What better place to take your pets on a holiday than the quiet and scenic Eastern Shores of Virginia? This coastal area offers wide-open grounds for running and playing fetch with your dogs. You can visit the lovely Chincoteague Island, where majestic horses freely walk around, and near-empty beaches welcome you. But if your pet gets uneasy around horses, you can instead visit the paradisical Assateague Island and the historical Tangier Island. For more sightseeing, you can take your furry friends to the old town of Cape Charles, a member of the National Register of Historic Places. There are a plethora of amazing things to do in Cape Charles. Visit its picturesque parks, shop at vintage shops, sail in its deep waters, and dine at restaurants by the harbor. For accommodation choices, check out the top pet-friendly vacation rentals on the Eastern Shore of Virginia.
We handpicked these listings carefully, considering (wherever possible) host status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and pet-friendly rules and regulations. The image galleries get refreshed with the latest updates regularly. They were last updated on October 24, 2025.
1. Gorgeous waterfront house for 12
Your vacationing group of 12 has plenty of recreational activities to enjoy in this gorgeous dog-friendly beach rental on the East Coast. It comes with an expansive deck, a games room, and a private boat ramp. Here, you can also access community facilities, such as the swimming pools, children’s playground, 18-hole golf course, clubhouse, and dog park. Yes, the host welcomes one to two dogs for a fee. But you must note that this furnished property sits on a canal, so please watch over your pets closely. Be more cautious when you travel with them to nearby attractions, such as Chincoteague & Assateague Islands (20 minutes away).
Greenbackville, Virginia, United States
42.58 km (26.5 mi) from Shore History/Eastern Shore of Virginia Historical Society
Top guest reviews
Location:
location was good close to many attraction areas especially assateaguehouse was amazing and great locationCleanliness:
overall happy with the property could have been a little more clean (overall floors were very clean)the property was clean and had very nice viewsRead more reviewsAmenities & Room:
lots of room and the sunrise is fantastic from this propertywe also enjoyed the game room with the pool and ping pong tables and the darts
Greenbackville, Virginia, United States
42.01 km (26.2 mi) from Shore History/Eastern Shore of Virginia Historical Society
Top guest reviews
Host:
awesome community people are very friendly and marina restaurant is great and very low keyrental agency very helpful came right out when we identified issuesRead more reviewsLocation:
good: walking distance to pool basket ball court golf course and marina
2. Lovely cottage with a fenced yard
This lovely cottage in a serene landscape is a haven for those seeking relaxation and features a pet-friendly policy. You can bring along your furry companions for a nominal fee and enjoy their company throughout your stay. The fenced yard provides a secure space to play and stretch their legs.
On warm days, the air conditioning will keep you cool while the heating ensures you stay comfortable. Curl up on the comfy couch in the living room and watch your favorite shows on the flat-screen TV, or retire to the master bedroom and enjoy the same amenity from the comfort of your bed. Outside, the patio beckons with its inviting seating area where you can sip your morning coffee.
Chincoteague Island, Virginia, United States
38.42 km (23.9 mi) from Shore History/Eastern Shore of Virginia Historical Society
Top guest reviews
Host:
rating details:the property manager was adequately helpfulrating details:the property manager was very helpfulLocation:
beautiful home convenient close to restaurants and beach and a safe and quiet neighborhoodi was very happy with the locationi was more than happy with the locationCleanliness:
rental was clean and well- appointedit was immaculately cleanthe vacation rental was very cleanloved the place was very pleasant and clean had fully equipped kitchen to useall in all it was clean quiet (next to a very small cemetery) reasonably pricedRead more reviewsAmenities & Room:
it was clean with fully functioning kitchen and a washer/dryeri love the layout of the cottage because the kitchen dining room and living room layout is open
3. Gwynn's Island Cottage on the Chesapeake Bay
Have a peaceful stay in this pet-friendly oceanfront rental on the East Coast. This charming accommodation is situated in Mathews County and offers spectacular water views, and a private beach on the Chesapeake Bay. The small cottage has two bedrooms that can accommodate four people. Boating, swimming, fishing, and birdwatching are some of the activities you can enjoy here.
The property welcomes pets, but you must request pre-approval by sending the manager a message with information about your pet, including its age, breed, gender, and weight. All pets together are subject to a 150 USD pet fee. Additionally, the property provides kayaks, watersports gear, and bicycles to explore the local area.
