Chesapeake Bay is a large estuary in the Mid-Atlantic region of the United States. It is home to a diverse ecosystem, including over 3,000 species of plants and animals. Chesapeake Bay is a popular destination for recreation, including boating, fishing, swimming and bird watching. The bay is also home to a number of historic sites, including Jamestown, the first permanent English settlement in North America. It boasts an incredible variety of beaches, including the natural and woodsy ones. Stroll along the boardwalk with funnel cakes in hand, savouring the sweet aroma and the sound of crashing waves. Moreover, there are beaches that can only be reached by boat. Those are known as ‘secret beaches.’
If you’re seeking the ideal seaside experience, here is a brief list of some of the top beach resorts in Chesapeake Bay, United States.
We handpicked these listings carefully, considering (wherever possible) recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to beach. The image galleries get refreshed with the latest updates regularly. They were last updated on October 29, 2025.
1. The Tides Inn (from USD 404)
The Tides Inn is a beautiful and relaxing place to stay in Chesapeake Bay. The resort is located on a private peninsula and it offers stunning views of the bay and the surrounding islands. The resort has a variety of amenities, including a spa, a fitness centre, a golf course and several restaurants.
There are also a number of activities that guests can enjoy, such as fishing, boating and hiking. The Tides Inn is the perfect place to relax on the beach and escape the hustle and bustle of everyday life.
The Tides Inn
Address: 480 King Carter Dr
40.95 km (25.5 mi) from New Point Comfort Natural Area Preserve
Other beach accommodations in Chesapeake Bay, United States
2. Last Flight Out (from USD 1247)
Last Flight Out is a beachfront cottage with access to private beach space and endless bay views. Visitors can take a walk along the 2 miles (3.22 kilometres) of white sandy beach while they are here.
The host has provided a beachfront deck where you can enjoy barbeque gatherings. As for activities, there’s something for everyone. Several beach toys, bikes and kayaks are exclusively included in the cottage amenities for guests to enjoy the beach life.
Port Haywood, Virginia, United States
854 meters (0.6 ft) from New Point Comfort Natural Area PreserveSuperhost
Accommodates: 6
Top guest reviews
Host:
brandon was a wonderful hosthosts were very responsive and helpfulthis spot is incredible brandon is a great hostbrandon is always an excellent host and we will be backbrandon was an excellent hostLocation:
the location is perfectthis house and location are divinesuch a peaceful and beautiful locationgreat place to get away from allbrandon was very responsive and provided extra details about the locationCleanliness:
was very clean and peacefulthe house was clean and welcomingthe house was clean and had everything we neededgreat location ease of access well equipped peaceful & serene modern clean and just plain relaxingRead more reviewsAmenities & Room:
the house is well stocked with lots of beach towels a washer dryer and a nice kitchen
3. Saint Salty (from USD 1743)
This beautiful house on Bavon Beach boasts 4 spacious bedrooms with a capacity to host up to 14 people. This beach-facing home is perfect for family vacations and large gatherings. You can witness the nearby New Point Comfort Lighthouse’s rich history by taking a short stroll along the shore. Feel free to take your coffee in the morning and enjoy the beauty of nature and serene bay on the front porch while catching a sight of dolphins swimming by.
Port Haywood, Virginia, United States
664 meters (0.5 ft) from New Point Comfort Natural Area PreserveAccommodates: 12
Top guest reviews
Cleanliness:
great place to stay nice and cleanRead more reviewsAmenities & Room:
family room view is incredible and allowed us to enjoy the beach and water even on cold days
4. Thicket Point Fish Camp (from USD 817)
A secluded fish camp located just 5 miles (8.05 kilometres) from downtown Onancock is a Chesapeake Bay waterfront property that’s the ideal getaway for exploring the Eastern Shore’s greatest attractions. This vintage-style home has endless water views and fishing opportunities as well.
Visitors can enjoy crabbing on the bay front or explore the town of Onankok, which is a short drive away from the property. Exotic seafood is a must-try from the popular Island House Seafood Restaurant, which is less than 20 miles (32.19 kilometres) away from the accommodation.
