Vacation rentals with a kayak in Northampton County

Vacation home in Cape Charles

A charming bungalow is embraced by lush greenery and colorful flowers, featuring a welcoming front porch with seating. A palm tree adds a tropical touch, while the pathway leads to the entrance, inviting guests to explore the comforts within.

5 out of 5 average rating, 71 reviews

Down By The Bay - Cape Charles -1st Floor Primary

🏖Come visit this updated 1930's bungalow. 5 blks to restaurants, shops & beach end of our street 🏠 First Floor master, w/ large bunky upstairs sleeps up to 8 (+ pack and play & air mattress) 🛶 Take stroll/ride to the beach, hose off in outdoor shower, grill on patio & cozy up to a fire. Or relax in the clawfoot tub! 💻 Staying the week & work remote? Work space ready for you! Wifi/Netflix. Updated kitchen & laundry space in your home away from home! 🐶 Dogs <50lbs (2 max) ☀️ Sunday-Sunday June -Aug

Farm stay in Cape Charles

The spacious kitchen features a large island with seating for six, modern appliances, and ample counter space. A bright window above the sink offers views of the surrounding landscape, while soft lighting complements the contemporary design. Light wood flooring enhances the welcoming atmosphere.

5 out of 5 average rating, 392 reviews

Guesthouse at Vessel Farm & Winery, Waterfront

Just 5 miles from Cape Charles and 30 minutes from Virginia Beach, our contemporary Guesthouse gives you the peace and solitude characteristic of the Eastern Shore along with the convenience of being close to town. Our twenty acre waterfront farm, home to both a Vineyard and an Oyster Farm, has plenty of nearby walking or biking and a dock on a secluded arm of the Chesapeake Bay. Our farm is perfect for solo travelers, couples or small families looking for a memorable trip to the Eastern Shore.

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.

4.89 out of 5 average rating, 18 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 classic brick duplex features a large front porch supported by white columns. A ceiling fan hangs in the shaded area, while steps lead up to the entrance. Lush greenery lines the porch, and a clear blue sky complements the welcoming design.

4.94 out of 5 average rating, 149 reviews

Harbor View- (Sun - Sun rental June- Aug.)

Harbor View is an early 1900's brick duplex with high ceilings, transom windows, and crown molding. Best of all, this home is located in a quiet neighborhood just one block from the beach and two blocks from Mason Ave. where you can find unique shops, restaurants and other amenities. It's an easy walk to the pier for a magnificent sunset, or to Brown Dog's for homemade ice cream. We invite you to enjoy our comfortable home, and explore the quiet ambience of a historic beach town vacation!

4.98 out of 5 average rating, 85 reviews

A serene outdoor area is surrounded by tall trees, providing shade and tranquility. Four turquoise chairs are arranged around a central table, enhancing the inviting space for gatherings. A glimpse of the water can be seen in the background, offering a calming natural view.

Treehouse in Machipongo

The Waverly Treehouse

Reconnect with nature and sway with the trees in this rustic treehouse nestled away in the woods with a gorgeous view of Hungar's creek. Enjoy the view from the front porch or while relaxing around the fire pit. Visit the adorable beach town of Cape Charles, complete with a beautiful beach, brewery, distillery and plenty of restaurant options, or stop by the nearby vineyard for some local wine. Usage of dock, kayaks, grill, and fire pit all included. Beach towels and cooler also provided.

4.97 out of 5 average rating, 120 reviews

Four black Adirondack chairs are positioned in a grassy area facing a tranquil body of water. Lush green reeds frame the water's edge, with a blue sky and scattered clouds above. A small dock is visible in the distance, adding to the serene setting.

Home in Belle Haven

Bay Breeze Home on private waterfront

On Virginia's beautiful Eastern Shore, the Bay Breeze Home on Occohannock Creek is the ultimate getaway for two or a large family desiring outside adventures. This 1970's spacious home has plenty of room. Experience the water with our three kayaks or family canoe and watch the abundant wildlife. Right outside your door, you may see Ospreys, Great Blue Herons, Eagles, wild ducks, porpoises, deer, geese, otters, & more. Be our guest and forget your worries in this spacious and serene spot.

5 out of 5 average rating, 88 reviews

A two-story beach house stands amidst lush greenery, featuring a spacious wrap-around porch with multiple seating areas. Large windows allow for ample natural light, while the light-colored exterior complements the serene surroundings. The property is partially surrounded by trees, enhancing privacy.

Home in Machipongo

Private Country Beach Retreat

Welcome to Mason Jar Retreats Beach Home. Our home is a private beachfront property with the best of both country and beach living. Located on 6 acres on a private road with only a few steps to take to your private oasis on the Chesapeake Bay. Enjoy sunsets from the beautiful porches while taking in the natural surroundings. Our home is only three miles from a vineyard and winery and 20 minutes to Cape Charles with lots of shopping and dining in a quaint beach town. *LGBTQ+Friendly Home

Vacation home in Cape Charles

The exterior features a welcoming front porch, accessed by brick steps. Two mint green doors lead to separate entrances, with elegant lanterns providing ambient light. A white railing frames the porch, complemented by dark mulch and neatly planted greenery, creating an inviting approach.

4.97 out of 5 average rating, 32 reviews

Parkside South, Cape Charles

Parkside offers the perfect getaway for families and/or friends! Conveniently located next to Central Park, 2 blocks from the beach and the main street (Mason Ave). In peak summer we have full weeks available (Sun-Sun) or partial (Sun-Thurs). We open corresponding weekends once the Sun-Thurs books. Check our calendar or social media for weekend openings! We recommend a max of 4 adults or 2 adults and 3 (possibly 4) children, depending on their ages. Our family of 5 stays comfortably!

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.

4.98 out of 5 average rating, 327 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.

A charming two-story house features pastel-colored shutters and a welcoming front porch with white pillars. Lush greenery and blooming flowers surround the property, while the stone pathway leads to the entrance. A well-maintained yard enhances the inviting exterior.

4.94 out of 5 average rating, 31 reviews

Seaville. Cozy 3bed/3bath home. Stunning backyard

The whole group will be comfortable in this spacious and unique space. Fully stocked large spacious kitchen/dining that will make family gatherings a breeze. Big living area with plenty of seating, large screen TV and dozens of games. 3 bedrooms and 3 full baths. Large front porch and a backyard described as an “oasis” by past guests. Outdoor “she shed” fun room with 65” TV, split HVAC system. Storage side has bikes, cornhole, beach chairs and much more beach stuff.

An inviting front porch features a pastel blue-green siding with a vibrant coral door. Two white adirondack chairs sit beside a small potted plant, while a pink swing offers a warm touch, enhancing the welcoming entrance to the home.

4.93 out of 5 average rating, 70 reviews

The Peach House: close to the shops, beach + park

READY TO BOOK FOR AWESOME FALL STAYS! Loads of historic charm - between the park, downtown & the beach • Contact us to rent our 4-seater golf cart more affordably than in town! • Newly remodeled upstairs bath • Two screened porches, outdoor shower, front porch • Kayak/Paddleboard/Life vests included • Two king bedrooms & a bunk room for four w/ smart TV & NES Classic Please read through our totally honest disclaimer below!

An aerial view captures the single-story ranch home positioned across from the beach. Sandy shores extend alongside the calm water, while charming residential streets and greenery surround the property, highlighting its prime coastal location.