Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities
House in Chesapeake Bay, NC
8 guests · 3 bedrooms · 3 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Free cancellationFull refund if you change your mind
Great for petsBring all your friends and family, even the furry ones
About this house rental
The privacy of a waterfront home welcomes you to pause and enjoy the beauty of the Chester River. Water views from every window connects you to the flowing water and the expansive outdoors. The southern exposure welcomes spectacular sunrises and sunsets. Relaxation and inspiration is abundant in this buffer zone!
Located close to both Chestertown and Rock Hall, it is an ideal gathering space for families and friends with many activities available in the area. By boat, this energetic space is located near Comegy Byte, the Langford Creek and the Corsica River. There is a boat launch within 1/4 mile of the house and a boat slip at the house; water depth is 2.5 feet MLT. Fishing from the 70 ' dock does not require a license.
For outside gathering, there is a large deck by the water with tables for dining, a picnic table under the shade of a holly tree and a water view bistro table and pergola beside the house.
For cooking, you can enjoy our amazing chef's kitchen with single oven, dishwasher, and fully stocked with dishes and utensils, including toaster and coffee/tea bar. You can also cook outside on our gas grill or charcoal grill. If dining inside, you can entertain guests at our kitchen table/dining bar or enjoy the water views at our second dining table.
For relaxation and amenities, we have a fantastic living room and dining area with water views, full size washer and dryer, 2 TVs with Direct TV, high speed internet, books, games and more! We also have an outdoor fire pit and indoor fireplace for entertaining. Firewood is available for your use.
We provide kayaks and paddle boards for you to enjoy the water around the property. We also have bicycles for you to explore the surrounding landscape. A few crab pots are available to try your luck for the famous Maryland blue crab. Bring your own fishing gear to fish directly from our private pier!
Three large bedrooms. Entry level bedroom has a king bed with two single day beds. En suite bathroom with shower and soaking tub. Perfect for families with smaller children.
The second bedroom has a king bed and the third bedroom is a queen. Both have chairs for reading and large closets. One hall bathroom has full bath while the other contains a shower stall. Linens (bed sheets, bath towels and hand towels) are provided with the rental contract. Please contact us if you are interested in opting out of the linen rental during your stay.
Come and fall in love with this retreat; return often!
Keywords: Self-catering, one-story water front cottage
Located close to both Chestertown and Rock Hall, it is an ideal gathering space for families and friends with many activities available in the area. By boat, this energetic space is located near Comegy Byte, the Langford Creek and the Corsica River. There is a boat launch within 1/4 mile of the house and a boat slip at the house; water depth is 2.5 feet MLT. Fishing from the 70 ' dock does not require a license.
For outside gathering, there is a large deck by the water with tables for dining, a picnic table under the shade of a holly tree and a water view bistro table and pergola beside the house.
For cooking, you can enjoy our amazing chef's kitchen with single oven, dishwasher, and fully stocked with dishes and utensils, including toaster and coffee/tea bar. You can also cook outside on our gas grill or charcoal grill. If dining inside, you can entertain guests at our kitchen table/dining bar or enjoy the water views at our second dining table.
For relaxation and amenities, we have a fantastic living room and dining area with water views, full size washer and dryer, 2 TVs with Direct TV, high speed internet, books, games and more! We also have an outdoor fire pit and indoor fireplace for entertaining. Firewood is available for your use.
We provide kayaks and paddle boards for you to enjoy the water around the property. We also have bicycles for you to explore the surrounding landscape. A few crab pots are available to try your luck for the famous Maryland blue crab. Bring your own fishing gear to fish directly from our private pier!
Three large bedrooms. Entry level bedroom has a king bed with two single day beds. En suite bathroom with shower and soaking tub. Perfect for families with smaller children.
The second bedroom has a king bed and the third bedroom is a queen. Both have chairs for reading and large closets. One hall bathroom has full bath while the other contains a shower stall. Linens (bed sheets, bath towels and hand towels) are provided with the rental contract. Please contact us if you are interested in opting out of the linen rental during your stay.
