Vacation rentals with a pool in Gloucester County

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Top-rated rentals with a pool in Gloucester County

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Farm stay in Gloucester

5 out of 5 average rating, 12 reviews

Farmhouse stay at upscale equestrian estate

Relaxation at its finest for up to 10 guests at Serenity Farm in historic Gloucester County, VA. We are a working private farm that overlooks groomed pastures and luscious gardens while offering views of a private equestrian estate. You will have private access to this beautifully decorated farmhouse while enjoying the views, amenities, and proximity to history, golf, shopping, and theme parks! *Stays longer than 20-days will receive one complimentary breakfast platter & (1) clean during stay.

Guest favorite

Home in Cobbs Creek

4.91 out of 5 average rating, 134 reviews

Millionaire $ Views No Xtra Charge! Hot Tub! POOL!

Welcome to The Cottage at Misti Cove, where you can experience the epitome of relaxation and tranquility. Immerse yourself in the serene ambiance of our cottage, aptly named for its simplicity, which belies the luxurious amenities that await you. At The Cottage at Misti Cove, we understand that the essence of a fulfilling vacation lies in the delicate balance between embracing the simple life and indulging in modern comforts. Here, you will discover a haven that seamlessly blends these elements

Guest favorite

Home in Gloucester Point

4.99 out of 5 average rating, 171 reviews

York River Vacation Home

This lovely, spacious waterfront home is located on the York River in Gloucester County Virginia. It is the perfect get away to enjoy the relaxing sounds and sights of nature. The views are spectacular! Keep an eye out for osprey and dolphins as you enjoy watching the sunrise and set over the water. There is plenty to do! Relax in the salt water pool overlooking the water, bring a pole & fish and crab right off of the private dock, or venture out on the kayaks. 16 ton boat lift, Jet ski lifts.

Guest favorite

Home in Cobbs Creek

4.98 out of 5 average rating, 150 reviews

Blue Heron WaterSide

Blue Heron Waterside awaits you...Private Hot Tub and Pool!Waterfront and Pier- Kayaks included! This retreat is set up with you in mind for a special get away.Relax.Enjoy being together plus space to have quiet time. Sunroom, spacious deck, private Pool, Hot tub and Pier create a waterfront living experience. Grab a book, go for a swim or lounge by the pool. Explore the water with a variety of Kayaks plus a Stand Up Paddle Board.Great location to fish and crab from the pier. Are you ready?

Guest favorite

Barn in Cobbs Creek

4.95 out of 5 average rating, 111 reviews

The Barn at Pond Point - Riverfront Home

The Barn at Pond Point is perfectly situated on the Piankatank River, a salt water arm of the Chesapeake Bay. It shares 19 acres of wooded and waterfront property with the owner's main home. A unique space, Barn was converted from a working horse barn into a residence in the 1980's. With a quarter mile of private, sand beach and a large pool (May-Sept), the Barn is an ideal space for time with family and friends, swimming, hunting for prehistoric shark's teeth, or simply enjoying the view.

Guest favorite

Home in Deltaville

5 out of 5 average rating, 14 reviews

Berryville Shores : Deltaville Riverfront Escape

This 4 bedroom, quiet and cozy home right on the water is perfect for the off season get away or extended stay to "work from home". It can accommodate the crew for a quick fishing trip, provide a break from the fast-paced city grind, or just a cozy weekend surrounded by nature. We are all about relaxing and making memories at your own pace. So, if you’re looking for somewhere easygoing to hit “reset” for the weekend, this is it. It's comfortable, spacious and this time of year..cheap!

Guest favorite

Home in Hartfield

5 out of 5 average rating, 23 reviews

Maddie's Place

Relax with the whole family or a group of friends at this newly constructed home in Piankatank Shores, a golf cart community on the piankatank river. Plenty of space for 8 and a porta-crib available. Garage features a bar, big screen smart tv, a poker table, dart board & pool table. Relax on one of the local beaches. Plenty of parking for multiple vehicles and a boat. 12 mi to Urbanna, 1 Mi to the piakatank river golf club/steamboat restaurant. golf groups MUST BE 21 years old to book!

Superhost

Vacation home in Gloucester County

4.8 out of 5 average rating, 41 reviews

Waterfront 4 bedroom home with marina facilities

Stunning river views from this spacious family home. The quiet, peaceful setting is perfect for taking in nature and wildlife. The open floor plan that spills onto the patio is great for entertaining. Wonderful spot to enjoy boating, crabbing, fishing, kayaking - all the Severn River has to offer. Home features first floor BR and BR w/ shower, upstairs 3 BR and 2 full BR. Award-Winning Busch Gardens, Historic Colonial Triangle (Yorktown / Williamsburg / Jamestown) Nearby.

Guest favorite

Farm stay in Gloucester

5 out of 5 average rating, 28 reviews

Colonial Farmhouse on 14 serene acres w/ huge pool

"Patriot Plantation" circa 1750's is perfect for family gatherings! A seasonal pool/party barn is adjacent to the 20x40 inground pool (pool open June-August). Enjoy fresh eggs, and we invite you to pick seasonal herbs, fruit and nuts: blackberries, pawpaw, black walnut and pecans. Relax and unwind on our 14 tranquil acres! Close to amenities: 10 minutes to Walmart; 45 minutes to Colonial Williamsburg/historic triangle; and 20-30 minutes to local wineries.

Guest favorite

Rental unit in Gloucester

4.93 out of 5 average rating, 41 reviews

Eclectic and Cozy Apartment

Close to many historical sites; Williamsburg, Yorktown, and the Northern Neck. Located on the Middle Peninsula. Close to the Tri- Rivers... fun family filled atmosphere with festivals all year long. Fully furnished. You only need your clothes and food. Full kitchen with all amenities. Owners on premises. Large dogs that are friendly. Pool available, with family and friends in and out. Small Par 3 practice space. Nice, quiet neighborhood.

Guest favorite

Guesthouse in Gloucester

5 out of 5 average rating, 132 reviews

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.

Superhost

Guesthouse in Gloucester

4.93 out of 5 average rating, 97 reviews

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.