Vacation rentals with a kayak in Chesapeake

4.85 out of 5 average rating, 134 reviews

The image presents a large outdoor pool surrounded by a deck, sun loungers, and a gazebo. Lush greenery lines the background, complementing the serene waters of Back Bay visible in the distance under a bright blue sky with scattered clouds.

Home in Sandbridge

Stunning Views of Back Bay & Seconds to the Beach

Be our guest and enjoy some of the most spectacular views in all of Virginia Beach. Lounge in the pool and watch the sun set over Back Bay or enjoy exploring Back Bay with fishing and site seeing. With the beach being a block away, you can get your feet wet with surfing or snorkeling or simply relax on the beach with your favorite beverage. Little Island Park, Back Bay Wildlife Refuge & The Baja are just a few minutes away as well. This 6 bedroom home, with 11 beds will be the perfect get away.

4.95 out of 5 average rating, 132 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, 198 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, 400 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 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, 151 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!

Guesthouse in Virginia Beach

A deck is furnished with four blue Adirondack chairs, facing a scenic waterfront view. Lush greenery and a pond are visible in the background, with trees framing the landscape under a clear blue sky. The outdoor space offers a tranquil setting for relaxation.

4.93 out of 5 average rating, 41 reviews

The Sportman's Lodge

The Sportsman’s Lodge is a rustic and relaxing modern getaway with all the conveniences you are accustomed to but surrounded by the gorgeous Back Bay Wildlife Refuge. Enjoy the relaxing countryside at this waterfront property, while still being only a short drive away from Sand Bridge Beach. If you are looking to get away from the standard Virginia Beach Boardwalk tourist experience and get back to nature, this is the place for you. Free kayaking to Back Bay, access to fishing and crabbing.

4.87 out of 5 average rating, 157 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.

4.91 out of 5 average rating, 420 reviews

The kitchen features modern appliances, including a stainless steel refrigerator and an oven with a cooktop. Rich wooden cabinets provide ample storage, while a large granite countertop offers space for meal preparation. A circular skylight allows natural light to enhance the inviting atmosphere.

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

A view from a deck showcases an open area leading to the beach, with a decorative arrangement of flowering plants in white planters. An American flag stands proudly in the background, while the calm waters of the bay reflect the clear blue sky.

4.91 out of 5 average rating, 190 reviews

Poseidon - Beach Carriage House - 120 Years Old

Your Bayfront Vacation Spot. If you want to spend good family time, a romantic getaway, or live in a cool place while working here, this is your spot. Our neighborhood is located on the shores of the historic Chesapeake Bay. Step onto our beach and you will see that we are the perfect spot for sunrises/sunsets, fishing/crabbing, sunbathing, grilling & hot tubbing. The rental isnt on the beach-side of the property so walk around the building to the beach which is only 30 feet away.

4.95 out of 5 average rating, 123 reviews

A sunset casts warm hues over the calm waters of the bay, with silhouettes of a shaded gazebo and a hammock. Weathered pilings and a single bird in flight can be seen against the vibrant sky, enhancing the tranquil atmosphere.

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 local fresh 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!

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, 143 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.

Cottage in Gloucester Point

A serene view of a wooden dock extending into the calm waters of Sarah's Creek, surrounded by trees. Two kayaks, one green and one blue, are positioned on the grassy shore, with a charming cottage visible in the background.

4.94 out of 5 average rating, 278 reviews

The Cottage on Sarah's Creek

Nestled on the waters of Sarah's Creek, this cozy cottage is just a short drive from historic Williamsburg and Yorktown. Fully furnished with a new kitchen, dining area, 1 bedroom, 1 bathroom, and a large loft with a queen bed and a pool table. Whether spending your days relaxing on the beach, exploring historic sights, or taking a tour of a local vineyard, you can look forward to the quiet comfort this cottage has to offer during your stay.

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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, 72 reviews

Home in Buckroe Beach

The Canary Island … Keep Calm and Fish On

4.93 out of 5 average rating, 88 reviews

A single-story house is framed by vibrant flowering bushes and trees. A red flag is prominently displayed near the entrance. The front yard is spacious with grassy areas, and a paved driveway leads to a single-car garage.

Home in Newport News

1-Bedroom Home Near Christopher Newport University

5 out of 5 average rating, 12 reviews

The blue, three-story house is viewed from the side, showcasing multiple windows with white trim. A well-maintained path lined with stones leads to the entrance. Two individuals walk towards the house, and a cart is positioned neatly beside plants in the foreground.

Home in Norfolk

Beachfront Getaway, pet friendly

A private pool is surrounded by comfortable lounge chairs with decorative cushions. A vibrant pink flamingo float is situated in the clear water. The space is framed by lush trees, and a two-story house is visible in the background.