Come and fall in love with this retreat; return often!
Keywords: Self-catering, one-story water front cottage
Amenities
Air conditioner
Pets allowed
Kitchen or Kitchenette
Internet / Wifi
Fireplace
Parking
Laundry
Balcony or Patio
Dishwasher
TV
Garden
Family friendly
Map of Chesapeake Bay, NC
$$$$
Ratings and reviews
5.0 / 5.0
Great location and property. Our family enjoyed the experience and fishing on the dock. We caught several cat fish and was a enjoyable experience. Some good restaurants 15 minutes away. Only thing was we couldn't check in at 4pm because cleaning wasn't completed yet, but wasn't a big deal.
5.0 / 5.0
Perfect place for our reunion of old friends- 3 couples.
-Explored the river and bay cove in the kayaks provided along with paddles and life jackets.
-Caught crabs in the cages and rode bicylces provided.
-So much space to gather for good conversation, meals, enjoying the water activity and especially the sunsets and stars.
Hope to have opportunity to visit this beautiful piece of Maryland again.
5.0 / 5.0
Such a wonderful place to spend time with family. We had all we could ask for, plus such a beautiful view! This is our second stay here, but first time in the summer season. Such a treat to be able to enjoy the water so easily!
5.0 / 5.0
The place was clean. cozy, and well stocked for cooking and dining. We loved how the dock was set up and would have morning coffee out there, as well as dinner while watching the sunset. We took advantage of the kayaks, and at one time the kids had 5 kayaks out for a race around the nearby fishing shack and back. At night we were able to have a fire and make s'mores, followed by all the kids just laying in the dark at the end of the dock watching the stars. The home also had fun yard games stored in the garage, which we took out and played with. We tried catching crabs with our manual lines and their cages, but we didn't get any. We brought fishing poles with us and were able to fish off the dock - all the kids caught fish, though we unhooked and threw them all back since they were all smallish fish about 5 inches or so. I did snag a big fish when we went out on the kayak - alas, I was fighting for close to 10 minutes I think trying to reel it in until it snapped my line and taking my lure along with it. Maybe the next time were back, I'll meet the same fish again and have better luck.
5.0 / 5.0
There’s a magic to this place that keeps us coming back. We enjoyed our stay with our family and pups. The house is clean and well-stocked and the beds are very comfortable. Feels like a home away from home. Thank you again. We will be back!
5.0 / 5.0
We have stayed at this gorgeous property many many times and it feel like home away from home. Our pets have a blast. So relaxing and recharging. We already booked for 2 weeks in June 2025.
5.0 / 5.0
This house has a beautiful, peaceful setting with a vista of sparking waters. The inside is welcoming with eye catching details. The dock is sturdy with lots of seating. Birds and wildlife abound! Just lovely.
5.0 / 5.0
The property is lovely with coffee amenities, toy amenities and comfort galore. The landscaping is so beautiful and the water feature with comfortable and abundant seating is extraordinary. We had a lovely stay!!
5.0 / 5.0
Gorgeous cottage with to die for views and charming, well maintained grounds. Will come again!
5.0 / 5.0
Awesome place. My family had fun.
5.0 / 5.0
We booked a short mid week stay to “get away” for a family get together and what a perfect place! Stunning views, beach house nautical themed throughout and absolutely stocked with anything you could possibly need. The attention to detail was beyond anywhere we have stayed. Comfortable beds, detailed instructions and where to go binders and Jared was responsive to all questions. The kitchen is the best stocked I have ever experienced with a rental. We loved the area - peaceful little harbor town- and the residents were so friendly. We fished off the dock, kayaked and had bonfires at night. It was a perfect trip and a much needed, serene get away for all of us. Thank you for sharing your beautiful home!
5.0 / 5.0
We have stayed at Cliff Point many times and always feel right at home there! The views are beautiful, the home is inviting, and it’s always so wonderful to have quiet time with family! Even on a rainy weekend, we thoroughly enjoyed our time there! Thank you, Jared!
