Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
5.0
Outstanding(32 Reviews)House in Chesapeake Bay, NC
12 guests · 8 bedrooms · 10 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Includes essentialsGarden, Pool, Kitchen or Kitchenette and more
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental
About this house rental
TREMEZZO STAY - CHEASAPEAKE MANSION
Our properties are owned, managed, and hosted by us. We deliver personally hosted luxury rental experiences in St. Michaels, MD.
If you do not see availability for your dates or are looking for a more moderate price point please visit our other listings!
Ranch at Royal Oak:
https://www.vrbo.com/2697100?unitId=3267863
Punch Point:
https://www.vrbo.com/3887202?dateless=true
Spencer Creek Cabin:
https://www.vrbo.com/1342430?unitId=1900766
Chesapeake Mansion is the premier Eastern Shore destination.
Voted #1 mansion rental in the state of Maryland by “Trips to Discover”!
Voted "Coolest ABNB in the state of Maryland" by Conde Nast Traveler (December 2021).
Also was host to the Bravo TV Network’s Real Housewives of Potomac.
The pool is open from mid-March to mid-October and to answer your question.. YES, it is heated :) This enormous 12,000 sqft. home sits on a private 30 acres just outside of St. Michaels. We spent 2 years updating this home with all of your rental needs in mind. This home sleeps the county maximum of 12 guests.
Please take a look at the virtual tour if you have a moment!
•August 2022- New playground surround installed
•October 2021- 160’ pier installed with 5’ MLW
•August 2021- New poly-wood mega playground installed
•March 2021- Atlantic Broadband has officially been added along with an EXTENSIVE MESH WiFi network!!!
Talbot County Rental License: ST-214-LYT
Our properties are owned, managed, and hosted by us. We deliver personally hosted luxury rental experiences in St. Michaels, MD.
If you do not see availability for your dates or are looking for a more moderate price point please visit our other listings!
Ranch at Royal Oak:
https://www.vrbo.com/2697100?unitId=3267863
Punch Point:
https://www.vrbo.com/3887202?dateless=true
Spencer Creek Cabin:
https://www.vrbo.com/1342430?unitId=1900766
Chesapeake Mansion is the premier Eastern Shore destination.
Voted #1 mansion rental in the state of Maryland by “Trips to Discover”!
Voted "Coolest ABNB in the state of Maryland" by Conde Nast Traveler (December 2021).
Also was host to the Bravo TV Network’s Real Housewives of Potomac.
The pool is open from mid-March to mid-October and to answer your question.. YES, it is heated :) This enormous 12,000 sqft. home sits on a private 30 acres just outside of St. Michaels. We spent 2 years updating this home with all of your rental needs in mind. This home sleeps the county maximum of 12 guests.
Please take a look at the virtual tour if you have a moment!
•August 2022- New playground surround installed
•October 2021- 160’ pier installed with 5’ MLW
•August 2021- New poly-wood mega playground installed
•March 2021- Atlantic Broadband has officially been added along with an EXTENSIVE MESH WiFi network!!!
Talbot County Rental License: ST-214-LYT
Amenities
Pool
Air conditioner
Kitchen or Kitchenette
Internet / Wifi
Fireplace
Parking
Laundry
Balcony or Patio
Dishwasher
TV
Wheelchair accessible
Gym or Fitness Center
Garden
Family friendly
Map of Chesapeake Bay, NC
Reviews
5.0
Outstanding(32 Reviews)5.0
Great stay
5.0
The Property Owners were both responsive and accommodating. The home is a lovely property and the venue is very nice with sweeping views of the Bay. There was plenty of space for our group of 10 to relax and congregate. Nice recreational areas with billiards, lovely pool and a fire pit as well as good beds, linens, dishes and appliances. The library of books was quite impressive as well.
5.0
Host and property were great
5.0
This property is just gorgeous inside and out! We were rained in a few days and did not have any trouble finding our fun! Lots of indoor activities and beautiful views! The kitchen is a fun family friendly atmosphere where all can hang out. Amazing time with our family in the prestigious home!