Grimstead, Virginia, United States
54.39 km (33.8 mi) from Shore History/Eastern Shore of Virginia Historical Society
Top guest reviews
Read more reviewsCleanliness:
it was clean overallit's a very relaxing vacation home clean and well stockedthe property was very clean and close to town
4. Nature house with a private beach
Enjoy a quiet beach getaway in this exquisite apartment with a courtyard that leads to a private beach where you can enjoy kayaking and fishing. Additionally, there is a fish pond with a waterfall to help you unwind. It has a private balcony where you can sip tea in the morning. Bald eagles can be seen here frequently in the mornings. This place allows up to two small pets.
All the necessities are present within the house, including high-speed WiFi, a fully functional kitchen, air conditioning, and heating. You can find beach chairs, kayaks, canoes, bicycles, and equipment for water sports outside.
Exmore, Virginia, United States
31.06 km (19.3 mi) from Shore History/Eastern Shore of Virginia Historical Society
Top guest reviews
Host:
property owner was really nice and helpfulchristi is a fantastic hostvery friendly and accommodating hostschristi the host was the best she really made us feel like we belonged therechristi & rick are wonderful kind considerate pplLocation:
great stay in an amazing beach side locationwe just wanted to relax and walk the dogs on the beach and around the wooded neighborhoodcape charles main street shops were nice to perusegreat place for a young familyRead more reviewsAmenities & Room:
the air conditioning was cold the bed was comfortable and there were plenty of pillowsthe apartment was clean and had a lot more amenities than any hotel i have ever stayed in
5. Upscale duplex near carnival grounds
The tasteful minimalist furnishings of this fully equipped duplex create such a desirable low-key, elegant ambiance. Despite its posh interior, your host warmly welcomes pets. Your rental includes a dog run, bowls, and a 24-inch crate. Regarding fees and conditions, you will have to contact the host directly. Besides that, you also have access to indoor entertainment: toys, board games, DVDs, music, and beach supplies like umbrellas and folding chairs. There are also business facilities that include WiFi, a scanner, and a printer. You can also participate in the annual Chincoteague carnival, Pony Penning, as this house sits close to the venue.
Chincoteague Island, Virginia, United States
39.71 km (24.7 mi) from Shore History/Eastern Shore of Virginia Historical Society
Top guest reviews
Host:
katy was a wonderful host and her home was perfect for our familykaty was very accommodating and easy to contact when we had questions or concernswe feel rejuvenated our host is really wonderfulkaty was immediately responsive when neededthe owner was very fast to respond and the house was in very good conditionLocation:
what a wonderful home and great location for our familya great place for friends or family to vacationloved the town the park the beaches and katy’s placeCleanliness:
the house was very organized and cleanwe had a wonderful time in this clean well-kept seaside retreatvery clean well organized and had lots of extrasi can't say enough about this property it is comfortable so clean and so well-0rganizedi can't say enough good things about our stay the house was super clean and well stockedRead more reviewsAmenities & Room:
the house had a good amount of space lots of amenities and was just warm and cozythe furniture was comfortable and the kitchen and bathrooms were stocked with all of the necessitieswe could see the beautiful birds from the living room which i enjoyed every morningwe had such a comfortable stay here over the weekend
6. Beautiful remote estate
This gorgeous three-bedroom estate in Chesapeake Bay defines your dream holiday vacation. It sits on a private peninsula property, so you have spacious grounds for outdoor games, direct access to boat ramps and waterways, free use of canoes and kayaks, and surrounding woods for hunting and hiking. This 1817 house was renovated and refurbished to give your family (six guests maximum) a beautiful rustic space to sleep. This quiet location amidst nature will appeal to your pets, but you need to follow the rules and deposit fees. For instance, you can’t bring them upstairs or allow them to sit on the furniture.
Hacksneck, Virginia, United States
14.14 km (8.8 mi) from Shore History/Eastern Shore of Virginia Historical Society
Top guest reviews
Host:
the owner is very responsiveRead more reviewsLocation:
it is quiet unique and extremely beautiful
7. Charming home with a grill
This charming home is the perfect getaway for those seeking a tranquil retreat, and with the added benefit of pets being allowed, guests can bring along their furry friends. The property charges only a one-time 20 USD pet fee per pet per stay, ensuring a hassle-free and enjoyable stay with your furry friends.
