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Vacation rentals with a kayak in Cumberland

Find and book unique kayak rentals on Airbnb

Top-rated kayak rentals in Cumberland

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Treehouse in Sanford

4.9 out of 5 average rating, 479 reviews

Luxury Year-round Treehouse with private hot tub

The Canopy is one of 5 luxurious tiny homes that make up Littlefield Retreat, a tranquil woodland village of 3 treehouses and 2 hobbit houses – each with its own private hot tub and dock. To see all five dwellings, click on the photo to the left of “Hosted by Bryce”, then click “Show more…”. This 15-acre forest retreat on Littlefield Pond offers our guests an experience that feels like a trip up to the woods of northern Maine, but is closer to home and to all the attractions of southern Maine.

Cottage in Topsham

4.95 out of 5 average rating, 244 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.

Loft in West Gardiner

4.97 out of 5 average rating, 152 reviews

Cozy, Efficiency Apartment with Hot Tub

Keep it simple at this peaceful, centrally-located efficiency apartment. 15 minutes to Gardiner and Augusta, 15 minutes to I95/295. Less than one hour from Portland. Walk along the stream, listen to the loons or enjoy relaxing in the hot tub. If you want to paddle in a kayak, you can do that too! Eagles regularly soar overhead. Queen size bed, love seat and room enough for a pack and pay or twin air mattress. A/C, full kitchen, Keurig, microwave, toaster, dishes. Wifi and cable. Roomy parking.

Home in Windham

4.93 out of 5 average rating, 115 reviews

Waterfront Gem walkable to Restaurants!

Waterfront Oasis on Pettingill Pond. You couldn't get any closer to the water, it's steps away. There are 3 Kayaks, and a paddleboat, firepit and dock for guest use! This a great spot for swimming and watersports! This home has been newly renovated, the effect results in a simple, stylish, comfortable space for guests to enjoy. Walk to Franco's Bistro for from Scratch Italian food, or Bob's Seafood for a fish taco! This is a piece of paradise on sweet Pettingill Pond in the heart of Windham.

Guest suite in Freeport

4.97 out of 5 average rating, 205 reviews

Waterfront Private Apartment just 5 min to LL Bean

Guest apartment with private entrances, king bed, pull out sofa, kitchenette, walk-in shower, and porch facing the water providing the perfect relaxing coastal Maine experience! Custom built home on 7.5 acres tucked away in the woods with waterfront access to Harraseeket Cove & South Freeport Harbor, great for kayaking! Located 5 minutes from LL Bean and Freeport's many shops, restaurants, bars, etc. Wolfes Neck State Park and its stunning coastal trails and forests are less than a mile away.

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!

Cottage in Brunswick

5 out of 5 average rating, 148 reviews

Lobstermen's ocean-front cottage

Be our guests and experience the life & beauty of Midcoast Maine. Relax and enjoy the views, warm up in the sauna or go for a refreshing dip. The cottage is part of an over 100 year old working lobstering property right on historic Route 24, a busy thoroughfare between Brunswick & the islands of Harpswell. All rooms have ocean views. There is a beach for your kayaks and the dock (May-Dec) is ideal for seasonal fishing, exploring and swimming. Check out @gurnetvillage for recent photos.

Tiny home in Bowdoinham

4.91 out of 5 average rating, 107 reviews

Sweet Fern Cabin on Merrymeeting Bay

Nestled in the woods on 2.5 waterfront acres where the Muddy River meets Merrymeeting Bay. The cabin is 350 square feet of simple living with a panoramic view. There is a three season hot water outdoor shower and wood burning stove with plenty of wood included. Kitchen is fully stocked with cooking supplies and has off grid cold water sink. Outbuilding with composting toilet is right out the back door. Kayaks and stand up paddle board are available to rent for an additional fee.

Treehouse in Georgetown

4.98 out of 5 average rating, 421 reviews

Modern Tree Dwelling w/Water Views+Cedar Hot Tub

Stay in our custom designed tree dwelling w/ wood-fired cedar hot tub up among the trees! This unique structure is perched atop a 21-acre wooded hill sloping to water views. Enjoy stunning views from the King size bed through a wall of windows. Located in a classic coastal Maine village w/ Reid State Park's miles of beaches + famed Five Islands Lobster Co. (See 2 other tree dwellings on our 21 acre property listed on AirBnb as "Tree Dwelling w/Water Views." See our reviews!).