Onancock, Virginia, United States
59.02 km (36.7 mi) from New Point Comfort Natural Area PreserveAccommodates: 10
Top guest reviews
Host:
matt was quick to respond when we sent messages and was a great host all aroundLocation:
this was a beautiful house in a beautiful locationpeaceful and beautiful for sure great location right on the watergreat location and super communicative hostsgreat location lots to do and amazing homeplace is big enough for extended family or two groups of friendsCleanliness:
the bedrooms and bathrooms were all spotless and we were very comfortableit is unbelievably beautiful peaceful and spotlessRead more reviewsAmenities & Room:
the house has amazing views and is cozypeaceful relaxing sunrise and sunsets r gorgeous - very comfortable
5. A tucked-in Airbnb in White Sone (from USD 1721)
This two-story house is a vintage structure built on a deck with a rustic and colourful interior. The property includes an outdoor kitchen and dining area, perfect for your barbecue dinners on the private beach. The guests can enjoy fishing blue crabs in the bay or a beach picnic.
Some of the outdoor activity essentials included are kayaks, paddle boards, beach chairs, umbrellas, inflatables and a hammock. Enjoy the calmness of the waters, the shade of the pine trees on the deck and the private patio of this beautiful house.
White Stone, Virginia, United States
37.27 km (23.2 mi) from New Point Comfort Natural Area PreserveAccommodates: 8
Top guest reviews
Host:
the hosts are responsive and accommodatingthe hosts were welcoming and communicated clearlythe hosts are great to communicate withsusan was a great hostgreat place and great hostsLocation:
we loved this locationthe best location you’ll ever findsuch a great place and locationa great house in a lovely location - highly recommendwe loved every minute of being so close to the waterCleanliness:
house was clean and has some unique beach touchesinside was clean well-stocked and very comfortablethe kitchen is incredible and the rooms are impeccably cleanwe had a great visit the house is well equipped with everything you may need and is very cleanRead more reviewsAmenities & Room:
great views fully stocked tv & wifi comfy surroundingsthe amenities from the outdoor kitchen to the garage filled with beach toys/tools were better than we imaginedthe accommodations and amenities were super and we loved the beach and outdoor kitchen the mostthe beach is just feet away from the deck and offers comfortable hard packed sand for playingand the location speaks for itself - right on the water private beach great deck and outdoor kitchen
6. The Baydreamer (from USD 679)
This accommodation is a blend of a beach house and a cottage. The house has ample space and multiple sitting areas to relax. It has the capacity to house up to six people at once. The baby safety gates, books and toys make it a suitable vacation house for families with children. Moreover, the cosy kitchen and dining area are equipped with a freezer, electric cooker, oven, blender and more for all your cooking needs.
Kilmarnock, Virginia, United States
44.66 km (27.8 mi) from New Point Comfort Natural Area PreserveAccommodates: 6
Top guest reviews
Read more reviewsHost:
the house is comfortable and welcoming very kid and family friendly
7. Lovely waterfront house with bay view (from USD 1377)
Located on the northern neck of Chesapeake Bay, this cosy house comes with four spacious bedrooms, three baths, a kitchen, as well as indoor and outdoor living areas. You’ll never be short on space here! The highlight of this Airbnb is the outdoor fire pit, where you can gather and enjoy the bay views with a bonfire.
The kitchen is well-equipped and comes with a barbecue grill, baking sheet, toaster, oven and stove for your daily cooking needs. Moreover, the private balcony’s view of the forest canopy creates the impression that you’re up in a treehouse!
White Stone, Virginia, United States
37.74 km (23.5 mi) from New Point Comfort Natural Area PreserveAccommodates: 8
Top guest reviews
Host:
rebecca was a great host loved itRead more reviewsLocation:
this place is absolutely breathtakingmy family had a great time at rebecca's place in white stone
8. Sunset Bay Cottage (from USD 1993)
If you are a family of four or looking for a private retreat by the bay, then Sunset Bay Cottage is for you. This rental has two bedrooms, one bathroom and a fully furnished kitchen. The covered bayfront outdoor deck is a perfect spot to read a book and relax. The location of this cottage has easy access to many local Eastern Shore activities and site-seeing opportunities.
Moreover, explore the bay and surrounding attractions on a kayak trip up Nassawadox and Church Creeks.
