Vacation rentals with a pool in Mathews County

The open-concept living space is shown, featuring a comfortable seating area with a queen sleeper sofa and two armchairs. A wood-burning fireplace is adjacent to the large TV, while a dining table is set for six. Wall-to-wall glass doors provide views of the outdoors.

4.95 out of 5 average rating, 122 reviews

Kingsmill 2bd2ba Condo on Golf Course 9th Fairway!

KristenRating, 5 stars3 weeks ago

I had a fantastic stay in Williamsburg! The room was exactly as described—clean, comfortable, and had all the comforts of home. The hosts were incredibly communicative and helpful, making the entire experience seamless. Their attention to detail and hospitality really stood out. I would absolutely love to return for another visit. Highly recommend!

4.9 out of 5 average rating, 148 reviews

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

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

JessicaRating, 5 stars1 month ago

This was a great stay for a weekend away to celebrate my birthday with my husband. It was very quiet & peaceful, and the view was beautiful. We wish we could have spent more time outside to enjoy it, but it was just a bit too chilly. We did have an opportunity to sit by the fire pit and watch the swans! We found some good restaurants not too far away and overall we were very happy with everything. The heated floor in the bathroom was awesome!

4.63 out of 5 average rating, 19 reviews

A spacious home is set among lush greenery, featuring large windows that allow natural light to flood the interior. A private, inviting saltwater pool is surrounded by a deck, with steps leading up to the house and shaded areas provided by patio umbrellas.

Home in Lancaster

Peaceful bay retreat. Hot tub,water views,fire pit

SjaloomRating, 5 stars4 months ago

A spacious home by the water. We celebrated Thanksgiving at this location and it was very special. The views are beautiful, had a fire right by the water and relaxed by the beach. A perfect getaway with family and friends. It has everything you need, the living room is super comfortable and great to relax with the family. The kitchen was spacious making it easy to cook and entertain the family. We loved the hot tub, playing pool and having family dinner. Overall a fabulous experience!! Great host- great communication. Highly recommend

4.99 out of 5 average rating, 112 reviews

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

The Rosé Retreat: Pool-Screened Porch-RELAX

LaurenRating, 5 stars5 days ago

We loved our stay at the Rosé Retreat and are so sad to leave! The place was spacious and beautiful- we felt right at home. The surroundings were so peaceful and serene. Roxanne and Tara were very responsive and helpful. This was the perfect place for our family to spend a fun weekend together. When we come back to Irvington, we will absolutely stay at the Rosé Retreat again!

4.98 out of 5 average rating, 152 reviews

Home in Cobbs Creek

Blue Heron WaterSide

JamesRating, 5 stars3 months ago

Absolutely beautiful overlook to the water from the entire rear of the house. Huge deck with plenty of seating and things to do. The inside is very spacious and had plenty of room for our group. We would visit again in the future without hesitation!

4.89 out of 5 average rating, 117 reviews

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

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

AshtonRating, 5 stars5 days ago

My bf and I stayed here for 2 nights and had the best time. We’re looking to get an RV/ Travel van for ourselves so it kinda gave us an idea of what that would look like ☺️ We traveled to this Dog Park in Kilamarnock about 20 mins from the Rv and got burgers and lobster rolls in town at Small Town Burger (kinda pricey but their curly fries cooked in beef tallow was amazing). We spent most of the day just walking our pup around and basking in the sun. It was a peaceful stay, we will definitely be back.

4.97 out of 5 average rating, 129 reviews

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

Waterfront Cottage Getaway Pool/Kayaks/Fireplace

MarilynRating, 5 stars3 weeks ago

Our only complaint is we wish our stay could have been longer! Gorgeous views, lovely home and so many thoughtful details for guests. 10/10, no notes. We felt right at home and will stay here next time we’re in the area for sure!

4.99 out of 5 average rating, 136 reviews

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

Escape to magical wooded cottage with hot tub

SummerRating, 5 stars1 month ago

Maria’s space was a perfect getaway! The house is clean and welcoming! They even had pet bows and toys which I thought was so sweet! Maria was very kind and responsive and gave a lot of great recommendations ! We had Brenda come to the house for a private dinner, and she was also amazing ❤️ 10/10 would stay here again

Vacation home in Gloucester County

A vibrant sunset casts a warm glow over the water, with rich hues of orange, pink, and purple reflected in the calm surface. A dock extends into the scene, framed by grassy edges, contributing to the serene atmosphere along the river.

