Holiday rentals with a kayak in Cape Charles

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, 409 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.

4.8 out of 5 average rating, 166 reviews

A sunlit living area is surrounded by large windows offering expansive views of the water. Floral-patterned armchairs and a wooden coffee table provide comfortable seating. A small lamp and light-colored couch enhance the inviting space, while wooden flooring adds warmth.

Home in Onancock

Charming Waterfront Cottage on Cedar Creek

Come unwind in this comfy cottage right on the water. Situated on a 2 acre wooded lot, this colonial home offers peaceful seclusion and unbelievable water views from every room. This 1930’s cottage has modern updates and plenty of room, with two large bedrooms downstairs and a delightful bedroom suite upstairs. Restaurants and shopping await in the historic town of Onancock, only a 5-minute drive or an even quicker boat ride away. Private dock for swimming and fishing, two kayaks for guest use.

Place to stay in White Stone

The image captures a waterfront view of the lighthouse-style home set on a spacious lot. A private dock extends into the water, featuring a vibrant red umbrella providing shade over seating. Surrounding lush trees add to the serene outdoor setting.

5 out of 5 average rating, 106 reviews

Unique style, Waterfront Dock,Yard,Kayaks,SUP,King

Nestled on Little Oyster Creek in the charming small town of White Stone, is Beacon Bay Getaway. This lighthouse style home is situated on 3 private acres and has 3 water views: the Creek, the Chesapeake Bay and the Rappahannock River all which can be viewed from the wrap @ deck and top observation lookout. Enjoy the large yard with fire pit. Launch a kayak/SUP from our dock or bring your fishing rods to catch Croaker. Have fun catching blue crabs with our crab traps. Follow @beaconbaygetaway

Guest house in White Stone

A serene view of the water showcases the Rappahannock River and surrounding landscape. The horizon blends various shades of blue with green grass and patches of marshland, inviting a sense of tranquility. Wisps of clouds drift across the expansive sky.

5 out of 5 average rating, 280 reviews

Waterfront Guesthouse II on the Rappahannock

The “Beach House” is a guest cottage at Snug Harbor, a 2 acre private property overlooking the Rappahannock River and Chesapeake Bay. Perfect for a couple’s getaway, this well-appointed cottage has beautiful water views and includes access to our private beach & dock (with guest slip) with use of our paddle boards and kayaks. The cottage’s 1st floor features an open liv/din/kit area, full bath with large shower and a covered patio. The 2nd floor features a large loft bedroom with a queen bed.

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, 155 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, 164 reviews

A spacious deck extends towards the waterfront, surrounded by lush trees. Lounge chairs and seating areas are positioned for relaxing views of the calm water. A sunroom is visible to the right, offering additional indoor space. The overall setting invites outdoor leisure and tranquility.

Home in Cobbs Creek

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?

4.95 out of 5 average rating, 140 reviews

A Victorian cottage sits on a private island, surrounded by a serene lake. The green roof contrasts with the pastel exterior, while a footbridge leads to the shore. Lush grass and scattered trees create a peaceful landscape, with distant water views enhancing the setting.

Cottage in Hacksneck

Pretty Byrd Cottage, a Victorian Bayfront Getaway!

Imagine getting away from it all by crossing a footbridge to a private island with a Victorian cottage on your own private 3-acre lake! This property is a unique oasis that combines today's modern conveniences with the charm of elegant decor. Enter the front door and be taken in by the surrounding water views, and enjoy charming verandas and a balcony that overlook the lake and gardens surrounding the cottage. Guests can also enjoy the use of a private beach, fishing, kayaks and a paddleboat!

4.99 out of 5 average rating, 300 reviews

A wooden deck is shown overlooking a serene pond, framed by lush trees. A dining table with chairs is set for outdoor enjoyment, while soft natural light reflects off the water's surface, creating a peaceful ambiance.

Farm stay in Onancock

Private romantic pet friendly waterfront cottage

On Virginia’s beautiful Eastern Shore, The Birdhouse at Windfall Farm is the ultimate romantic getaway. Just steps from Pungoteague Creek (a short boat ride to the Chesapeake Bay)on one side and a picturesque large stocked pond on the other, The Birdhouse is a charming 1 bedroom hideaway, with abundant wildlife, walking trails on our 62 acre working farm, kayaking, fishing, crabbing, and stargazing, all amid Nature’s beauty. Be our guest for an unforgettable time on Virginia’s Eastern Shore!

