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Vacation rentals with a kayak in Cumberland County

Find and book unique kayak rentals on Airbnb

Top-rated accommodations with a kayak in Cumberland County

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

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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!

Guest favourite

Home in Naples

4.99 out of 5 average rating, 105 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.

Guest favourite

Home in Shapleigh

4.96 out of 5 average rating, 135 reviews

Secluded Lakehouse/2 private docks*Hottub*big yard

Bring your family or friends for a fun and relaxing stay on Mousam Lake this summer! With 3 bedrooms, and additional loft and a basement sleeping area, there's room for everyone! Explore the lake with canoes, kayaks and paddleboards available to you or bring your own boat, the public boat launch is across from our front dock! When you are not enjoying the lake, the house provides many spaces for your favorite yard games, a screen house to play cards or have a drink and unwind in large hot tub!

Guest favourite

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.

Guest favourite

Cottage in Topsham

4.93 out of 5 average rating, 247 reviews

Cozy waterfront home on Merrymeeting Bay.

Our cozy cottage is the perfect romantic getaway or quiet retreat in any season. Located on a private rd with scenic waterfront view. Guests can enjoy sitting on the dock (May- October) or the jetty, watch the eagles and Osprey, use our kayaks, do some fishing, walking or biking. Sit by the propane fueled fireplace on a chilly night. Brunswick, home of Bowdoin College and a # of great restaurants and unique shops is just 5 mi. Travel by bus or train to/from Boston. Portland is @ 30 min away.

Guest favourite

Cabin in Denmark

4.98 out of 5 average rating, 101 reviews

Lake Front with Private Dock - BRAND NEW Furniture

Our waterfront haven can be your personal retreat. Just 35 minutes to Downtown North Conway, our home takes you away from the noise for quiet relaxation. In the summer enjoy: - Tying your boat off to our private dock. - Bass fishing and water sports. - Fryeburg Fair minutes away - Hiking In the winter have fun: - Skiing at Shawnee Peak (15-mins away) - Snowmobiling (Trail directly across the street) - Ice Fishing - Snowshoeing - Bring your trailers, snowmobile & hit the trails

Guest favourite

Home in Buxton

4.88 out of 5 average rating, 126 reviews

Charming 4 bedroom lake front, with private beach

Will not consider less than weekly rentals for July and August and the last week in June.The house sits 80 ft off the lake. It has over 150 ft of lake shore and own private beach. We supply several kayaks paddle boards canoes and tubes . You will be required to sign a waiver to use them and you Must wear lifejackets .The home is located down a private gravel road .We are only 20 miles from the city of Portland, Old Orchard beach, Lake Sebago. Come explore and relax. 2 hours from Boston

Home in Harpswell

4.94 out of 5 average rating, 120 reviews

Brand new Scandinavian cottage: dock & kayaks!

Brand new architectural cottage and detached 'boathouse' with sweeping elevated ocean views both east and west, private waterfront lawns and deep water dock with kayaks. This property was built in 2020 so expect a fresh and clean experience on one of Harpswell's most private peninsulas. Watch the sunrise from the cantilevered 2nd floor deck, sit by the campfire on your private lawn oceanside, or walk down to the dock for a paddle in the west facing protected cove. The best of coastal Maine!

Home in Harpswell

4.89 out of 5 average rating, 114 reviews

Rising Tide Times - quintessential Maine cottage

Out of State guests please read the Maine State COVID-19 restrictions currently in affect. Classic Maine cottage on the end of a point, surrounded by water on 3 sides provides stunning views. The perfect backdrop for the quintessential cottage vacation. Features spacious decks, direct tidal access for kayaking, and outdoor firepit. 15 min to downtown Brunswick/45 min to Portland. We even have Kayaks onsite for guests to paddle around Cards Cove. Perfect for couples and families!

Guest favourite

Cabin in Harrison

4.99 out of 5 average rating, 123 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

Guest favourite

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.