5.0
My friends and I had a spectacular time at this truly amazing property. The house is gorgeous and has every amenity you could possibly dream of wanting. Everything was clean, comfortable and the views were incredible. The hosts were responsive and everything was in perfect working order. Thank you for letting us stay in such wonderful accommodations!
5.0
Amazing house in an amazing location with wonderful owners! Fun house for a weekend with friends. Highly recommend. Fully stocked kitchen and so many amenities.
5.0
For my 50th and 60th birthday, I celebrated with 10 dear girlfriends in Bethany and then Annapolis. Now it was my 70th and I wanted something extra special with plenty of room and comfortable sleeping arrangements. Wow, I definitely found it at the Chesapeake Mansion! We spent 5 days doing yoga in the early morning while watching the eagles and osprey overhead. We cooked fabulous meals in the beautiful, fully equipped kitchen. We sang karaoke in the fabulous bar as we had cocktails and then watched the sun go down around a bonfire eating s’mores. It was sooooo perfect and Marissa was just amazing. Everyone wants to return, although we will definitely not wait 10 years!!!
Next, my family arrived for another 5 days. It was totally different but also just PERFECT! My grandchildren swam everyday in the heated pool and played on the perfect playground. When we had a rainy day, the large playroom stocked with toys and a great play kitchen kept everyone happy. When the kids went down, the adults had plenty of space to have drinks, play pool, ping pong and some more karaoke! We also caught some crabs off the pier…..my grandchildren had a ball and can’t wait for my next birthday LOL!!! What a fantastic experience!
5.0
Perfect spot for families with little kids. Great host and beautiful home.
5.0
This is a beautiful and well-maintained house with an incredible view, amazing pool, and great amenities for kids including one of the best private playgrounds I've ever seen and a lovely playroom stocked with toys. Our group had 5 kids ranging from 6 months to 5 years old, and we were very comfortable. Marisa was extremely communicative and helpful. It's a 15 min drive to St. Michael's but the property is extremely private and secluded so it's a great getaway from the city. The only thing that would have made our stay better is improved water pressure (it's fine if one person is using the shower at a time, but otherwise it gets quite low) -- but this wasn't a huge deal. Highly recommend.
5.0
House was great, as advertised. The owner was very responsive, which is a huge plus for a rental house.
5.0
Great place for two generations of family to gather. House and grounds were beautiful. All rooms very comfortable. Plenty of dishware and cooking equipment. Day trips to the ocean, Washington DC and Baltimore. St. Michaels, Easton and Tilghman Island were wonderful nearby spots. Host was very communicative and everything went perfectly smoothly.
5.0
This is a wonderful property for bigger families. It has plenty to do for all ages.
5.0
The property and home are beautiful and so comfortable! Our family had a wonderful gathering.
Marissa was very helpful and always available.
Thank you!
5.0
We were a party of 8 old girlfriends who have gotten pickier and pickier with age for our annual get together. The house, location and Marissa were all incredible. Beautifully appointed, kitchen well stocked with everything including consumables and so much space both inside and out. Comfort, quiet and privacy. So many bathrooms! Yeah! While likely designed for families (fantastic playground, pool, huge yard and lots of fun activities inside and out) it works well for all kinds of groups. Excellent prompt communication. The sunsets and the grand white oak as we winded down the day. A flock of turkeys, bald eagle, great blue herons, Bluebirds etc and the power of a thunderstorm one evening allowed lots of connection between friends and nature. Incredible.
5.0
This property is even nicer in person than the pictures show online. Every guest was simply impressed with the size, cleanliness, and interior design of the property. The house came with everything you need to have fun playing lawn games (e.g., cornhole and croquet) make world class dinners, and keep the children occupied with a fully stocked game room and playground in the backyard.
We had a ton of questions for the host and Melissa was super quick to reply with all the information we needed.
We utilize VRBO quite often, and this was, by far, the nicest property we've stayed at. Even at the price point offered, it exceeded our expectations. We look forward to booking again in the future.