5.0 / 5.0
Such a wonderful property! You can really tell that the owners put a LOT of care into making sure it’s as enjoyable as possible for their guests. House was clean and well stocked. The use of outdoor items was a serious bonus and ensured we always had something to do. We would definitely come again and highly recommend to anyone else.
Side note, it’s obvious an artist lives here which made for such a beautiful setting. 😊
5.0 / 5.0
The property has everything that we needed to relax and enjoy our stay. It is clean and beautiful. The host Jared Miller is very flexible, responds to and accommodated our request when he can, had thought of every detail and everything needed. We have been there a few times before, we love it, we will be back.
5.0 / 5.0
My husband and I and our 2 dogs took a long-needed break in February. The house, amenities, location and weather were perfect. The constant calming views of the water and walks down to the Cliff City boat ramp each morning and evening were just what we all needed. The location is peaceful but provides easy access to Chestertown, Rockhall and other points.
5.0 / 5.0
Perfection
5.0 / 5.0
4th year in a row we’ve stayed here as a group of 8. Perfect layout of seating, sleeping and accommodations! We’ll be back again!
5.0 / 5.0
This is a great house to gather with multiple areas to relax. We enjoyed the fireplace! The views are outstanding. We witnessed one spectacular sunrise and several sunsets. Chestertown is a cute, historic town. This was our second time staying at Cliff Point Retreat and we will probably be back!
5.0 / 5.0
Thanks for sharing this amazing place. It was a perfect place for our family holiday. The beauty and serenity is unique, ducks, geese, river, bay - always a part of the view- nature at its best.
Merry Christmas!
5.0 / 5.0
Sunset views are spectacular from this waterfront gem. The house is spotless and extremely well stocked both in kitchen and outdoor equipment. Owner communication was top notch.
5.0 / 5.0
Such a perfectly designed space! We were happy with the seating areas, the outside area, and of course the views. We loved the fully stocked kitchen- thank you! The sea glass collection was beautiful, allowing for reflection and mindfulness. We look forward to our return!
5.0 / 5.0
We always enjoy staying! The views are stunning. You can see sunrise and sunset from the dock.
5.0 / 5.0
Extremely well stocked home with beautiful view. Great area for walking or biking. Quiet with an awesome deck and pier.
5.0 / 5.0
My group and I have been to Cliff Point Retreat many times beginning in the 1990's. There must be a reason. Many, actually. The house of three/four bedrooms with great mattresses, three complete bathrooms, full, well equipped modern kitchen and located dead on one of the widest points on the Chester River is simply spectacular. A beautiful "L" dock extends into the river (fishing or crabbing anyone?) and will accommodate your party as it sits to view sunrises and sunsets. Perfectly quiet location on a near dead end road. The VRBO listing will list details amenities. Jared Miller manages the property and is a gem to work with.
Go to Cliff Point Retreat. You won't regret it.
5.0 / 5.0
We love to come here. There are so many extras. It feels like home away from home. Jared is a terrific property manager. He is very responsive and provides excellent details about the property. Everything was perfect and we will be back.
5.0 / 5.0
Beautifully appointed home - clearly the owners care very much about their property. Tastefully decorated. Everything is in tip top shape - inside and out. Super clean. Nothing is lacking - everything you need is here. Jared - the property manager - is very responsive. Peaceful, quiet neighborhood. Thoroughly enjoyed our stay. Thank you!
5.0 / 5.0
This is our fourth time staying at Cliff Point and we can’t wait to come back. We enjoyed the beautiful sunrises and sunsets, and how comfortable we feel in this home.
5.0 / 5.0
We had a wonderful time at this place. The house & view was spectacular!! We will definitely come back again!
5.0 / 5.0
The property manager Jared, is the best at answering questions, adding helpful information - the best! We have vacationed at this amazing property, we love it so much we have returned on 4 vacations!
The kitchen is pretty much fully stocked if you like to cook during your stay, I did and loved it. Being a foodie and cook, I brought my own knives, thats just me!
