
Beachfront holiday rental in Chesapeake Bay
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Top-rated beachfront accommodation in Chesapeake Bay
Guests agree: These beachfront homes are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for Chesapeake Bay beachfront rentals
Pet-friendly beachfront home rentals

Shore to Please-11 Beds-Beach View
wonderful place by the bay to spend Christmas with the family! lots of bedrooms as well as a bunkbed room made it really convenient and nice

Cozy beach cottage! One block to the beach!
House was great! Small but not too small and perfect for vacation rental. Med sized dog, husband, and toddler loved it. Kenzie leaves you everything you need from a raised double dog dish to dishwasher and laundry pods….awesome attention to detail. Pics don’t do it justice as more outside and living room seating have been added. Fire pit was really cute and everything to get it started and have a fire were there even though we didn’t get a chance. Reasonable driving distance to VA beach, zoo, and playgrounds. Food easily accessible both driving and walking. Grocery store is close drive but don’t forget your butter. The corner store sees you coming! It was super clean well done and would love to stay again. Thank you Kenzie for being a great host!

Delaware Beach Bliss, steps from the sand & surf!
Well equipped house within very short walking distance to quite, private beach. Great amenities -- including bikes, kayak and paddle board. Private beach was gorgeous and very dog friendly, water was calm and shallow. Short driving distance to Lewes for great food, including terrific crabs.

Modern. Spacious. Pets Yes! 2Min Walk to Beach
Space was perfect for us staying as a family of 6. Bedrooms were great and the home offered plenty of space throughout. Awesome backyard, although we did not really use - very close beach access. Had all the amenities we needed for a long weekend!

Quiet East Beach Bungalow, 1 block to beach!
Beautiful place with modern upgrades. Access to the beach was super close and just a block away. Neighborhood is quiet and we enjoyed walking our dog in the nearby park. We look forward to returning.

The Happy Place-Quiet, North End 1 block to ocean!
We had the most wonderful stay at this beach house! Walking into the home was like walking into your own home - stocked with everything you could possibly need, and then some. I love that we didn't have to pack all the bulky beach gear and bikes! They provided EVERYTHING you would want. All we needed were our clothes and personal items. The game cabinet was a huge hit as was the Wii which had all the best games! I'm always concerned renting homes that allow pets, but you would never know this was a pet home - there was no pet odor or stains, and the fenced front yard was very convenient. A short walk to a beautiful beach, and an access rode for easy bike riding made this the perfect location. Mary was an amazing host - responsive and very kind. Loved our stay so much we are hoping to return some day.

Steps From The Ocean & Boardwalk On Surf Ave.
Lovely, calming place and location! Place is as shown, and you can hear the ocean and watch sunrise from one of the bedrooms. The front porch was great for relaxing and reading. The fenced yard perfect for our dog; she had so much fun sniffing the ocean air and playing ball. The house is in a quieter part of town, but a 10 min easy walk via beach or boardwalk to shops and restaurants. We misread the kitchenette description: there are no pots/pans for cooking, but making toast or reheating leftovers was easy (and there was also a BBQ grill). Place was clean, and Carol was a great host. Would love to stay again!

Harbor View- (Sun - Sun rental June- Aug.)
This is the perfect home base to explore charming Cape Charles! The location simply can’t be beat - one block in one direction to the beach and one block in the other to the quaint downtown area with shops and restaurants. We never used the car once while there - such a nice change of pace! The house is also so roomy and comfortable, gets beautiful light, and is well stocked with everything you might need! We especially enjoyed sitting on the front porch rocking chairs and watching the world go by. Highly recommend - will definitely come back!
Beachfront home rentals with a pool

Villa Positano
Roger’s beach house was charming. It was an older-style home with many modern updates. Quick and easy walking path to the beach. The pool in the backyard was lovely. It was a little dirty upon arriving and Roger came right over and got it all cleaned up for us during our stay. The neighborhood was a little rough we did have a few uncomfortable encounters with homeless people being two girls alone it was a little unsettling. Overall, I would definitely come back again. The weather was absolutely beautiful for our stay.

Beachfront on Pooldeck 9400 Bldg
This condo was in a great location. Steps to the pool and right on the beach! The place was beautifully decorated in a beachy theme. It was clean. The beds were very comfortable. Across from a grocery store and had a variety of restaurants within walking distance. Would love to book this place again!

Highly Rated Oceanfront Condo w/ Pool & Pick Ball
A haven of peace right next to the sea. Very clean and big enough for 6 people. My boys loved the pool and the pickelball court. Finally, there are plenty of activities to do in this city and the condo is close to everything. We will come back for sure ☺️

IslandCoveParadise: Luxury-NewlyBuilt/Brdwalk/Pool
We loved our stay at Tom’s place! It was spacious, beautiful and we were close to everything yet still had the privacy we were looking for! We will be staying again in the future!