5.0
I recently stayed at the Chesapeake Mansion with my extended family for a week-long reunion. The property was accurately represented in the listing and provided an amazing experience for everyone in our group. The house was well-maintained, spacious, and had plenty of amenities to keep everyone entertained. The location was beautiful, with stunning sunsets in the evenings.
One of the best things about our stay was communication with the owners. They were very responsive to any questions we had and made sure our stay was enjoyable. We appreciated their prompt communication and willingness to accommodate our needs.
Overall, the Chesapeake Mansion was an incredible place to reconnect with family and create lasting memories. I would highly recommend this property to anyone looking for a large house to spend quality time with their loved ones.
5.0
11 family members, age range 8 moths to 88 years stayed in this beautiful home. Wonderful facilities for both adults and little ones. Marissa is a superb host. Very highly recommended.
5.0
You can't want for more from the multitude of king BRs with ensuite baths to a milk froth machine for your morning cup of joe. The kitchen was extremely well equipped. Our group consisted of 5 couples that met in college 40+ years ago. We've somewhat scattered to other states and have never gotten together more than one evening at a wedding for many years. Besides the pool and ping pong table and a foos ball table, they had a karaoke machine which while using created many memories that'll last a lifetime. Our only issue was the weather! We were there during the last dregs of Hurricane Ian but thankfully this property provided lots of entertainment options. We had no issues with the house other than not being able to find the firewood for the outdoor fire pit. A quick text that was responded to immediately sent us on our way. Can't say enough good things about this property. We didn't have any children with us but it is extremely well equipped to handle a gaggle of kids.
5.0
The property is beautiful; the views beautiful!
Marissa was very responsive to any questions or requests. The pool and property are great. The house is stocked with basically anything you need - from pool towels, games, toys, and then the view!!
5.0
This is a beautiful home with an amazing view that has everything you could want for a restful vacation.
5.0
Well maintained and recently updated with lots of room for a big family group. The house has plenty of amenities to keep everyone occupied inside and out. Everything works and the owner is very responsive.
5.0
This was a family vacation of 10 (6 adulats and 4 kids 6-9) celebrating our 50th anniversary. The house had so much room that everyone could spread out and do their own thing. The pool was incredible, sunset views, wildlife (on one tree alone, I took pictures of a bald eagle, 2 osprey and a great blue heron). The recreational amenities were super: playroom, games, billiards, foosball, karyoke, wifi speakers for music, cable tv with all the premium networks, a gym, etc.
We all said we would stay for a week more if we could.
Marissa and Brandon were amazing hosts. Very accommodating and responsive. Our only regret was that we really couldn't go into the bay with paddleboards or swim but the hosts made alternative arrangements for us to do that.
5.0
Wonderful week. Great host!
This was a family vacation of 10 (6 adulats and 4 kids 6-9) celebrating our 50th anniversary. The house had so much room that everyone could spread out and do their own thing. The pool was incredible, sunset views, wildlife (on one tree alone, I took pictures of a bald eagle, 2 osprey and a great blue heron). The recreational amenities were super: playroom, games, billiards, foosball, karyoke, wifi speakers for music, cable tv with all the premium networks, a gym, etc.
We all said we would stay for a week more if we could.
Marissa and Brandon were amazing hosts. Very accommodating and responsive. Our only regret was that we really couldn't go into the bay with paddleboards or swim but the hosts made alternative arrangements for us to do that.
