Vacation rentals with a pool in Mathews County

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Top-rated rentals with a pool in Mathews County

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

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Guest favorite

A cozy bedroom features a king-size bed with crisp white linens and decorative pillows. A large window offers a view of a green space beyond, with a sitting area including a chair and small table. A 50" TV and coffee station are positioned on a wooden dresser.

Condo in Williamsburg

4.94 out of 5 average rating, 173 reviews

Kingsmill 1bed/1ba on Golf Course 9th Fairway

This beautiful 1 bed-1 bath unit is a cozy 400 sq.ft. and is located in the exclusive Kingsmill neighborhood. This first floor unit offers a king-size bed with a private patio that walks out onto the 9th Fairway of the River Course at Kingsmill. You'll enjoy the luxurious full bathroom with shower/tub combination and upgraded finishes. In the bedroom, you'll also find a computer desk, an over-sized sitting chair, a mini-fridge, a microwave, a Keurig coffee maker, and 50" Roku Smart TV w cable!

Guest favorite

A refreshing outdoor pool is surrounded by a spacious deck. Lounge chairs are positioned around the pool, set against a backdrop of lush greenery and distant buildings. Clear blue skies and gentle clouds enhance the serene atmosphere of the area.

Home in Cobbs Creek

4.9 out of 5 average rating, 159 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

Top guest favorite

A spacious waterfront home is showcased with a well-maintained lawn and blooming yellow flowers near the entrance. A large driveway leads to a brick facade, complemented by a garage. Clear blue skies can be seen in the background, enhancing the welcoming appearance of the property.

Home in Gloucester Point

4.99 out of 5 average rating, 194 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.

Top guest favorite

A refreshing swimming pool is visible, bordered by a concrete deck. Two charming structures resembling small cottages stand nearby, complemented by several white lounge chairs and vibrant umbrellas. Lush greenery surrounds the area, creating a serene backdrop.

Home in Irvington

4.99 out of 5 average rating, 119 reviews

The Rosé Retreat: Pool-Screened Porch-RELAX

Escape to The Rosé Retreat for peace and relaxation. Enjoy a romantic getaway sipping wine on the screened porch, unwind by the refreshing pool, navigate the waterways by kayak, and stroll to great restaurants/shopping. Savor local oysters and explore nearby wineries. Bring the family for a memorable NNK adventure. The Rosé Retreat is a place to get away from it all. Enjoy a bottle (or more, we're not judging) of Rosé while you're here. Follow on IG:roseretreatva Irvington Occupancy Tax #500

Top guest favorite

A spacious deck extends towards the waterfront, surrounded by lush trees. Lounge chairs and seating areas are positioned for relaxing views of the calm water. A sunroom is visible to the right, offering additional indoor space. The overall setting invites outdoor leisure and tranquility.

Home in Cobbs Creek

4.98 out of 5 average rating, 160 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

A large outdoor swimming pool is nestled within a stone patio, surrounded by lush greenery and tall trees. Sunlight reflects off the clear blue water, while comfortable lounge chairs are positioned nearby, offering a relaxing space to enjoy the serene outdoor setting.

Barn in Cobbs Creek

4.94 out of 5 average rating, 120 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.

Superhost

A vintage pull-behind camper sits by the water's edge, featuring a striking teal color that contrasts with the clear blue sky. Grassy surroundings provide a natural setting, inviting views of the serene shoreline and distant water.

Camper/RV in White Stone

4.88 out of 5 average rating, 128 reviews

“Old Smokey”A cozy, single bedroom, unique getaway

"Old Smokey" is a 1965 pull-behind camper that has been beautifully remodeled. It is cozy, rustic and has been restructured with lots of love. You can enjoy breathtaking sunrises and sunsets. The camper has both air conditioning and a wood stove. "Old Smokey" is a unique and romantic glamping experience. You can cook delicious meals on the propane stove/grill or visit one of our charming local restaurants. This is the perfect location to relax and reset, either solo or with someone special.

