
Family-friendly holiday rentals in Eastern Shore of Virginia
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Top-rated family-friendly rentals in Eastern Shore of Virginia
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Popular amenities for Eastern Shore of Virginia family-friendly rentals
Family-friendly home rentals with a hot tub

Sea Colony Premier Family Resort
Great place to stay at Sea Colony. The place was very nice and looked just like the pictures, and the amenities at the resort were excellent. My husband loved the open pickleball play and we both liked the pools and tram. Great location between many beach towns and boardwalks.

Horses-Views-Dog Friendly-4WD Area
Terra’s place was beautiful. We saw the horses everyday. Her house is an easy walk to the beach. We enjoyed our stay. Terra was very responsive and quick to respond to our questions. She had food and water bowls for our fur babies. 10/10 recommend!!

Historic Powhatan Resort- 2 bedroom condo!
Second time staying at this resort and it was great. Place was very clean and as described in the listing. The check in process is easy and the staff is always very friendly and helpful. Will stay again next time I’m back in Williamsburg.

Beautiful Beach-View Condo
We loved Raj’s place! We have two young children and his place was fully equipped to entertain them with books, toys, etc. Best Airbnb we have stayed in so far 😊

Westgate Historic Williamsburg One Bedroom
We had a great stay at Eddie's place! Very close to restaurants, Colonial Williamsburg, and Busch Gardens. The unit we stayed in was spotless and had all of the amenities that we needed during our stay. Highly recommended!

Featured on HGTV! Bethany Beach Ocean Front Condo
Better view than the pic shows! The private beach was clean and very close to the condo. Rentable chairs and umbrellas available on the beach. There are 2 chairs and umbrellas in the condo to use. Some of the furnishings could use a freshen-up. Mattress was excellent and we are picky! The place was very clean upon arrival and the owner was very responsive to any questions we had! Bethany Beach Boardwalk is less than a mile and a delightful treat with great restaurants and shops along with beach access- something we did not expect and thoroughly enjoyed!

Dodd House Beach Home w/private pool and hot tub
Our family enjoyed the Dodd home. There was adequate space for everyone. We loved the location which was in close proximity to Dewey and Rehoboth beach. The kids really enjoyed having a pool. They said they don’t want to go to a hotel ever again. We enjoyed cooking on the grill & playing games in the evening. We can’t forget to mention the wonderful hot tub. It was such a great added attraction. We will return next year for sure.

Lakefront slps 6; beach, pools, tennis, gym, view!
Sherri’s place is awesome and the community and surroundings are beautiful. The kitchen is furnished with everything you need for cooking. The deck is such a plus, with the view of the pond and the ducks, as well as the private little beach. The community is very friendly and walkable, and the different options for pools were very fun for us to explore. Taking walks in the morning was amazing. It is very close to Bethany “downtown” and 6 min drive to the beach. You can also walk or take the tram. I had a great time with my kids and would definitely recommend and come back!
Family- and pet-friendly home rentals

Villa Positano
We had an amazing time. The house was perfect for us. We really enjoyed the pool and short walk to the beach. We could hear the ocean from the master suite. The upstairs deck had view of the water. Everything about our stay was perfect. The area was nice and was quiet and peaceful. We will definitely go back and stay longer next year. Thank you!!!

Water Oaks at Chic's Beach
Amazing experience. This was the very best Airbnb I have ever stayed. Felt at home. Absolutely above and beyond my dreams Anything and everything you would need from your home, they have. I didn't need to go out and purchase 1 item. The kitchen was completely stocked with all pots, pans, and more. The kindest host. Thank you for the most amazing and 1st Grandkids vacation. Appreciate the opportunity to enjoy your amazing home. Thanks for the amazing, loving, beautiful memories we made. Namaste Carolyn and Soul Tribe

The Little House at Waveland
Had such a lovely stay at the Little House to attend a wedding at the Maritime Museum which is virtually next door. We hope to be back again when we have more time to enjoy the gorgeous view, little beach, and walk to a restaurant or two. Perfect location and we were in awe at how many stars we could see with so little light pollution compared to our home in the suburbs. 🩷 Even with summer temps the screen porch with fan was the best way to wind down in the evening. They’ve thought of everything you could possibly need!

Walk to famous Tiki Bar on Solomons Island!
Such a cute spot for me and my husband to stay. I wanted a place walkable to Tiki for my birthday and I got the perfect place.

Williamsburg Hide-A-Way Creekside
Anne was wonderful! Accommodating and very responsive. The property was beautiful and very well stocked. We did not want for a thing! Anne has thought of everything anyone may need. We would definitely stay here again!! Shirley

Rivah View
Relaxing, well-kept property and house with a view. Plenty of good food in next town over. If you haven't been to Northern Neck, stay here and enjoy some peace and quiet.

Stunning private waterfront suite
We came for peace and quiet, and Julie's place delivered! We came to see the Assateague horses, and just relaxation, and we were totally happy here in Ocean Pines. Our private ground floor of a beautiful house at the end of the lagoon, was in a perfect location to get to Ocean City and Assateague easily. Julie gives a lot of information in her listing, and everything was just the way she described. Checking in and out was seamless. We had a wonderful time relaxing in Julie's hideaway at the lagoon. We loved it!

