Vacation rentals with a kayak in Cumberland County

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Top-rated kayak rentals in Cumberland County

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Guest favorite

Home in Naples

4.99 out of 5 average rating, 150 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

Two kayaks, one yellow and one blue, are positioned side by side on a calm riverbank. The surface of the water reflects the overcast sky and surrounding trees, creating a serene scene perfect for outdoor activities.

Cottage in Buxton

4.97 out of 5 average rating, 157 reviews

Peaceful Cottage on Maine Flower Farm

Overlooking the gardens at Ferris Farm, our family-owned specialty cut flower farm, this charming cottage offers a peaceful retreat to relax and reconnect with nature. Take in garden views, sip coffee on the deck, wander through the flowers, kayak the river, and end your day with a cozy bonfire under the stars. Use the cottage as your home base to explore beaches, or head into Portland for breweries, coffee shops, and great dining. Perfect for a solo retreat, romantic escape, or work getaway.

Top guest favorite

A wooden dock extends into the calm waters of Littlefield Pond, surrounded by lush greenery. The still surface of the water reflects the blue sky and trees, creating a serene atmosphere. Delicate plants can be seen in the water near the dock, enhancing the natural beauty.

Treehouse in Sanford

4.9 out of 5 average rating, 543 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.

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 Naples

4.98 out of 5 average rating, 173 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

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, 272 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

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, 129 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.

Guest favorite

Home in Windham

4.95 out of 5 average rating, 164 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

Cottage in Brunswick

5 out of 5 average rating, 183 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

A modern lakehouse is visible from the sandy beach, featuring multiple levels with large windows. Pathway lights illuminate steps leading to the entrance. Surrounding the fire pit, several lounge chairs offer a relaxing space, complemented by shaded seating under umbrellas.

Home in Oxford

5 out of 5 average rating, 214 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.

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

4.93 out of 5 average rating, 167 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 bright living room features a gray sofa with orange accent pillows, paired with an orange armchair and matching ottoman. Natural light streams in through large windows, illuminating the hardwood floor and a circular woven area rug that adds texture to the space.

Apartment in Cape Elizabeth

4.98 out of 5 average rating, 120 reviews

Beautiful Kettle Cove Apt Steps to Beaches

Enjoy some of the Portland area’s best destinations year-round. This sunny, 1 BR ground floor apt in Cape Elizabeth has seasonal water views and is nestled between Kettle Cove, Crescent Beach, and Two Lights State Parks. Fields, forests and ponds are a stroll away while downtown Portland is an easy 15-minute drive. The apartment is a great base to explore Southern Maine from and an equally great location to chill out and soak in coastal Maine’s restorative water and air.