Waterfront Property, kayaks, private dock, near town
4.8
Outstanding(146 Reviews)House in Chesapeake Bay, NC
6 guests · 4 bedrooms · 3 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Includes essentialsGarden, Pool, Pets allowed and more
About this house rental
Cranford on the Miles is an historic waterfront home located on 3+ acres, in St. Michaels, and 1+ mile from the beginning of town. Fully renovated, with WI-Fi, there is a Master Bedroom with king bed, sitting room, private bathroom and private balcony; Second Bedroom with a double bed; Third Bedroom with both a double and twin bed; and a Den with a trundle bed with 2 twins beds and a second balcony. Downstairs there is a queen sofa bed. Every room has a view of the water.
Linens, towels, beach towels, blankets and pillows provided.
Provided are two kayaks (one single, one double) for exploring the Chesapeake.
From the private dock you can watch wildlife, fish or crab. Roast marshmallows over the fire pit, or cook your fish on the grill. Bring your boat and launch from the public boat ramp within walking distance.
Or just relax on either the screened porch with ceiling fans, cushioned sofa and chairs, or the front porch rocking chairs. Indoors, every bedroom has a TV, large TV is genie ready, books, and music CDs for all ages. The second family room has a fireplace.
Talbot County Short Term Rental License Number ST-119-SAN 2018.
There is also a community pool about 1 mile from the house.
Linens, towels, beach towels, blankets and pillows provided.
Provided are two kayaks (one single, one double) for exploring the Chesapeake.
From the private dock you can watch wildlife, fish or crab. Roast marshmallows over the fire pit, or cook your fish on the grill. Bring your boat and launch from the public boat ramp within walking distance.
Or just relax on either the screened porch with ceiling fans, cushioned sofa and chairs, or the front porch rocking chairs. Indoors, every bedroom has a TV, large TV is genie ready, books, and music CDs for all ages. The second family room has a fireplace.
Talbot County Short Term Rental License Number ST-119-SAN 2018.
There is also a community pool about 1 mile from the house.
Amenities
Pool
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
Reviews
4.8
Outstanding(146 Reviews)4.8
Very nice place! Everything was perfect! Lisa is a great host! Our plane was cancelled so she let us extend our stay free of charge! We will be back!!
Thanks Lisa!
4.8
We stayed here at the end of March with our family of 3 kids ages 3 to 13 and Grandma. Crabbing season doesn’t start until April so we found some things in the area were closed for the season, but it didn’t matter because we had a fantastic time at this magical waterfront property. They have taken great care of this historical property and filled it with so many interesting artifacts! We enjoyed fishing off the dock, and seeing ospreys, bald eagles, herons and numerous song birds. We brought our bikes and enjoyed several rails to trails bike paths in the area. Just a short drive to town and all of its charming shops. Owner was wonderful, beds comfortable, great communication. We hope we can return soon!
4.8
A true original Chesapeake Bay Eastern Shore estate with terrific water access via nice dock into the beautiful Miles River. The house is filled with so very many historic and labeled artifacts and antiques. Lots of sitting areas throughout the home and a wonderful wrap around screened in porch overlooking the water. We will be back!
4.8
We enjoyed our time spent at Cranford on the Miles. The house and property was well provided for. The screened in porch was enjoyed all weekend by all of us even our four legged friends. We would definitely recommend this property for a relaxing stay at St. Michaels.
4.8
We just recharged at this lovely, thoughtfully restored and thoroughly modernized historic house on the water. From watching spectacular sunrises, working crab boats and a magnificent great heron perched on the dock to learning more about the area and being surrounded by articles and items from the house’s historical era, our stay was a delight.
4.8
We just recharged at this lovely, thoughtfully restored and thoroughly modernized historic house on the water. From watching spectacular sunrises, working crab boats and a magnificent great heron perched on the dock to learning more about the area and being surrounded by articles and items from the house’s historical era, our stay was a delight.
4.8
We thoroughly enjoyed the time we spent at this property. The setting and grounds are beautiful; the house was spacious and well-appointed; and Lisa was a very attentive and gracious host. Thank you!
