Holiday rentals with a pool in Northampton County

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.

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.

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.

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!

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!

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.

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.

Coastal Soul | Spacious Family Beach Retreat

Bring family and friends to Coastal Soul, a spacious, updated home just steps from a private beach and a short walk to the public beach, shopping, and dining. Guests enjoy complimentary access to the community pool, tennis and pickleball courts, and a second private beach. This 4-bedroom, 3-bath retreat is well equipped for extended family stays and features an outdoor shower, game room, and comfortable outdoor living space—everything you need for a relaxing Cape Charles getaway.

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.

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.

Oyster Point Cabin

Go glamping in one of our Deluxe Cabins. There is enough space for the whole gang featuring a queen bedroom, a room with a twin over full bunk bed, and a sleeper sofa in the living room. The full kitchen comes with a cooktop and the essentials for dining. Relax on the screened porch and enjoy time together. A fire ring and a picnic table are included with most Deluxe Cabins. You will enjoy our private beach, onsite restaurant, and a private resort pool!

NiceBay Getaway Coastal Retreat in Bay Creek

Discover your perfect coastal getaway in Bay Creek, located in the charming seaside town of Cape Charles, VA. This beautifully situated home offers the ideal blend of relaxation and adventure, just minutes from a private beach, resort-style pools, and premier golf courses.