4.92 out of 5 average rating, 13 reviews

Stunning Views | Kayaks | Pet-Friendly | Sunsets

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, 67 reviews

York River | Chesapeake Bay Bliss: Fishing Retreat

5 out of 5 average rating, 15 reviews

A bright and airy living space showcases large windows framing views of lush greenery. A child is seen setting up a chess board on a central table, while comfortable seating options invite relaxation in the cozy atmosphere.

Home in Spring Grove

Analog Private Beach on 10 Acres

A spacious dining area features a large wooden table surrounded by several wooden chairs. Arched windows allow natural light to flood in, providing views of the lush greenery outside. A decorative ceiling fixture with multiple bulbs adds a warm touch to the space.

5 out of 5 average rating, 12 reviews

Eden Lake House Cape Charles

5 out of 5 average rating, 12 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!

Cottage rentals with a kayak

A wooden pier extends into calm waters, leading toward a distant marina. A sandy beach lies in the foreground, inviting relaxation. Soft clouds float above a clear blue sky, creating a serene atmosphere that emphasizes the natural beauty of the waterfront setting.

Cottage in Surry

4.78 out of 5 average rating, 9 reviews

James River Beach Retreat - Private Beach & Pier

4.95 out of 5 average rating, 57 reviews

The cottage is positioned atop a riverbank, surrounded by greenery. Stairs lead down to a sandy beach along the James River. The home’s exterior features a simple design, and the area displays a mixture of natural vegetation and the beach below.

Cottage in Surry

Riverfront Oasis | Kayaks, Private Beach, & More

A serene beach view captures the sun rising just above the horizon, casting warm orange and pink hues across the sky. Gentle waves ripple onto the shore, creating a soft white foam. A wooden pier extends into the water, framing the tranquil scene.

4.79 out of 5 average rating, 153 reviews

Historical Cottage - On Beach Wrap Around Porch

A vibrant sunset casts warm hues over the Chesapeake Bay, while silhouettes of people are seen along the sandy beach. The sun descends slowly toward the horizon, with soft clouds reflecting shades of orange and pink, creating a serene coastal view.

4.78 out of 5 average rating, 129 reviews

Beach Cottage-Bay Views Loft on Beach & Veranda

5 out of 5 average rating, 27 reviews

A serene view from a wooden dock extends over calm water at dusk. Two Adirondack chairs are positioned to face the horizon, where soft orange light meets a gradient of deep blue sky, reflecting on the water's surface.

Cottage in Sandbridge

Sunsets | Beach + Pool + Pickleball | Pet Friendly

4.93 out of 5 average rating, 56 reviews

A private dock extends over calm waters, reflecting hues of blue and orange from the setting sun. The sky is adorned with soft clouds, creating a serene backdrop for an inviting sunset view over the Currituck Sound.

Cottage in Coinjock

WaterView | Private Dock | Kayaks | Chef's Kitchen

A well-kept garden is framed by flowering hydrangeas in shades of pink and blue. The cottage features large windows with colorful accents, providing a view of the water and nearby pier. Lush greenery complements the serene waterfront setting.

Cottage in Surry

5 out of 5 average rating, 4 reviews

James River Beach Cottage - Private Beach & Pier!

Other vacation rentals with a kayak

4.99 out of 5 average rating, 79 reviews

A spacious pool area is highlighted, featuring a clear blue pool surrounded by a decorative fence. Brightly colored lounge chairs are positioned on the patio, with a shaded gazebo and lush greenery visible in the background.

Home in Sandbridge

The Golden Hour Pool is Open until October 5th!

4.83 out of 5 average rating, 29 reviews

Baydream Believer: Luxurious 7BR Oasis w Pool&Pier

The exterior view of a two-story house is showcased, featuring wood siding and a staircase leading to the upper deck. A United States flag waves proudly from a flagpole. Lush greenery surrounds the property, creating a natural setting.

5 out of 5 average rating, 24 reviews

Lazy Palm Carova 4x4 Beach

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.

4.94 out of 5 average rating, 31 reviews

FREE Luxury Golf Cart - across from CC Beach

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

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.

4.9 out of 5 average rating, 21 reviews

Hot Tub - Massage Chair - Golf Cart - Beach Gear

4.79 out of 5 average rating, 39 reviews

Two wooden Adirondack chairs are positioned on a sandy area beside the calm water. Lush green plants surround the chairs, while a bridge and boats can be seen in the distance reflecting on the water's surface.

Home in Norfolk

Wil-O-Bay Getaway

A newly built coastal home stands elevated on stilts, featuring a spacious lower deck with a pool and hot tub enclosed by a wooden fence. Multiple balconies extend from the upper floors, inviting views of the surrounding natural landscape.