4.79 out of 5 average rating, 42 reviews

Waterfront 4 bedroom home with marina facilities

ElizabethRating, 5 stars5 months ago

This Airbnb was very convenient to Severn Yachting Center. We were able to work on our boat all day and enjoy being in a home at night. The area is beautiful and peaceful. Super safe area that is right on the water! Communication with owner was top notch! Highly recommend staying here!!!

Tiny home in Cape Charles

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.

4.98 out of 5 average rating, 309 reviews

The Laughing King Retreat Honeymoon Island Cottage

AndrewRating, 5 stars6 days ago

The Laughing King (and the Honeymoon Island Cottage in particular) were fantastic! A wonderful quick getaway from DC for couples. The property is gorgeous - a farm with a historic old house that is the main lodge, surrounded by hundred-year-old oak trees, a standalone cottage (that we stayed in for 3 nights), open fields, a saltwater pool, and private beach with dock and a boat and SUPs for guest use. MJ serves up gourmet breakfasts (eggs Benedict, avocado toast, French toast, quiche, etc. over the course of our stay) + coffee in the morning and also dished out recommendations on local spots to visit. 100% will be back!

0 of 0 items showing

What guests are saying

Individual quaint 3 bedroom cottage

4.69 out of 5 average rating, 13 reviews11 months ago

The cottage was perfect for our purposes. We traveled to Williamsburg to celebrate our daughter’s graduation from William and Mary. The main room provided plenty of space for family gatherings and the kitchen was stocked with basic cookware, dishes, and cutlery. Since we rented both units, we borrowed chairs and kitchen items from the smaller unit so we could all eat together in the larger unit. The beds were very comfortable. There was parking for three cars for the two units.

Apartment in Williamsburg

What guests are saying

Family Retreat, In-Ground Pool, plus Private Beach

4.77 out of 5 average rating, 78 reviews8 months ago

This house and stay were exactly what we needed! We are a quiet family that loves peaceful spaces. The home was beautiful, well maintained, clean, updated, and extremely well appointed. Access to both the beach and lake was easy, as was getting into and out of town. Jack proactively reached out to us when we got there to ensure everything was in order and offered assistance if we needed anything. We didn’t need anything during the week but we felt good knowing he was available. We met some of the neighbors in passing and they were friendly and welcoming, too. Wonderful experience!

Home in Cape Charles

What guests are saying

The Cottage @ Captain Genes - Secluded Waterfront

4.95 out of 5 average rating, 132 reviews4 months ago

Our stay in this home was such a treat! We enjoyed utilizing the kayaks to boat around in Chesapeake Bay. The hot tub was an absolute delight, perfect for evening stargazing, saw lots of shooting stars, and could see the water of the bay from the hot tub. We also enjoyed doing November cold plunges from the hot tub to the pool. While the living room is not expansive, it fit our needs for family game & movie nights. The bed linens were so comfortable, and Lori was beautifully responsive & friendly when we would reach out with a question. We also enjoyed the nearby Sandy beaches.

Cottage in Chesapeake

What guests are saying

Eclectic and Cozy Apartment

4.93 out of 5 average rating, 43 reviews4 months ago

We loved the place. It was very clean, spacious, relaxing, kid friendly, and has all the necessary amenities. Rebecca is a great host, being very proactive and friendly. It was easy to get to the sites in the Virginia Historic Triangle. We hope to be back someday.

Apartment in Gloucester

What guests are saying

Williamsburg King's Creek Plantation 1BR, 1BA Unit

5 out of 5 average rating, 3 reviews14 months ago

We used this space while our home was being worked on, do it was more of a “staycation” and did not use all of the amenities. The space was clean and newly renovated, so we were pleased with how nice things were. I highly recommend it for people visiting the Williamsburg area. Great location to Busch Gardens, W&M, etc. The only negative is that it is a time share, and they don’t take no for an answer.

Apartment in Williamsburg

What guests are saying

CHARMING COTTAGE, 3 AND FULL 3, KAYAK DOCK, POOL

4.85 out of 5 average rating, 39 reviews9 months ago

Lovely home in a serene neighborhood. The pool was such a blessing as it was very hot and muggy the week of our stay. We also appreciated the central air conditioning! The house had everything we needed and made our stay very easy and comfortable. The neighbors were very friendly and welcoming as well!

