
Family-friendly holiday rentals in Middlesex County
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Top-rated family-friendly rentals in Middlesex County
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Popular amenities for Middlesex County family-friendly rentals
Family-friendly home rentals with a hot tub

Colonies at Williamsburg: 2-BR, Sleeps 6, Kitchen
was very spacious and clean! we really enjoyed our stay. was very comfortable. maintenance staff was extremely responsive to two small issues we had - they came within 5 minutes both times! would definitely stay here again.

Colonies at Williamsburg: 2-BR, Sleeps 6, Kitchen
Great location. Igor was very responsive. We did Busch Gardens and Water Country from here. The pool was a great place to hang out on days we didn't have plans. The apartment was spacious and decently equipped kitchen. Our only complaint is squeaky bed which were fairly disruptive, but we still really enjoyed stay. Great value considering what it costs to rent a house these days. Highly recommend Igor's place.

The Colonies at Williamsburg: 2-BR, Sleeps 6
Awesome place and the host was very responsive and kind. We will definitely come back again. +++

The Colonies: 4-BR, Sleeps 12, 2 Full Kitchens
Fantastic area to vacation with family and kids. The waterpark/pool is a lot of fun. Staff was responsive with any questions or concerns (we had a wasps nest on the back patio that was quickly terminated by the on-call maintenence crew). Lots to do in the area, shopping, dining, breweries/wineries, theme parks, local parks, mini golf, etc. Highly recommended!

Williamsburg Colonies Resort, 4BR, 4BA
Great place, Great pool area, Great location, Great host, and great experience. We will be back.

The Colonies at Williamsburg: 4-BR, Sleeps 12
We had a great stay at the colonies. It was a very convenient location close to lots of things to do. The pool area was super fun for all ages! The condo itself was set up nice and worked well for our group of 9

Colonies at Williamsburg - Gorgeous suite for 4
Family- and pet-friendly home rentals

Thelma's Dawn Getaway. No Drama Zone
We had an absolutely wonderful stay at Rick and Christi's Airbnb. The location is perfect for anyone looking to enjoy a peaceful getaway, with direct access to the beautiful sandy beaches of Chesapeake Bay. Whether you’re into water activities, fishing, or just taking quiet walks around the serene neighborhood, this place has it all. One thing to note is that this spot is not for those seeking nearby restaurants or bars because there aren’t any in the vicinity—and that’s exactly what makes it so special. It’s a perfect escape from the hustle and bustle. Our family, including my wife and 14-year-old child, thoroughly enjoyed our time here. But what truly sets this place apart is the warm and friendly hospitality from Christi. She went above and beyond to make sure we had everything we needed to enjoy our stay. A lovely touch was the fresh jalapeño pepper she gave us, which we’re still using in our meals. Thank you, Christi and Rick, for making our vacation memorable.

Private House 4BR -Eastern Shore VA Wachapreague
Location, location, location! This was our second stay this year in this property. It’s the perfect location in town. Close to the restaurant, boat ramp, and friends at the campground. We thoroughly enjoyed our stay again. Clean property with responsive hosts. We will be back!

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

Waterfront 3BR/3BA Getaway: Beach, Dock, Firepit!
We took a small vacation with my sister’s family and we loved the location. Our kids enjoyed the small play area in the basement with the arcade machine and foosball table. We cooked every night and they had all useful appliances. We used the Ninja air fryer and Keurig machine every day. Since we went in January after a snowstorm the road was a little hazardous to use and the lake was completely frozen, so we spent most times indoors. We did enjoy going to the dock and looking at the frozen lake. This will be a great place to visit during the summer, they had Kayaks to use and a nice dock to jump from and fish. We would definitely come back.

The Bird's Nest at Holly Bluff-Riverfront. Beach.
T’s place was absolute perfection! It was beautiful, tastefully decorated and the homemade muffins and cookies were amazing! She and John were so lovely and accommodating. Relaxing on the dock on the river was a sublime experience as well! I really can’t say enough about my time spent there and if I’m ever in the area again I will definitely be staying at T’s! Why would you stay anywhere else!?

A "True" Chesapeake Bay Waterfront Experience!
Awesome house and location. Very nicely furnished and stocked with more items that I am accustomed to for an air bnb.

Moss Side Manor
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.

Historic Ware River Cottage at Glebefield
Incredible stay on a beautiful property. It’s quiet, private, VERY well maintained and just awesome. I truly hope to stay at this location again in the future because it was that great! You can tell the history in the cottage yet it’s updated and cozy. Also I’ve NEVER stayed at a location so clean!!!! From the cottage itself to the grounds, everything was very well taken care of.
Family-friendly home rentals with a pool

Unique Yurt Nestled in Williamsburg, Virginia
Stayed at a few KOAs, this one was the cleanest, best maintain and had the most things to do. Had a 9 hole disc golf course, nature trail, petting zoo, moon bounce, full amenities store, and it was 4 miles from all restaurants. Awesome place

Pet Friendly Deluxe Cabin in Williamsburg, VA
I needed a pet friendly place to stay to attend a local graduation and this was the perfect place. I didn’t get to enjoy the amenities at the campground, but saw them and it looked like the pictures. Had a nice, quiet stay.

Handicap Accessible Deluxe Cabin in Williamsburg
Really a great place to unwind. Very casual and relaxing.

The Colonies at Williamsburg
Really nice hotel resort with a great kids pool and close to the parks. We had a wonderful stay in a 2 bedroom unit…no smart TVs so consider bringing a fire stick but other than that it was lovely. Would definitely stay there again

Deluxe Cabin in Historic Williamsburg, Virginia
we enjoyed our stay! wifi isn't always available but given it's location and the fact that you are sharing with so many people so we didn't mind. a good reason to put the electronics down and get quality time!

Pet Friendly Classic Camping Cabin in Williamsburg
Our family had a wonderful stay, we will definitely be back in the future!
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- Chesapeake Bay
- Busch Gardens Williamsburg
- Buckroe Beach
- Water Country USA
- Buckroe Beach and Park
- Kingsmill Resort
- Grandview Beach
- Outlook Beach
- Jamestown Settlement
- Haven Beach
- Sarah Constant Beach Park
- Ragged Point Beach
- Wilkins Beach
- Royal New Kent Golf Club
- Kiptopeke Beach
- Golden Horseshoe Golf Club
- Sandyland Beach
- Salt Ponds Public Beach
- Cape Charles Beachfront
- James River Country Club
- The Poe Museum
- Lane Beach
- Piney Point Beach
- Guard Shore