Vacation rentals with a pool in Cape Charles

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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

Condo in Williamsburg

4.95 out of 5 average rating, 129 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!

Aug 2 – 9

G$32,205 GYD per night

Guest favorite

Apartment in Cape Charles

4.98 out of 5 average rating, 182 reviews

Cape Charles Plantation Home “Nevill’s Nook Suite”

Sorry We do NOT cook Breakfast, We offer a SELF catered SUITE & INCLUDES a welcome package of champagne, wine, OJ, 1/2 & 1/2, butter Bagel, Eng. muffins, crm. cheese, yogurt, jam,coffee. Counter top convection oven *Lge. microwave *Keurig coffee * ENLARGE pics 2 read captions w/needed info Click show more We help guests stay safe by disinfecting frequent touch surfaces* light switches, doorknobs, cabinet knobs, remotes, etc. before arrival. Under kitchen & bathroom sinks are Disinfectant wipes

Jan 1 – 8

G$42,401 GYD per night

Guest favorite

Cottage in Irvington

4.99 out of 5 average rating, 149 reviews

Peaceful Haven

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. **Take advantage of our limited time SPECIAL PRICES**

Aug 27 – Sep 3

G$67,031 GYD per night

Guest favorite

Home in Cobbs Creek

4.99 out of 5 average rating, 133 reviews

Blue Heron WaterSide

Blue Heron Waterside awaits you...Private Hot Tub, 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?

Nov 24 – Dec 1

G$73,012 GYD per night

Guest favorite

Home in Irvington

5.0 out of 5 average rating, 101 reviews

Escape to magical wooded cottage with hot tub

Escape to our enchanting woodland haven where gothic architecture meets sun-drenched luxury on 2 acres of tranquility. Indulge in sunlit rooms, a private bathroom for each bedroom, and starlit hot tub nights. Sip local wines, savor oysters, and dive into the community pool. Explore markets, dine on sea-to-table delights, and relish our historic water town. Unwind at Tide's Inn, shop Kilmarnock, and cruise into sunset bliss. Your idyllic retreat awaits—book now for a soul-reviving escape!

Aug 25 – Sep 1

G$72,922 GYD per night

Guest favorite

Guest suite in Chesapeake

4.95 out of 5 average rating, 479 reviews

Sweet Suite!

Private attached MOTHER IN LAW suite (not the whole house) in a quiet neighborhood in the heart of Hampton Roads. We offer keyless entry and a private parking space, private pool and backyard grill area. All are welcome here, including pets. We ask that you tell us if you are bringing a pet(s) and I'll message you about the added pet fee. We are minutes away from all major attractions and less than 5 minutes from major highways. Our location gives you easy access to the Outer Banks.

Jan 3 – 10

G$23,784 GYD per night

Guest favorite

Home in Accomac

4.98 out of 5 average rating, 218 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.

Oct 14 – 21

G$32,741 GYD per night

Guest favorite

Farm stay in Cardinal

4.95 out of 5 average rating, 108 reviews

Wtrfrnt aptmnt w/pool/dock on private farm

Come enjoy all the outdoors has on offer at this secluded, waterfront estate. The spacious studio apartment is fully equipped for comfort. 12 acres of waterfront grounds to enjoy including great outdoor seating, fabulous bayside salt water pool. Fish, canoe and kayak right off the farms private dock. Grill and fire pit. Just 10 mins from the charming villages of Mathews and Gloucesters farm to table amenities. Great local food, music, history and shopping right on the bay!

Aug 3 – 10

G$35,885 GYD per night

Guest favorite

Tiny home in Cape Charles

4.98 out of 5 average rating, 273 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.

Jan 5 – 12

G$53,676 GYD per night

Guest favorite

Apartment in Virginia Beach

4.91 out of 5 average rating, 231 reviews

VB. Oceanfront/ Boardwalk,Beach, Pool, Balcony

Nestled on the desirable north end of the boardwalk, close to the area’s best attractions, the top restaurants and bars. Just steps to the boardwalk, beach and ocean. Enjoy a nice meal or a early morning cup of coffee on the balcony while enjoying a beautiful view of the Atlantic Ocean. Our studio includes a reserved parking space, saltwater pool, large BBQ deck area and a lawn on the beach. This small oceanfront complex is a great place for couples or a small family.

Jan 2 – 9

G$23,672 GYD per night

Guest favorite

Home in Cobbs Creek

4.9 out of 5 average rating, 117 reviews

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

"Now this is the life!" "A little piece of paradise!" "Livin the Dream!" "It doesn't get any better than this!" Just a few thoughts that may cross your mind when you come for a stay at The Cottage at Misti Cove. While the name may be simple, don't let that fool you, for so are the best things in life! Getting a taste of the simple life doesn't mean you have to sacrifice amenities. Here, you'll enjoy resort-like amenities without resort crowds.

Oct 4 – 11

G$45,650 GYD per night

Guest favorite

Cottage in Chesapeake

4.95 out of 5 average rating, 110 reviews

The Cottage @ Captain Genes - Secluded Waterfront

Get away from the crowds! Private, secluded upscale waterfront cottage on ~5 acres; pool/hot tub feet from the back door (hot tub open year round). Waterview from most rooms. Direct Chesapeake Bay access on property via dock / kayak launch. ~15 mins to downtown. Fish/crab, kayak, screened porch views, relax by the pool, fire pit or hot tub with a drink. Bring your boat - marina ~4 mi away - put-in there & tie-up at our pier!

Mar 11 – 18

G$57,422 GYD per night