Vacation rentals with a kayak in Hampton Roads

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Top-rated kayak rentals in Hampton Roads

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Guest favorite

Condo in Williamsburg

4.98 out of 5 average rating, 103 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!

Jan 12 – 19

G$68,411 GYD per night

Guest favorite

Home in Newport News

4.93 out of 5 average rating, 45 reviews

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.

Apr 20 – 27

G$28,369 GYD per night

Guest favorite

Home in Gloucester Point

4.99 out of 5 average rating, 146 reviews

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.

Nov 13 – 20

G$73,485 GYD per night

Superhost

Home in Portsmouth

4.82 out of 5 average rating, 28 reviews

3D Theater ~ Firepit ~ Fishing

Make some memories at this unique and family-friendly home! Enjoy a movie night with our 120" movie screen and high end 3D projector, as well as a selection of 3D movies and rechargable 3D glasses. Relax in the backyard with outdoor dining, a firepit - and best of all, excellent fishing and kayaking from our own private dock! At bedtime, we have a very comfortable king size bed in the master, and two, also very comfortable, double beds in the secondary bedroom. Plus top of the line pillows!

Oct 9 – 16

G$43,339 GYD per night

Guest favorite

Boat in Poquoson

4.93 out of 5 average rating, 92 reviews

Invictus: A Romantic Sailboat

We can't adequately describe how romantic & carefree it feels to step aboard our sail boat. We purposely chose this marina location for the incredible seafood restaurant only steps from the boat. You must try their amazing SheCrab soup! Afterwards, snuggle up together on deck to watch the sunset turn the sky pink & purple. The marina atmosphere is simply magical & you'll love sleeping to the gentle sway of calm waters. Come enjoy a night aboard this amazingly cozy & romantic sail boat. ;)

May 12 – 19

G$35,599 GYD per night

Guest favorite

Farm stay in Cape Charles

5.0 out of 5 average rating, 332 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.

Oct 7 – 14

G$33,139 GYD per night

Guest favorite

Home in Hampton

5.0 out of 5 average rating, 42 reviews

The Canary Island … Keep Calm and Fish On

Relax with your family at this peaceful home on the waterfront. Enjoy expansive views of the Salt Ponds inlet with deep water boating access, and miles of kayaking waters. Immerse yourself in the “low country” lifestyle and spend your days fishing, crabbing, boating or sunning at the beaches. The kitchen is stunning, coffee on the deck is a must, the bedrooms are comfortable and the master bath is a retreat to enjoy the amazing inlet surroundings. Pool table, video game table … and more

Sep 29 – Oct 6

G$108,331 GYD per night

Guest favorite

Cottage in Norfolk

4.94 out of 5 average rating, 113 reviews

110 Year Old Beach Carriage House @ Poseidon 902CH

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.

Oct 23 – 30

G$37,324 GYD per night

Guest favorite

Tiny home in Cape Charles

4.98 out of 5 average rating, 275 reviews

The Laughing King Retreat Honeymoon Island Cottage

Honeymoon Island Cottage is an adults-only lodging experience like no other. You and your guest will stay in a charming tiny farmhouse that is located just steps from the Chesapeake Bay on a USDA certified organic farm. Enjoy access to a private saltwater pool, private beach, Chesapeake Bay water access for boating, swimming, paddleboarding, fishing or just soaking, dig for clams, collect wild oysters, or just sit and marvel at the beauty. We look forward to welcoming you.

Jan 21 – 28

G$53,739 GYD per night

Guest favorite

Home in Lanexa

4.95 out of 5 average rating, 172 reviews

Williamsburg Hide-A-Way Creekside

Cozy home, updated decor, full kitchen, 3 bedrooms, 2 baths overlooking a gorgeous creek that is too beautiful to describe. Minutes from Colonial Williamsburg, Busch Gardens yet rural, private and quaint. Screened, 3 season porch with heat and A/C, gated deck for kids and pet containment, propane grill, fire table, swingset, boat ramp, kayaks. Enjoy a totally relaxing experience with homelike accommodations. **Pet friendly upon owner approval of breed, age, etc.

Jul 16 – 23

G$57,251 GYD per night

Guest favorite

Home in Charles City

4.99 out of 5 average rating, 231 reviews

Hutch's Bluff - Waterfront near Williamsburg

Charming riverfront A-Frame home on 2 acres overlooking the Chickahominy River. Completely updated interior, including all furnishings and appliances. Wake in a King bed loft space with a majestic view of the river, or choose one of the two Queen bedrooms below. First floor all tile bathroom with a walk in shower. Stainless appliances and granite countertops. Bring your fishing gear, relax at the end of the pier, or enjoy the views from the large deck and fire pit.

Mar 23 – 30

G$56,104 GYD per night

Guest favorite

Home in Virginia Beach

4.78 out of 5 average rating, 130 reviews

Quaint 2 Bedroom Cottage in Chicks Beach

2 bedroom 1 bathroom quaint cottage, walking distance only 2 blocks to the beach . The beach is great for families with children . This unit is connected to a 1 bedroom unit . 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 $75 pet fee with pre approval. Starting June 25th 7 night min check in on Friday only !

Oct 2 – 9

G$35,031 GYD per night