We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Airbnb your place

Vacation rentals with a kayak in Greenwood

Find and book unique kayak rentals on Airbnb

Top-rated kayak rentals in Greenwood

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

0 of 0 items showing

1 of 3 pages

Cottage in Windham

4.91 out of 5 average rating, 85 reviews

Tranquil waterfront cottage

A private clean tranquil cottage, dock, parking, deck, grill, hammock, kitchen & all amenities, bathroom, 2 bedrooms, sleeps 5, futon, WIFI, cable, bidet, washer & dryer, granite outdoor table, kayaks, paddle boards, floats, fire pit and fireplace. Minutes from great restaurants, bars, hiking trails, and shopping. The most amazing sunsets. 30 minutes from Portland. Winter rentals as well. 40 min. from Shawnee Peek, 1 mile from Seacoast tubing. This place is privately yours. Smoke free please!

Home in Naples

4.99 out of 5 average rating, 106 reviews

LUX Designer Private Waterfront

Waterfront GLASS cabin with privacy professionally designed, escape to somewhere really special. Crooked river acres surrounding the house with the river wrapping around the property. Dock with direct access to Sebago lake and state park just minutes away, Outdoor shower, hot tub, hammocks, BIG walk-in shower w/ window. Heated bath floors, ac. See through Fireplace. The property has its own sandy swimming beach, pets are welcome. Come enjoy privacy and the space to run around seconds to Sebago.

Home in Naples

4.98 out of 5 average rating, 159 reviews

Kayak to the Causeway-50s cottage with modern vibe

Find out why the Maine life is the best life at Moonstone Cottage. Play on the shores of Long Lake, stroll the Naples Causeway, eat your way around Portland, and hike the mountains of western Maine before coming home to relax around the fire pit, lounge on the deck, and get a feel for the way life should be. Kayaks are waiting for you on the private association beach, or rent a boat from the marina to explore 40 miles of open water. Restaurants, live music, and the market are a short walk away.

Cabin in Woodstock

4.96 out of 5 average rating, 146 reviews

Sunday River & Lake Chalet, 2 Kitchens, Hot Tub

Family-friendly Chalet-Style cabin on three acres. Minutes away from world class skiing and across the street from Glover's Marsh Wildlife Sanctuary and beautiful North Pond, with lake access minutes away. Kayaks available for rent during summer months! Updated recently with upgrades including luxurious Egyptian cotton sheets, memory foam mattress toppers, & plush down alternative comforters. Hot Tub with Pavilion next to new stone firepit! Come relax and enjoy the beautiful Maine landscape!

Cabin in Naples

5 out of 5 average rating, 10 reviews

Cabin at Sunshine on Long Lake

You can't get any closer to Long Lake! The Cabin at Sunshine is a few short steps to the sandy bottom of this crystal clear lake. The Cabin at Sunshine was recently remodeled to give the home a relaxed, lake feeling with unobstructed views of Long Lake. All new mattresses and appliances throughout the cabin. A new Webber grill is outside for those days when you want to spend every second outside. Walk into Naples for ice cream, cocktails, shopping, entertainment, boat rentals, and dinner.

Cottage in Fryeburg

5 out of 5 average rating, 14 reviews

Waterfront Cabin close to all the N Conway Fun

Best of both worlds ...lake and mountain fun!! Relax and play with family and friends at this peaceful spot on Lovewell Pond. Sitting on your own 110 feet of waterfront with kayak access right into the Saco River. All this and just minutes to the all the action in North Conway and the Maine lakes region …shopping, restaurants, and mountain fun! Weekly rentals only! 1 King, 2 Queen Access to 4 kayaks/paddleboard Firepit & Grill BYO boat or rent ours, jet ski available to rent as well

Cottage in Parsonsfield

4.87 out of 5 average rating, 146 reviews

Riverpine Retreat - clean&bright waterfront home

Tucked away in a small town, minutes away from the New Hampshire border, located 2 minutes off of rt. 25 (direct route from Portland ME to NH) The ultimate family or couples getaway. Plenty of room in the back yard for any and all yard games, while also enjoying the firepit, "game shed" and 75ft of water frontage where you can swim, fish, or launch your kayaks from the dock into the Ossipee River. Wireless internet is available and reaches the back yard. The 'cabin' has 2 bedrooms.

Cabin in Harrison

4.99 out of 5 average rating, 124 reviews

Get away at Crystal Lake

Escape the lake region crowds on the calm water of Crystal Lake. Watch the sunset from the private waterfront/dock, kayak to take tour of the lake. Steps away from the center of Harrison and 2 boat launches, and only a short drive from downtown Bridgton. If you'd like a hike or bike instead, it's also a short drive to the mountains. Relax lakeside while your family enjoys the small beach, 2 kayaks, dock, or simply float about with a drink in hand. Note: waterfront across street

Chalet in Naples

4.96 out of 5 average rating, 105 reviews

The Chalet~ 4 bed Lakefront Family Vacation

Welcome to your secluded slice of paradise on the shores of Sebago Lake! Nestled amidst towering pines and overlooking the tranquil waters of Seabgo Cove, our 4-bedroom waterfront chalet promises a serene escape like no other. Whether you're seeking adrenaline-pumping thrills from the local excursions, or peaceful moments surrounded by nature and a book, The Chalet offers endless opportunities for unforgettable experiences and cherished memories in the heart of Naples.