5.0
Beautiful Waterfront with Heated Pool and Family Fun Favorites
After four years our large family was under the same roof for the first time. This beautiful VRBO had enough bedrooms and bathrooms to provide the privacy and vacation feel for all. We used the billard room almost every evening and the home is large enough that the noise did not disturb sleeping children. We had a couple of folks who were working from home and they had private quiet space for virtual meetings. They experienced a brief wi-fi outage but after sending a text to the host it was fixed within minutes. Phew! The children had a stocked playroom, our nightly family cooking challenge competition was a lot of fun in the large open kitchen (Sushi night was the winner with fresh tuna sourced from the local Wittman seafood store that was only 5 minutes away). The heated pool was a big hit and right next to the large playground so it kept us all together. The host had a multitude of yard games and we used croquet, can jam, and cornhole. Our 50 ft boat charter with captain was able to pick us up from the dock- no worries with water depth. We tried our luck at fishing from the dock and crabbing- no luck. Haha. We ordered crabs from nearby Chesapeake Landing restaurant for our last night and the kitchen was stocked with everything we needed to host our own crabfeast at home. This property sits directly on the open bay so swimming and paddleboarding were not possible. Having the boat charter allowed us to find nearby swimming holes and explore the area. We enjoyed the firepit, smores, beautiful sunsets, and morning country side walks/runs. The VRBO hosts were very responsive and helpful. Don’t hesitate to book it. This property is worth it :)
5.0
We had such a lovely time at the Chesapeake Mansion. The property is beautiful - just like the pictures. We were three families, and found the space perfectly suited to deliver fun for all ages. The look on the kids' faces after exploring the property was priceless. "Mom, no one at school is going to believe that I stayed in a MANSION!" The kids were so happy setting up a cafe in the playroom toy kitchen, wandering the shore line, walking to see the animals at the farm, and playing endless games of hide-in-go seek (which usually resulted in the seekers giving up - there are just too many places for hiding!) The pool really is heated well - the heater could deliver warm bath-like temperatures after just 30 minutes. The views of the Chesapeake are just stunning, and we thoroughly enjoyed stargazing while using the firepit at night. Each morning we were happily greeted by deer grazing, and we thoroughly enjoyed watching the swallows swoop down from their nests throughout the day. We were worried that the location would be too remote, but found that it was easy to hop over to St. Michael's for dinner or ice cream. We stopped in Easton on our way in for groceries and a propane tank for the BBQ, and then we were set for the weekend. The rooms were spacious and the beds and linens were comfy. It was a lovely weekend, and we definitely recommend this property.
5.0
Beautiful views and wonderful family memories
We had such a lovely time at the Chesapeake Mansion. The property is beautiful - just like the pictures. We were three families, and found the space perfectly suited to deliver fun for all ages. The look on the kids' faces after exploring the property was priceless. "Mom, no one at school is going to believe that I stayed in a MANSION!" The kids were so happy setting up a cafe in the playroom toy kitchen, wandering the shore line, walking to see the animals at the farm, and playing endless games of hide-in-go seek (which usually resulted in the seekers giving up - there are just too many places for hiding!) The pool really is heated well - the heater could deliver warm bath-like temperatures after just 30 minutes. The views of the Chesapeake are just stunning, and we thoroughly enjoyed stargazing while using the firepit at night. Each morning we were happily greeted by deer grazing, and we thoroughly enjoyed watching the swallows swoop down from their nests throughout the day. We were worried that the location would be too remote, but found that it was easy to hop over to St. Michael's for dinner or ice cream. We stopped in Easton on our way in for groceries and a propane tank for the BBQ, and then we were set for the weekend. The rooms were spacious and the beds and linens were comfy. It was a lovely weekend, and we definitely recommend this property.
5.0
We had a grand time using the pool, and our 3 year old love the play gym in the yard. The sunsets were great.
5.0
Family get together
We had a grand time using the pool, and our 3 year old love the play gym in the yard. The sunsets were great.
5.0
This host and home was beyond 5 stars from start to finish! This sets the bar for all vacation rentals without a doubt. We went into this trip thinking that our visit to Saint Michaels was going to be a one-time thing. After our experience with this home we have decided we will not go through another summer without a trip to this luxurious waterfront sanctuary. We have already booked a week for 2022!! We cannot wait! Thank you for everything! PS - the new playground was worth it’s wait in gold… the kids were occupied the entire trip :)
5.0
Sets the bar for all vacation rentals! My friends and family almost couldn’t believe it.