Lovely Ocean View Cottage
We loved our stay at this location, it felt like a home away from home. Everything was exactly as described in the booking. Our fur kids loved the extra treats Chuck left and we enjoyed the basket of goodies as well. The place was very clean and the neighborhood extremely quiet. We had such a pleasant stay we booked for next year too. Would recommend anyone looking for a getaway to seek out this place. Can't wait to come back next year. Thanks to Chuck and his team for having such a nice clean and updated place to share with others. It was very home like.
Family-friendly home rentals with a pool

True St. Michaels 6 Acre Waterfront w/heated pool
WOW. This was one of the most wonderful homes we’ve ever stayed in. Everything was clean, comfortable and accessible. Marissa was so helpful with recommendations, flexible check-in times so we could get my little one down for a nap, my three-year-old love the pool, dedicated playroom, toys, swing set and s’mores that were such a perfect gift from Marissa. My son asked if we could move there! My husband and I loved the kayaks and pond. We saw bunnies in the morning - it’s truly magical. It’s so private and just 2 mins away from town. We made so many memories and I can’t recommend staying at this property enough.

Right on Silver Lake walk to the beach and town!
I can't say enough good things about Ana and this lovely condo. First things first, Ana as a host is everything you'd wish for- friendly, sincere, gracious, patient and very helpful! A week and a half before check-in, my sister had a specific question about parking in town so I asked Ana. She took the time to point me in the right direction and also suggested Salt Air for the kind of restaurant we wanted. And she was right! This condo is lovely, I've been going to turtle bridge for years so the proximity to the bridge and Silver Lake was wonderful. We are already daydreaming of when we'll come back. Nothing is more soothing than sitting with your morning tea and checking emails with the lake moving so close to you. We were able to go out and play badminton, walk to the market, walk into town and visit our old friends- just a dream. I even had to leave half a day early, unexpectedly- everything was smooth. I forgot to throw away my mouthwash bottle in the bathroom when leaving- sorry!

Oceanfront Family Oasis: Pool, Beach & Parking!
Great place to stay in Ocean City! clean and wonderful place situated right off the beach secluded and quiet. had lots of beach materials for use. would stay again.

OC MD trip bayside, great amenities
I arrived after dark, on a Friday, so I was thinking I’d have some challenge to find the house. I was wrong! There was a guard at the gate who was quite friendly and helpful, gave me the parking pass for my stay and a map with outlined directions to find the street and the house. I found it first time through. Keys were in the lockbox, instructions were clear and the gate pass card was in the dish on the table. I had a lovely quiet night in a very comfortable bed with no noise or distractions. After a 10 hour drive I needed that! In the morning I had a small convenience issue, which Terri and Shawn were immediately responsive to, offered me a self service solution which worked fabulously and I had no other problems during my stay for a total of 8 nights. I especially loved the water pressure in the shower! Love that the house is a short hop from both OC and Assateague! I would definitely stay here again!

🏖 *Ocean *Ocean *Ocean* 🏖 Beautiful Condo!!
We had a fantastic stay at Adam’s place. Location was amazing and the description of the unit was exactly on point. Place was clean and comfortable and even had some toys and games for the kiddos! Great communication with the host and we’ll definitely be back!!

Secluded beach beauty with private, heated pool
This is a great property! The house is gorgeous, the grounds are clean, kept and very private. The house was fully stocked with kitchenware, pool accessories, & decorated tastefully. A lot of delicate artwork and intentional decor- (if traveling with a young child, one needs to watch them closely :) Re: the beds- my 7 year old described it as “sleeping on clouds!” - very comfy! The area is close (2-3 min) to outlet shops and a bunch of restaurants on Costal Highway 1 and about a 6 min drive to the Rehoboth pier. It’s also a central location to other neighboring beach towns.

"Shangri-La", of Hampton, Virginia
It’s a great location and was the perfect size for my friends and I. We loved having a pool table and access to the pool. Everything was super nice and well taken care of and they have the SuperHost title for a reason. 10/10 experience all around

3 BR Cottage on Mallardee Farm in Williamsburg
The house was adorable and comfy! Can’t think of a thing that we needed we didn’t have available! Great location to Busch Gardens and Colonial Williamsburg! Everything is just a very short drive!
Destinations to explore
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- Chesapeake Bay
- Virginia Beach Oceanfront
- Resort Beach
- Assateague Island National Seashore
- Busch Gardens Williamsburg
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Buckroe Beach and Park
- Grandview Beach
- Haven Beach
- Assateague Beach
- Outlook Beach
- Snead Beach
- Norfolk Botanical Garden
- Sarah Constant Beach Park
- Kiptopeke Beach
- Grove Beach
- Little Creek Beach
- Salt Ponds Public Beach
- Cape Charles Beachfront
- Parramore Beach
- Bow Beach
- Saint Jerome Beach