Vacation rentals with a kayak in Cumberland

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Top-rated kayak rentals in Cumberland

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Guest favorite

The cabin's exterior is captured through a flickering flame, showcasing large glass windows that invite natural light. Surrounded by lush trees, the cozy structure features a modern design, blending seamlessly with the serene outdoors.

Home in Naples

4.99 out of 5 average rating, 146 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 favorite

A collection of five kayaks and one canoe is positioned along the shore, next to tall grasses. The vibrant colors of the kayaks contrast against the calm water of Merrymeeting Bay. The serene landscape is framed by trees in the background, illustrating a peaceful outdoor setting.

Cottage in Topsham

4.94 out of 5 average rating, 268 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 favorite

A wooden dock extends into the tranquil lake, surrounded by lush greenery and distant forested hills. The calm water reflects the clear blue sky, creating a serene setting for relaxation and outdoor activities.

Farm stay in Norway

4.96 out of 5 average rating, 211 reviews

Waterfront Home on Norway Lake - Hillcrest Farm

Serene parklike setting on 11-acres with 1,300-ft of frontage on Norway Lake. Newly renovated 1 bedroom apartment with full kitchen in historic farmhouse has separate access for complete independence. Only 35 min to Sunday River & 1 mile to downtown Norway. Direct connection to miles of hiking, biking & ski trails on Shepherd's Farm Preserve. Fish from our dock, use our canoes and kayaks, rent boats from the local marina or watch abundant wildlife from the deck - unlimited outdoor activities!

Top guest favorite

A charming waterfront cottage is presented with a bright blue door and two red chairs on a stone patio. Lush greenery surrounds the property, enhancing its inviting exterior. The tranquil waters of Pettingill Pond can be seen in the background, reflecting the sky.

Home in Windham

4.94 out of 5 average rating, 158 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.

Top guest favorite

A serene waterfront scene features a small boat gliding across calm waters, reflecting the surrounding buildings. A cluster of white cottages stands on pilings, with a dock visible, under a soft pastel sky as day transitions to evening.

Cottage in Brunswick

5 out of 5 average rating, 180 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, 245 reviews

Waterfront Private Apartment just 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.

Guest favorite

The modern lakehouse structure is framed by tall trees, featuring large windows that provide ample natural light. A spacious deck is equipped with lounge chairs and picnic tables, while the lower level includes a hot tub. A clear lawn extends towards a serene backdrop.

Home in Oxford

5 out of 5 average rating, 213 reviews

The Modern Lakehouse

This modern lakehouse is situated on Hogan Pond in Oxford Maine. Here you can stay with all the comforts of a beautiful lakehouse built in 2020 while being feet from the water. This is a great place to vacation whether you prefer the private sandy beach, the A/C inside complete with Smart TV cable and Wifi, or the hottub! Sip a drink at the bar while watching the game or use the grill on the deck but be sure to use the built in sound system to play your music throughout the house and deck.

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, 248 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 serene lakeside view reveals a wooden dock with a reclining chair near the water's edge. Vibrant autumn leaves frame the scene, contrasting with the clear blue sky and calm lake. Rocky terrain adds natural texture to the tranquil environment, inviting relaxation.

Cabin in Raymond

4.93 out of 5 average rating, 164 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

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.

Guest favorite

The two elevated structures of the tree dwelling are connected by a rope bridge, surrounded by lush green trees. Natural materials are utilized in the design, which includes a balcony and multiple levels that create a unique, inviting silhouette against the forest backdrop.

Treehouse in Georgetown

4.98 out of 5 average rating, 445 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!).

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, 448 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.