
Vacation rentals with a kayak in Chesapeake
Find and book unique kayak rentals on Airbnb
Top-rated accommodations with a kayak in Chesapeake
Guests agree: these accommodations with a kayak 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.

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 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.

Eden Guest Suite on Lake Allure
Relax and recharge in nature at this unique and peaceful getaway. Private access to one of Virginia’s best freshwater fishing lakes, with kayaks and SUP included. Just 15 minutes south of Cape Charles and 5 minutes from Kiptopeake, it’s a perfect base for exploring the Shore. Surrounded by trees and just 3 minutes’ drive to Pickett’s Harbor Farm and beach access. The guest suite is separated from the main house, with a private entrance and beautiful garden views for a truly tranquil stay.

3 bedroom 3 bathroom beach house pets welcome
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

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 7 night min check in on Friday only !

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.

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!

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.

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

The Canary Island … Keep Calm and Fish On

Lazy Palm Carova 4x4 Beach

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

Waterfront on the James 4,100 SF near Williamsburg

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

Splash of Lime Carova 4x4 Beach Cottage

Silver Strand, Pool, Dock w/ Kayaks, Sunset Views

Bay and Sea
Cottage rentals with a kayak

James River Beach Retreat - Private Beach & Pier

Riverfront Oasis | Kayaks, Private Beach, & More

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

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

Sunsets | Beach + Pool + Pickleball | Pet Friendly

WaterView | Private Dock | Kayaks | Chef's Kitchen

Captain’s Cottage at Willoughby Spit Beach

James River Beach Cottage - Private Beach & Pier!
Other vacation rentals with a kayak

Better at the Bay

Bells Island, w/pool on the water.

Serene waterfront retreat w/ private dock & kayaks

Waterfront Hot-Tub, Canoe & Firepit w/ Dock

Incredible 4BR Oceanfront 1st-Floor | Balcony

Wil-O-Bay Getaway

Cozy Home in Barco, NC

Sandbridge Ocean Paradise
Quick stats about vacation rentals with a kayak in Chesapeake

Nightly prices starting at
Chesapeake vacation rentals start at $84 CAD per night before taxes and fees

Verified guest reviews
Over 560 verified reviews to help you choose

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 Cinemark Chesapeake Square
Destinations to explore
- New York City Vacation rentals
- Washington Vacation rentals
- Jersey Shore Vacation rentals
- Myrtle Beach Vacation rentals
- Philadelphia Vacation rentals
- South Jersey Vacation rentals
- Charlotte Vacation rentals
- Outer Banks Vacation rentals
- Jersey City Vacation rentals
- Cape Fear River Vacation rentals
- Ocean City Vacation rentals
- Rappahannock River Vacation rentals
- Mansion rentals Chesapeake
- Private suite rentals Chesapeake
- Rentals with lake access Chesapeake
- Rentals with beach access Chesapeake
- Waterfront rentals Chesapeake
- Rentals with pools Chesapeake
- Fitness-friendly rentals Chesapeake
- Townhouse rentals Chesapeake
- Rentals with a firepit Chesapeake
- Family-friendly rentals Chesapeake
- Beachfront rentals Chesapeake
- Rentals with a patio Chesapeake
- Pet-friendly rentals Chesapeake
- Rentals with a hot tub Chesapeake
- Smoking-friendly rentals Chesapeake
- Beach house rentals Chesapeake
- Condo rentals Chesapeake
- Rentals with outdoor seating Chesapeake
- Rentals with a fireplace Chesapeake
- Cottage rentals Chesapeake
- Rentals with a washer and dryer Chesapeake
- Rentals with an EV charger Chesapeake
- House rentals Chesapeake
- Apartment rentals Chesapeake
- Guesthouse rentals Chesapeake
- Rentals with breakfast Chesapeake
- Rentals with a kayak Virginia
- Rentals with a kayak United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Carova Beach
- Buckroe Beach
- Corolla Beach
- Water Country USA
- First Landing State Park
- Haven Beach
- Buckroe Beach and Park
- Grandview Beach
- Jamestown Settlement
- Bethel Beach
- Outlook Beach
- Kiptopeke Beach
- Virginia Beach National Golf Club
- Ocean Breeze Waterpark
- Norfolk Botanical Garden
- Golden Horseshoe Golf Club
- Chrysler Museum of Art
- Cape Charles Beachfront
- James River Country Club
- Wilkins Beach
- Little Creek Beach
- Red Wing Lake Golf Course