Home in Limerick

4.8 out of 5 average rating, 15 reviews

Sokokis Cottage Lakefront cottage w/ dock kayaks

Just 2 hours from Boston and 1 hour from Greater Portland, ME, Sokokis Lake is a fantastic ice fishing spot! Relax under our majestic willow tree with stunning lake views at every turn. During the warmer months, explore the lake in our 2 kayaks or launch your own boat from the public ramp neaby. Enjoy evenings by the fire pit while watching the sunset. Plus, a supermarket, ice cream, fried seafood, and pizza are just a short walk away. Your lakeside escape awaits!

Vacation rentals for every style

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Houses

A space that's all yours, with room for everyone

Cabins

Kick off your hiking boots at these rustic lodgings

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Cumberland County kayak rentals

Free parking on premises

Air conditioning

House rentals with a kayak

Guest favourite

Home in Brunswick

5 out of 5 average rating, 13 reviews

Coastal Mere Point Home

Guest favourite

Home in Sabattus

4.88 out of 5 average rating, 16 reviews

The Cliff House

Guest favourite

Home in Harrison

5 out of 5 average rating, 37 reviews

Long Lake Gorgeous Views & Private Sandy Beach #1

Guest favourite

Home in Windham

4.93 out of 5 average rating, 117 reviews

Waterfront Gem walkable to Restaurants!

Guest favourite

Home in Falmouth

4.95 out of 5 average rating, 80 reviews

Beautiful lake-side home close to Portland Maine

Guest favourite

Home in Harpswell

4.94 out of 5 average rating, 49 reviews

Maine Ocean Waterfront - Family, Rustic Getaway!

Guest favourite

Home in Windham

4.9 out of 5 average rating, 39 reviews

The Lake House

Guest favourite

Home in Casco

4.93 out of 5 average rating, 14 reviews

Waterview Lake House

Cottage rentals with a kayak

Guest favourite

Cottage in Falmouth

5 out of 5 average rating, 42 reviews

Cobb Cottage: Lake Beachfront Fri-Fri June-Aug

Guest favourite

Cottage in Oxford

5 out of 5 average rating, 20 reviews

Sandy Ridge Cottage: Your Tranquil Maine Getaway

Guest favourite

Cottage in Windham

4.91 out of 5 average rating, 43 reviews

Cozy cottage

Guest favourite

Cottage in Gray

4.96 out of 5 average rating, 51 reviews

Charming 3 bedroom cottage on Notched Pond

Cottage in Lyman

4.82 out of 5 average rating, 99 reviews

RK North : All season Waterfront cottage with dock

Guest favourite

Cottage in Harpswell

4.95 out of 5 average rating, 63 reviews

Private oceanfront cottage, great views, and float

Guest favourite

Cottage in Windham

4.9 out of 5 average rating, 77 reviews

Covered Bridge Cottage - Maine woods and river

Cottage in Waterboro

4.95 out of 5 average rating, 20 reviews

Quintessential Maine Lakefront Cottage

Cabin rentals with a kayak

Guest favourite

Cabin in Windham

4.92 out of 5 average rating, 205 reviews

Private Hilltop Cabin, Lakes and Trails Abound..

Guest favourite

Cabin in Harrison

5 out of 5 average rating, 21 reviews

Charming Lakefront Cabin Getaway

Guest favourite

Cabin in Oxford

4.93 out of 5 average rating, 27 reviews

A Serene A-Frame Cabin with Hot Tub

Guest favourite

Cabin in Oxford

4.94 out of 5 average rating, 127 reviews

Thompson Lake, winter discount. Pine Point Cottage

Guest favourite

Cabin in Waterford

4.94 out of 5 average rating, 158 reviews

Lakeside Cabin Nestled in the Pines

Guest favourite

Cabin in Bridgton

4.93 out of 5 average rating, 117 reviews

Private cabin w hot tub,skiing,firepit & mountains

Guest favourite

Cabin in Oxford

4.87 out of 5 average rating, 54 reviews

Private Lakefront Cottage, Excellent location!

Cabin in Otisfield

4.91 out of 5 average rating, 47 reviews

Charming log cabin on Crooked River in Maine

Destinations to explore