This host and home was beyond 5 stars from start to finish! This sets the bar for all vacation rentals without a doubt. We went into this trip thinking that our visit to Saint Michaels was going to be a one-time thing. After our experience with this home we have decided we will not go through another summer without a trip to this luxurious waterfront sanctuary. We have already booked a week for 2022!! We cannot wait! Thank you for everything! PS - the new playground was worth it’s wait in gold… the kids were occupied the entire trip :)
5.0
Hi, Marissa,
I just wanted to say thank you for the experience of the last week. Simply put the house is fabulous. There were 10 of us and we (and I) had an amazing vacation. Comfort and convenience were the everyday experience. We were never cramped and always had space to do what we ever we wanted and that certainly included the pool. Photography is a hobby of mine and the sunsets from the back yard over the water were spectacular. Thank you. I’m certainly hoping to do it again.
The Shelton's
This wonderful oasis sits right on the water. The house which is truly a mansion has all the amenities plus more for an enjoyable, relaxing getaway. All the rooms are spacious and well appointed, which includes a fitness room, library, multiple family rooms, bedrooms with their own bathrooms and a swimming pool. Highly recommend!
Our Guest
5.0
This home was the perfect place for our family vacation. It has something for every age group. Inside and out! Every room is impeccably designed and decorated. I took pictures to give me inspiration for my own home, I am so in love. The kitchen is HUGE, open, airy, and the perfect gathering spot for everyone to have a meal together. You will be blown away at the beauty.
5.0
An Oasis
Hi, Marissa,
I just wanted to say thank you for the experience of the last week. Simply put the house is fabulous. There were 10 of us and we (and I) had an amazing vacation. Comfort and convenience were the everyday experience. We were never cramped and always had space to do what we ever we wanted and that certainly included the pool. Photography is a hobby of mine and the sunsets from the back yard over the water were spectacular. Thank you. I’m certainly hoping to do it again.
The Shelton's
This wonderful oasis sits right on the water. The house which is truly a mansion has all the amenities plus more for an enjoyable, relaxing getaway. All the rooms are spacious and well appointed, which includes a fitness room, library, multiple family rooms, bedrooms with their own bathrooms and a swimming pool. Highly recommend!
Our Guest
5.0
Wholeheartedly recommend this AMAZING home!
This home was the perfect place for our family vacation. It has something for every age group. Inside and out! Every room is impeccably designed and decorated. I took pictures to give me inspiration for my own home, I am so in love. The kitchen is HUGE, open, airy, and the perfect gathering spot for everyone to have a meal together. You will be blown away at the beauty.
5.0
Talk about absolutely breathtaking! We had a fabulous time at the Chesapeake Mansion. Everything about our stay was an A++! We had high hopes when reading about this home and everything exceeded our expectations from the privacy of the home to over 12,000sqft of creative design elements and beautiful decor. The view is spectacular, especially from the crystal clear heated pool. The amenities were endless with plenty of options to keep both kids and adults entertained for our entire stay. The chef’s kitchen was incredible and plenty of room for all 12 of us! The Mansion is the perfect location to plan a reunion with family or friends. Marissa was available at all times and was a great communicator with any questions we had. Highly recommend! 5 stars plus!
5.0
The property is gorgeous inside and out! No detail has been missed.
There is something for all age groups from the toy room for babies/toddlers to karaoke in the bar with the pool table for adults and fun card games too! There are also lawn games outside for young and old.
It’s in a great location! Close to St. Michaels if you want to shop or get dinner. We also had a few meals in Tilghman island. The kids loved watching the fishing boats go under the bridge.
Definitely a trip we won’t forget. I can’t wait to go back next year!
5.0
Heaven on Earth!
Talk about absolutely breathtaking! We had a fabulous time at the Chesapeake Mansion. Everything about our stay was an A++! We had high hopes when reading about this home and everything exceeded our expectations from the privacy of the home to over 12,000sqft of creative design elements and beautiful decor. The view is spectacular, especially from the crystal clear heated pool. The amenities were endless with plenty of options to keep both kids and adults entertained for our entire stay. The chef’s kitchen was incredible and plenty of room for all 12 of us! The Mansion is the perfect location to plan a reunion with family or friends. Marissa was available at all times and was a great communicator with any questions we had. Highly recommend! 5 stars plus!