4.8
The location of this property is fantastic It is on a quiet river with a dock for fishing, a little beach for young children and a beautiful space for kayaking. The house is well equipped and beautifully furnished. The kitchen had every appliance and tool that anyone would need. We ate our dinners on the wraparound porch while enjoying the breezes. There is plenty of space for everyone inside and out. While we spent most mornings at the house, we also took advantage of the opportunities nearby. St. Michael's is only a few miles away for meals out and shopping. Our family particularly enjoyed the Chesapeake Bay Maritime Museum in St. Michaels and ferry trip from Bellevue to Oxford for ice cream. This three generations of family is still talking about how much fun this vacation was and are still recounting memories of the best moments. The owners of this property have made this a really special destination house.
4.8
Everything was as described and photos were accurate. Lots of nice space and we enjoyed watching the horseshoe crabs on the beach and saw a tiny jellyfish and what may have been dolphins in the river. The wifi worked fine and we really enjoyed the cute town of St. Michaels and the maritime museum.
4.8
This was the perfect place for our Memorial Day girls trip! We spent the weekend doing yoga on the dock, cooking meals together in the large kitchen, eating dinner on the screen porch, and watching the sunrise. It was also very quick and easy to get into town in St Michaels for restaurants and shopping. We would love to come back!
4.8
We had a lovely Thanksgiving with our family - and it was perfect for all of us. Close to town and restaurants and grocery. Great communication with owners and overall was delightful!
4.8
This place was the perfect getaway for our girls trip. Everyone had plenty of space, kitchen was well stocked, and the views can’t be beat. Would highly recommend.
4.8
Historic, relaxed, comfortable, and spacious house on gorgeous, expansive waterway. The views from the entire house are beautiful, and the screened wraparound porch is the perfect place to have a meal, or morning coffee, or to sit and relax while enjoying the view. The house has its own pier and sits on a large lot surrounded by trees. St Michaels' restaurants are 3 mi away and the lovely Tilghum Island is half an hour away via a country drive. Just perfect. Lisa was a wonderful and attentive host.
4.8
We had the most amazing time at this unique home situated on the Miles River 3 miles from town. Our daughter was getting married at the Inn at Perry Cabin. The house was perfect for a small luncheon for her bridesmaids with a beautiful dining room that easily seats 8 people. There are four air conditioning units keeping the house cool during a very hot period in August. We crabbed off the pier, my husband went kayaking, our two small dogs were welcomed and there was ample room for three couples to stay, the owner was very accommodating for the changes in my schedule since I needed to stay a few extra days and was fortunate to be able to extend last minute. I would definitely recommend to families or several couples who want to have the experience of staying in a historic home on the eastern shore with beautiful water views and privacy with the ability to get into town easily for shopping, dining and water activities.
4.8
Incredible Stay
beautiful property and great location. We plan to stay here again.
4.8
My family stayed here for a family reunion. The check-in process was efficient and the host contacted me to make sure everything was okay upon arrival and departure. The property is very nice, albeit old-timey--this is clear in the description. Air conditioning works, as do the kitchen appliances. Only complaint was that I killed 15-20 flies in the kitchen over the course of 3 days. My sense is that this is par for the course for the Eastern Shore climate, but if that is a dealbreaker for you, consider elsewhere. Otherwise the unit was totally clean. I would stay here again.
4.8
Good for long weeknd
My family stayed here for a family reunion. The check-in process was efficient and the host contacted me to make sure everything was okay upon arrival and departure. The property is very nice, albeit old-timey--this is clear in the description. Air conditioning works, as do the kitchen appliances. Only complaint was that I killed 15-20 flies in the kitchen over the course of 3 days. My sense is that this is par for the course for the Eastern Shore climate, but if that is a dealbreaker for you, consider elsewhere. Otherwise the unit was totally clean. I would stay here again.
4.8
St Michaels
Roomy Historic home with screened-in porch for relaxing and eating meals. Very clean home with every kitchen gadget imaginable. Kayaking, fishing, relaxing (in Adirondack chairs overlooking the water). Short drive to town for shops and restaurants.
4.8
If we could give this fabulous property 6+ stars we would! It was a real home from home with every amenity and comfort we could possibly want, beautifully clean and will presented, extremely large and private with spectacular views over the Miles River and its own dock. We simply didn't want to leave! We had the best long weekend ever with our family congregating from NJ and GA to attend the wedding of a close family friend. We felt very relaxed and comfortable, the property was very private and we enjoyed every moment! Thank you to our wonderful super host Lisa who made everything so special for us and who was so responsive to the couple of questions we had. This is a real home from home and we loved everything about it and it's location. We would return in a heartbeat and hope to do so again very soon! Thank you from the bottom of our hearts!
