Vacation rentals with a pool in Northampton County

5.0 out of 5 average rating, 29 reviews

New Build-1st Floor King Suite &Kid Friendly Loft!

Escape to your brand-new coastal beach retreat! This home features seaside decor and a serene atmosphere, blending comfort and elegance. Your kitchen is a chef's dream with a gas stove, granite countertops, and a bar area with a wine and drink fridge. You'll love the private beachfront access and community pool. Play pickleball or tennis, then relax with a drink on the front porch or play cards on the screened-in back porch. Shops and restaurants are just a 5-minute drive or golf cart ride away.

The exterior of a vibrant orange house is shown, featuring multiple balconies and a spacious patio area with outdoor seating. A hot tub is visible on the patio, surrounded by landscaping. Nearby, additional homes can be seen, highlighting the neighborhood's character and layout.

4.88 out of 5 average rating, 41 reviews

New Hot Tub~1st Floor King Bed~Fire Pit~Bunk Room!

Escape to where Bay Views Meet Coastal Comfort Welcome to your home away from home in one of America’s happiest seaside towns. Nestled within a peaceful, gated community, the Majestic Mermaid is more than just a house, it’s the backdrop for your family’s favorite memories. Whether you’re here to watch the legendary Cape Charles sunsets from your third-story deck, cruise the charming streets in a golf cart, or walk just a few steps to the sand, this is the coastal retreat you’ve been looking for.

Home in Exmore

Bayfront Retreat w/ Game Room + Outdoor Pool!

An excursion to the Eastern Shore of Virginia is your perfect chance to unwind and enjoy a waterside getaway! Settled on 3 acres in Exmore, this 4-bedroom, 3-bathroom house gives you the solitude you need to relax with loved ones. Spend time soaking in the pool, playing foosball in the game room, kayaking on the bay, or simply watching the sunset on the dock. Plus, this abode offers the chance to explore beaches, farmers’ markets, and local shops in the nearby towns of Cape Charles and Onancock.

4.77 out of 5 average rating, 35 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.

4.93 out of 5 average rating, 61 reviews

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!

A cozy living area features two white sofas with dark blue cushions, facing a wooden coffee table. A wall-mounted artwork with floral tones adds color above a simple fireplace. Natural light fills the space, while a sliding door provides access to another room.

5.0 out of 5 average rating, 14 reviews

Shore Is Fun: Private Beach, Pool & Bunk Room!

Tucked away on a private drive, this spacious getaway offers breathtaking sunsets, exclusive beach access, and all the comforts of home. Just steps away, enjoy a swim in the community pool or take a short stroll to the private beach. Nearby Cape Charles has something for everyone, including miniature golf, pickleball and tennis courts, boutiques, restaurants, and confectionaries. Whether you’re seeking beach days or small-town charm, this rental is the ideal place to make lasting memories.

4.92 out of 5 average rating, 12 reviews

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, a Resort Condo in Cape Charles

A luxurious 1550 sq foot 2nd floor resort condo that offers comfort and tranquility in a private beach and country club setting. Imagine your most prefect beach vacation: sun, sand, morning walks, pool, time with the family, relaxing, exploring nature, great restaurants, golf cart rides around town, romantic sunset walks, and evening ice cream. Experience these things and so much more when you stay at Rendezvous in Cape Charles on the Virginia Eastern Shore. Come experience it for yourself!

A single-story house is presented with a welcoming exterior, featuring a covered porch and large front windows. The well-maintained yard includes neatly trimmed bushes and a paved walkway leading to the entrance. A bright blue sky with scattered clouds complements the serene setting.

4.93 out of 5 average rating, 86 reviews

Bay Creek (Pool!) Meets Historic Cape Charles!

New outdoor shower! Best of both worlds - first house off the historic district, but part of the gated Bay Creek with access to exclusive amenities including pool, tennis, and PRIVATE beaches! Single floor living with handicap access from the two car garage. TONS of space! Great front porch for lounging. Walkable to both public and private beaches. Closest house in town to mini golf, Cape Charles Welcome Center (includes a train museum - always a hit with the kids) and the brewery!

An aerial view captures a vibrant Victorian-style home featuring teal and yellow siding. A striped awning provides shade over the front porch, where two chairs sit beside potted plants. Neatly trimmed hedges line the walkways, and a neighboring home adds to the charming streetscape.

5.0 out of 5 average rating, 49 reviews

East of the Sun Victorian - Private Pool

Back after a 2-year hiatus! East of the Sun is a fully-restored ca. 1890 Victorian (3 en-suites) with a large screen porch and private, 12' round plunge pool. Our place is ideally suited for 3 couples or families with older children. We welcome younger children as long as parents confirm they're okay with 3 floors/2 sets of stairs, antiques, and a pool. We have a strict limit of 6 guests (however, children under 2-years do not count). We offer a 3-night minimum both low and high season.

4.71 out of 5 average rating, 83 reviews

Oysterman's Pearl Golf Cart Included

Luxury Home with Golf cart included! Spacious beach house with a luxury touches. Great place to escape and enjoy the private amenities of Bay Creek while being a short walk or golf cart ride to downtown Cape Charles. Relax on the screened in porch or enjoy the breeze from the crows nest on the 3rd floor. This home has everything you need to have a relaxing beach vacation with the comforts of feeling at home. Bay Creek HOA pool, tennis courts, and YMCA pool and gym passes included.

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.

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.

4.98 out of 5 average rating, 360 reviews

An outdoor space features a wooden deck surrounding a V-bottom saltwater pool. Sun loungers and patio tables are arranged for relaxation. In the background, a play structure and swing set can be seen among lush greenery, enhancing the family-friendly atmosphere.

4.79 out of 5 average rating, 84 reviews

Family Retreat, In-Ground Pool, plus Private Beach

5 bedrooms and 3 full baths plus an outdoor shower. Sleeps 10 adults. 1/2 mile walk, bike, or drive to our private community beach. Kiptopeke Park, Cape Charles, VA Beach, and Williamsburg. Ideal family get-a-way. Modern and private. Please note: Parties, loud music, or lots of screaming in the yard, are not allowed or tolerated. This is a peaceful and quiet community and we need you to honor that. Otherwise, please book another home for your vacation. Thank you.