Family-friendly holiday rentals in Eastern Shore of Virginia

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.

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.

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 😊

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!

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!

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!

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.

We have stayed here many times & wouldn't consider any place else. The home is very well furnished. The kitchen is very well supplied. It is minutes from Lewes, Rehoboth Beach, and Delaware State Parks and provides a very large swimming pool + hot tub. And you can't beat it for privacy which is very important to our large family. I'd give then place more stars if they were available.

Comfy cottage nicely decorated. Comfortable bed and furniture. Close to everything and the host was great.

Our stay was fantastic! The location couldn't be better, just a stone's throw from the beach. The property itself was clean and well-stocked with everything we needed. Mary was prompt and helpful in addressing the one minor issue that came up. We highly recommend this spot for a worry-free beach getaway!

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!

Our second time here! An absolutely adorable gem of an Airbnb with the nicest hosts and most beautiful garden and dock on the River! Great restaurant recommendations, super comfortable beds, and lovely living room. Perfect for families visiting the beloved St. Mary’s River.

House and ground were beautiful! The vast estate was very well manicured and well kept. It was a unique house being 160 years old and having the kitchen in a separate house but did enjoy the time era furniture. House had been updated and was done well. Fireplaces in all rooms was awesome even though we only used the one in the kitchen as the pilot light wasn’t lit in the others. House had all of the items needed for a vacation and we would go back in the future if we are in the area.

Cute place in a small community of vacation homes. They don't call the area Tall Timbers for nothing. I like the corner market up the road, the restaurant and bar are old school, friendly, and lively - packed with locals.

I’ve never had a nicer host. John had to help me through reservations because of some weird Airbnb accounts thing (two accounts??) but was so patient and was able to troubleshoot the problem. What a lovely spot!

The place is quaint and very well supplied. Maybe a bit too much but I'm sure it is used for other purposes beside just overnight guest based on the China, glassware, etc. The only thing I didn't care for was the size and location of the bathroom. But it was just my husband and I, so it wasn't an issue. Now, the shower is very small and I'm a 5'1" female. My husband is 6 foot, so it was more of an issue for him. But everything else was great. The dogs loved the fenced in yard and all the windows they could look out. It's not a place for multiple couples, but it's fine for parties of 2 adults and maybe a couple of kids as long as you do not need a tub. There is only the small shower and only 1 bathroom at this location. But Sharon and Doreen are excellent host.

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!!!

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!

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.

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!

Everything was great! The room was comfortable, clean, and the view was beautiful. It is in a great location with many restaurants in walking distance. Parking is close and convenient. We had a great trip and would recommend to others!

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!!

Great location and host. The home was the perfect size for my family and friends.

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!