5.0
Exceeded our expectations!
The property is gorgeous inside and out! No detail has been missed.
There is something for all age groups from the toy room for babies/toddlers to karaoke in the bar with the pool table for adults and fun card games too! There are also lawn games outside for young and old.
It’s in a great location! Close to St. Michaels if you want to shop or get dinner. We also had a few meals in Tilghman island. The kids loved watching the fishing boats go under the bridge.
Definitely a trip we won’t forget. I can’t wait to go back next year!
FAQs
How much does this house cost compared to others in Chesapeake Bay?
The average price for a rental in Chesapeake Bay is $408 per night. This rental is $1,532 above the average.
Is parking included with this house?
Yes, parking is listed as an amenity at Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND. For more information, we encourage you to contact the property about where to park.
Is there a pool at this house?
Yes, a swimming pool is available for use at Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND. Enjoy the water!
Is Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND pet friendly?
Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"
What amenities are available at Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND?
We found 14 amenities for this rental. This includes pool, air conditioner, kitchen or kitchenette, internet / wifi, and fireplace.
Explore similar vacation rentals in Chesapeake Bay
Explore all rentals in Chesapeake BayStart earning One Key rewards
Historic Oxford Waterfront Estate
House
in Oxford12 guests · 7 bedrooms · 6 baths
Garden · Pool · Kitchen or Kitchenette
When traveling to Chesapeake Bay, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $1,616 per night.
$$$$
Start earning One Key rewards
Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28
House
in Cambridge28 guests · 7 bedrooms · 7 baths
Pool · Pets allowed · Kitchen or Kitchenette
The best choice in Chesapeake Bay for House, for $2,083 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)
$$$$
Eagle Haven - Waterfront Estate on the Choptank with Pool and Pier - Sleeps 18
House
in Cambridge18 guests · 5 bedrooms · 5 baths
Garden · Pool · Pets allowed
Are you ready to indulge in a relaxing getaway? Our House in Chesapeake Bay has everything you need for a rejuvenating stay. Treat yourself to Eagle Haven - Waterfront Estate on the Choptank with Pool and Pier - Sleeps 18's exceptional amenities, such as Air conditioner, Dishwasher and Internet / Wifi.
$$$$
Chesapeake Bay View
House
in Cape Charles14 guests · 6 bedrooms · 5 baths
Garden · Kitchen or Kitchenette · Air conditioner
Indulge in a peaceful retreat at Chesapeake Bay View, our elegant House in Chesapeake Bay. Enjoy amenities including Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Private 2 Acre Waterfront Family Retreat with Pool & Pier
House
in Cambridge22 guests · 8 bedrooms · 7 baths
Garden · Pool · Pets allowed
Looking for a memorable stay in Chesapeake Bay? Our House might just be what you're looking for. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more during your stay.
$$$$
Waterfront Paradise on the Eastern Shore of Chesapeake Bay
House
in Rock Hall14 guests · 6 bedrooms · 4 baths
Pool · Kitchen or Kitchenette · Air conditioner
Experience the best of Chesapeake Bay with this House available for $1,675. This property is equipped with amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.
$$$$
Start earning One Key rewards
A WATERFRONT ESTATE ON THE CHESAPEAKE BAY, "THE DRIFTWOOD LODGE".
House
in Tracys Landing20 guests · 7 bedrooms · 5 baths
Garden · Pets allowed · Kitchen or Kitchenette
Discover the beauty of Chesapeake Bay with a stay at A WATERFRONT ESTATE ON THE CHESAPEAKE BAY, "THE DRIFTWOOD LODGE". , a top rated House with amenities such as Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Just Steps to the Beach!
House
in Virginia Beach21 guests · 8 bedrooms · 8 baths
Garden · Pool · Pets allowed
Most favorited
Experience vacation in Chesapeake Bay with our House, Just Steps to the Beach!. Enjoy amenities such as Air conditioner, Dishwasher and Internet / Wifi, and more.
$$$$
Start earning One Key rewards
Amazing Waterfront Retreat On The Chesapeake Bay Private Pool Private Beach
House
in Cambridge12 guests · 6 bedrooms · 3 baths
Garden · Pool · Pets allowed
Business stays, family stays, couples stay, getaway vacation, and rental in Chesapeake Bay at Amazing Waterfront Retreat On The Chesapeake Bay Private Pool Private Beach for $1,569 for your next trip.
$$$$
Prestigious Historic Annapolis home, parking for 5 cars, walk to everything!
