Kid-friendly holiday rentals in Gloucester County

The Nook; Peaceful 2 bedroom cottage by the bay

Relax or go-for-it! The Nook is a stylish cozy cottage with great indoor/outdoor space. With water view and access including pier and boat ramp enjoy your coffee on the deck before taking to the water in one of the two kayaks or canoe or enjoying a bike ride (4 available) to get up close with nature. Catch fish, crabs or just a sunburn while enjoying time on the water. When ready there's plenty of shopping, eating and beaching to do in nearby towns! All topped off with a sunset over the water!

Little Cove Cottage, Couples Retreat/Mathews

Little Cove Cottage: a charming studio in Mathews County with private entrance. Mathews is a rural town with several beautiful beaches close by and many areas to access the water. This apartment offers a small water view of the North River, with a pier and boat ramp just 400 yards away. Bring your Kayaks or use ours. . We are just minutes away from the Mobjack and Chesapeake Bays. Mathews is home to great restaurants with fresh seafood. We also have a wonderful farmer's market. Come enjoy!

Bee Humble Cottage Entire Home

Curious about what makes Gloucester so wonderful? Live like a local at "Bee Humble Cottage" and find out for yourself at our newly renovated 2 bedroom cottage. Super homey and spacious living allows for guests to have memorable family & friend time. Sit around with the windows open, sipping morning coffee. Our street is quiet & very safe with free parking spaces. Shops, restaurants, hiking, lovely beaches & Colonial Williamsburg all within a short driving distance of our home.

Elm Grove Farm Guest Cottage

Our guest cottage is the perfect retreat for a quiet getaway or a quick commute to local historical sites. We are located on a family farm property dating back to the 1880's. Although the old farmhouse is gone our home with attached cottage is filled with decor built by the owner with reclaimed wood from the original home. We are adjacent to Beaverdam Park and located 2 miles from Main Street which boasts the historic Gloucester Courthouse dating back to 1651.

Wooded Cabin retreat on fresh water pond

If your looking for a quiet place in a wooded setting, this is it. Cabin has view of private 7.5 acre pond, deck and walking trail to the scenic Dragon Run, with canoe portage. You are welcome to bring your canoe/kayak. Bird watchers, wildflower enthusiasts will enjoy what the Dragon Run has to offer. If shopping or history is your interest, this cabin is only 45 min away from Williamsburg, and will give you a place to relax. This is a pet friendly cabin.

Historic Ware River Cottage at Glebefield

Come visit this quiet and peaceful setting on the Ware River in historic Gloucester VA. The cottage sits on a 65 acre waterfront property. This fully updated cozy cottage is a great home base for exploring Williamsburg, Yorktown, Jamestown and Richmond. Pets are welcome with a small fee and pre-approval. There are serval buildings and gardens to enjoy so please take note of the picture captions for details on the cottage and other dependencies.

The Bee Goode House on Main Street

Welcome to the Bee Goode House! We want our future and returning guests to know of our diligence in sanitizing and cleaning every surface after each guest. Linens are fresh and clean, and there is plenty of private space with a large yard surrounding the house. Relax and enjoy Gloucester Main Street from a 1950's renovated home. From Mid Century Modern furniture and renovated retro appliances, you will be comfortable and hip in our home.

Creekside Guesthouse - Dock and Pool on 10 acres

With stunning views overlooking Bland Creek, this guesthouse is the perfect place to unwind or start your adventure. This two-bedroom apartment is nestled high in the treetops, perfectly situated on 10 acres of wooded and coastal beauty. When the time comes to explore, guests are only minutes away from eclectic shopping and dining in historic downtown Gloucester, with Williamsburg and Richmond an easy 45 minutes away.

Clay Bank River Front Cottage

Recently updated waterfront cottage 2 bedroom - 2 queen beds, a pull out sofa, 28 private acres on the York River in Gloucester, Va. Great remote getaway with a pool, kayaks and private pier for fishing/crabbing. Lightly traveled river. Access to Yorktown, Newport News, Williamsburg, Jamestown, Richmond, Norfolk, Urbanna. Shares the property with the main house where owner lives.