You can stock up the fridge at the grocery stores in Chestertown and be ready to cook crabs if you crab out front, we bring our boat. Our family loves taking the boat out to fish and crab, we had a bushel in 2 days!
The beds are all comfortable and there are plenty of blankets if you need them as well as pillows. The bathrooms are stocked with things you may have forgotten - love that.
The game closet is great, the kids loved it - old and young! The views while sitting at the dining table are amazing. The boat ramp is just down the road for easy in and out.
I used the gas grill one night to cook chicken - oh baby, the grill is great, I need a new grill like this one : )
Thanks Jared for keeping this property a gem - close to perfection.
5.0 / 5.0
I am adding to a long list of positive reviews. The property was perfect for our family to gather. The place was clean and well stocked with everything we needed. The grounds, deck and outdoor toys - kayaks, paddle boards etc. made the trip fun and easy. We even did some crabbing! Jared was helpful along the way and we appreciate the opportunity to use the space. The location was the right mix of private and accessible -15 min to a nice town with an amazing bakery!! We hope to return again soon! Heather
5.0 / 5.0
We loved our time at Cliff Point Retreat. The owners had every amenity you could think of and then some. Even down to the showering products and q tips. The kitchen was fully stocked with every pot, pan, dish and seasoning plus storage containers. Our kids loved using the kayaks and we brought our fishing gear. The 7-11 in Chestertown sold bait which we needed a lot of because we easily caught 70 fish during the week. We were able to swim half the time as the jellyfish came early this year. There were tubes and floats all in the garage. Also the beds were the most comfortable I have slept on in any rental! I could go on but we would absolutely stay again.
5.0 / 5.0
This outstanding quiet property sets the stage for an amazing family vacation. It has EVERYTHING you could want for a relaxing stay and dreamy fun on the river. We lived on the dock from morning coffee to sunsets, enjoying the kayaks & paddle boards, fishing, crabbing, meals and more. The house is equally well appointed from comfy beds, ample seating for everyone to stretch out & a fully equipped kitchen where we made all but one meal for 11 days. Loved the grill too. Fast internet and quiet workspace for our son that had to work during the day.
Seriously - it exceeded my already high expectations from the listing and reviews. Excellent communication. Absolutely Perfect! Still smiling.
5.0 / 5.0
My husband and I love this property so much which is why we have rented it multiple times. The view is unbelievable, it is quiet and private. The house itself is ultra clean and fully stocked. The property manager is beyond helpful and a pleasure to deal with. We look forward to our return next year.
5.0 / 5.0
Gorgeous riverfront property with amazing sunsets. Dog friendly, spacious rooms and fully stocked kitchen. Plenty of water sports -kayaks, paddleboards- to keep busy. Great restaurants-highly recommend Luisa’s. We will return!
5.0 / 5.0
This is the most beautiful and serene vacation spot we frequent. It’s so quiet and peaceful. The accommodations could not be better!
5.0 / 5.0
Great places nearby, however you don’t need to leave the property. Everything you could possibly need is available.
5.0 / 5.0
We’ve been coming here for a decade and will return every time we are in the area!
5.0 / 5.0
Friends and I love staying here year after year because it is a clean and efficient property, but an excellent home on the river with "things" to do -- both be on the water in kayaks or paddle boards or swimming, or relaxing and playing games or puzzles in the house, sharing meals, or heading into the quaint town of Chestertown.
5.0 / 5.0
Loved this property. The house was comfortable and well-appointed. Especially nice was the dock right on the water, where we could put out the fishing pole during the day and have a fire at the fire pit in the evening. There were birds nesting at one end of the dock, right near the honeysuckle, which was fragrant during our stay. There is also a picnic table which was perfect for our steamed crab dinner (we called Clark's Seafood, who steamed them ahead for us, and provided advice on how to eat them). Highly recommended property. We hope to come again.