4.8
A little slice of heaven with fabulous, private water frontage and every amenity/comfort imaginable
If we could give this fabulous property 6+ stars we would! It was a real home from home with every amenity and comfort we could possibly want, beautifully clean and will presented, extremely large and private with spectacular views over the Miles River and its own dock. We simply didn't want to leave! We had the best long weekend ever with our family congregating from NJ and GA to attend the wedding of a close family friend. We felt very relaxed and comfortable, the property was very private and we enjoyed every moment! Thank you to our wonderful super host Lisa who made everything so special for us and who was so responsive to the couple of questions we had. This is a real home from home and we loved everything about it and it's location. We would return in a heartbeat and hope to do so again very soon! Thank you from the bottom of our hearts!
4.8
This house is charming and welcoming from the moment you drive up the long driveway and see the large porches and beautiful bay in the background! My family came for three nights, knowing that if the weather wasn't fantastic we'd want a house we could enjoy spending time in. Cranford did not disappoint!! Much bigger than we expected, the house is well appointed with period furniture and art, but feels incredibly comfortable and homey. Lisa was the most wonderful, gracious host who made herself available and helped us feel welcome without being overbearing at all. We enjoyed the house immensely - from the gorgeous views in the bedrooms (the sunrise over the water is spectacular) to the kayaks my husband took out in the morning. We came with our two kids - 10 mos & 4.5 years - as well as our dog, and everyone was welcome (there was even a fresh bowl of water for our pup and Lisa had messaged that there would be beanie babies for the kids to play with). Highly recommend!!
4.8
A very special getaway
This house is charming and welcoming from the moment you drive up the long driveway and see the large porches and beautiful bay in the background! My family came for three nights, knowing that if the weather wasn't fantastic we'd want a house we could enjoy spending time in. Cranford did not disappoint!! Much bigger than we expected, the house is well appointed with period furniture and art, but feels incredibly comfortable and homey. Lisa was the most wonderful, gracious host who made herself available and helped us feel welcome without being overbearing at all. We enjoyed the house immensely - from the gorgeous views in the bedrooms (the sunrise over the water is spectacular) to the kayaks my husband took out in the morning. We came with our two kids - 10 mos & 4.5 years - as well as our dog, and everyone was welcome (there was even a fresh bowl of water for our pup and Lisa had messaged that there would be beanie babies for the kids to play with). Highly recommend!!
4.8
Despite continually overcast skies and rainy weather, our family of five (ages 28-60+) and 2 dogs enjoyed welcoming 2022 (and ushering out 2021!) during our post-Christmas stay at Cranford on the Miles. We had stayed at another (1980s) house nearby, last December. Cranford was much more charming and interesting! Lisa has put a lot of effort into highlighting examples of furnishings and decor of the mid-nineteenth century period, when the house was first built. These were essentially out of reach for small children, although I did manage to break a more day-to-day wine glass that fell from a counter top.
The layout allows for a lot of privacy and quiet spaces, as well as very functional areas for group gatherings. A 15-step staircase with a carved, period railing leads from the living room and dining room side of the original house to the master bedroom. The mbr is large with a comfortable king-size bed, a balcony/porch (above part of the first floor wrap around porch) with an outstanding view overlooking the Miles, and more built-in storage than we could ever use! A laundry and linen storage space (with doors on both sides) separates the master from a second cozy and well appointed bedroom with a high, full-size bed. One step down from that bedroom's door is a full bathroom and the third bedroom with 2 artfully decorated twin beds. Going back up a step there is a large landing/sitting area with a chair and trundle daybed opening on to a second balcony/porch. The landing is at the top of what may have been the location of the back kitchen staircase to the second level, which is reached from the large family/TV room that opens to the kitchen.