Cottage in Irvington

What guests are saying

Cape Charles Plantation Home “Nevill’s Nook Suite”

4.98 out of 5 average rating, 188 reviews9 months ago

Charming Cape Charles getaway! I was so happy to find this gem and even more thrilled when I arrived. From the beautiful landscape of the gated community, to the southern charm of this glorious suite…I wanted for nothing. This enormous suite has all the comforts of home and the location was spectacular. The property offered not only a private beach on the bay , a community pool, a beautiful well maintained golf course, it was also a short drive to the charming town of Cape Charles. Dawn offered endless advice to her favorite restaurants, activities to do and places to see while we visited. She was just a text or call away if I needed anything. Her hospitality was beyond measure. I look forward to coming back.

Apartment in Cape Charles

What guests are saying

Seabreeze Cottage ... explore the Eastern Shore!

4.98 out of 5 average rating, 55 reviews5 months ago

This was a very peaceful location. I truly appreciate the fenced backyard, the solitude, and of course the local coffee! The home was pristine and welcoming, and we had everything we needed. The area was a great place to get away. We traveled to Norfolk twice, and spent time in the Cape Charles downtown. We had no trouble with wireless connections and streaming. The Food Lion was close by for groceries, and when we asked the hosts about a particular kitchen tool, the response and delivery of the tool was immediate! It was a lovely vacation, and if we go back to the area, I wouldn’t hesitate to book the same home.

Cottage in Cape Charles

What guests are saying

Gulway

5 out of 5 average rating, 42 reviews9 months ago

Just returned from an amazing stay at Preston's home! From the absolutely beautiful sunsets, dolphins in the Piankatank, fab fishing on the dock, comfortable beds, incredible salt water pool, kitchen with everything, to delightful surprises at every turn -- we loved our trip! This wonderful vintage house is full of love, books, games and private spaces for all. Bonus: the tap/bath water is great...not the usual hard water in the Northern Neck, and the air conditioning was very welcoming during this heat wave. Preston answered our questions immediately. Everyone in our group raved about our experience and we'd love to return!

Home in Cobbs Creek

What guests are saying

Wtrfrnt aptmnt w/pool/dock on private farm

4.89 out of 5 average rating, 156 reviews1 week ago

I had to cancel unfortunately because of the weather emergency Arkansas was going through. I gave Shelli five stars because of her graciousness and kindness when I to cancel. I will definitely be booking her place when I get to take my trip next year! Thanks Shelli!

Farm stay in Cardinal

1 of 12 pages

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Hotels

Stylish accommodations and amenities

Popular amenities for Mathews County rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 15 reviews

Home in White Stone

Waterfront panoramic point with pool

RobinRating, 5 stars9 months ago

Wow! My toddler daughter nicknamed this place “The Pretty House.” It is beautiful inside and out and is pretty near perfection. Kitchen is well stocked, beds are comfortable, linens were nice and we enjoyed our time in the beautiful pool. You can see water from just about every window and the place feels very private. There’s plenty of space for everyone to spread out but we also enjoyed the selection of games and outdoor toys during our together time. This has been our best stay ever and we hope to return again and again in the future. Thank you for hosting us!

4.67 out of 5 average rating, 3 reviews

A deck overlooks the tranquil waterway, with picturesque views of grassy areas and the shoreline. Brightly colored chairs provide seating options, while a wooden railing frames the outdoor space. The clear blue sky enhances the inviting atmosphere.

Home in Cape Charles

Hot Tub - Massage Chair - Golf Cart - Beach Gear

DanielleRating, 5 stars4 days ago

The house was wonderful, the location was beautiful. We enjoyed watching the sunrise and listening to the birds on the back deck. So peaceful! We were away from the crowds but could easily bike or ride the golf cart into town to walk, shop, or visit the restaurants and bars. Highly recommend!

5 out of 5 average rating, 24 reviews

A spacious living area is furnished with comfortable sofas and a coffee table, surrounded by natural light from the large windows. The open layout transitions into a modern kitchen with white cabinetry and stainless-steel appliances, enhancing the welcoming atmosphere for gatherings.

Home in Hartfield

Maddie's Place

AdamRating, 5 stars6 months ago

The place is perfect for a group. Comfortable rooms, kitchen and couch area. Add in the games room and you have everything you need for fun nights. We were in the area for a sports competition and this location is only 10 minutes away.

4.88 out of 5 average rating, 25 reviews

A bright and inviting living area features a spacious navy sofa and two matching armchairs. A coffee table sits in front, while a wood-burning fireplace adds warmth. A flat-screen TV is mounted on the wall, and a staircase leads to the upper level. Light enters through large windows.