5.0 / 5.0
We came for our sons college graduation weekend! The house is exactly as pictured… they have everything you can imagine from cookware to bug spray… if you need it it’s there! The lower deck on the water is very comfortable and the views stunning! We had a few people over for a luncheon and the house is set up for easy entertaining too! Highly recommend this gem on the Eastern Shore!
FAQs
How much does this house cost compared to others in Chesapeake Bay?
The average price for a rental in Chesapeake Bay is $236 per night. This rental is $208 above the average.
Is parking included with this house?
Yes, parking is listed as an amenity at Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities. For more information, we encourage you to contact the property about where to park.
Is there a pool at this house?
We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.
Is Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities pet friendly?
Yes! This house is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.
What amenities are available at Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities?
We found 12 amenities for this rental. This includes air conditioner, pets allowed, kitchen or kitchenette, internet / wifi, and fireplace.
Explore similar vacation rentals in Chesapeake Bay
Explore all rentals in Chesapeake Bay
2 blocks to CNU-5 bedroom house with First floor Master
Villa
in Newport NewsGarden · Kitchen or Kitchenette · Air conditioner
Looking to create some memories in Chesapeake Bay? Look no further than our Villa, 2 blocks to CNU-5 bedroom house with First floor Master. Enjoy top-rated amenities including Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Inn at Perry Cabin
Hotel
in St. Michaels5star
2 guests · 1 bedroom · 1 bath
Garden · Pool · Air conditioner
Looking to create some memories in Chesapeake Bay? Look no further than our Hotel, Inn at Perry Cabin. Enjoy top-rated amenities including Air conditioner, Internet / Wifi and Laundry, and more.
$$$$
Inn at Perry Cabin
Hotel
in St. Michaels5star
1 queen bed
Garden · Pool · Air conditioner
Looking to create some memories in Chesapeake Bay? Look no further than our Hotel, Inn at Perry Cabin. Enjoy top-rated amenities including Air conditioner, Internet / Wifi and Laundry, and more.
$$$$
PERFECT LOCATION in the heart of history
House
in Annapolis8 guests · 3 bedrooms · 3 baths
Kitchen or Kitchenette · Air conditioner · Internet / Wifi
Experience the best of Chesapeake Bay with this House available for $441. This property is equipped with amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.
$$$$
Start earning One Key rewards
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
House
in Ridge10 guests · 3 bedrooms · 3 baths
Garden · Pets allowed · Kitchen or Kitchenette
The best choice in Chesapeake Bay for House, for $385 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)
$$$$
Start earning One Key rewards
Very private riverfront, beach, nature for all to enjoy. High Speed Internet!!
House
in Bohannon12 guests · 6 bedrooms · 4 baths
Garden · Pool · Pets allowed
Nestled in Chesapeake Bay, this House is perfect for your next vacation. Enjoy Very private riverfront, beach, nature for all to enjoy. High Speed Internet!!'s top-rated amenities, including Air conditioner, Dishwasher and Internet / Wifi, and more.
$$$$
Beachfront
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
House
in Stevensville26 guests · 5 bedrooms · 4 baths
Garden · Pool · Pets allowed
Looking for a memorable stay in Chesapeake Bay? Our House might just be what you're looking for. Enjoy amenities including Air conditioner, Dishwasher and Fireplace, and more during your stay.
$$$$
Island Life! Kent Island Waterfront with Pool-Bring your boat!
Bed and Breakfast
in Stevensville12 guests · 3 bedrooms · 3 baths
Garden · Pool · Kitchen or Kitchenette
Looking to create some memories in Chesapeake Bay? Look no further than our Bed and Breakfast, Island Life! Kent Island Waterfront with Pool-Bring your boat!. Enjoy top-rated amenities including Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Chesapeake Bay House with Dock & Private Beach
House
in Elkton12 guests · 5 bedrooms · 4 baths
Kitchen or Kitchenette · Air conditioner · Internet / Wifi
Looking for a memorable stay in Chesapeake Bay? Our House might just be what you're looking for. Enjoy amenities including Air conditioner, Dishwasher and Fireplace, and more during your stay.
$$$$
As seen on HGTV! 4 BR, 2 blocks to beach. Newly renovated. Golf Cart Included.