4.99 out of 5 average rating, 101 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

4.91 out of 5 average rating, 206 reviews

A serene waterfront view features two kayaks resting on the grass under tall trees. A wooden dock extends into the water, surrounded by lush greenery and a clear blue sky. The area offers a peaceful setting for outdoor activities.

Farm stay in Cardinal

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.

4.94 out of 5 average rating, 122 reviews

The serene outdoor view captures a vibrant sunset over the water, framed by two waterfront pavilions. Silhouetted trees stand on either side, while the grassy expanse leads down to the beach, creating a peaceful atmosphere for relaxation.

Home in White Stone

Coastal Farmhouse Getaway

Take it easy at this unique and tranquil getaway. This fully renovated historic farmhouse sits on 4 acres on Windmill Point. Spend the day on the expansive yard or our private beach on the Rappahannock/Chesapeake Bay. Perfect for fishing, crabbing, kayaking or just relaxing! The waterfront pavilions and tiki bar are the perfect oasis to set up camp. The house was completely renovated historic home that offers unmatched comfort and charm. Enjoy water views from almost every room!

4.99 out of 5 average rating, 126 reviews

An inviting outdoor fire pit area features turquoise Adirondack chairs arranged around a stone fire ring. The charming blue farmhouse, with a metal roof, is partially shaded by trees, and sprawling green grass surrounds the property, enhancing the space for relaxation.

Home in White Stone

1891 Coastal Charmer: fully renovated farmhouse

Built in 1891, this farmhouse has been totally renovated by a professional designer. The Cottage is filled with coastal colors and accessories so it feels fun and updated but still retains the feeling of walking into a well loved family beach cottage. We are pet friendly as any beach cottage should be and love seeing our guests and their pets enjoying the cottage. Follow the cottage on social media @ BlueOysterCottage for more pictures, design ideas and local places to visit.

Popular amenities for kayak rentals in Cape Charles

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

5 out of 5 average rating, 48 reviews

A private sandy beach is featured alongside a 100-foot wooden dock extending into the water. Several seating options are arranged in the sand, offering a spot to relax while enjoying the scenic water views and gentle waves.

Home in Kilmarnock

Fall Weekends -Waterfront, Beach, HotTub, GameRoom

4.94 out of 5 average rating, 49 reviews

A beachfront cottage is situated on sandy terrain, framed by beach grass. The structure features a spacious porch overlooking the water, and the coastline extends toward a secluded jetty in the distance. Clear skies enhance the serene coastal atmosphere.

Home in Port Haywood

Anne's Beachfront Shangri-La

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, 29 reviews

Hot Tub - Massage Chair - Golf Cart - Beach Gear

A historic Victorian home is depicted with a red brick exterior and white trim. The large wrap-around porch features multiple columns, offering ample shaded seating space. The well-maintained lawn and surrounding greenery complement the home's stature, creating a welcoming facade.

4.95 out of 5 average rating, 40 reviews

Beach Front Home 5 Bedrooms 9 beds 2 kings 3 baths

4.96 out of 5 average rating, 94 reviews

A grand deck is viewed, featuring two white rocking chairs overlooking a vibrant sunset over the water. The sky is filled with shades of pink and orange, reflecting on the calm ocean surface. A dark wicker seating area is visible to the right.

Home in Buckroe Beach

Exclusive Beachfront Home w/ 180° Views & Hot Tub!

Home in Gloucester County

A wooden dock extends into the tranquil waters, bordered by smooth stones along the shore. Bright blue skies with scattered clouds enhance the natural beauty of the scene, inviting leisurely activities by the water.

4.96 out of 5 average rating, 78 reviews

York River | Chesapeake Bay Bliss: Fishing Retreat

4.96 out of 5 average rating, 163 reviews

The exterior of a single-story house is shown, featuring gray siding and black shutters on each window. A welcoming front door is adorned with a decorative wreath. Lush green grass surrounds the property, contributing to a serene outdoor environment.

Home in Deltaville

The Oyster House

5 out of 5 average rating, 14 reviews

The exterior of a spacious house displays a multi-level design with a sloping roof and large windows. Balconies adorn the upper levels, offering outdoor seating areas. Lush green trees surround the property, enhancing the natural appeal of the waterfront setting.

Home in Onemo

Spacious waterfront home, private dock

Cottage rentals with a kayak

4.88 out of 5 average rating, 58 reviews

Aerial view of a peaceful coastal retreat set on a spacious property surrounded by lush greenery and water. A sandy beach extends along the shoreline, complemented by tranquil marshlands and distant woodlands. The house is positioned towards the center, offering a sense of privacy amidst nature.