Like any nearly 200-year old house, there are some quirks that I found charming, and maintenance is always an ongoing thing. Lisa has taken the time, clearly, to address things as they might come up. She was very accessible by phone and very easy to talk with. Cranford has a mix of casual, child-friendly furnishings and some more “adult-friendly”, but still comfortable pieces. The views are lovely — although we had a lot of wet weather, the morning mist on the water was beautiful. The kitchen was equipped with an abundance of cookware and tableware (especially anything necessary for eating crab!), a large Kitchenaid cooktop, a new-looking dishwasher, and soapstone counters. The washer & dryer also looked new. The house is in a terrific location between Easton and St. Michaels, both with excellent restaurant
4.8
Happy New Year
Despite continually overcast skies and rainy weather, our family of five (ages 28-60+) and 2 dogs enjoyed welcoming 2022 (and ushering out 2021!) during our post-Christmas stay at Cranford on the Miles. We had stayed at another (1980s) house nearby, last December. Cranford was much more charming and interesting! Lisa has put a lot of effort into highlighting examples of furnishings and decor of the mid-nineteenth century period, when the house was first built. These were essentially out of reach for small children, although I did manage to break a more day-to-day wine glass that fell from a counter top.
The layout allows for a lot of privacy and quiet spaces, as well as very functional areas for group gatherings. A 15-step staircase with a carved, period railing leads from the living room and dining room side of the original house to the master bedroom. The mbr is large with a comfortable king-size bed, a balcony/porch (above part of the first floor wrap around porch) with an outstanding view overlooking the Miles, and more built-in storage than we could ever use! A laundry and linen storage space (with doors on both sides) separates the master from a second cozy and well appointed bedroom with a high, full-size bed. One step down from that bedroom's door is a full bathroom and the third bedroom with 2 artfully decorated twin beds. Going back up a step there is a large landing/sitting area with a chair and trundle daybed opening on to a second balcony/porch. The landing is at the top of what may have been the location of the back kitchen staircase to the second level, which is reached from the large family/TV room that opens to the kitchen.
Like any nearly 200-year old house, there are some quirks that I found charming, and maintenance is always an ongoing thing. Lisa has taken the time, clearly, to address things as they might come up. She was very accessible by phone and very easy to talk with. Cranford has a mix of casual, child-friendly furnishings and some more “adult-friendly”, but still comfortable pieces. The views are lovely — although we had a lot of wet weather, the morning mist on the water was beautiful. The kitchen was equipped with an abundance of cookware and tableware (especially anything necessary for eating crab!), a large Kitchenaid cooktop, a new-looking dishwasher, and soapstone counters. The washer & dryer also looked new. The house is in a terrific location between Easton and St. Michaels, both with excellent restaurant
4.8
Thanksgiving escape
We had a wonderful stay. The house is beautiful and perfectly located. It was quiet and private yet very close to downtown St. Michaels and all the restaurants and shopping. The views from the house and grounds are amazing!
The owner was so friendly and helpful. Highly recommend this property!
4.8
Stayed with wife and 18 month old son. The house is very well located off a quiet driveway on the road into St. Michael’s. The house feels very private and secluded even though it’s only 5 minutes drive into St. Michael’s. The backyard is directly on the waterfront with beautiful views out of multiple rooms in the house.
The house is very well appointed with supplies including everything you need in the kitchen. The cleaning service had everything in great shape and the linens were all cleaned and ready, including towels and sheets on the beds.
Lots of room for a baby to run around. The owners also provided a gate and some other baby proofing items.
Would definitely stay again!
4.8
Great home in perfect location
Stayed with wife and 18 month old son. The house is very well located off a quiet driveway on the road into St. Michael’s. The house feels very private and secluded even though it’s only 5 minutes drive into St. Michael’s. The backyard is directly on the waterfront with beautiful views out of multiple rooms in the house.
The house is very well appointed with supplies including everything you need in the kitchen. The cleaning service had everything in great shape and the linens were all cleaned and ready, including towels and sheets on the beds.
Lots of room for a baby to run around. The owners also provided a gate and some other baby proofing items.
Would definitely stay again!
4.8
We stayed in the property to visit the Waterfowl Festival in Easton. The location was great as it was close to both Easton and St Michaels. The view was beautiful and we watched heron and eagles on the dock. . This is an old house so the layout is different. The bedrooms are arranged that you can walk through to get to the other but also able to close doors for privacy. My issue was the one bedroom you had to step down into the hallway to the bathroom which is tough to navigate when getting up in the middle of the night to use the bathroom. I recommend this house for 4 adults at the most or 2 adults with children because of the layout of the bedrooms. I never rented a property with so many rules.
