Vacation rentals with a pool in Gloucester County

4.9 out of 5 average rating, 155 reviews

Home in Cobbs Creek

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

4.99 out of 5 average rating, 185 reviews

Home in Gloucester Point

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.

5 out of 5 average rating, 28 reviews

Home in Deltaville

Waterfront 4BR | Pool & Peaceful Deltaville Views

This spacious 4-bedroom, 2.5-bathroom home offers the perfect blend of comfort, relaxation, and outdoor adventure. Wake up to stunning river views, and spend your days lounging by the private pool, kayaking, fishing, or exploring the serene surroundings. Whether you're looking for a fun-filled family vacation, or a friends' getaway, this serene stay provides unmatched tranquility Book now for spring & summer, and experience warm breezes, golden sunsets, and the ultimate waterfront experience!

4.98 out of 5 average rating, 156 reviews

Home in Cobbs Creek

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?

4.94 out of 5 average rating, 116 reviews

Barn in Cobbs Creek

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.

5 out of 5 average rating, 14 reviews

Home in Gloucester

Serenity Farm Equestrian Retreat in Historic VA

Relaxation at its finest for up to 16 guests at Serenity Farm in historic Gloucester County, VA. We are a working barn that overlooks groomed pastures and luscious gardens while offering views of a private equestrian estate. You will have full private access to this beautifully decorated farmhouse while enjoying the views, amenities, and proximity to history, golf, shopping, and theme parks! Historic Museums, Shopping, Restaurants, Local Breweries, and Art Galleries are only minutes away!

5 out of 5 average rating, 32 reviews

Home in Hartfield

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!

Apartment in Williamsburg

4.67 out of 5 average rating, 3 reviews

Modern Studio Comfort at Burgesses Way

Built on the lush grounds of a former golf course, this quiet resort community is surrounded by the stunning landscape and historic spirit of Williamsburg. A great retreat any time of year, its central location also provides convenient access to explore all the area has to offer. • Guest checking in must be 21+ with valid ID. • Guest must have debit/credit card to put $250 refundable security deposit on hold at resort check-in. • Name on reservation must match photo ID at check-in.

Vacation home in Gloucester County

4.8 out of 5 average rating, 45 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.

4.94 out of 5 average rating, 49 reviews

Apartment in Gloucester

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.

5 out of 5 average rating, 29 reviews

Farm stay in Gloucester

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). 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.

5 out of 5 average rating, 133 reviews

Guesthouse in Gloucester

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.

Vacation rentals for every style

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Popular amenities for Gloucester County rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.89 out of 5 average rating, 18 reviews

Home in Deltaville

Get away to the heart of Deltaville!

AnnRating, 5 stars9 months ago

Such a beautiful place! The pool was fantastic!! The house is so much better than the pictures even are!!

4.8 out of 5 average rating, 5 reviews

Our Home Away from Home

SheilaRating, 5 stars2 weeks ago

Sue was very communicative throughout our experience. She responded quickly to my initial message and each message thereafter. My trip was a bit last-minute, but it sure didn't feel that way! The cottage was perfect in every way! It was clean and cozy. It was just the right size. It truly felt like a home away from home. The resort was peaceful and included many activities. The resort staff was friendly, too! If I travel to Williamsburg for pleasure again, I would absolutely see if this cottage is available.

5 out of 5 average rating, 3 reviews

Lovely 3 bed cottage sleeps 10

CathyRating, 5 stars11 months ago

The cottage was clean and uncluttered. It was very comfortable, from the table to the couch to the beds. It had all the amenities needed for a week-long stay. It was in a safe and friendly gated resort neighborhood. As a group of four adult women, we loved the four bathrooms (3 full, 1 half) and four comfortable beds.

Home in Gloucester

4.73 out of 5 average rating, 11 reviews

Squeaky Shores on the York River

OncaRating, 5 stars1 month ago

super sweet host !! totally bailed us out last minute!!

4.5 out of 5 average rating, 4 reviews

Lovely 3 bedroom cottage

MargaritaRating, 5 stars23 months ago

Beautiful cottage in a beautiful area. Would stay here again. Our layout was a bit different from the pictures, but it work great to have a space for the teens and another one for the adults. I would love to stay here again.

5 out of 5 average rating, 3 reviews

Parkside Williamsburg | 3BR Next to Busch Gardens!

BeckyRating, 5 stars18 months ago

Great location! Easy check in! Perfect for our family of 5. No issues!

Home in Gloucester County

4.63 out of 5 average rating, 52 reviews

Private 5-acre Waterfront Peninsula with Beach

TroyRating, 5 stars1 month ago

This was a short trip for a bachelor/bachelorette party. Everyone who was coming was so impressed and was like we wish we were staying here longer than one night! Mary was very responsive and even popped out and said welcome when we arrived! Definitely would recommend this place for a fun get away! The bonfire was definitely a recommended opportunity! Thank you again Mary!!

4.73 out of 5 average rating, 11 reviews

Cheerful free standing 4 bed 4 1/2 bath home

ChuckRating, 5 stars12 months ago

The check-in process, with the resort, includes repeated attempts to sign up for a timeshare presentation. The resort's activities center staff was rude when we signed up for an activity. The indoor and outdoor pools are great. The resort has a gym, but it's small and has limited equipment. The accommodations are clean and offers everything we were looking for. The furnishings could use updating though. The location is perfect for Colonial Williamsburg, Jamestowne Settlement, Water Country USA and Busch Gardens Williamsburg.

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Condo rentals with a pool

MeganRating, 5 stars36 months ago

Close to Theme Parks & Attractions!

Our trip was great and the property was exactly as described. Very nice and clean.

4.58 out of 5 average rating, 12 reviews

Wyndham Patriots Place | King Bed Studio

ToriRating, 5 stars8 months ago

We had a great stay here. Check in was easy and the suite had everything you need to feel at home. Staff was also very nice and helpful. Would recommend!

4.83 out of 5 average rating, 18 reviews

Colonial Williamsburg Patriot's Place - 2 Bedroom

StaciRating, 5 stars6 months ago

a perfect stay to experience Christmas in Williamsburg

5 out of 5 average rating, 8 reviews

Wyndham Patriots' Place one bedroom

AdamRating, 5 stars12 months ago

This place was in a great home base for our day trips to Williamsburg, Jamestown, and Yorktown. It was surprisingly roomy, with ample space in the living room, dining room and bedroom. The two sinks and two showers were a nice feature. We were warned that the Wyndham employees would try to get us to go to a timeshare pitch, and they did during check-in and again by phone the next day, but we told them we weren't interested and they didn't bother us. All in all, we were pleased with our stay.

4.92 out of 5 average rating, 25 reviews

King's Creek Plantation: 2-BR, 2.5 Baths, Sleeps 6

HunterRating, 5 stars2 months ago

Good location next to the water park and Target. Quick response for short notice trip. Stronger than. Good quality furniture and new flooring.

4.67 out of 5 average rating, 12 reviews

Wyndham Patriots Place | King Bed Studio

MichaelRating, 5 stars1 month ago

David’s place was great. The grounds are beautiful, the unit itself was clean and roomy, the bathroom was spotless, and the kitchenette was equipped with a coffee maker, refrigerator, small oven with stove top, microwave, some cups, and dishes. The bed and couch were comfortable as well. Reception had no problem checking us in a little before 10pm and allowed us to store our bags there after checkout. The unit itself is part of a timeshare, but honestly the staff member was not too pushy in asking if we wanted to come see a presentation (we declined). The place is a little far to recommend walking from Colonial Williamsburg, however, by car it is only 5-6 mins away. David was a responsive host and I’d stay again.