Vacation rentals with a kayak in Eastern Shore of Virginia

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Top-rated kayak rentals in Eastern Shore of Virginia

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Guest favorite

Guest suite in Lusby

4.99 out of 5 average rating, 303 reviews

Riverfront Chalet Kayak/Canoe, pier, breakfast!

This is a two room above the garage apartment with a dedicated side entrance for guests separate from the main house by screens down and a barn door up. Once upstairs you have your own completely private space. Your mini fridge will always be stocked with an assortment of beverages and snacks as well as breakfast items. Enjoy, our kayaks, fire pit or sunset viewing on the pier. Lots of hiking and water sports abound in the area. A short drive south is beautiful Solomon’s island. Boaters welcome!

Apr 27 – May 4

R2,475 ZAR per night

Guest favorite

Tiny home in Saint Inigoes

4.98 out of 5 average rating, 294 reviews

Historic St.Mary's City at the Lazy Bear Cottage

Inquire first on pets, there is a 40 lb. weight limit total, can be split up between 2 small dogs or 1 at 40lbs or less,must be house broken and friendly. Close to Saint Mary's historic city, Pt. Lookout State Park, Sotterley Plantation. Great hiking trails, restored colonial village,a replica of the Maryland Dove. Tour a lighthouse. Great restaurants , or spend a day over in Solomons Island, about 20 miles from us. Peaceful settings for relaxing right on the water,or kayak on the river.

Sep 15 – 22

R1,525 ZAR per night

Guest favorite

Bungalow in Belle Haven

4.92 out of 5 average rating, 178 reviews

Stay Waterfront-Private Dock Belle Haven Bungalow

Come explore the Eastern Shore - Waterfront bungalow with fishing / crabbing pier. Our two bedroom, two bath bungalow sleeps up to 7 guests comfortably. Open floor plan and large screened porch / deck make our modest bungalow feel like a much bigger place. Perfect setting for a family vacation you will never forget. Kayaks, Fishing / crabbing gear and yard games are all available for use during your stay. 35 minute drive to Cape Charles beach and many other adventures in every direction.

Nov 12 – 19

R3,361 ZAR per night

Guest favorite

Farm stay in Onancock

4.99 out of 5 average rating, 177 reviews

Private romantic pet friendly waterfront cottage

On Virginia’s beautiful Eastern Shore, The Birdhouse at Windfall Farm is the ultimate romantic getaway. Just steps from Pungoteague Creek (a short boat ride to the Chesapeake Bay)on one side and a picturesque large stocked pond on the other, The Birdhouse is a charming 1 bedroom hideaway, with abundant wildlife, walking trails on our 62 acre working farm, kayaking, fishing, crabbing, and stargazing, all amid Nature’s beauty. Be our guest for an unforgettable time on Virginia’s Eastern Shore!

Jan 9 – 16

R3,293 ZAR per night

Guest favorite

Cottage in Onancock

4.96 out of 5 average rating, 138 reviews

A "True" Chesapeake Bay Waterfront Experience!

Get away from it all... The Thicket Point Fish Camp is a true Chesapeake Bay waterfront property and the perfect place to escape for the best of the Eastern Shore. Located just 5 miles from downtown Onancock, VA, and everyday conveniences, this property is one of a kind! This is the "Sunset House" expanded and completely renovated in May 2018, It is complemented by our "Bayside House" - also available on Airbnb. Be ready for the smell of the salt air and to enjoy million-dollar sunsets!

Sep 6 – 13

R6,348 ZAR 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 20 – 27

R2,934 ZAR per night

Guest favorite

Home in Chincoteague Island

4.97 out of 5 average rating, 179 reviews

★ Jay’s Waterfront Retreat: Private Dock- Kayaks-Fire Pit-Bikes-Beach-Pet Friendly ★

Fully equipped 1000 sf home-3 Bdrm residence-with fire pit, 2 kayaks, 4 bikes & Private Dock. Linens & towels included Jay's Retreat is at nature's front door within a few miles from Assateague National Seashore (the beach), home of the world famous Chincoteague Ponies. Enjoy: Swimming in the bay and ocean Bicycling Fishing, crabbing, clamming Kayaking, paddle boarding; boating Hiking Bird Watching Nature photography Hunting Nature Trails Great Restaurants & Brew Pub Boat Tours Ponies

Feb 26 – Mar 5

R2,615 ZAR per night

Guest favorite

Loft in Lusby

5.0 out of 5 average rating, 315 reviews

Coastal Treetop Retreat w/ Private Beach Access

Come experience our tucked-away loft 5 minutes from beaches, 10 minutes to Solomons, and Calvert Cliffs. Private garage apartment with 17 stairs. Our open-concept space, has a bedroom area, bathroom, workspace, & kitchen (convection oven, induction stove, microwave, refrigerator, and Keurig). Enjoy quick Wi-Fi, a 40" Smart TV, a cozy queen bed, and comfy lounge chairs. Bring S'mores fixings to roast over the fire and wrap yourself in a blanket. Choose to stay in or adventure out.

Mar 14 – 21

R2,527 ZAR per night

Guest favorite

Cottage in Westover

4.99 out of 5 average rating, 182 reviews

Rumbley Cottage on the Tangier Sound-Private Beach

Winter time is a great time at Rumbley! Rumbley Cottage, a custom-built home, provides a quiet stay in nature. Views from all window. Look out to the mouth of the Manokin River at Tangier Sound on one side; wetlands on the other side. NO CLEANING OR PET FEE. Rumbley Cottage is enjoyed year- round with a great fireplace. WE PROVIDE THE FIREWOOD AND STARTERS. Many amenities including Wifi, Molton Brown toiletries, kayaks, SPBs, bikes, beach equipment; well-stocked kitchen.

Apr 1 – 8

R6,861 ZAR per night

Guest favorite

Guesthouse in White Stone

5.0 out of 5 average rating, 188 reviews

Waterfront Guesthouse II on the Rappahannock

The “Beach House” is a guest cottage at Snug Harbor, a 2 acre private property overlooking the Rappahannock River and Chesapeake Bay. Perfect for a couple’s getaway, this well-appointed cottage has beautiful water views and includes access to our private beach & dock with use of our paddle boards and kayaks. The cottage’s 1st floor features an open liv/din/kit area, full bath with large shower and a covered patio. The 2nd floor features a large loft bedroom with a queen bed.

Feb 14 – 21

R3,974 ZAR per night

Guest favorite

Farm stay in Cardinal

4.95 out of 5 average rating, 111 reviews

Wtrfrnt aptmnt w/pool/dock on private farm

Come enjoy all the outdoors has on offer at this secluded, waterfront estate. The spacious studio apartment is fully equipped for comfort. 12 acres of waterfront grounds to enjoy including great outdoor seating, fabulous bayside salt water pool. Fish, canoe and kayak right off the farms private dock. Grill and fire pit. Just 10 mins from the charming villages of Mathews and Gloucesters farm to table amenities. Great local food, music, history and shopping right on the bay!

Nov 3 – 10

R2,548 ZAR 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.

Apr 10 – 17

R4,758 ZAR per night