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Holiday rentals with a kayak in Delmarva Peninsula

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Top-rated rentals with kayak in Delmarva Peninsula

Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.

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Tiny home in Cambridge

4.89 out of 5 average rating, 500 reviews

Blackwater Tiny Cabin on Snakehead Creek

The Solar Powered Tiny Cabin is located on a farmette 5 min away from Blackwater Refuge! It is an affordable and unique way to visit and enjoy all that Cambridge and Blackwater Refuge have to offer! Staying the cabin will make your visit even more memorable!The Tiny Cabin is now located 50 steps away from Pitcher Dam Creek which leads to the Little Blackwater! Kayaks on site! Bring your fishing rod to catch popular Snakeheads! 15 minute drive to Route 50, downtown Cambridge, shopping and dining!

31 Jul – 7 Aug

€ 87 per night

Guest favourite

Tiny home in Saint Inigoes

4.98 out of 5 average rating, 295 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.

15–22 Sep

€ 88 per night

Guest favourite

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!

15–22 Nov

€ 185 per night

Guest favourite

Farm stay in Cape Charles

5.0 out of 5 average rating, 333 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.

4–11 Sep

€ 195 per night

Guest favourite

Loft in Lusby

5.0 out of 5 average rating, 316 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.

31 Jan – 7 Feb

€ 140 per night

Guest favourite

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.

23–30 Dec

€ 333 per night

Guest favourite

Home in Chincoteague

4.98 out of 5 average rating, 196 reviews

★ Pearl in the Pines: Kayaks-Fire Pit-Bikes-Beach-Pet Friendly

Fully equipped 1200 sf home-3 Bdrm residence-with fire pit, 2 kayaks, 4 bikes, towels & linens. Pearl in the Pines is literally 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

5–12 Feb

€ 133 per night

Guest favourite

Guest suite in Chestertown

4.99 out of 5 average rating, 193 reviews

Beautiful Waterfront Chestertown Getaway

Lovely three room waterfront apartment/guest suite conveniently located minutes from historic Chestertown and Washington College. Beautiful water views, full kitchen, wooded lot, quiet neighborhood, bird watching, biking, running, kayaking. Friendly pets (comfortable with people and our medium rescue dog) are welcome. We donate 5% of proceeds to Kent Attainable Housing, the Animal Care Shelter of Kent County or ShoreRivers conservation—your choice. Make it your home away from home.

9–16 Jul

€ 140 per night

Guest favourite

Guest house 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.

9–16 Nov

€ 218 per night

Guest favourite

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.

15–22 Aug

€ 270 per night

Guest favourite

Cottage in Saint Michaels

4.99 out of 5 average rating, 138 reviews

La Casita on Harris Creek, St. Michaels

Newly constructed architecturally unique guesthouse inspired by the historic barns of the Chesapeake. Stay in luxury on a secluded 40 acre farm on Harris Creek, be at one with nature & still only 5 min from town's fine dining, shops & charm . With 360 views, TV/Wi-fi, full bath/shower, galley kitchen w/ microwave, fridge w/ice maker, washer/drier, patio fire pit, private pool & kayaks. We comply with Talbot County's zoning that requires a 3 night minimum ST-934-HUD 2020.

12–19 May

€ 530 per night

Guest favourite

Guest suite in Tilghman Island

4.96 out of 5 average rating, 114 reviews

Black Walnut Cove Retreat, Tilghman Island

Our waterfront studio retreat is a birdwatchers paradise. Located on beautiful Black Walnut Cove at the southern tip of Tilghman Island, you will be in a quiet neighborhood surrounded by water. Enjoy a quiet walk or bike ride along the Chesapeake Bay shoreline. You will have access to our dock and small boat ramp. Crabbing and fishing are a delight. Please note: 1) There is a 3-nt. minimum on holiday weekends. 2) Children between the ages of 1 and 5 are not permitted

22–29 Dec

€ 128 per night

Holiday rentals for every style

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Popular amenities for kayak rentals in Delmarva Peninsula

Free parking on premises

Air conditioning

House rentals with a kayak

Guest favourite

Home in Heathsville

4.93 out of 5 average rating, 122 reviews

Water ft Chesapeake Bay DREaM Vacation Dock Kayaks

12–19 Jan

€ 363 per night

Guest favourite

Home in TYLERTON

4.95 out of 5 average rating, 118 reviews

3 bedroom/2.5 bath Smith Island bungalow with dock

20–27 Oct

€ 155 per night

Guest favourite

Home in Lusby

4.98 out of 5 average rating, 261 reviews

Cove Point Beach Cabin

26 Dec – 2 Jan

€ 182 per night

Guest favourite

Home in Cambridge

4.99 out of 5 average rating, 143 reviews

Sunset Breezes - quiet waterfront retreat

27 Apr – 4 May

€ 447 per night

Guest favourite

Home in Deltaville

5.0 out of 5 average rating, 104 reviews

"No Bad Days" in this Fabulous Beachhouse w/ Dock!