4.8
Nice location and great view
We stayed in the property to visit the Waterfowl Festival in Easton. The location was great as it was close to both Easton and St Michaels. The view was beautiful and we watched heron and eagles on the dock. . This is an old house so the layout is different. The bedrooms are arranged that you can walk through to get to the other but also able to close doors for privacy. My issue was the one bedroom you had to step down into the hallway to the bathroom which is tough to navigate when getting up in the middle of the night to use the bathroom. I recommend this house for 4 adults at the most or 2 adults with children because of the layout of the bedrooms. I never rented a property with so many rules.
4.8
The place was perfect for us….plenty of space, indoors and outdoors. Views were wonderful. Everything was clean and easy. Definitely a great place!
4.8
This was a perfect house for our long weekend, wishing we could of stayed longer! Spacious and everything you need with old world charm. The view can't be beat, beautiful sunrises. Highly recommend.
4.8
Miles River
This was a perfect house for our long weekend, wishing we could of stayed longer! Spacious and everything you need with old world charm. The view can't be beat, beautiful sunrises. Highly recommend.
4.8
Perfect!
The place was perfect for us….plenty of space, indoors and outdoors. Views were wonderful. Everything was clean and easy. Definitely a great place!
4.8
The house, property, and views of the water are incredible. The communication was great and we had no issues at all with the house. The house has everything you need. We would love to stay again!
4.8
Beautiful Home and Property
The house, property, and views of the water are incredible. The communication was great and we had no issues at all with the house. The house has everything you need. We would love to stay again!
4.8
We attended a wedding in St Michaels over the long weekend. The house was a perfect fit for us, with plenty of room, beautiful water views, idyllic screen-in porch where we enjoyed our meals. Lisa was very responsive and even set up crab traps for us!
4.8
Labor Day weekend
We attended a wedding in St Michaels over the long weekend. The house was a perfect fit for us, with plenty of room, beautiful water views, idyllic screen-in porch where we enjoyed our meals. Lisa was very responsive and even set up crab traps for us!
4.8
A wonderful property
My family and I had an amazing time at this property. The owner was extremely helpful and pleasant to deal with, the home was very well-equipped, and both the interior and exterior of the home were beautiful. There was plenty of yard space for lawn games and my daughter’s dog had a great time running around; the owners even had some pet supplies there! The home had its own dock for fishing and crabbing and had all kinds of equipment for those activities as well. I would highly recommend this spot for a St. Michael’s stay!
4.8
Great location and great space.
Beautiful setting, incredible sunrise and perfect for sunsets
4.8
Christmas in July
Great location and great space.
Beautiful setting, incredible sunrise and perfect for sunsets
FAQs
How much does this house cost compared to others in Chesapeake Bay?
The average price for a rental in Chesapeake Bay is £212 per night. This rental is £432 above the average.
Is parking included with this house?
Yes, parking is listed as an amenity at Waterfront Property, kayaks, private dock, near town. 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 Waterfront Property, kayaks, private dock, near town. Enjoy the water!
Is Waterfront Property, kayaks, private dock, near town 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 Waterfront Property, kayaks, private dock, near town?
We found 13 amenities for this rental. This includes pool, air conditioner, pets allowed, kitchen or kitchenette, and internet / wifi.
Explore similar vacation rentals in Chesapeake Bay
Explore all rentals in Chesapeake Bay
Charming Historic Annapolis Home With Two Off-street Parking Places!
House
in Annapolis8 guests · 4 bedrooms · 3 baths
Kitchen or Kitchenette · Air conditioner · Internet / Wifi
Most favorited
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.
££££
Start earning One Key rewards
Award Winning Ocean Front Architectural Gem [Home Share per VA Beach Zoning]
House
in Virginia Beach12 guests · 4 bedrooms · 6 baths
Garden · Pool · Pets allowed
This House in Chesapeake Bay, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!
££££
Start earning One Key rewards
Perfect weekend getaway
House
in Annapolis6 guests · 3 bedrooms · 4 baths
Kitchen or Kitchenette · Air conditioner · Internet / Wifi
Soak up the beauty of Chesapeake Bay in our House, Perfect weekend getaway. With a range of amenities such as Air conditioner, Dishwasher and Fireplace, you'll feel right at home.