Home in Cape Charles

Sunshine Baydream Cape Charles

LorrieRating, 5 stars2 weeks ago

We were in town for our son’s wedding and enjoyed our stay very much. Jason responded quickly to the few questions we had. We would definitely stay again.

4.92 out of 5 average rating, 79 reviews

A clear blue pool is depicted, bustling with activity. A child is seen jumping into the water, wearing a safety vest. Surrounding the pool, a spacious deck provides ample room for lounging. A building is visible in the background, offering changing facilities and amenities.

Home in Cape Charles

Bay Creek (Pool!) Meets Historic Cape Charles!

MeghanRating, 5 stars1 week ago

Our family really enjoyed our stay in Cape Charles. Chris’s home was more than enough space for our family of 5. It rained one day and we were able to comfortably spread out and watch a movie, read, play board games, etc. The sizable yard was also lovely! It was nice to sit and have a coffee in the Adirondack chairs while our children played. Great spot for an evening cocktail too. The home is a quick golf cart or bike ride into town. We walked to dinner our first night and it was a leisurely 10-12 mins. There is mini golf across the street and the brewery is located down from mini golf. We ate breakfast at the pharmacy which is across the way as well. We enjoyed having access to the tennis courts at Bay Creek. If it was summer, I know we would have loved the pool. We can’t recommend Chris’s home enough!

An in-ground pool boasts clear turquoise water, surrounded by lush greenery and palm trees. The serene view of the water extends in the background, creating a tranquil outdoor space for relaxation.

Home in Gloucester

4.78 out of 5 average rating, 9 reviews

Squeaky Shores on the York River

MarcusRating, 5 stars8 months ago

Perfect location. The sunsets were absolutely beautiful. If we weren’t at Busch Garden or Water Town, we enjoyed the pool and did some fishing right from the back yard. We will definitely stay again when we are back in the area.

5 out of 5 average rating, 12 reviews

A private pool area is surrounded by lush greenery and decorative plants, providing a serene outdoor setting. A shaded seating area with a table and umbrella complements the space, while a charming shed is visible in the background. Sunlight creates a bright and inviting atmosphere.

Home in Gloucester

Serenity Farm Equestrian Retreat in Historic VA

ZackRating, 5 stars6 months ago

Stayed with 4 friends for a wedding and we absolutely loved the place. Also, if you like horses this is the spot for you. Billy was very timely with communication which I really appreciated. 5/5 stars.

Show all

Condo rentals with a pool

An indoor pool area is featured, with a water volleyball net positioned in the center. Comfortable lounge chairs border the pool, and natural light streams in through large windows, creating a serene environment. The ceiling is adorned with wooden beams, contributing to the spacious feel.

4.79 out of 5 average rating, 14 reviews

King's Creek Plantation: 3-BR, Sleep 10, 2 Kitchen

JCRating, 5 stars4 months ago

Igor’s place was excellent! The space was clean, in a fantastic location, and exactly as described in the listing. Everything went smoothly, and we had a wonderful stay. Highly recommend!

A sweeping view of the lush green fairway and the sparkling water at sunset, with tall trees lining the edges. A sand bunker can be seen on the left, while sculpted landforms curve gently, leading towards the horizon.

5 out of 5 average rating, 9 reviews

Upscale condo with Golf Course views

MaryRating, 5 stars8 months ago

The condo is well appointed with everything I needed. Kingsmill is a special place. Rodica was very quick to reply when I had a few different questions. Very comfortable bed and reading chairs. Top notch.

5 out of 5 average rating, 24 reviews

The exterior of a two-story house is shown, featuring a gray shingle facade and a welcoming front porch. Neatly trimmed shrubs and manicured lawns frame the driveway, while flowering plants add subtle color. A double garage with white doors is visible on the left.

Condo in Cape Charles

Bay Creek Blessed at The Fairways

PaulaRating, 5 stars7 months ago

We loved our weekend stay in Cape Charles and this rental was absolutely perfect for our family. Very well equipped home with lovely decor. Angela communicated every detail that we needed for a seamless check in. Would definitely recommend!

A comfortable living area features two armchairs and a spacious sofa arranged around a coffee table. Natural light filters through window treatments on a large window. A television is mounted above a fireplace, and framed nautical-themed artwork adorns the walls.

4.83 out of 5 average rating, 6 reviews

Live Like A King @ King's Creek Resort 2 bedroom

TerezkaRating, 5 stars45 months ago

Very clean and spacious. Friendly staff and the pools are fun for younger kids. Jamestown beach about a 20 min drive, (river not the ocean) is especially nice, warm water and lots of sand.