Vacation rentals with a kayak in Chesapeake

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Top-rated kayak rentals in Chesapeake

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Guest favorite

Condo in Williamsburg

4.96 out of 5 average rating, 115 reviews

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!

Guest favorite

Townhouse in Newport News

5 out of 5 average rating, 21 reviews

Waterfront suburban oasis with theater room

Our lakefront apartment suite boasts extraordinary sunsets of the James River! Surrounded by wildlife: herons, egrets, owls, deer, otters, ducks, geese, turtles, squirrels galore! This large 1 bedroom apartment contains 3 beds and 1 bathroom. Featuring a movie room with a 75" Smart TV. Full kitchen, W/D in unit, fast WiFi, pet-friendly, front-of-the-unit parking spot. Quiet and serene yet centrally located in the best of Newport News. Midway between colonial Williamsburg and Virginia Beach.

Guest favorite

Tiny home in Sandbridge

5 out of 5 average rating, 25 reviews

New! Spectacular Sunsets! Back Bay Waterfront

Enjoy the best of both worlds – the beach and the bay – at Bay Dream Believer a charming new tiny home (RV) located waterfront on the Back Bay in Sandbridge Beach, Virginia in Surfside at Sandbridge. 180 degree bay views and amazing sunsets await! There is a private queen bedroom and a loft area with two additional twin beds. After enjoying the sun and surf at the beach, retreat to your own private waterfront oasis. We have tried to think of everything you need to enjoy the perfect getaway.

Guest favorite

Home in Knotts Island

4.94 out of 5 average rating, 104 reviews

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!

Guest favorite

Guesthouse in Virginia Beach

5 out of 5 average rating, 10 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.

Guest favorite

Camper/RV in Portsmouth

4.92 out of 5 average rating, 127 reviews

“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.

Guest favorite

Home in Portsmouth

4.96 out of 5 average rating, 105 reviews

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.

Guest favorite

Farm stay in Cape Charles

5 out of 5 average rating, 363 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 urban centers. Our twenty acre waterfront farm, which has plenty of nearby walking or biking, and a dock onto a secluded arm of Plantation Creek, an inlet of the Chesapeake Bay, is perfect for solo travelers, couples or small families looking for a memorable trip to the Eastern Shore.

Guest favorite

Cottage in Norfolk

4.94 out of 5 average rating, 145 reviews

Poseidon - Beach Carriage House - 120 Years Old

Your Beachfront Vacation. 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.

Guest favorite

Cottage in Norfolk

4.99 out of 5 average rating, 116 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.

Superhost

Tiny home in Sandbridge

4.81 out of 5 average rating, 26 reviews

Meredith's Mini Mansion.

Welcome to Surfside at Sandbridge!!! Sandbridge is the northern most portion of the OBX!!! Location location location. this tiny home is 3 years old and was previously a vacation property. This will be it's first year on airbnb. there is a queen adjustable bed in the master and two twins in the loft. There is room for a air mattress in the loft also. This unit comes fully stocked for everything you'd need for a beach vacation. Towels..chairs..beach canopy..boogie boards..ect.

Guest favorite

Home in Chesapeake

4.95 out of 5 average rating, 20 reviews

Charming waterfront home in Chesapeake

Come enjoy a relaxing stay at our riverfront home! Our home is in a safe, quiet neighborhood in Chesapeake right off the Elizabeth River! Feel free to enjoy the water views from the sunroom and dock or take the kayaks for a paddle down the river! This listing is for our entire home, completely private, not shared with any other guests or hosts! Downtown Portsmouth - 10 min Waterside / Downtown Norfolk - 15 min VA beach Oceanfront - 30 min