The home features a grill, making it easy for guests to cook barbecue. The property also has WiFi, allowing guests to stay connected with loved ones. For entertainment, guests can watch their favorite shows on Roku TV, perfect for unwinding after a day of outdoor activities. Parking is available on the gravel pad, providing convenience and peace of mind for guests traveling by car. In the evenings, guests can gather around the fire pit and enjoy the warmth of the fire.
Franktown, Virginia, United States
28.45 km (17.7 mi) from Shore History/Eastern Shore of Virginia Historical Society
8. Elegant bayfront house in Captain's Cove
Captain’s Cove is known for its elegant neighborhood and upscale community facilities: swimming pools, golf courses, tiki bars, fitness centers, restaurants, playgrounds. This luxe four-bedroom house in Captain’s Cove, fronting deep waters, is fully furnished. It also features a private boat dock, which appeals to the interests of your water-adventure-seeking group of 12. You can take up to two dogs (less than 50 pounds or 23 kilograms) on your adventures. Just cover the extra fees required and supervise them.
Greenbackville, Virginia, United States
42.2 km (26.3 mi) from Shore History/Eastern Shore of Virginia Historical Society
Top guest reviews
Location:
the property was beautiful and was a great place to get away during the pandemicRead more reviewsAmenities & Room:
gorgeous location with beautiful views and very comfortable in all waysthe rooms were spacious and the common areas were perfect to hold large family gatherings
9. Historic waterfront farmhouse
Are you thinking of organizing a vacation for 15 guests? This waterfront farmhouse, which has adjacent cottages and large green fields, can accommodate large groups and a maximum of two dogs of any size. Whether these dogs need to be leashed or kept outdoors, you need to clarify with the host. The dainty furnishings of this historic vacation rental create a relaxing country ambiance, more so its waterfront location. You can enjoy pleasant views of Onancock and Parker’s Creek from the screened-in porch and living rooms inside. Here, you are free to swim, kayak, and fish as your energy allows. You have a full kitchen where you can cook your freshly caught fish and crabs.
Onancock, Virginia, United States
5.88 km (3.7 mi) from Shore History/Eastern Shore of Virginia Historical Society
Top guest reviews
Host:
the property manager is extremely helpful and responsivethank you to the hosts and hope to return back again soonthe property is beautiful and the hosts and property manager are very friendly and accommodatinghe was a gracious and accommodating host and we'd revisit in a heartbeatanne was very friendly in our communication and quick to reply to my questions prior to our arrivalLocation:
we went on an amazing family trip at this placethis place was as listed relaxing fun cozyCleanliness:
we found it clean and comfortable with a lived in feelRead more reviewsAmenities & Room:
we also liked the small mudroom with sink and laundry by the side doorthe kitchen was recently renovated and was fantastic
10. Delightful family retreat
This charming Vrbo vacation rental in Cape Charles, originally built in the 1600s, is a fully furnished accommodation for 11 guests. It boasts 14 acres (5.7 hectares) of land, including private wide-open grounds, where you can set up tents for private group events. The interior of the house is cozy and classic, which will make you and your pets feel right at home. Plus, this house by Cherrystone Creek has a beautiful, peaceful setting and it is close to Cape Charles town center (5 miles or 8 kilometers). You may contact the host for inquiries about fees and conditions for checking in your pets.
Cape Charles, Virginia, United States
50.9 km (31.7 mi) from Shore History/Eastern Shore of Virginia Historical Society
Top guest reviews
Location:
loved being close but not too close to cape charlesit was nice being close to cape charlesit was perfect location for putting boats in at kiptopeake state park it had beautiful viewsCleanliness:
the whole house was beautifully decorated and very cleanthe bedrooms were very comfortable and everything was very cleanagain the property was beautiful but the house could have been cleanerRead more reviewsAmenities & Room:
the water views are lovely and the house is spacious and comfortableit was nice having all the tools pots pans and a few spices in the kitchenwe had no idea how much we'd love having the foosball table therean incredibly relaxing enjoyable and comfortable retreatwe had our dogs with us and the yard was perfect for them to run free and swim
A vacation with your pets
Trips can also be stressful for your pets. The long rides and often tight restrictions can put them in a bad mood. You can be grateful that many vacation rentals are friendly and easy on pets, and they’re found in the scenic and serene outdoor setting of the Eastern Shore.
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