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Vacation rentals with a kayak in Delmarva Peninsula

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Top-rated kayak rentals in Delmarva Peninsula

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Tiny home in Cambridge

4.89 out of 5 average rating, 498 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!

Jul 8 – 15

R1,556 ZAR per night

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.

Aug 8 – 15

R1,525 ZAR per night

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!

Oct 16 – 23

R3,293 ZAR per night

Loft in Cape May Court House

4.97 out of 5 average rating, 591 reviews

Quiet Lakefront Studio - Close to the Beach

Discover Cape May County - the hidden gem of Southern New Jersey. Be our guest on a crystal clear lake surrounded by tall pines and wetlands, creating a vast wildlife habitat in a sanctuary of natural artistry. Great care has been taken to nurture a secluded environment to explore, restore and create; all on a hidden lake with its own sandy beach. Local beach passes, hiking trails, direct access to the county bike path, fire pit, hammocks, water sports, etc. are all included in your stay.

Nov 10 – 17

R2,468 ZAR per night

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.

Sep 20 – 27

R2,712 ZAR per night

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.

Mar 7 – 14

R6,227 ZAR per night

Guest suite in Chestertown

4.99 out of 5 average rating, 192 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.

Sep 13 – 20

R2,563 ZAR per night

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.

Jan 3 – 10

R3,991 ZAR per night

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

R4,758 ZAR per night

Cottage in Saint Michaels

4.99 out of 5 average rating, 137 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.

Aug 6 – 13

R10,323 ZAR per night

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

Aug 6 – 13

R2,733 ZAR per night

Apartment in Frankford

4.98 out of 5 average rating, 123 reviews

Cozy Cottage Getaway

Enjoy this newly remolded 1 bedroom apartment tucked away on 2+ acres 3 miles from Bethany beach. Close to Rehobeth beach for outlet tax free shopping or Ocean City MD just 13 miles. You’ll be minutes away from lots of restaurants, stores, mini golf, arcade, night life etc. Property includes a 1/4 mile walking/running trail, fire pit and basket ball court. This is the perfect place to escape away from the busy Beach life but close enough to enjoy everything fully.

Oct 20 – 27

R2,734 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Houses

A space thats all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Delmarva Peninsula kayak rentals

Free parking on premises

Air conditioning

House rentals with a kayak

Home in TYLERTON

4.95 out of 5 average rating, 118 reviews

3 bedroom/2.5 bath Smith Island bungalow with dock

Oct 4 – 11

R2,662 ZAR per night

Home in Heathsville

4.93 out of 5 average rating, 122 reviews

Water ft Chesapeake Bay DREaM Vacation Dock Kayaks

Feb 16 – 23

R6,645 ZAR per night

Home in Lusby

4.98 out of 5 average rating, 261 reviews

Cove Point Beach Cabin

Feb 27 – Mar 6

R3,194 ZAR per night

Home in Chincoteague

4.98 out of 5 average rating, 195 reviews

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

Mar 6 – 13

R2,561 ZAR per night

Home in Cambridge

4.99 out of 5 average rating, 142 reviews

Sunset Breezes - quiet waterfront retreat

Mar 28 – Apr 4

R8,254 ZAR per night

Home in Kent Narrows

5.0 out of 5 average rating, 279 reviews

Chester Riverfront At Kent Narrows

Nov 2 – 9

R5,729 ZAR per night

Home in Deltaville

5.0 out of 5 average rating, 104 reviews

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

Oct 27 – Nov 3

R6,493 ZAR per night

Home in Woolford

4.93 out of 5 average rating, 118 reviews

Waterfront Getaway with Dock

Oct 21 – 28

R4,180 ZAR per night

Cottage rentals with a kayak

Cottage in Leonardtown

4.97 out of 5 average rating, 126 reviews

Beach Front and 'Perfectly Placed'

Jan 24 – 31

R3,343 ZAR per night

Cottage in Urbanna

4.99 out of 5 average rating, 134 reviews

Little Dipper -private beach,Kayaks & paddleboards

Oct 24 – 31

R3,837 ZAR per night

Cottage in Lower Township

5.0 out of 5 average rating, 146 reviews

Octopus Cottage: Hot Tub | Kayaks | Fire Pit

Mar 4 – 11

R8,491 ZAR per night

Cottage in Reedville

4.9 out of 5 average rating, 162 reviews

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

Sep 11 – 18

R8,787 ZAR per night

Cottage in Saint Leonard

4.99 out of 5 average rating, 102 reviews

Captain Jack's Bay Hideaway

Jul 11 – 18

R3,164 ZAR per night

Cottage in Onancock

4.96 out of 5 average rating, 138 reviews

A "True" Chesapeake Bay Waterfront Experience!

Dec 6 – 13

R6,348 ZAR per night

Cottage in Gwynn

4.96 out of 5 average rating, 200 reviews

Mystic Seahorse Cottage & game room

Jul 17 – 24

R3,005 ZAR per night

Cottage in Chincoteague

4.98 out of 5 average rating, 130 reviews

Waterfront-CI Bay sunsets-Amazing views

Dec 27 – Jan 3

R6,347 ZAR per night

Cabin rentals with a kayak

Cabin in Reedville

4.97 out of 5 average rating, 190 reviews

Dinna Fash-3 BR Waterfront Log Cabin

Mar 15 – 22

R2,959 ZAR per night

Cabin in Lusby

4.91 out of 5 average rating, 210 reviews

Peaceful Waterfront Retreat on The Bay

Sep 16 – 23

R3,323 ZAR per night

Cabin in Lusby

4.94 out of 5 average rating, 145 reviews

Hideaway on the Bay: Waterfront Vintage A Frame

Jul 17 – 24

R6,023 ZAR per night

Cabin in Galloway

4.89 out of 5 average rating, 173 reviews

ROMANTIC GETAWAY Scenic Lakefront home peaceful

Dec 22 – 29

R4,403 ZAR per night

Cabin in Dinwiddie

5.0 out of 5 average rating, 87 reviews

Dinwiddie Couples Getaway- Wells Cabin @WeldanPond

Jul 27 – Aug 3

R2,515 ZAR per night

Cabin in Worton

4.94 out of 5 average rating, 65 reviews

Cabin on the Creek ~ Kayaks and Fire Pit

Feb 18 – 25

R4,752 ZAR per night

Cabin in Reedville

4.94 out of 5 average rating, 71 reviews

Coastal Cabin - hot tub, private beach & kayaks

Feb 9 – 16

R4,983 ZAR per night

Cabin in Newport

4.83 out of 5 average rating, 82 reviews

Dyers Cove

Nov 10 – 17

R4,571 ZAR per night

Destinations to explore