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 April 11, 2024.
1. Gorgeous waterfront house for 12 (from USD 300)
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).
Top guest reviews
Amenities & 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 dartsCleanliness:
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 reviewsLocation:
location was good close to many attraction areas especially assateaguehouse was amazing and great location
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
Premier Host
2. Charming three-level house near Cape Charles Beach
This 3-level property has 5 bedrooms, 4 baths, and several common areas that your family of 12 will find charming and cheerful. With homey facilities (kitchen, dining, parking), you should consider holding your family reunion vacations here. There is a dedicated children’s room upstairs with toys, mats, and board games for entertainment. Plus, it sits within walking distance of the beach, carting zone, golf course, and bike lane. Pets are welcome on a case-by-case basis. That said, you need to contact the host before booking and clearly describe your pet.
54.95 km (34.2 mi) from Shore History/Eastern Shore of Virginia Historical SocietyAccommodates: 12
Minimum Nights: 7
Refund Policy : 100% refund if you cancel at least 60 days before check-in.
Top guest reviews
Amenities & Room:
has an amazing kids room that can easily sleep 4 kids if not more with games and spacethe only improvement would be an upgrade to the kitcheneat formal or casual and enjoy breakfast in the nookcould not have been more comfortable cozy or enjoyableHost:
lots of helpful items like beach umbrellas boogie boards even a slip n slideour pugs enjoyed the house too thanks for being pet friendlyRead more reviewsLocation:
the location of the house was great close proximity to the beach and to the main streetgreat house in a perfect location we really enjoyed our staylocation to downtown and proximity to the beach were excellentclose to the beach comfy and great back yard for the kiddos and pupssea gate is a wonderful place for a family vacation with a big family
Top guest reviews
Host:
owners response was to thank us so it could help later peopleRead more reviewsLocation:
beautiful well-equipped house close to the shops restaurants and water
3. Beachfront cottage with Chesapeake Bay views
Your family will enjoy the beachfront location of this lovely cottage with panoramic views of Chesapeake Bay. It’s cozy, fully furnished, and directly accessible to the beach. Your group of six can then enjoy unlimited swimming, kayaking, and fishing. Alternatively, you can engage in less strenuous activities like crabbing, shelling, and walking barefoot on the sand. The property also has a grass area where your pets and kids can play around. Since the yard is not fenced-in, you need to look after them. It’s best to ask the owner before check-in for pet admissions and conditions.
44.86 km (27.9 mi) from Shore History/Eastern Shore of Virginia Historical SocietyAccommodates: 6
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 14 days before check-in.
Top guest reviews
Amenities & Room:
sleeping was very comfortablethe kitchen very basic; it inspires a frontier mentality that works for mewould be nice to have a better equipped kitchenCleanliness:
and this is exactly it the cottage was clean and well stockedHost:
owners very nice and accommodating good at communicatingthe owners are fantastic - quick to communicate and accommodating very friendly and personablethe owners were responsive and helpful and the property was largely cleanRead more reviewsLocation:
the location is just outright amazingquiet neighborhood with excellent beach trail 5 min drive awayone could easily get a three-to-four mile walk inrelax and reset we loved this place in the winter and can’t wait to visit in the summergreat location right on the water with a beautiful private clean beach
Top guest reviews
Cleanliness:
we really enjoyed our stay the house was very clean and equipped with everythingRead more reviewsLocation:
such a wonderful duplex in a great locationgreat location for the house very easy to check in and outeasy access to a park playground and beach
4. Lovely cottage with a fenced yard (from USD 96)
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.
Top guest reviews
Amenities & 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 openCleanliness:
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 pricedHost:
rating details:the property manager was adequately helpfulrating details:the property manager was very helpfulRead more reviewsLocation:
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 location
5. Charming home with a grill (from USD 91)
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.
6. Gwynn's Island Cottage on the Chesapeake Bay (from USD 245)
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.
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
7. Nature house with a private beach (from USD 157)
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.
Top guest reviews
Amenities & 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 inHost:
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 pplRead more reviewsLocation:
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 family
8. Elegant bayfront house in Captain's Cove (from USD 589)
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.
Top guest reviews
Amenities & 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 gatheringsRead more reviewsLocation:
the property was beautiful and was a great place to get away during the pandemic
9. Upscale duplex near carnival grounds (from USD 245)
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.
Top guest reviews
Amenities & 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 weekendCleanliness:
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 stockedHost:
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 conditionRead more reviewsLocation:
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 place
10. Delightful family retreat (from USD 309)
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.
Top guest reviews
Amenities & 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 swimCleanliness:
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 reviewsLocation:
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 views
11. Historic waterfront farmhouse (from USD 450)
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.
Top guest reviews
Amenities & Room:
we also liked the small mudroom with sink and laundry by the side doorthe kitchen was recently renovated and was fantasticCleanliness:
we found it clean and comfortable with a lived in feelHost:
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 arrivalRead more reviewsLocation:
we went on an amazing family trip at this placethis place was as listed relaxing fun cozy
12. Beautiful remote estate (from USD 250)
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.
Top guest reviews
Host:
the owner is very responsiveRead more reviewsLocation:
it is quiet unique and extremely beautiful
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.
History
Get Trip101 in your inbox
Unsubscribe in one click. See our Privacy Policy for more information on how we use your data
Create an account to