££££
Modern St. Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks & More
House
in Easton10 guests · 5 bedrooms · 4 baths
Garden · Pool · Pets allowed
Looking for a House in Chesapeake Bay, this House for £656 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.
££££
Start earning One Key rewards
Top of the Chesapeake - 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 £519 per night.
££££
Start earning One Key rewards
Blue Heaven - A Dog Friendly North End Beach Cottage - Private Walk to Beach!
Cottage
in Virginia Beach9 guests · 3 bedrooms · 4 baths
Pool · Pets allowed · Kitchen or Kitchenette
Business stays, family stays, couples stay, getaway vacation, and rental in Chesapeake Bay at Blue Heaven - A Dog Friendly North End Beach Cottage - Private Walk to Beach! for £623 for your next trip.
££££
Beachfront
Grand Escape - Featured on HGTV's Beachfront Bargain Hunt
House
in Cape Charles11 guests · 5 bedrooms · 6 baths
Pets allowed · Kitchen or Kitchenette · Air conditioner
House in Chesapeake Bay, for £520 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)
££££
Start earning One Key rewards
Inchgarth at Scotland Yards
House
in Scotland14 guests · 7 bedrooms · 6 baths
Pets allowed · Kitchen or Kitchenette · Air conditioner
Nestled in Chesapeake Bay, this House is perfect for your next vacation. Enjoy Inchgarth at Scotland Yards's top-rated amenities, including Air conditioner, Dishwasher and Fireplace, and more.
££££
Start earning One Key rewards
80 Five Star Reviews & located in a quiet neighborhood in the City of Annapolis!
House
in Annapolis8 guests · 4 bedrooms · 4 baths
Garden · Kitchen or Kitchenette · Air conditioner
The best choice in Chesapeake Bay for House, for £567 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)
££££
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
House
in Easton10 guests · 6 bedrooms · 5 baths
Garden · Pool · Kitchen or Kitchenette
Looking for a House in Chesapeake Bay, this House for £581 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.
££££
Start earning One Key rewards
Spacious Luxury 6 BR Home, Sleeps 15, Private Pool, In Nature, Convenient to DC
House
in Harwood15 guests · 6 bedrooms · 6 baths
Garden · Pool · Kitchen or Kitchenette
This House in Chesapeake Bay, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!
££££
Historic Beach Front Home: Victorian Elegance. Large Rooms with AMAZING bay view
House
in Cape Charles12 guests · 5 bedrooms · 3 baths
Garden · Pool · Kitchen or Kitchenette
Looking to create some memories in Chesapeake Bay? Look no further than our House, Historic Beach Front Home: Victorian Elegance. Large Rooms with AMAZING bay view. Enjoy top-rated amenities including Air conditioner, Dishwasher and Fireplace, and more.
££££
Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.
House
in Stevensville14 guests · 4 bedrooms · 3 baths
Garden · Kitchen or Kitchenette · Air conditioner
Indulge in a peaceful retreat at Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill., our elegant House in Chesapeake Bay. Enjoy amenities including Air conditioner, Dishwasher and Fireplace, and more.
££££
Charming Annapolis Victorian
House
in Annapolis12 guests · 6 bedrooms · 5 baths
Garden · Kitchen or Kitchenette · Air conditioner
Looking to create some memories in Chesapeake Bay? Look no further than our House, Charming Annapolis Victorian. Enjoy top-rated amenities including Air conditioner, Dishwasher and Fireplace, and more.
££££
Peaceful Waterfront Retreat ~ 23 Private Acres With Dock & Pool
House
in Cambridge17 guests · 6 bedrooms · 5 baths
Garden · Pool · Pets allowed
Indulge in a peaceful retreat at Peaceful Waterfront Retreat ~ 23 Private Acres With Dock & Pool, our elegant House in Chesapeake Bay. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.
££££
Start earning One Key rewards
Beachfront Luxury Home w/ Fabulous Garden & Sunset Views!
House
in Cape Charles14 guests · 5 bedrooms · 4 baths
Garden · Kitchen or Kitchenette · Air conditioner
Business stays, family stays, couples stay, getaway vacation, and rental in Chesapeake Bay at Beachfront Luxury Home w/ Fabulous Garden & Sunset Views! for £561 for your next trip.