Cabin in Oxford

4.94 out of 5 average rating, 125 reviews

Thompson Lake, Maine. discount winter rate Cottage

A refurbish 1967 knotty pine Cottage a short walk to lake and has lake rights. Located 400 feet from lake access. For swimming, FREE docking for your boat to fish, water ski or just cruise in Thompson lake. 14 miles one of Maines cleanest lakes. 6 Bicycles, 2- kayaks, 2-16 ft canoes, a 14 ft rowboat, and a paddle boat, fishing gear, firewood available for guest at no charge for fire pit. Propane and charcoal barbeques available at cottage. THERE IS NO WIFI.

Home in Hollis

4.99 out of 5 average rating, 401 reviews

Birch Ledge Guesthouse--Four Season Maine Getaway

Both rustic and elegant, the Birch Ledge Guest House offers a cozy place to relax and recharge, whatever the season. The first floor features a spacious living room (with queen sized pull-out-couch), dining area, and small kitchen. The bathroom has a walk-in shower. The second floor is a loft accessible by a spiral staircase and has a comfy queen and two twin sized beds. The guesthouse is surrounded by quiet forest and is an easy 30 minute drive to Portland.

Rental unit in Windham

4.99 out of 5 average rating, 136 reviews

The Roost - lovely one bedroom efficiency unit

Staying at the Roost means you will be 15 minutes to the ocean, the airport and to the Old Port; 10 minutes to nearby lakes and rivers; 5 minutes to everything downtown Westbrook has to offer, including many restaurants, parks, live music venues, shopping and a movie theater: what you are looking for is nearby! Kick back and relax in this calm, stylish space with a queen-sized bed, kitchenette, dining/work area, excellent wifi, a full bathroom and a big yard.

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Popular amenities for Cumberland kayak rentals

Free parking on premises

Air conditioning

House rentals with a kayak

Home in Limerick

4.93 out of 5 average rating, 115 reviews

Lakefront Getaway

Home in Greenwood

4.98 out of 5 average rating, 105 reviews

Maine lake front getaway!

Home in Bridgton

4.98 out of 5 average rating, 101 reviews

Fish Tales Cabin

Home in Greenwood

4.96 out of 5 average rating, 132 reviews

Bright, Vintage Maine Home, Awaiting Adventure!

Home in Wakefield

4.98 out of 5 average rating, 145 reviews

Lakefront Home-Stunning Views-Hot Tub, 3100 sqft!

Home in Old Orchard Beach

4.96 out of 5 average rating, 134 reviews

Luxury Beach House Old Orchard Beach Maine

Home in Naples

4.98 out of 5 average rating, 156 reviews

Kayak to the Causeway-50s cottage with modern vibe

Home in Pittston

4.99 out of 5 average rating, 142 reviews

Riverside

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 Middleton

4.99 out of 5 average rating, 101 reviews

Lovely cottage on Sunrise Lake, Middleton, NH.

Cottage in Fayette

4.97 out of 5 average rating, 101 reviews

Classic Lakefront Maine Cabin

Cottage in Kennebunkport

4.98 out of 5 average rating, 107 reviews

Charming Designer Cottage on Marsh

Cottage in Standish

4.92 out of 5 average rating, 116 reviews

Peaceful Lakeside Maine Retreat

Cottage in Windham

4.89 out of 5 average rating, 75 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

Cottage in Buxton

4.98 out of 5 average rating, 142 reviews

Peaceful Cottage Retreat on Maine Flower Farm

Cabin rentals with a kayak

Cabin in Woodstock

4.96 out of 5 average rating, 138 reviews

Sunday River & Lake Chalet, 2 Kitchens, Hot Tub

Cabin in Windham

4.92 out of 5 average rating, 204 reviews

Private Hilltop Cabin, Lakes and Trails Abound..

Cabin in Dresden

4.98 out of 5 average rating, 238 reviews

Merrymeeting Midcoast Cabin

Cabin in China

4.89 out of 5 average rating, 171 reviews

Rustic Family Cabin on China Lake

Cabin in Waterford

4.94 out of 5 average rating, 158 reviews

Lakeside Cabin Nestled in the Pines

Cabin in Harrison

4.99 out of 5 average rating, 121 reviews

Get away at Crystal Lake

Cabin in Bridgton

4.93 out of 5 average rating, 111 reviews

Private cabin w hot tub,skiing,firepit & mountains

Cabin in Georgetown

4.82 out of 5 average rating, 95 reviews

Cozy log cabin on private pond, near Reid St Park!

Quick stats about vacation rentals with a kayak in Cumberland

Total rentals
20 properties
Nightly prices starting at
$100 before taxes and fees
Total number of reviews
940 reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace

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