Vacation rentals with a pool in Cape Charles

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Cape Charles

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

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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, 148 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

Superhost

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

4.63 out of 5 average rating, 19 reviews

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

Peaceful get away on the sandy shores of the Corrotoman "Rivah" full of water activities. Fast WiFi, private saltwater pool(open May-Sept), kayaks, canoe, private sand beach, hot tub, full kitchen, pool table, firepit, deck with grill, outdoor dining tables. Deep water dock bring or rent a boat. Yankee Point Marina offers boat rentals, live music & restaurant w/in walking distance! Ride free ferry into Kilmarnock for shopping, restaurants & wineries. Kayak w/dolphins, watch Rock fish from dock

Top guest favorite

Home in Gloucester Point

4.99 out of 5 average rating, 177 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, 112 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

Guest favorite

Home in Cobbs Creek

4.98 out of 5 average rating, 152 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

4.95 out of 5 average rating, 112 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

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

4.89 out of 5 average rating, 116 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 from the patio. 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 grill or visit one of our charming local restaurants. This is the perfect location to relax and reset, either solo or with someone special.

Top guest favorite

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.

Apartment in Hampton

4.96 out of 5 average rating, 378 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!

Top guest favorite

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

4.98 out of 5 average rating, 257 reviews

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.

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

4.99 out of 5 average rating, 136 reviews

Escape to magical wooded cottage with hot tub

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.

Superhost

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.

Vacation home in Gloucester County

4.79 out of 5 average rating, 42 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.

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, 307 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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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 Point"-Luxury-Waterfront-Pool-Dock-Fire pit-

5 out of 5 average rating, 8 reviews4 months ago

We enjoyed a wonderful stay over Thanksgiving with our family. The home was as advertised - the location is beautiful, even in the colder months. The large living room makes it easy to enjoy time together, and there is plenty of room for guests to spread out in bedrooms and smaller spaces.

Home in Weems

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

Waterfront Getaway w/ Pool, Firepit, Kayaks, Dock

5 out of 5 average rating, 3 reviews5 months ago

Wow!! What an amazing stay! We spent the weekend here with some friends from church and three babies! The place was great for entertaining everyone and the babies had a blast hanging out in the open space of the kitchen! The kitchen was well stocked with everything we needed. The house was beautifully maintained and had super cute decor! We enjoyed the amazing views from the house and deck overlooking the water! Amy’s suggestion book was super helpful for finding niche spots to explore downtown! She was quick to respond to any questions we had throughout our stay! Hoping we can stay here again soon!!!

Home in White Stone

What guests are saying

Inn at Sandy Creek

5 out of 5 average rating, 23 reviews8 months ago

First I think Donna 100% underrated the place. My Grandson loved all the animals that are free to see and pet. She evens provides feed for the animals. The Pool was nice and private and clean. The loft was clean and stocked with everything you will need for a stay. We used the kitchen to cook breakfast, lunch and dinner. Had enough utensils for all. She undersold the grilling. Had a large gas grill with a flat grill attached. Charcoal grill and a gas smoker by pool. You have a private entrance from the garage and she has plenty of tools for a quick fix. Donna was great and every time see saw you she checked to make sure everything was ok. She even put snacks and drinks in fridge for us. She even paid attention that we had a child and got juice for him. DoorDash does deliver to house if you don’t feel like cooking.Patriot Grill and Sweet Tooth was our favorite. Wish I got a flight of beers at the Brewery because the one I got was just ok. Donna does adopt animals so we got so vegetable

Loft in James Store

What guests are saying

Northern Neck Waterfront

4.8 out of 5 average rating, 10 reviews8 months ago

Our stay at Brian's Place Aug 17-24, 2024 was just what we needed. The area was quiet, peaceful, and restful. The pool was used everyday; we skimmed it daily and it easily stayed clean for the whole week. My husband and sons crabbed everyday from the docks; lots of crabs caught for the week. The house was quite comfortable. The kitchen was, by far, the best equipped for a vacation rental; felt like I was right at home. The beds were quite comfortable. The whole house had lots of light. There was no TV but the internet (Starlink) was blazing fast so we brought our own devices including a TV and a Firestick...voila...access to TV! I very much appreciated the house being pet friendly as we always want to travel with our sweet pup. Restaurants we visited were Great Fortune Chinese (Kilmarnock), Horn Harbor (3 - 4 minutes from the house!) , Los Patrones (Burgess), and Crazy Crab (Reedville) ---- all with varying price points, all we would gladly re-visit. Great week, highly recommend!

Vacation home in Burgess

What guests are saying

East of the Sun Victorian - Private Pool

5 out of 5 average rating, 23 reviews32 months ago

We love East of the Sun! It’s well-appointed to create a better vacation experience - great linens, well-stocked kitchen (that you can actually cook in!), and that amazing plunge pool. Our adult kids flip a coin for the guest cottage and its bonus privacy. Cynthia and Tucker are always just a text away, and they know all the ins and outs of Cape Charles to make the visit special. After many weekend trips to town, we found this lovely home as it debuted early during the pandemic - and this was our third summer for a weeks stay since then. We love this home - it’s so much more than a house.

Home in Cape Charles

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

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