
Vacation rentals with a kayak in Chesapeake
Find and book unique kayak rentals on Airbnb
Top-rated kayak rentals in Chesapeake
Guests agree: these kayak rentals are highly rated for location, cleanliness, and more.

1-Bedroom Home Near Christopher Newport University
Sip a bourbon while you listen to a record on the vintage player. Create your CD playlist to pop in the 90s 5 disk changer while you cook on a seasoned cast iron on the new stove. Check out the coffee bar for home roasted beans. Soak in the hot tub, or get a high score on Dig Dug. Centrally located in Newport News near CNU. 25-30 minute drive to Busch Gardens, Water Country, and Colonial Williamsburg. 45 minute drive to the ocean front. Great neighborhood with sidewalks for running and walking.

Exclusive Beachfront Home w/ 180° Views & Hot Tub!
If you enjoy majestic ocean views from almost every room & your own exclusive beach just steps below, Bay Bliss is for you! The panoramic views from this luxury home are unmatched & sure to relax you! Sip coffee from the grand deck or take a soak in the hot tub w/ breathtaking views. Cook/eat in the high-end chef's kitchen or watch a movie on a 75" TV all with stunning views! Wake up in the plush, king-sized bed and enjoy views of the water without having to get up. Your bliss at the bay awaits!

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.

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!

The Great River Escape *Hot Tub!
Welcome to the River Escape, where the sun is hot and river breezes are cool! Located on the Hampton River, on a big fenced lot, with easy river access and just a 10 minute drive to sandy toes and the sound of crashing waves, this fantastic river house is made for the best family vacations around. It is furnished to comfortably sleep 6, featuring a spacious, well-stocked kitchen, private in-ground pool, hot tuband a gas grill in the backyard! Just add family, and you've got instant vacation fun!

3 bedroom 3 bathroom beach house pets welcome
Welcome to your vacation getaway! This remodeled 3-bedroom, 2.5-bath ranch house is just a mile away from the ocean front. It's an ideal destination for families, friends & pets. All bedrooms have queen beds and smart tvs. Pet-Friendly (fee)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

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.

“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.

Beach Front with Paddle Boards and Kayaks
You have your own private access to the beach AND water views of the Chesapeake Bay that no other home in the area has. The sunrises and sunsets are breathtaking! Paddle boards and kayaks are provided. 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.

Quaint 2 Bedroom Cottage in Chicks Beach
This 2 bedroom 1 bathroom quaint cottage is the perfect small family getaway. Located 2 residential blocks to the beach. The beach is great for families with children. This unit is connected to a 1 bedroom rental. Back yard has a single detached unit also . Great for small families. There is a fenced in front yard Back yard and laundry area is shared with guest suite next door. 2 Car max allowed $100 pet fee with pre approval. ***Summer 2026 check in on Friday only ****

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!

Beachfront 2 Dwellings EV charger
Blue Marlin is a private beachfront home on the Chesapeake Bay in Hampton, VA! This home has two dwellings. The 4th bedroom is located in the 2nd dwelling. All four bedrooms are located on the second floor and require climbing stairs. Nestled within 30 miles to the attractions of Busch Gardens, Colonial Williamsburg, and Virginia Beach; our location offers the perfect blend of relaxation and adventure.
Popular amenities for Chesapeake kayak rentals
House rentals with a kayak

Oceanfront Cozy Beach Duplex

Lazy Palm Carova 4x4 Beach

New! Sandbridge Beach, 5bd/3Bth, Boat, Surf, Swim

Grace Haven

4x4 Carova, WaterFront, Dock, Wild Horses, Hot Tub

Bay and Sea

The Cool Change: Carova Beach (4x4 area)

Emperor’s Nest Upstairs
Cottage rentals with a kayak

902 B Historical Beachfront Duplex Sauna & Hot Tub

902C Coastal King Retreat Steps from Beach + Sauna

900 A Seaside 2BR Duplex Steps to Bay w/ Veranda

900 B Seaside 2BR Cottage w/ Bay Views & Veranda

Waterfront Cottage w/ Dock/Kayaks + Dog Friendly

WaterView | Private Dock | Kayaks | Chef's Kitchen

902 CH Historic Carriage House 20 Steps to Beach

Captain’s Cottage at Willoughby Spit Beach
Other vacation rentals with a kayak

The Barefoot Bungalow-Unit B-Steps From The Sand!

Lakeview Retreat: Private 2BR Guest Suite

Cape Charles Home: Private Pier & Beach-Front Deck

5BR Beach Home with Pool & Hot Tub & Rooftop Deck

Soundfront | Log Cabin | Near OBX | Dock | Kayaks

Sandbridge Ocean Paradise, Pool, Hot Tub,

Wil-O-Bay Getaway

Cozy Home in Barco, NC
Quick stats about vacation rentals with a kayak in Chesapeake

Total vacation rentals
Explore 10 vacation rentals in Chesapeake

Nightly prices starting at
Chesapeake vacation rentals start at G$12,552 GYD per night before taxes and fees

Verified guest reviews
Over 1,320 verified reviews to help you choose

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
10 of Chesapeake vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Chesapeake rentals

4.9 Average rating
Chesapeake stays are highly rated by guests—averaging 4.9 out of 5!

Nearby attractions
Chesapeake's top spots, include Chrysler Museum of Art, Nauticus, and Cinema Cafe-Greenbrier Mall
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- Rentals with a kayak Virginia
- Rentals with a kayak United States
- Busch Gardens Williamsburg
- Virginia Beach Oceanfront
- Corolla Beach
- Carova Beach
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Cape Charles Beachfront
- Norfolk Botanical Garden
- Outlook Beach
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- Nauticus
- Colonial Williamsburg's Merchants Square
- Virginia Zoological Park
- First Landing Beach
- Hampton University
- Town Point Park
- Regent University
- Old Dominion University
- Currituck Club
- Currituck Beach Lighthouse
- Currituck Beach