15–22 Dec

€ 367 per night

Guest favourite

Home in Charles City

4.99 out of 5 average rating, 233 reviews

Hutch's Bluff - Waterfront near Williamsburg

14–21 Dec

€ 287 per night

Guest favourite

Home in Woolford

4.99 out of 5 average rating, 199 reviews

Newly Renovated Modern 3 bed 2 bath Water Front

10–17 Mar

€ 385 per night

Guest favourite

Home in Kent Narrows

5.0 out of 5 average rating, 280 reviews

Chester Riverfront At Kent Narrows

2–9 Nov

€ 323 per night

Cottage rentals with a kayak

Guest favourite

Cottage in Westover

4.92 out of 5 average rating, 142 reviews

Heaven on the Bay - A Peaceful Waterfront Retreat

26 Mar – 2 Apr

€ 249 per night

Guest favourite

Cottage in Leonardtown

4.97 out of 5 average rating, 126 reviews

Beach Front and 'Perfectly Placed'

27 Sep – 4 Oct

€ 208 per night

Cottage in Reedville

4.88 out of 5 average rating, 60 reviews

Private point on the Bay🌤hammock, hot tub, kayaks❤️

20–27 Mar

€ 393 per night

Guest favourite

Cottage in Lower Township

5.0 out of 5 average rating, 147 reviews

Octopus Cottage: Hot Tub | Kayaks | Fire Pit

26 Feb – 5 Mar

€ 411 per night

Guest favourite

Cottage in Urbanna

4.99 out of 5 average rating, 135 reviews

Little Dipper -private beach,Kayaks & paddleboards

17–24 Oct

€ 230 per night

Guest favourite

Cottage in Onancock

4.96 out of 5 average rating, 138 reviews

A "True" Chesapeake Bay Waterfront Experience!

8–15 Nov

€ 382 per night

Guest favourite

Cottage in Chincoteague

4.98 out of 5 average rating, 131 reviews

Waterfront-CI Bay sunsets-Amazing views

25 Nov – 2 Dec

€ 366 per night

Guest favourite

Cottage in Gwynn

4.96 out of 5 average rating, 200 reviews

Mystic Seahorse Cottage & game room

21–28 Oct

€ 170 per night

Cabin rentals with a kayak

Guest favourite

Cabin in Reedville

4.97 out of 5 average rating, 190 reviews

Dinna Fash-3 BR Waterfront Log Cabin

15–22 Nov

€ 178 per night

Guest favourite

Cabin in Lusby

4.91 out of 5 average rating, 211 reviews

Peaceful Waterfront Retreat on The Bay

12–19 Dec

€ 156 per night

Guest favourite

Cabin in Lusby

4.94 out of 5 average rating, 146 reviews

Hideaway on the Bay: Waterfront Vintage A Frame

20–27 Jul

€ 342 per night

Cabin in Galloway

4.89 out of 5 average rating, 174 reviews

ROMANTIC GETAWAY Scenic Lakefront home peaceful

7–14 Jan

€ 181 per night

Guest favourite

Cabin in Egg Harbor City

4.96 out of 5 average rating, 109 reviews

Pinelands Riverfront Home

21–28 Aug

€ 347 per night

Guest favourite

Cabin in Reedville

4.94 out of 5 average rating, 71 reviews

Coastal Cabin - hot tub, private beach & kayaks

3–10 Dec

€ 285 per night

Guest favourite

Cabin in Worton

4.94 out of 5 average rating, 65 reviews

Cabin on the Creek ~ Kayaks and Fire Pit

6–13 Oct

€ 271 per night

Guest favourite

Cabin in Saint Leonard

4.96 out of 5 average rating, 82 reviews

Cozy Cedar Cottage~Beach Retreat

5–12 Jun

€ 191 per night

Destinations to explore