House
in Cape Charles10 guests · 4 bedrooms · 2 baths
Garden · Pets allowed · Kitchen or Kitchenette
This inviting House in Chesapeake Bay can fit your needs for many types of vacations, at $459 per night.
$$$$
Start earning One Key rewards
THE LIGHTHOUSE INN..Imagine Walking 2 Blocks And Having Your Feet In The Sand!!!
House
in Cape Charles14 guests · 4 bedrooms · 5 baths
Garden · Kitchen or Kitchenette · Air conditioner
Business stays, family stays, couples stay, getaway vacation, and rental in Chesapeake Bay at THE LIGHTHOUSE INN..Imagine Walking 2 Blocks And Having Your Feet In The Sand!!! for $515 for your next trip.
$$$$
Start earning One Key rewards
*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay
House
in Perryville8 guests · 3 bedrooms · 3 baths
Garden · Pets allowed · Kitchen or Kitchenette
When traveling to Chesapeake Bay, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $373 per night.
$$$$
Start earning One Key rewards
Private, 7-acre waterfront retreat on Winter Harbor Haven
House
in Port Haywood8 guests · 4 bedrooms · 2 baths
Garden · Pets allowed · Kitchen or Kitchenette
Discover the beauty of Chesapeake Bay with a stay at Private, 7-acre waterfront retreat on Winter Harbor Haven, a top rated House with amenities such as Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Heart of Historic District!
House
in Annapolis10 guests · 5 bedrooms · 3 baths
Garden · Kitchen or Kitchenette · Air conditioner
Looking to create some memories in Chesapeake Bay? Look no further than our House, Heart of Historic District!. Enjoy top-rated amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.
$$$$
Start earning One Key rewards
5-bedroom vacation home 5 minutes from historic Charlestown
House
in Perryville13 guests · 6 bedrooms · 2 baths
Garden · Pets allowed · Kitchen or Kitchenette
When traveling to Chesapeake Bay, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $398 per night.
$$$$
Beach House on Chesapeake Bay!
House
in Hudgins8 guests · 3 bedrooms · 2 baths
Garden · Pool · Kitchen or Kitchenette
Enjoy the best of Chesapeake Bay in our House, Beach House on Chesapeake Bay!. A stunning property with amenities including Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Waterfront Cottage with Fishing Dock and Fireplace!
House
in HeathsvillePets allowed · Kitchen or Kitchenette · Air conditioner
Looking for the perfect place to call home during your trip to Chesapeake Bay? This House offers a comfort and style with top-notch amenities, including Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Start earning One Key rewards
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
House
in Cambridge15 guests · 4 bedrooms · 2 baths
Garden · Pets allowed · Kitchen or Kitchenette
When traveling to Chesapeake Bay, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $501 per night.
$$$$
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
House
in Chester8 guests · 4 bedrooms · 2 baths
Garden · Kitchen or Kitchenette · Air conditioner
Experience the best of Chesapeake Bay with this House available for $413. This property is equipped with amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.
$$$$
Sisters 3 by the Sea, 400 Feet To The Beach
House
in Cape Charles8 guests · 4 bedrooms · 2 baths
Garden · Kitchen or Kitchenette · Air conditioner
Indulge in a peaceful retreat at Sisters 3 by the Sea, 400 Feet To The Beach, our elegant House in Chesapeake Bay. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.
$$$$
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
House
in Port Republic8 guests · 3 bedrooms · 2 baths
Garden · Pets allowed · Kitchen or Kitchenette
This attractive House in Chesapeake Bay, $398 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)
$$$$
Enjoy The Hideaway in Hays Beach on the Chesapeake Bay with Broadband Internet!
Cottage
in Scotland8 guests · 3 bedrooms · 2 baths
Garden · Pets allowed · Kitchen or Kitchenette
This Cottage for $375 in Chesapeake Bay, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)
$$$$
Bay House with Amazing View & Swimming Pool (open May- Sept.)
