Vacation rentals with a kayak in Cumberland

Find and book unique kayak rentals on Airbnb

Top-rated kayak rentals in Cumberland

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

0 of 0 items showing

1 of 3 pages

Guest favorite

Home in Naples

4.99 out of 5 average rating, 151 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.

Top guest favorite

An aerial view of Long Lake reveals a sandy beach bordered by trees and a gentle shoreline. Kayaks are arranged on the beach, while docks extend into the water. Nearby, residential buildings provide a sense of community along the lake's edge.

Home in Pleasantdale

4.98 out of 5 average rating, 174 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 favorite

The lakehouse is viewed from the water, showcasing its two-story structure with large windows reflecting on the lake's surface. A private shoreline is framed by lush greenery and suggests areas for outdoor relaxation, while kayaks are visible by the water's edge.

Cottage in Sabattus

4.95 out of 5 average rating, 131 reviews

Maine lakehouse 2.5 hrs from BOS, 40 min Portland

Beautiful lake living: 2.5 hours from Boston, 40 min. from Portland. This cozy 2-bedroom home on Lake Sabattus with 110 feet of private lake frontage, sleeps four. All the amenities of home incl. a SS kitchen with newer appliances, air conditioning. Minutes to Lewiston/Auburn - close to dining and stores. Spend your days swimming, canoeing, kayaking and fishing, use our grills or lobster pot to prepare your dinner and relax by the fire pit, toasting s'mores while watching the gorgeous sunsets.

Top guest favorite

Cottage in Brunswick

5 out of 5 average rating, 184 reviews

Lobstermen's ocean-front cottage

Be our guests & experience the life & beauty of Midcoast Maine. Relax & 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, and now oyster farming property we call, Gurnet Village. Located right on historic Route 24, we are conveniently situated between Brunswick & the islands of Harpswell. All rooms have ocean views. The tidal beach & the floating dock (May-Dec) is ideal for seasonal fishing, lounging & swimming.

Top guest favorite

An aerial view captures a custom-built home nestled within a dense wooded landscape. Surrounding trees create a natural border, while the waters of Harraseeket Cove are visible, showcasing the blend of forest and coastal scenery.

Guest suite in Freeport

4.97 out of 5 average rating, 249 reviews

Waterfront Private Apartment only 5 min to LLBean!

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 8 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.

Top guest favorite

A spacious yard features a hammock set up for relaxation, accompanied by a fire pit area. The light yellow house stands in the background, offering multiple levels and direct access to outdoor spaces. Lush greenery surrounds the property, contributing to a serene outdoor setting.

Guest suite in Westbrook

4.93 out of 5 average rating, 250 reviews

Awesome open space in Westbrook near Portland, ME!

Welcome!! We're excited to share our house with you! You'll get the whole ground level of the house - two very large clean modern rooms with a private entrance, bathroom, and direct yard access to the hammock, fire pit, and wildlife. Off-street parking for 2 cars, kitchenette, fast wifi, smart TV, heat or A/C, and much more! We will give you awesome tips on everything in the area and beyond! 15 mins downtown Portland (Uber/Lyft available) 1 mile from I-95 11 mins from the airport

Guest favorite

A blue kayak is positioned alongside the cabin's exterior, with paddles resting above it. Various life jackets are hung nearby, showcasing bright colors. The surroundings are shaded by tall trees, creating a natural setting for outdoor activities.

Cabin in Raymond

4.92 out of 5 average rating, 169 reviews

Rustic, cozy cabin on Sebago Lake. A hidden gem.

Step out of the screened in patio to lakeside relaxation. Dive into crystal waters, snorkel or float with a cool beverage. Kayak or canoe out to Turtle Cove and enjoy the wildlife in this natural waterway teeming with birds to include our resident Blue Heron, ducks, geese, and loons who make this place their home. We have the fortune of bald eagle pairs in several tall pines. Turtles sunning on doting rocks and lily pads in bloom greet us each day. It is a natural water landscape.

Guest favorite

A cabin featuring a wooden exterior is nestled among tall trees and lush greenery. Large windows allow natural light to illuminate the interior, while ferns grow densely at the base, enhancing the serene, forested setting.

Tiny home in Bowdoinham

4.91 out of 5 average rating, 132 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.

Top guest favorite

A private dock extends over calm waters, surrounded by vibrant autumn foliage. A flag is displayed proudly atop the dock, which features a ladder for easy access to the lake. Reflections of trees are visible on the water's surface.

Cabin in Oxford

4.95 out of 5 average rating, 146 reviews

Thompson Lake, No Cleaning Fee Pine Point 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.

Top guest favorite

The Birch Ledge Guest House is a two-story structure nestled among trees, featuring a rustic exterior with a metal roof. A small patio with two chairs is positioned at the entrance, and a staircase leads to the loft area. Lush greenery surrounds the home.

Home in Hollis

4.99 out of 5 average rating, 452 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.

Top guest favorite

A compact sleeping area features a queen-sized bed with a decorative white throw. Flanking the bed are two bedside tables, each topped with a lamp. Neutral-colored walls and soft lighting create a calm and inviting ambiance.

Apartment in Windham

4.99 out of 5 average rating, 165 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.

Guest favorite

The image captures a serene lakeside view, showcasing the calm water reflecting the vibrant blue sky. Tall trees provide a natural backdrop to a white house set back from the shore, with a wooden deck visible among the greenery.

Cottage in Windham

4.83 out of 5 average rating, 151 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!