Exmore, Virginia, United States
33.82 km (21.1 mi) from New Point Comfort Natural Area PreserveAccommodates: 4
Top guest reviews
Host:
the hosts are very responsive and kindeveryone is very friendlythe property manager is a nearby neighbor she is helpful if you need anythingdennis was very communicative and helpful before out stayvery peaceful and locals are very friendly and inviting offering recommendations and advice on places to goLocation:
great location for a quiet relaxing vacationgreat secluded location right on the beachthis house has an amazing location and everything you need for a perfect vacationthe beach is wonderful to walk on and just get away mentallywe loved the location perfect for the vacation that we hoped forCleanliness:
thanks for providing a clean and cozy placethe beds have clean white hotel-like sheets with a bedspreadthe water and sand is cleangreat host very cleanRead more reviewsAmenities & Room:
can’t wait to return for another visit we also appreciated the addition of wifioverall the cottage is cozy comfortable (mattresses are comfy) and thoroughly cleaned
9. Three-bedroom beachfront cottage (from USD 567)
A private beach cottage located on the secluded Gwynn’s Island in Virginia. The house overlooks Chesapeake Bay from this small island region. The house comes with a kitchen, living and dining area, full bathroom, master bedroom and screened porch on the first floor. The second floor offers two more bedrooms and a full bath. The private deck and porch on the house provide added space for sitting.
The location is only 15 minutes from downtown Mathews for Food Lion supermarket, restaurants and more. Guests can pick up their groceries and shop around the town leisurely.
Gwynn, Virginia, United States
18.93 km (11.8 mi) from New Point Comfort Natural Area PreserveAccommodates: 6
Top guest reviews
Host:
renee is an excellent hostrenee is indeed a super hostrenee was very helpful and responsiverenee was super responsive and easy to communicate with prior to and during our staythe host is in touch and makes sure you have what you needLocation:
great location for private beach access with small childrenrenee's house is in a beautiful location and very comfythis rental is just as advertised- secluded beautiful location and some nice new flooringyou can expect a great stay in a perfect locationwe had an amazing time staying at this placeCleanliness:
very clean and updatedit was clean and nicely decoratedthe house was clean and orderlyclean and right on the watervery clean we will definitely go back to this placeRead more reviewsAmenities & Room:
big beautiful open deck with lots of space toys and puzzles for little ones and comfy bedsthe house is cozy and having a beach for a back yard is so beautifulthe view is practically three-sided the screened-in porch was lovely and the new outdoor shower was very nice
10. The Salt Box (from USD 356)
One half of a historic duplex from 1915, The Salt Box is located in Cape Charles. This two-story house has its own front and back doors and is completely private. It has a capacity to accommodate six guests with three bedrooms and two full bathrooms. The first floor has a dining room in the front of the house, the den/TV room in the middle and the kitchen, bathroom and laundry room in the back. If some members of your group go to bed and others wish to linger out downstairs, the den can be partitioned off from the dining room and upstairs.
Only a block away from the beach, on a quiet, leafy street in the Historic District, the rental is a short walk to nearby shops, the pier and more.
Cape Charles, Virginia, United States
23.37 km (14.6 mi) from New Point Comfort Natural Area PreserveAccommodates: 6
Top guest reviews
Host:
anna was a wonderful hostanna was friendly & responsive with our questionsanna was also a very helpful and informative hostanna was helpful and responsiveanna was an amazing host and very accommodating for our familyLocation:
cute house the location is greatthe location was perfectgreat place within a 10 minute walk from most shopping and restaurants in the townsuch a great location and lovely place to stay in cape charlesperfectly located for walking to the beach and shops/restaurantsCleanliness:
the house was very clean and exactly as advertisedthe place was very clean and super convenientit was clean and chic and just what we wantedanna’s home was clean and comfortable for the 6 of us (all adults)it was very clean we really liked the fact that the interior pieces were historicRead more reviewsAmenities & Room:
beds were comfortable and the two zone a/c unit was a huge plusoutdoor shower on the back porch is a nice addition for those sandy feetgreat place with everything we needed to make our group of four adults comfortable
Have a beachside vacation in Chesapeake Bay
With such a variety of cottages available near Chesapeake Bay, your vacation plans can be sorted. Additionally, they frequently provide better value and more privacy than hotels do. So gather your beach toys and book the ideal private beach resort for your upcoming vacation!
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