House
in Reedville9 guests · 4 bedrooms · 2 baths
Garden · Pool · Pets allowed
Experience vacation in Chesapeake Bay with our House, Bay House with Amazing View & Swimming Pool (open May- Sept.). Enjoy amenities such as Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Start earning One Key rewards
𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻 𝐇𝐀𝐘𝐒 𝐁𝐄𝐀𝐂𝐇 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘
Cottage
in Scotland8 guests · 3 bedrooms · 1 bath
Kitchen or Kitchenette · Air conditioner · Internet / Wifi
When traveling to Chesapeake Bay, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $386 per night.
$$$$
Start earning One Key rewards
Stunning New Construction in Historic Cape Charles 3 1/2 Blocks to the Beach
House
in Cape Charles9 guests · 3 bedrooms · 3 baths
Garden · Kitchen or Kitchenette · Air conditioner
Soak up the beauty of Chesapeake Bay in our House, Stunning New Construction in Historic Cape Charles 3 1/2 Blocks to the Beach. With a range of amenities such as Air conditioner, Dishwasher and Fireplace, you'll feel right at home.
$$$$
Start earning One Key rewards
Chesapeake Bay Beachfront Retreat
House
in White Stone12 guests · 4 bedrooms · 5 baths
Kitchen or Kitchenette · Air conditioner · Internet / Wifi
Nestled in Chesapeake Bay, this House is perfect for your next vacation. Enjoy Chesapeake Bay Beachfront Retreat's top-rated amenities, including Air conditioner, Dishwasher and Internet / Wifi, and more.
$$$$
American Four-Square completely renovated, easy walk to the beach!
House
in Cape Charles9 guests · 3 bedrooms · 3 baths
Kitchen or Kitchenette · Air conditioner · Internet / Wifi
House in Chesapeake Bay, for $366 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)
$$$$
Stunning Custom Home in Maritime Annapolis - Million dollar row in Eastport
House
in Annapolis9 guests · 4 bedrooms · 4 baths
Garden · Pets allowed · Kitchen or Kitchenette
Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Chesapeake Bay, at $494 per night for your next great vacation.
$$$$
Beachfront
Beachfront w/ Private Access & 2 Decks - Spacious & Well-Equipped Home 🏖️
House
in Norfolk8 guests · 4 bedrooms · 3 baths
Garden · Pool · Kitchen or Kitchenette
Are you ready to indulge in a relaxing getaway? Our House in Chesapeake Bay has everything you need for a rejuvenating stay. Treat yourself to Beachfront w/ Private Access & 2 Decks - Spacious & Well-Equipped Home 🏖️'s exceptional amenities, such as Air conditioner, Dishwasher and Fireplace.
$$$$
Great Entertaining Spot for any Occassion!
House
in Edgewater10 guests · 2 bedrooms · 1 bath
Garden · Pool · Pets allowed
Are you ready to indulge in a relaxing getaway? Our House in Chesapeake Bay has everything you need for a rejuvenating stay. Treat yourself to Great Entertaining Spot for any Occassion!'s exceptional amenities, such as Air conditioner, Dishwasher and Internet / Wifi.