House
in Annapolis12 guests · 5 bedrooms · 4 baths
Garden · Kitchen or Kitchenette · Air conditioner
Looking to create some memories in Chesapeake Bay? Look no further than our House, Prestigious Historic Annapolis home, parking for 5 cars, walk to everything!. Enjoy top-rated amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.
$$$$
Sunset Lodge on the Bay
House
in Rock Hall14 guests · 6 bedrooms · 4 baths
Garden · Kitchen or Kitchenette · Air conditioner
Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Chesapeake Bay, at $1,719 per night for your next great vacation.
$$$$
Beachfront
Beachfront Villa - Private Beach with Hot Tub
Villa
in Cape Charles16 guests · 5 bedrooms · 5 baths
Garden · Pets allowed · Kitchen or Kitchenette
Villa in Chesapeake Bay, for $1,739 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)
$$$$
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Villa
in Rock Hall25 guests · 9 bedrooms · 8 baths
Garden · Pool · Kitchen or Kitchenette
Top rated
Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Chesapeake Bay, at $1,972 per night for your next great vacation.
$$$$
Exquisite Water Front Estate. Pool, Crabbing off private dock and sunset kayaks.
House
in White Stone12 guests · 4 bedrooms · 4 baths
Garden · Pool · Kitchen or Kitchenette
Looking to create some memories in Chesapeake Bay? Look no further than our House, Exquisite Water Front Estate. Pool, Crabbing off private dock and sunset kayaks.. Enjoy top-rated amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.
$$$$
Veazey Cove | 8,000 sq ft Waterfront Home w/ Pool + Hot Tub!
House
in Earleville16 guests · 6 bedrooms · 7 baths
Pool · Pets allowed · Kitchen or Kitchenette
Are you ready to indulge in a relaxing getaway? Our House in Chesapeake Bay has everything you need for a rejuvenating stay. Treat yourself to Veazey Cove | 8,000 sq ft Waterfront Home w/ Pool + Hot Tub!'s exceptional amenities, such as Air conditioner, Dishwasher and Fireplace.
$$$$
Life Just Got Better
House
in Cape Charles20 guests · 6 bedrooms · 5 baths
Garden · Pool · Kitchen or Kitchenette
Looking for a memorable stay in Chesapeake Bay? Our House might just be what you're looking for. Enjoy amenities including Air conditioner, Dishwasher and Fireplace, and more during your stay.
$$$$
Classic Eastern Shore Waterfront Manor House - ST-936
House
in St Michaels12 guests · 6 bedrooms · 5 baths
Garden · Pool · Kitchen or Kitchenette
This attractive House in Chesapeake Bay, $2,183 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)
$$$$
RANCH AT ROYAL OAK- Exclusive waterfront pool pier
House
in Royal Oak12 guests · 6 bedrooms · 6 baths
Garden · Pool · Kitchen or Kitchenette
Are you ready to indulge in a relaxing getaway? Our House in Chesapeake Bay has everything you need for a rejuvenating stay. Treat yourself to RANCH AT ROYAL OAK- Exclusive waterfront pool pier's exceptional amenities, such as Air conditioner, Dishwasher and Internet / Wifi.
$$$$
Renovated dog-friendly bayfront home with private hot tub & pool, grill, & dock
House
in Annapolis18 guests · 8 bedrooms · 6 baths
Garden · Pool · Pets allowed
Are you ready to indulge in a relaxing getaway? Our House in Chesapeake Bay has everything you need for a rejuvenating stay. Treat yourself to Renovated dog-friendly bayfront home with private hot tub & pool, grill, & dock's exceptional amenities, such as Air conditioner, Dishwasher and Internet / Wifi.
