Vacation rentals with a pool in Cape Charles

4.9 out of 5 average rating, 155 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!

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, 184 reviews

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

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.

4.99 out of 5 average rating, 116 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

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

4.9 out of 5 average rating, 10 reviews

A spacious living area features a large sectional couch, a coffee table, and a massage chair. Natural light floods the space through sliding glass doors, illuminating the wood flooring. The open layout connects to a kitchen and dining area, enhancing the communal feel.

Home in Cape Charles

Hot Tub - Massage Chair - Golf Cart - Beach Gear

Whether you are looking for some rest and relaxation, a home-base for the beach or water activities, or a place that comfortably allows you to bring your pets, you are sure to find your desired experience at Paws at the Beach. Open concept space with large glass doors and window to bring in natural light. Sunset room with multiple entertainment options, a massage chair in the living room and a Hot Tub. Four bedrooms that comfortably sleep 10. Rental includes access to a four-seater golf cart!

4.81 out of 5 average rating, 146 reviews

An Olympic-sized pool is visible, surrounded by numerous white lounge chairs with blue cushions. Tall trees rise in the background, providing shade alongside a clear sky. A lifebuoy hangs on the fence, and a serene atmosphere is evident around the pool area.

Bungalow in Horntown

Nature's retreat @ the Bug-a-Boo. Beaches nearby

We're inside a lovely gated campground community with full amenities @ the Club House: Wi-Fi, pool, fishing n crabbing, boat ramp, laundry, and bath houses. The Bug-a-Boo is a lovely single dwelling home. It is ADA handicap accessible. There's an outdoor fire pit and space for camping. We are 20 miles from Chincoteague National Wildlife Refuge with miles of protected beaches. This is a peaceful place for soul searching & social distancing. We are also 42 mi from Assateague Is. Nat. Seashore.

4.98 out of 5 average rating, 155 reviews

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

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?

4.95 out of 5 average rating, 115 reviews

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

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.

4.88 out of 5 average rating, 123 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

"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.

Apartment in Downtown Hampton

A charming gazebo is set beside a sparkling blue pool, surrounded by lush greenery and colorful flowers. The fenced area provides a sense of privacy, while the clear sky above creates a serene atmosphere. Sunlight reflects off the water's surface, enhancing the tranquil scene.

4.96 out of 5 average rating, 381 reviews

"Shangri-La", of Hampton, Virginia

2nd story 1200 square foot apartment with 2 BR's, Wi-Fi, microwave, fridge and bar with sink. Walk in glass enclosed shower & soaker tub. Private deck with gas grill down the spiral stairs below on ground level patio. Pool table in BnB. We share our pool with our BnB guests seasonally. Please inquire about pool availability if important to your booking. Local history, sites, nature and beaches abound. Security cameras surround the exterior of our home for our protection as well as yours!

4.98 out of 5 average rating, 267 reviews

A green pasture is featured, where a group of five horses graze peacefully. The background showcases a wooded area with tall trees, under a clear blue sky. A small shelter is visible in the distance, complementing the tranquil rural setting.

Home in Accomac

Heartsong Farmhouse , a nature lover's retreat.

Heartsong Farmhouse was completely renovated in 2019. Beautiful hardwood floors, brand new furniture, in a modern farmhouse style with a Boho vibe. The entire home is filled with beautiful natural light and the brick walls ensure a peaceful nights sleep. The yard is completely surrounded by a 15ft hedgerow of holly, magnolia and camellias, like walking into a secret garden. You will feel welcome from the moment you drive up. The Farmhouse is also beautifully decorated for the holidays.

4.98 out of 5 average rating, 138 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

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.

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, 317 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.

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Popular amenities for Cape Charles rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.67 out of 5 average rating, 21 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

Great Family Vacay! Dock, pool, fire pit, hot tub

KateRating, 5 stars3 weeks ago

Our family and friends had a lovely time in Cynthia's home. The setting is very pretty, the dock was a great place to fish and crab from and the beach offers another great hangout spot. The added bonus is that her home is just a 10-minute walk to a cute little restaurant in a marina with great oysters and cocktails.

