Vacation rentals with a kayak in Chesapeake

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, 68 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

4.95 out of 5 average rating, 123 reviews

The open-concept living space is shown, featuring a comfortable seating area with a queen sleeper sofa and two armchairs. A wood-burning fireplace is adjacent to the large TV, while a dining table is set for six. Wall-to-wall glass doors provide views of the outdoors.

Condo in Williamsburg

Kingsmill 2bd2ba Condo on Golf Course 9th Fairway!

This beautiful, 2B2Ba condo is 1400 sq.ft. in the exclusive Kingsmill neighborhood. This 1st floor unit has two master suites w/ king beds. One features a luxurious bathroom w/ a walk-in shower & dual shower heads, the other has a shower/tub combo as well as a private patio, stepping out onto the 9th Fairway. The open-concept living space has dining for 6, a queen sleeper sofa, a fully stocked kitchen, and an additional private patio. Golf course views from anywhere in the main living space!

4.99 out of 5 average rating, 177 reviews

A spacious waterfront home is showcased with a well-maintained lawn and blooming yellow flowers near the entrance. A large driveway leads to a brick facade, complemented by a garage. Clear blue skies can be seen in the background, enhancing the welcoming appearance of the property.

Home in Gloucester Point

York River Vacation Home

This lovely, spacious waterfront home is located on the York River in Gloucester County Virginia. It is the perfect get away to enjoy the relaxing sounds and sights of nature. The views are spectacular! Keep an eye out for osprey and dolphins as you enjoy watching the sunrise and set over the water. There is plenty to do! Relax in the salt water pool overlooking the water, bring a pole & fish and crab right off of the private dock, or venture out on the kayaks. 16 ton boat lift, Jet ski lifts.

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, 377 reviews

Private Guesthouse on Secluded Waterfront Farm

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 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.

4.95 out of 5 average rating, 139 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!

4.95 out of 5 average rating, 112 reviews

Three kayaks are displayed in a garage setting, featuring turquoise, orange, and blue colors. Each kayak is equipped with seating and storage areas. Light is present from a nearby window, creating a functional space for outdoor adventures.

Home in Knotts Island

Island Lotus Yoga & Spa

A nature lover’s dream! Waterfront, ample natural light, serene beauty, and privacy can be all yours at our charming ranch right on the bay. The bay faces east, giving you the most breathtaking views of the sunrise and moonrise. Relax in the spa, adventure on kayaks, and chill and grill over the fire-pit. You’ll also receive breakfast pastries & eggs, and a private yoga class. Check us out on insta @islandlotusyoga! PS we’re not actually an island. Reach us by driving through Virginia Beach!

4.9 out of 5 average rating, 134 reviews

The kitchen area features dark cabinetry and a modern design, with a large sink and stove. A microwave is mounted above the stove, and a mounted TV can be seen nearby. Marble-like countertops enhance the space, which is well-lit by natural light.

Camper/RV in Portsmouth

“Genevieve” the glam RV perfect for R & R!

Genevieve is a 30 foot stunning Design RV that is located in Parkview Portsmouth, Virginia. It provides a glamping experience and a comfortable stay while your on vacation. This beautiful modern RV provides an experience of unwinding, relaxation and style. Escape the stress of a busy schedule and experience this gem. We are situated on a private residence walking distance from the Elizabeth River. Olde Towne Portsmouth, scenic views & minutes away from restaurants, grocery shopping and more.

4.96 out of 5 average rating, 109 reviews

A panoramic view showcases a serene riverfront setting with lush green grass and a fenced backyard. A fire pit with seating is positioned in the foreground, while docks and a pier extend into the calm water, framed by trees and grasses along the shore.

Home in Portsmouth

The Captains Cottage KAYAK/FISH on Elizabeth River

“The Captains Cottage” offers a quiet private RIVERFRONT setting. Bring kayaks, paddle board, fish or just sit and bird watch! Enjoy the sunset at this 1500 sq. ft. quaint and cozy 2 story cottage. Hampton Roads has so much to offer, and the Portsmouth area is no exception! There’s a ‘historic downtown’ and a vibrant waterfront only 4 miles from the captains cottage! Need a break from the river? Virginia Beach OCEANFRONT is 30 minutes away! 6 guest limit. Guests of the 2 legged variety.

4.9 out of 5 average rating, 386 reviews

The living area is furnished with a spacious sectional couch and a coffee table, providing a comfortable space for relaxation. Natural light fills the room through a window adorned with sheer curtains. A dresser and a flat-screen TV complete the inviting layout.

Home in Virginia Beach

Pet friendly 3 bedroom beach house

Welcome to your perfect vacation getaway! This remodeled 3-bed, 2.5-bath ranch house is just a mile away from the ocean front. It's an ideal destination for families, friends & pets. Bedrooms are equipped with comfy beds. Pet-Friendly: The spacious backyard and deck are perfect for playtime and relaxation. Great location close to shopping and restaurants. You’ll feel right at home in this safe neighborhood. Please note: No parties. Only 9 people are allowed at the house at any time

Place to stay in Sandbridge

A blue kayak is shown gliding across calm waters during sunset. The sky is painted in soft shades of orange and pink, reflecting gently in the water's surface. The silhouette of a person in the kayak is visible, holding a paddle in a serene environment.