$$$$
Chesapeake Bay travel inspiration
Read our blogGuides
Best East Coast Beaches and Getaway Locations You Can’t Miss
Budget Travel
7 Most Affordable Snowbird Destinations for 2025
Guides
Top Activities to Try in Panama City Beach, Florida
Guides
Top Things to Do in Gulf Shores, Alabama: Adventure and Fun Await
Local Culture
Exploring Miami’s Wynwood District: Street Art, Food, and More
Guides
Fun Things to Do in Ocean City, Maryland
Local Culture
A Foodie’s Guide to the Best Dining in Orlando, Florida
Guides
Top Things to Do in Oahu and Honolulu
Keep exploring
- Kauai Villas
- Orlando Villas
- Kiawah Island Villas
- Miami Beach Villas
- Kissimmee Villas
- North Naples Villas
- Florida Keys Villas
- Phoenix Villas
- Los Angeles Villas
- St Petersburg Villas
- Palm Desert Villas
- Miami Villas
- Las Vegas Villas
- Venice Villas
- Key West Villas
- Palm Springs Villas
- Lake Tahoe Villas
- Hollywood Hills Villas
- Seabrook Island Villas
- South Lake Tahoe Villas
- Pocono Mountains Villas
- Scottsdale Villas
- Myrtle Beach Villas
- Hilton Head Island Villas
- Marco Island Villas
- North Miami Villas
- Sanibel Island Villas
- West Palm Beach Villas
- Fort Myers Beach Villas
- Haines City Villas
- North Las Vegas Villas
- Destin Villas
- Lake Tahoe Cabins
- Ruidoso Cabins
- Blue Ridge Cabins
- Estes Park Cabins
- Lake George Cabins
- Eureka Springs Cabins
- Branson Cabins
- Lake of the Ozarks Cabins
- Lake Arrowhead Cabins
- Lake Texoma Cabins
- Canyon Lake Cabins
- Sevierville Cabins
- Flagstaff Cabins
- Colorado Springs Cabins
- Hot Springs Cabins
- Bass Lake Cabins
- Buffalo River Cabins
- Possum Kingdom Lake Cabins
- Chattanooga Cabins
- Nashville Cabins
- Wears Valley Cabins
- Cloudcroft Cabins
- Deep Creek Lake Cabins
- Mammoth Lakes Cabins
- Anna Maria Islands Rentals
- Outer Banks Vacation Rentals
- Rosemary Beach Rentals
- Holden Beach Rentals
- Hilton Head Vacation Rentals
- Topsail Beach Rentals
- Kiawah Island Rentals
- Panama City Beach Rentals
- Ocean Isle Beach Rentals
- Folly Beach Rentals
- Dauphin Island Rentals
- Rehoboth Beach Rentals
- Bethany Beach Rentals
- Cape Cod Rentals
- 30A Rentals
- Seaside Florida Rentals
- Edisto Beach Rentals
- Fort Myers Beach Rentals
- Miramar Beach Rentals
- Port Aransas Rentals
- Emerald Isle Rentals
- Orange Beach Rentals
- Surfside Beach Rentals
- Hampton Beach Rentals
- Assateague Island Rentals
- Jacksonville Beach Vacation Rentals
- North Shore Vacation Rentals
- Ogunquit Vacation Rentals
- North Redington Beach Rentals
- Lido Key Vacation Rentals
- Sea Colony Rentals
- Pass A Grille Vacation Rentals
- Blue Ridge Mountain Rentals
- Vail Lodging
- Jackson Hole Lodging
- Winter Park Lodging
- Telluride Lodging
- Big Sky Rentals
- Aspen Lodging
- Park City Rentals
- Steamboat Springs Lodging
- Breckenridge Rentals
- Lake Tahoe Rentals
- Copper Mountain Lodging
- Mammoth Mountain Lodging
- Beech Mountain Rentals
- Crested Butte Rentals
- Sun Valley Lodging
- Keystone Lodging
- Taos Lodging
- Sugar Mountain Cabins
- Beaver Creek Lodging
- Deep Creek Lake Rentals
- Smith Mountain Lake Rentals
- Ocean Lakes Rentals
- Lake Anna Rentals
- Torch Lake Rentals
- Lake Winnipesaukee Rentals
- Norris Lake Rentals
- Lake Gaston Rentals
- Canyon Lake Rentals
- Lake Oconee Rentals
- Lake Wallenpaupack Rentals
- Lake Martin Rentals
- Lake Havasu Rentals
- Lake of the Ozarks Rentals
- Lake Michigan Vacation Rentals
- Lake Chelan Rentals
- Finger Lakes Rentals
- Lake Keowee Vacation Rentals
- Lake Conroe Rentals
- Lake Erie Vacation Rentals
- Lake Austin Vacation Rentals
- Sebago Lake Rentals
- Lake Tillery Rentals
- Keuka Lake Rentals