
Holiday 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.

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

The Rosé Retreat: Fireplace-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

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!

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?

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.

“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.

"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!

Gorgeous Vacation House
This is is the perfect home away from home! Enjoy cozy furnishings and modern amenities in this 3bed/2.5 bath house located in the vibrant city of Norfolk oceanview. The house is renovated with top notch material and artistic touch. The kitchen, living room, and private backyard with deck/patio swimming pool make it the ideal place to relax. Shopping, restaurants, and entertainment are all within minutes; plus onsite parking and self-check-in make this an ideal destination for travelers.

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.

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.

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.

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.
Popular amenities for Cape Charles rentals with a pool
House rentals with a pool

Waterfront panoramic point with pool

Waterfront Getaway w/ Pool, Firepit, Kayaks, Dock

Waterfront home-225' pier kayak firepit pool beach

14th & Hoos

Sunshine Baydream Cape Charles

Bay Creek (Pool!) Meets Historic Cape Charles!

East of the Sun Victorian - Private Pool

Waterfront 4BR | Pool & Peaceful Deltaville Views
Condo rentals with a pool

Rendezvous at the Bay Special Fall Rates

Updated Condo in Golf Community Featuring Access t

Spacious First Floor Condo in Golf Community With

Relaxing Condo in Golf Community With Access to Cl

Golf, Tennis, Pool, Beach - Bay Creek Caddy Shack

Ocean’s Eleven: A Steal of a Stay by the Bay

Bay Creek Blessed at The Fairways

Beautiful Condo in Golf Community Featuring Access
Other holiday rentals with a pool

Family Retreat, In-Ground Pool, plus Private Beach

Get away to the heart of Deltaville!

ShowTyme's Hampton Oasis

Chesapeake Bay Retreat Waterfront Indoor Pool

Waterfront Hot-Tub, Canoe & Firepit w/ Dock

Coastal Elegance Meets Small Town Charm

Spacious 4 bedrms, pool, close proximity to beach

Just two blocks away from private beach.
Quick stats about holiday rentals with a pool in Cape Charles

Total holiday rentals
Explore 40 holiday rentals in Cape Charles

Nightly prices starting at
Cape Charles holiday rentals start at $160Â NZD per night before taxes and fees

Verified guest reviews
Over 430 verified reviews to help you choose

Family-friendly holiday rentals
40 properties offer extra space and kid-friendly amenities

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
40 of Cape Charles holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Cape Charles rentals

4.9 Average rating
Cape Charles stays are highly rated by guests—averaging 4.9 out of 5!
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- House rentals Cape Charles
- Rentals with a patio Cape Charles
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- Condo rentals Cape Charles
- Family-friendly rentals Cape Charles
- Rentals with a fire pit Cape Charles
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- Cottage rentals Cape Charles
- Pet-friendly rentals Cape Charles
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- Apartment rentals Cape Charles
- Rentals with beach access Cape Charles
- Rentals with an accessible height toilet Cape Charles
- Rentals with pools Northampton County
- Rentals with pools Virginia
- Rentals with pools United States
- Chesapeake Bay
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Haven Beach
- Buckroe Beach and Park
- Jamestown Settlement
- Grandview Beach
- Bethel Beach
- Outlook Beach
- Kiptopeke Beach
- Golden Horseshoe Golf Club
- Virginia Beach National Golf Club
- Ocean Breeze Waterpark
- Norfolk Botanical Garden
- Chrysler Museum of Art
- James River Country Club
- Wilkins Beach
- Cape Charles Beachfront
- Red Wing Lake Golf Course
- Little Creek Beach
- Sarah Constant Beach Park