4.86 out of 5 average rating, 28 reviews

Back Bay Getaway Beach Retreat

You have found it! The perfect waterfront spot to enjoy the beauty of the Back Bay and Sandbridge oceanfront. Try one of our 5 kayaks (tandem, 3 singles and a fishing kayak), Jon boat, paddleboard and surfboard! Enjoy riding our bikes around the neighborhood or fishing off the porch. It's just a 5 minute walk to the beach to enjoy the sand and surf. And when you get back, our favorite spot is relaxing on the spacious porch with bay views at sunset to enjoy that peaceful, easy feeling!

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.

4.99 out of 5 average rating, 129 reviews

Private Beach Access at The OV Beach House

Here at the OV Beach House, you have your own private access to the beach and STUNNING water views of the Chesapeake Bay. The sunrises and sunsets are incredible! My husband and I renovated the interior of the house this past year. We poured all of our love (and sweat) designing and crafting a home away from home with you in mind!! You'll find the kitchen stocked with all of the essentials. Towels, soap, shampoo, and conditioner are all provided. Can accommodate up to 8 people.

Place to stay in Virginia Beach

A docking area is shown with a white boat attached to a floating dock. The water reflects the surrounding greenery and trees. In the background, a two-story home with a brown roof is visible, along with an open grassy space and a basketball hoop.

5 out of 5 average rating, 44 reviews

Peninsula Suite on the Lynnhaven River

Entire 2nd floor waterfront suite in shared home overlooks Lynnhaven river in residential neighborhood. Ideal launching pt for vacation adventures; 30 mins by boat to Chesapeake Bay, 10 mins by car to VA Bch Oceanfront, Chic’s Beach or 20 mins to Norfolk Airport. Kayaks, paddleboards, beach towels/cooler included. 2 bedroom/2-bath suite sleeps up to 5 & parking for 2 cars. Open concept kitchen to great room, 14-ft ceilings & wall-to-wall windows overlooks 600 sq ft deck & water.

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Houses

A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Popular amenities for Chesapeake kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

5 out of 5 average rating, 63 reviews

Home in Buckroe Beach

The Canary Island … Keep Calm and Fish On

5 out of 5 average rating, 16 reviews

A shaded deck area features two wooden rocking chairs with blue cushions and a small side table. Large windows are visible in the background, allowing natural light to brighten the space. The expansive wooden flooring complements the tranquil atmosphere.

Home in Corolla

Lazy Palm Carova 4x4 Beach

The exterior view of a charming two-story house is presented, showcasing a light-colored facade with green shutters. A covered front porch features seating and is surrounded by well-maintained landscaping, while a stone driveway leads to the entrance.

4.92 out of 5 average rating, 25 reviews

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

A deck overlooks the tranquil waterway, with picturesque views of grassy areas and the shoreline. Brightly colored chairs provide seating options, while a wooden railing frames the outdoor space. The clear blue sky enhances the inviting atmosphere.

4.67 out of 5 average rating, 3 reviews

Hot Tub - Massage Chair - Golf Cart - Beach Gear

4.78 out of 5 average rating, 36 reviews

The exterior of the duplex features a light grey façade with a striking blue front door. Steps lead up to the entrance, with one white chair positioned nearby. To the side, a tree provides shade, and the bay is visible in the background.

Home in Norfolk

Wil-O-Bay Getaway

5 out of 5 average rating, 3 reviews

A welcoming entrance features a light blue front door framed by two windows. A small porch, supported by wooden beams, is equipped with a railing. Potted plants line the side of the porch, while brick steps lead up to the entrance.

Home in Portsmouth

Escape to the water!

A charming brick duplex is showcased with a well-maintained front porch and white railings. American flags are displayed. Lush greenery is visible along the base of the porch, complementing the inviting entrance. The neighboring structure is painted in a vibrant green.

5 out of 5 average rating, 3 reviews

Sol Mate: Bayfront Bliss – Sunrise to Sunset

5 out of 5 average rating, 69 reviews

The exterior of a brick waterfront home is presented, featuring a multi-level deck with railing and several steps leading down to a stone shoreline. Lush greenery borders the property, and a large expanse of grass is visible, enhancing the outdoor space.

Home in Surry

Waterfront on the James 4,100 SF near Williamsburg

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Cottage rentals with a kayak

4.96 out of 5 average rating, 47 reviews

A kayaker is seen paddling in calm waters, surrounded by a vast expanse and a sky filled with white, fluffy clouds. Two bright green kayaks are visible in the foreground, emphasizing the tranquil outdoor setting.

Cottage in Surry

Riverfront Oasis | Kayaks, Private Beach, & More

The beach cottage presents a two-story blue exterior, framed by white trim and features. An American flag is displayed prominently on a pole. The surrounding sandy landscape adds to the coastal ambiance, with a few outdoor chairs visible on the front porch.

5 out of 5 average rating, 18 reviews

Beachfront Cottage

A charming outdoor area features a firepit surrounded by stone seating. A wooden deck leads to a screened porch, where a figure is visible. Lush greenery and a covered tiki bar can be seen in the background, providing a relaxing atmosphere.

5 out of 5 average rating, 6 reviews

Captain’s Cottage at Willoughby Spit Beach

A view of the sandy beach and the river from the sunporch shows children playing near the water's edge. The private pier extends into the river, with kayaks stacked nearby. A black grill and a white bench are visible in the garden area.

Cottage in Surry

4.78 out of 5 average rating, 9 reviews

James River Beach Retreat - Private Beach & Pier

4.8 out of 5 average rating, 138 reviews

Beach Cottage - On Beach with Wrap Around Porch

4.79 out of 5 average rating, 118 reviews

Beach Cottage-Bay Views Loft on Beach & Veranda