££££
When you want to get away from everything Magnolia shores 2 acres of tranquility
House
in Reedville18 guests · 8 bedrooms · 6 baths
Garden · Pool · Kitchen or Kitchenette
This attractive House in Chesapeake Bay, £674 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)
££££
Start earning One Key rewards
TRUE IN-TOWN ST MICHAELS 6 ACRE WATERFRONT - Heated Pool
House
in St Michaels8 guests · 6 bedrooms · 3 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 £724 per night.
££££
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
House
in Chestertown8 guests · 4 bedrooms · 4 baths
Garden · Pool · Pets allowed
This attractive House in Chesapeake Bay, £766 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)
££££
PET FRIENDLY-BEAUTIFUL APPOINTED HOME WITH BAY VIEWS AND PRIVATE COMMUNITY BEACH
House
in Cape Charles14 guests · 5 bedrooms · 5 baths
Pool · Pets allowed · Kitchen or Kitchenette
House in Chesapeake Bay, for £623 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)
££££
Multi-Generational Waterfront Retreat with Pool. No cleaning fees!
House
in Cambridge12 guests · 4 bedrooms · 3 baths
Pool · Kitchen or Kitchenette · Air conditioner
House in Chesapeake Bay, for £662 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)
££££
A Vacation Away From It All-Family And Pet Friendly
House
in Taylors Island12 guests · 5 bedrooms · 5 baths
Garden · Pets allowed · Kitchen or Kitchenette
Experience vacation in Chesapeake Bay with our House, A Vacation Away From It All-Family And Pet Friendly. Enjoy amenities such as Air conditioner, Dishwasher and Fireplace, and more.
££££
Start earning One Key rewards
Stunning Annapolis Home! Across from the library, walk to Naval Graduation
House
in Annapolis12 guests · 5 bedrooms · 5 baths
Garden · Kitchen or Kitchenette · Air conditioner
Business stays, family stays, couples stay, getaway vacation, and rental in Chesapeake Bay at Stunning Annapolis Home! Across from the library, walk to Naval Graduation for £739 for your next trip.
££££
Start earning One Key rewards
Charming 3 Bedroom 3 Bath Beach Front Property
House
in Stevensville8 guests · 3 bedrooms · 3 baths
Garden · Kitchen or Kitchenette · Air conditioner
Most favorited
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 £546 per night.
££££
Start earning One Key rewards
Breath-Taking Family Retreat On The Water!
House
in Upper Fairmount24 guests · 8 bedrooms · 4 baths
Kitchen or Kitchenette · Air conditioner · Parking
Discover the beauty of Chesapeake Bay with a stay at Breath-Taking Family Retreat On The Water! , a top rated House with amenities such as Air conditioner, Dishwasher and Laundry, and more.
££££
Start earning One Key rewards
Sweet Retreat - Close to the beach! Sleeps 12 comfortably
House
in Cape Charles12 guests · 6 bedrooms · 6 baths
Pets allowed · Kitchen or Kitchenette · Air conditioner
Discover the beauty of Chesapeake Bay with a stay at Sweet Retreat - Close to the beach! Sleeps 12 comfortably, a top rated House with amenities such as Air conditioner, Dishwasher and Fireplace, and more.
££££
Beachfront
Coastal Bliss: 3500 sqft Beachfront Haven, Steps Away from Your Private Beach - Your Ultimate Cape Charles Getaway
House
in Cape Charles15 guests · 6 bedrooms · 5 baths
Garden · Pets allowed · 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.
££££
Renovated Historic Waterfront Home with Pool, Dock, 200 acres
House
in Cambridge18 guests · 7 bedrooms · 5 baths
Garden · Pool · Pets allowed
Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Chesapeake Bay, at £713 per night for your next great vacation.
££££
Beachfront
Spacious beachfront home with decks, gas grill, wet bar, gas fireplace, and W/D
House
in Annapolis10 guests · 5 bedrooms · 4 baths
Garden · Kitchen or Kitchenette · Air conditioner
This inviting House in Chesapeake Bay can fit your needs for many types of vacations, at £637 per night.
££££
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows
House
in Chesapeake City15 guests · 7 bedrooms · 7 baths
Kitchen or Kitchenette · Air conditioner · Internet / Wifi
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 Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows 's exceptional amenities, such as Air conditioner, Dishwasher and Fireplace.
££££
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