Superhost

An aerial view captures the expansive, green grounds surrounding the property, featuring a rectangular salt-water pool with lounge chairs. A spacious outdoor area is noted, complemented by a nearby building and white fencing that outlines the property.

Farm stay in Cardinal

4.91 out of 5 average rating, 185 reviews

Wtrfrnt aptmnt w/pool/dock on private farm

Escape to this serene waterfront estate, offering a private, fully-equipped studio apartment with stunning cove views from every window. 14 acres of peaceful grounds—saltwater pool, fish from the private dock, or kayak right from the shore. 10 minutes from Mathews and Gloucester’s farm-to-table dining, and steps from the Peninsula's famed art scene with galleries, antiques, and local crafts. Plus, we're right on the doorstep of the Historic Triangle—Williamsburg, Yorktown, and Jamestown.

Guest favorite

The inviting pool area features a crystal-clear swimming pool bordered by a stone deck. A shaded table and chairs are positioned beside the pool, with vibrant flowers and a large umbrella enhancing the outdoor space. The cottage can be seen in the background, surrounded by lush trees.

Home in Locust Hill

4.97 out of 5 average rating, 145 reviews

Waterfront Cottage Getaway Pool/Kayaks/Fire Pit

A timeless cottage on a quiet property on the Rappahannock River with charming rose garden, relaxing pool, and quintessentially Virginia feel. Find us on IG @rosehilllcottagerappahannock! Explore nearby towns of Urbanna, White Stone, and Irvington, or stay close to home to enjoy sweeping views, waterfront adirondack chairs, and kayaks — perfect for a cocktail or coffee, or take a dip in the river or pool. With open living spaces and thoughtful decor, this is your waterfront retreat.

Guest favorite

A private hot tub is situated on a wooden deck surrounded by trees, offering a serene retreat. Sunlight filters through the branches, creating dappled shadows on the tub's surface. A wooden wall adds a rustic touch, featuring a decorative crab motif.

Home in Irvington

4.97 out of 5 average rating, 144 reviews

Magical wooded cottage pool +priv hottub walk2town

Set among the trees on 2 peaceful wooded acres, this cottage delights with gothic architecture, sun-filled rooms, and a bathroom for every bedroom. Relax in the hot tub under the stars, sip local wines, eat oysters. Take a sunset boat cruise or learn oystering and crabbing from a local waterman. Farm stands, markets, and sea-to-table local fare. Live life in an historic working water town with lots of personality. Close to Tides Inn, Kilmarnock, White Stone, Compass Entertainment.

Top guest favorite

A charming two-story cottage is set on a lush green lawn, with a clear view of the Chesapeake Bay in the background. The cottage features large windows and a sloped roof, with a small wooden addition on one side, surrounded by well-maintained grass.

Tiny home in Cape Charles

4.98 out of 5 average rating, 328 reviews

The Laughing King Retreat Honeymoon Island Cottage

Honeymoon Island Cottage is an adults-only lodging experience like no other. You and your guest will stay in a charming tiny farmhouse that is located just steps from the Chesapeake Bay on a USDA certified organic farm. Enjoy access to a private saltwater pool, private beach, Chesapeake Bay water access for boating, swimming, paddleboarding, fishing or just soaking, dig for clams, collect wild oysters, or just sit and marvel at the beauty. We look forward to welcoming you.

Top guest favorite

The Gothic Revival-style cottage is showcased from its charming exterior, featuring large arched windows and a welcoming front porch. Two wooden chairs sit invitingly on the porch, complemented by seasonal decorations. Surrounding trees provide a sense of tranquility within the peaceful setting.

Cottage in Irvington

5 out of 5 average rating, 211 reviews

Peaceful Haven: nature, pool & charming town

Do you want to get away from it all, change your surroundings and recharge yourself mentally and physically? Welcome to Peaceful Haven. Shops and restaurants of the lovely historic Village of Irvington are only a couple of minutes away. Hike just outside your door or in nearby parks, ride bikes around the meadows or to town, hang outside and listen to the birds, or just sink into the comfy couch to enjoy a movie on our large TV screen.