Cottage in Onancock

Peaceful 5 bedroom cottage on the Eastern Shore...

5 out of 5 average rating, 42 reviews

The waterfront cottage is set on a peninsula, surrounded by calm waters. Lush trees provide shade beside the house, while a stone patio is visible along the shoreline. The nearby dock is partially shown, offering access to the water for various activities.

Cottage in Topping

Locklies Innlet, A unique waterfront experience!

4.99 out of 5 average rating, 149 reviews

A bright sunroom features large windows that frame views of the Chesapeake Bay and surrounding natural landscape. Light-colored furnishings complemented by a wooden coffee table and a small plant enhance the airy feel. The serene atmosphere is accentuated by sunlight streaming through the glass.

Cottage in Bayview

Private Beach Access at The OV Beach House

4.94 out of 5 average rating, 176 reviews

A spacious deck offers breathtaking views of the water at sunset, with a stunning orange and pink sky. Four Adirondack chairs are arranged around a brown wicker coffee table, complemented by striped cushions. The serene water reflects the evening sky, creating a tranquil atmosphere.

Cottage in Onancock

A "True" Chesapeake Bay Waterfront Experience!

4.9 out of 5 average rating, 108 reviews

A serene sunset is captured over calm waters, with hues of orange and gold reflecting on the surface. Silhouettes of trees frame the scene, while a dock extends into the bay, creating a tranquil coastal atmosphere.

Cottage in Painter

Cottage by the bay (private peaceful surroundings)

5 out of 5 average rating, 100 reviews

A spacious cottage exterior is framed by vibrant green landscaping and a well-maintained lawn. American flags are displayed prominently, and a covered porch offers access to the home's entrance. Surrounding trees provide a natural backdrop, enhancing the peaceful setting.

Cottage in Kilmarnock

Cottage on Prentice Creek

4.93 out of 5 average rating, 104 reviews

An aerial view captures the farmhouse situated along the banks of Henry's Creek, surrounded by lush greenery. A dock extends into the water, providing access for outdoor activities. The rural landscape and nearby road are visible, emphasizing the peaceful setting.

Cottage in Kilmarnock

Creeks End Farmhouse

4.97 out of 5 average rating, 120 reviews

The exterior of a charming cottage is depicted, featuring a white wooden facade and a metal roof. A small stone patio with a bistro table and chairs sits at the entrance, surrounded by lush greenery and flowering plants. Two windows invite natural light into the space.

Cottage in Onancock

Little Cottage on the Creek

Other holiday rentals with a kayak

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, 33 reviews

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

4.92 out of 5 average rating, 24 reviews

An aerial view captures a serene cove on the Chesapeake Bay, showcasing the vacation home in the foreground. Surrounding landscapes include lush greenery and several residential properties along the water's edge, reflecting a peaceful and inviting atmosphere.

Home in White Stone

Relax Waterfront Hot Tub, Game Room, Frisbee Golf

4.96 out of 5 average rating, 71 reviews

A serene waterfront view is captured during sunset, with the sun dipping below the horizon. Reeds and grasses frame the foreground, while a private pier extends into the water, enhancing the peaceful atmosphere of the natural setting.

Home in Onemo

The Harbor House - Waterfront with private pier!

4.98 out of 5 average rating, 97 reviews

A rustic treehouse is elevated among tall trees, featuring a front porch with a railing and multiple windows. Below, a seating area is arranged with bright blue chairs and a black coffee table, surrounded by a natural forest setting.

Treehouse in Machipongo

The Waverly Treehouse

Holiday 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, 37 reviews

Parkside South, Cape Charles

4.95 out of 5 average rating, 55 reviews

A rustic cabin is surrounded by tall pine trees, featuring a spacious deck with multiple seating areas. An American flag is displayed, while a grill is positioned nearby. Large windows allow natural light into the interior, creating a welcoming exterior view.

Cabin in Onancock

Awesome private off grid cabin with creek view.

Place to stay in Machipongo

A rustic entrance showcases a wooden porch with a barrel and potted flowers. The doors are crafted from wood, featuring detailed carvings. Natural light filters through the surrounding greenery, enhancing the charm of this historic smokehouse converted into a unique accommodation.

5 out of 5 average rating, 85 reviews

Smokehouse on the Chesapeake Bay

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.