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Vacation rentals with a kayak in Cumberland County

Find and book unique kayak rentals on Airbnb

Top-rated kayak rentals in Cumberland County

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Treehouse in Sanford

4.9 out of 5 average rating, 480 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.

Home in Naples

4.98 out of 5 average rating, 156 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.

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.

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.

Home in Oxford

5 out of 5 average rating, 195 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.

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.

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.

Chalet in Naples

4.96 out of 5 average rating, 104 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 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.

Guest suite in Windham

4.92 out of 5 average rating, 172 reviews

Millers Private Studio on Highland Lake

If you're looking for a quiet, cozy getaway with private Highland Lake access this is the place for you. Private deck to enjoy your morning coffee, close to everything but in a country setting. 15 minutes from 95, Portland ME and Sebago Lake Region. Small boat launch available, Swimming & Fishing . Large back yard and a great window view of the lake. Wifi 100(mbps) for a work from home atmosphere.

Vacation rentals for every style

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Houses

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Cottages

Quaint homes, peaceful surroundings

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Cumberland County 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 Gray

4.97 out of 5 average rating, 33 reviews

Little Sebago Lakefront Getaway

Home in Sweden

4.98 out of 5 average rating, 51 reviews

New Waterfront Near the White Mountains and Skiing

Home in Windham

4.92 out of 5 average rating, 25 reviews

Lakehouse on Highland Lake

Home in Naples

4.9 out of 5 average rating, 39 reviews

Trickey Moose Family Retreat | Firepit Near Skiing

Home in Falmouth

5 out of 5 average rating, 28 reviews

Modern Maine Lake House near Portland

Home in Shapleigh

4.98 out of 5 average rating, 126 reviews

Secluded Lakehouse-2 private docks*Hottub*big yard

Home in Windham

5 out of 5 average rating, 34 reviews

Cozy Camp on the lake

Cottage rentals with a kayak

Cottage in Windham

4.91 out of 5 average rating, 85 reviews

Tranquil waterfront cottage

Cottage in Raymond

5 out of 5 average rating, 21 reviews

Red Bird Cottage

Cottage in West Bath

4.9 out of 5 average rating, 49 reviews

Coastal Waterfront in West Bath

Cottage in Standish

4.92 out of 5 average rating, 116 reviews

Peaceful Lakeside Maine Retreat

Cottage in Standish

4.95 out of 5 average rating, 87 reviews

The Loon's Nest Cottage

Cottage in Windham

4.89 out of 5 average rating, 75 reviews

Covered Bridge Cottage - Maine woods and river

Cottage in Buxton

4.98 out of 5 average rating, 142 reviews

Peaceful Cottage Retreat on Maine Flower Farm

Cottage in Sebago

5 out of 5 average rating, 84 reviews

Recently renovated waterfront! Cedar Side Cottage

Cabin rentals with a kayak

Cabin in Windham

4.92 out of 5 average rating, 204 reviews

Private Hilltop Cabin, Lakes and Trails Abound..

Cabin in Bridgton

5 out of 5 average rating, 13 reviews

Cozy Cabin at Beaver Pond, no cleaning fee

Cabin in Buxton

5 out of 5 average rating, 18 reviews

Brooksie's Bungalow

Cabin in Waterford

4.94 out of 5 average rating, 158 reviews

Lakeside Cabin Nestled in the Pines

Cabin in Brownfield

4.95 out of 5 average rating, 42 reviews

Amish built cabin on 280 acres near North Conway

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 Naples

4.85 out of 5 average rating, 40 reviews

Cabin on the Cove

Destinations to explore