Cottage in Windham

4.8 out of 5 average rating, 127 reviews

Cozy camp near highland lake

If you're looking for a quiet, cozy get a-way steps from the lake this is the place. Lake is private with no public access so it’s not crowded. Close to everything but far enough away; highway (95), Portland, Sebago Lake Area. Boating, swimming, fishing, hiking at your finger tips. 4 kayaks provided. Big yard, great for games, BBQ or sitting by the fire pit. Listen to the loons from the front deck. Sorry no pets so please don’t ask if you bring one!

Home in Greenwood

4.98 out of 5 average rating, 107 reviews

Holiday lakeside getaway by Sunday River

Located along Main Street, this beautifully restored lake front home had a private dock and yard facing the lake. Come enjoy summer on the lake with our canoes, kayaks and corn hole. In the winter come to ice skate in the front yard and ski at Sunday River (20mins) or Mt Abrams (5mins). House offers high speed internet, a smart TV and modern amenities. Custom dining nook, custom kitchen and modern, yet cozy finishes throughout.

Cottage in Fayette

4.97 out of 5 average rating, 101 reviews

Classic Lakefront Maine Cabin

This lakeside 3 bedroom retreat with huge quarried stone fireplace defines a "Maine cabin". My grandfather built the Big House in 1944 with rustic knotty pine walls, high ceilings, a modern kitchen, a spacious screened porch ten feet from the water, and spectacular lake views from every room in the house. Truly a rare and unique property in an age where newer buildings have large setbacks from the lake's edge.

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Popular amenities for Greenwood kayak rentals

Free parking on premises

Air conditioning

House rentals with a kayak

Home in Sabattus

4.88 out of 5 average rating, 16 reviews

The Cliff House

Home in Standish

4.96 out of 5 average rating, 68 reviews

Sebago Lake, ME *Lakeside*Hot Tub* just renovated

Home in Windham

4.93 out of 5 average rating, 117 reviews

Waterfront Gem walkable to Restaurants!

Home in Fayette

4.9 out of 5 average rating, 21 reviews

Lakehouse with 100ft of private waterfront

Home in Falmouth

4.95 out of 5 average rating, 80 reviews

Beautiful lake-side home close to Portland Maine

Home in Windham

4.9 out of 5 average rating, 39 reviews

The Lake House

Home in Turner

5 out of 5 average rating, 13 reviews

Little Wilson Pond

Home in Casco

4.93 out of 5 average rating, 14 reviews

Waterview Lake House

Cottage rentals with a kayak

Cottage in Conway

4.89 out of 5 average rating, 108 reviews

Cozy Pondside Retreat with direct water access!

Cottage in Falmouth

5 out of 5 average rating, 42 reviews

Cobb Cottage: Lake Beachfront Fri-Fri June-Aug

Cottage in Milan

4.9 out of 5 average rating, 59 reviews

Nay'tures Cottage

Cottage in Conway

4.94 out of 5 average rating, 325 reviews

20ft from the Water with Mountain View!

Cottage in Livermore

4.94 out of 5 average rating, 53 reviews

Loons Rest- Maine Quintessential Cottage

Cottage in Sumner

4.95 out of 5 average rating, 19 reviews

Private Cottage on Lake, Sauna & Hot Tub, Dogs OK

Cottage in Windham

4.9 out of 5 average rating, 77 reviews

Covered Bridge Cottage - Maine woods and river

Cottage in Livermore

4.95 out of 5 average rating, 148 reviews

Bass Point Lakeside Cottage: Livermore, Maine

Cabin rentals with a kayak

Cabin in Windham

4.92 out of 5 average rating, 205 reviews

Private Hilltop Cabin, Lakes and Trails Abound..

Cabin in Oxford

4.94 out of 5 average rating, 127 reviews

Thompson Lake, winter discount. Pine Point Cottage

Cabin in Waterford

4.94 out of 5 average rating, 158 reviews

Lakeside Cabin Nestled in the Pines

Cabin in Bridgton

4.93 out of 5 average rating, 118 reviews

Private cabin w hot tub,skiing,firepit & mountains

Cabin in Weld

4.94 out of 5 average rating, 108 reviews

Camp Bai Yuka/Little Camp (Log Cabin on Webb Lake)

Cabin in Parsonsfield

4.96 out of 5 average rating, 212 reviews

Riverfront cabin between Portland & White Mtns.

Cabin in Denmark

4.95 out of 5 average rating, 172 reviews

Maine Lakes-Pleasant Mt-Private Trails

Cabin in Woodstock

4.95 out of 5 average rating, 124 reviews

Private Cabin in woods on lake near Sunday River

Quick stats about vacation rentals with a kayak in Greenwood

Total rentals
30 properties
Nightly prices starting at
G$16,715 GYD before taxes and fees
Total number of reviews
1.2K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace

Destinations to explore