4.86 out of 5 average rating, 44 reviews

Home in Coliseum Central

Coastal Retreat @ Coliseum| Pool, Bonus Rm, Gazebo

AshleyRating, 5 stars3 weeks ago

Erin's place was awesome! The home was gorgeous, the amenities, everything was well worth the price! Will definitely rebook!

4.96 out of 5 average rating, 69 reviews

A two-story waterfront home is showcased, featuring a spacious deck and a heated pool. Lush greenery lines the gravel pathway, and well-maintained landscaping surrounds the property. Clear blue skies reflect a serene atmosphere, while the water glimmers nearby, enhancing the tranquil setting.

Home in Lottsburg

Heron Harbor

DianaRating, 5 stars34 months ago

All I can say is WOW! We were blown away at the beauty of the home AND the view! Relaxing and peaceful. The pool was to die for and Kathleen was one of the best hosts I’ve ever had in all our air bnb travel!!! Will definitely return AND will check out her other properties in the future. Thank you to Kathleen and her staff/team!!

5 out of 5 average rating, 31 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 stars5 days ago

Fun place with great activities. Had a good time shooting pool playing darts area was very spacious.

4.8 out of 5 average rating, 80 reviews

An exterior deck surrounds an above-ground pool, featuring a bright blue surface. A lounge chair is positioned on the deck, while a yellow inflatable float is visible in the pool. A private, fenced-in yard is situated in the background.

Home in Newport News

Cute Remodeled Rancher w/ Fenced in Yard and pool

CamilleRating, 5 stars23 months ago

Davina was very attentive and was always checking in to make sure things were going well. She quickly responded to messages and was very helpful.

4.88 out of 5 average rating, 26 reviews

A two-story blue house with white trim and black shutters is showcased. A covered porch is featured at the front, surrounded by manicured hedges and a spacious lawn. Neighboring houses are visible in the background under a clear blue sky.

Home in Cape Charles

Sunshine Baydream Cape Charles

LorrieRating, 5 stars2 months 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.

4.93 out of 5 average rating, 81 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!

MarinaRating, 5 stars1 month ago

My family had the pleasure of renting this wonderful home, and I must say it exceeded all our expectations. The location was ideal, with both private and public beach access a short drive away. This home is located on a peaceful street, allowing for a good night’s rest. The house itself was clean, spacious, and comfortable, with a warm and inviting atmosphere that made it feel like a second home. The attention to detail in terms of amenities and extras was impressive. What truly made our experience stand out was the exceptional communication and hospitality provided by the host. Their instructions were clear, concise, and extremely helpful, making it easy for us to settle in and make the most of our short stay. Cape Charles is a charming town, with its quaint shops, restaurants, and theater all conveniently located on Mason Avenue, making it easy to explore and find everything we needed. Thank you Chris and Clare for sharing your home! Rating: 10/10 would rent again!

5 out of 5 average rating, 14 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

LogynRating, 5 stars1 month ago

Great accomodations for a big group. The house is huge and super interesting. While on the patio we watched the horses frolick, and were visited by a shy little dachshund, and a not-so-shy little farm cat. Beds were comfy. Lots of amenities like coffee pots, plenty of seating, a theater room, big Jacuzzi tub, and lots of bedrooms. Overall an extremely peaceful visit that I would stay at again.

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Condo rentals with a pool

A serene beach sunset is captured over gentle waves, with vibrant hues of orange and pink reflecting off the water. The shoreline features soft sand, inviting relaxation and peaceful moments by the sea.

Condo in Cape Charles

Rendezvous at the Bay

KellyRating, 5 stars3 weeks ago

We had a wonderful stay here! The condo was clean and well appointed, and the location couldn’t be beat! Carol was very responsive and helpful as well. We will be back for sure!

A screened balcony features a table surrounded by comfortable seating with blue and white cushions. Scenic water views of the marina are visible, highlighting the peaceful atmosphere offered by this outdoor space.

Condo in Crisfield

Walk to Main St: Condo w/ Pool Access in Crisfield

VictoriaRating, 5 stars1 month ago

Stunning accommodations! The view was beautiful. The home was spotless. If it were not for the scheduled events I had to attend in the area, I would have relaxed in the condo for the entire stay!