$$$$
Beautiful, spacious waterfront home, an easy walk to historic Chestertown
House
in Chestertown14 guests · 6 bedrooms · 7 baths
Garden · Kitchen or Kitchenette · Air conditioner
This House for $2,244 in Chesapeake Bay, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)
$$$$
Start earning One Key rewards
Historic Manor House on Beautiful Eastern Shore Estate
House
in Chestertown13 guests · 6 bedrooms · 5 baths
Garden · Pool · Pets allowed
When traveling to Chesapeake Bay, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $2,069 per night.
$$$$
3-story, dog-friendly home near beaches with home theatre, grill & gaming tables
House
in Annapolis15 guests · 6 bedrooms · 7 baths
Garden · Pets allowed · Kitchen or Kitchenette
Experience vacation in Chesapeake Bay with our House, 3-story, dog-friendly home near beaches with home theatre, grill & gaming tables. Enjoy amenities such as Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Start earning One Key rewards
Blake House Historic Estate with Private Inn
Villa
in Centreville12 guests · 7 bedrooms · 6 baths
Garden · Pool · Pets allowed
Top rated
Discover the beauty of Chesapeake Bay with a stay at Blake House Historic Estate with Private Inn, a top rated Villa with amenities such as Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Start earning One Key rewards
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
House
in Cambridge27 guests · 12 bedrooms · 6 baths
Pool · Kitchen or Kitchenette · Air conditioner
Soak up the beauty of Chesapeake Bay in our House, Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!. With a range of amenities such as Air conditioner, Dishwasher and Fireplace, you'll feel right at home.
$$$$
Minutes from Downtown Cambridge | Private Dock | Pool | Kayaks
House
in Cambridge16 guests · 5 bedrooms · 4 baths
Garden · Pool · Pets allowed
Experience vacation in Chesapeake Bay with our House, Minutes from Downtown Cambridge | Private Dock | Pool | Kayaks. Enjoy amenities such as Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Newly renovated historic Annapolis house. walking distance to navy stadium, DTA
House
in Annapolis14 guests · 5 bedrooms · 3 baths
Kitchen or Kitchenette · Air conditioner · Internet / Wifi
Enjoy the best of Chesapeake Bay in our House, Newly renovated historic Annapolis house. walking distance to navy stadium, DTA. A stunning property with amenities including Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Chesapeake Point | Waterfront w/ HOT TUB + Beach!
House
in Elkton20 guests · 7 bedrooms · 5 baths
Kitchen or Kitchenette · Air conditioner · Internet / Wifi
Indulge in a peaceful retreat at Chesapeake Point | Waterfront w/ HOT TUB + Beach!, our elegant House in Chesapeake Bay. Enjoy amenities including Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Thorneton Point Estate
House
in Easton12 guests · 6 bedrooms · 5 baths
Garden · Pool · Pets allowed
Experience the best of Chesapeake Bay with this House available for $2,164. This property is equipped with amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.
$$$$
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
House
in Annapolis12 guests · 6 bedrooms · 4 baths
Kitchen or Kitchenette · Air conditioner · Internet / Wifi
Enjoy the best of Chesapeake Bay in our House, Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA. A stunning property with amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.
$$$$
Start earning One Key rewards
Bayfront White Stone Escape w/ Private Beach!
House
in White Stone19 guests · 6 bedrooms · 5 baths
Garden · Kitchen or Kitchenette · Air conditioner
When traveling to Chesapeake Bay, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $1,762 per night.
$$$$
Chesapeake Bay travel inspiration
Read our blogGuides
Top Things to Do in Oahu and Honolulu
Guides
Top Things to Do in Fort Lauderdale, Florida
Guides
Top Things to Do in Miami: From Beaches to Culture
Guides
The Best Things to Do in Orlando: Attractions, Food, and Family Fun
Guides
Things to Do in Galveston, Texas
Guides
Top Things to Do in Myrtle Beach
Guides
Ski Trip Packing List: What to Bring Skiing or Snowboarding
Trends
VacationRenter Holiday Travel Trends 2023