4 BR/2.5 BA, Oceanblock w/pool & fantastic view!
Great stay at a fantastic location. This property has a lot to offer with four bedrooms and three decks, lots of comfortable seating and just a 3-minute walk to the beach. We had an enjoyable weekend and would certainly come back again.

Amazing oceanfront view 3 blocks from boardwalk
We had a wonderful time at John‘s condo! The location can’t be beat and it offered everything we needed. We had little issue with the dishwasher and washing machine, but John responded very promptly and took care of everything quick as could be. Highly recommend!

YEAR ROUND Beachfront Pool Paradise Cape May Beach
10/10 beach home for family and friends. I don’t think I’ve ever stayed at a better Airbnb. Highly recommend staying here.

2BR- St. Tropez Condominiums- Ocean City, MD!
I really enjoy my stay here. It was very peaceful and affordable. Easy to check Definitely would stay here again when i come back .
Private beachfront home rentals

Oceanfront Getaway Private Beach & Stunning View
Had been dreaming about this place for a few years and finally got to go. It did not disappoint. Being right on the beach was so important for our family and the space was very cute and functional. Also had tons of chairs and activities.

Private Beach Getaway at Finest Chesapeake Bay
This home is absolutely beautiful. I loved being able to wake up early and watch the sun rise over the Chesapeake bay. Even though it was cold the kids enjoyed splashing in the water with their rain boots. We spent the Wednesday before Thanksgiving at colonial Williamsburg. Afterwards we ate at Captain George’s, a place Tas recommended. It was absolutely worth it. I was also pleased with being able to make a good Thanksgiving meal. The stay was relaxing and peaceful. We would love to come back in the near future.

Beachfront Home with Beautiful Views of the Bay
This place is such a gem! The home was exactly what we expected — and more! The location is amazing and the setting is so serene and peaceful. The house was well-equipped with towels, linens and kitchen essentials. Four bedrooms and two bathrooms make it perfect for a family! Tom and Jess answered our questions quickly and were laid back and respectful of our time there. We will definitely book again.

Anne's Beachfront Shangri-La
Our family Thanksgiving was great! What a beautiful home with a breathtaking view of the water!! Just waking up each day with that beautiful sunrise over the water was wonderful to see. What a hidden gem! Everything you possibly have needed was provided in the home. The fireplace was very nice especially on those cold evenings! We can't wait to return! Thank you Brandon for opening up your home to my family. We all felt relaxed & right at home!! Thanks Again Nicholas & Crouch family

Play by the Bay 1 MIN TO WATER
We had a wonderful stay at Diana’s Airbnb off Shore Drive on Denwiddie From the moment we walked in, we could tell how much thought and care went into this place. The attention to detail was incredible—from the beautifully curated décor to the small but thoughtful touches like Band-Aids, cooking essentials, and other convenient extras that made a big difference. The location was perfect, and the space truly felt like home. Thank you, Diana, for creating such a welcoming and comfortable space!

Waterfront Bay Cottage w/ Your Own Private Beach
We booked this beautiful beachfront home for my husband's birthday, and it was perfect. Check-in was seamless, and the breathtaking water view greeted us upon entry. The house was spotless and peaceful, with only the soothing sound of waves. We enjoyed most meals in the sunroom overlooking the water and took advantage of the outdoor seating as the weather warmed. Fawn, a great coffee and breakfast/lunch spot, was just five minutes away. The well-equipped kitchen allowed us to cook fresh seafood from Little River Seafood. Mornings were magical with stunning sunrises, and the nearby beach access was perfect for walks, yoga, and birdwatching. A highlight was Hughlett Point, a hidden nature preserve 30-40 minutes away, leading to a secluded beach with only 11 parking spots. Thank you for sharing your home—it made for a peaceful and unforgettable celebration!

Beach Front and 'Perfectly Placed'
It is the perfect location for a relaxed getaway. Several lovely state parks within a short distance. The space is well equipped and comfortable with magical sunsets over the Potomac. Theresa is super responsive.

Beach House with Private Beach, Kayak, and Canoe
This is our fourth? fifth? stay at Sundar's lovely spot. Private, gorgeous beach out back, great expansive views out front with ships in the distance. Home is very comfortable. We are always there in November so don't swim, or kayak, or fish. Just enjoy the comfortable home and the walks on the beach. Sundar is always very responsive and available. Kitchen has everything you need. Appliances are great. Beds are comfortable. No clutter of owner's cast-offs which many airbnb homes have. We will be back next year!!
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