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Vacation rentals with a kayak in Windham

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Quick stats about vacation rentals with a kayak in Windham

  • Total vacation rentals

    Explore 70 vacation rentals in Windham

  • Nightly prices starting at

    Windham vacation rentals start at ﺩ.ﺇ 294 per night before taxes and fees

  • Verified guest reviews

    Over 2,790 verified reviews to help you choose

  • Family-friendly vacation rentals

    60 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    70 of Windham vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Windham rentals

  • 4.9 Average rating

    Windham stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated kayak rentals in Windham

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

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Top guest favorite
A hobbit house is nestled among lush green trees, with a sloping earth-covered roof adorned with grass and ferns. The rounded front features a large window framed in white, complemented by a natural stone border, emphasizing the home's connection with its woodland surroundings.
Earthen home in Sanford

Luxury Year-round Hobbit House w/ private hot tub

Fern Hollow 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.

4.92 out of 5 average rating, 132 reviews
Top guest favorite
A fire pit area is surrounded by colorful Adirondack chairs on a gravel path. Large natural stones are placed near the pit. In the background, a cedar-shingled cottage is elevated with a spacious deck and features a green roof amidst a wooded setting.
Home in Naples

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.

4.98 out of 5 average rating, 188 reviews
Top guest favorite
A serene waterfront scene is presented, showcasing a calm lake framed by trees. In the foreground, a small dock extends into the water alongside a moored boat. Rocky shorelines feature boulders partially submerged, adding to the natural beauty of the landscape.
Guest suite in Raymond

Sebago Lake Waterfront Studio

Beautiful Lakehouse studio apartment located on Sebago Lake. A perfect spot to take in the gorgeous lake view w/sandy beach. The lake is great for swimming, boating, kayaking, and water activities. Backyard to enjoy lawn games, grill, and relax by the outdoor fire-pit. This space has a cozy modern feel, for a perfect summer vacation or fall leaf-peeping. Located within 40 minutes of Portland and the beautiful Maine coast. This space is furnished to sleep 4. Dock available for $100 per stay.

4.96 out of 5 average rating, 105 reviews
Guest favorite
A bright living area features a wooden floor and a cozy, gray sofa. A blue writing desk is positioned beside a window, adorned with decorative bookshelves and plants. A vintage-style wood stove is set against a brick wall, with warm light enhancing the inviting atmosphere.
Home in Freeport

Charming Historic Freeport House

Bring the whole family to this historic house just minutes from downtown Freeport and the LL Bean flagship stores. The cozy central kitchen and dining are flanked by two separate living rooms making plenty of room for fun and relaxation! With two twin beds, toddler bed and full-sized crib we can accomodate any family. Catch glimpses of the Harraseeket River from this updated 1840s home on a half acre. A wonderful jumping off point for both Portland and the natural beauty of Mid-coast Maine!

4.89 out of 5 average rating, 114 reviews
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

Lobstermen's ocean-front cottage

Be our guests & experience the life & beauty of Midcoast Maine. Relax with ocean views, warm up in the sauna or take a refreshing dip. Our cottage is part of Gurnet Village, an over 100-year-old working lobstering & oyster farming property on historic Route 24, between Brunswick & Harpswell. Expect boats, workers, road traffic, gear, and the occasional sounds & smells of a real Maine working waterfront. All rooms have ocean views, with access to the tidal beach & floating dock (May-Dec).

5.0 out of 5 average rating, 226 reviews
Top guest favorite
Home in Oxford

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.

5.0 out of 5 average rating, 248 reviews
Guest favorite
Home in Naples

LUX Designer Private Waterfront Hot Tub - Secluded

Escape to a luxurious, privately designed glass-walled waterfront cabin on 3+ secluded acres along the Crooked River in Naples, Maine. The river wraps around, offering total privacy, your own sandy beach, dock with direct Sebago Lake access, and state park minutes away. Unwind in the year-round hot tub, outdoor shower, hammocks, or by the see-through fireplace. Luxe bath with heated floors, huge walk-in shower w/ scenic window. AC, pets welcome. Perfect peaceful retreat—come recharge!

4.98 out of 5 average rating, 200 reviews
Top guest favorite
Two wooden chairs are situated on a dock overlooking a calm pond surrounded by dense trees. The water reflects the sky and greenery, creating a serene backdrop. A sense of tranquility is conveyed through the peaceful atmosphere of the natural setting.
Home in Oxford

Mirror Pond Cottage

A sweet space on a pond, this cottage is perfect for those looking for a quiet getaway. We offer swimming, kayaks and a canoe, life jackets along with a raft to float on. Endless fun in the water, with no motors to be heard. This is a quiet spot and we would hate to be responsible for ruining that. We are family friendly and kids are welcome, but please leave the party at the casino (5 minutes away)! The waterfront is sandy and shallow, perfect for young ones to splash around in.

4.92 out of 5 average rating, 150 reviews
Top guest favorite
An airy living space is highlighted by tall windows that bring in natural light and showcase views of the surrounding trees. A large sectional sofa faces a flat-screen TV, complemented by a wood stove for warmth. A dining area is visible in the background.
Home in Freeport

Waterfront 5 BR Home | On Casco Bay in Freeport!

Spacious waterfront 5BR coastal retreat on Harraseeket Cove and South Freeport Harbor, perfect for kayaking, wildlife, and relaxing coastal Maine getaways. Set on 3.5 private wooded acres, the home features fast WiFi, smart TVs, outdoor dining, grills, firepit, kayaks, and peaceful water views throughout the property. Enjoy the tranquility of Maine’s coast while being only 3 minutes from Freeport’s shops, restaurants, breweries, and LLBean, with Wolfe’s Neck Woods State Park nearby.

4.96 out of 5 average rating, 147 reviews
Top 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

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 eagles in several tall pines. Turtles sunning on doting rocks and lily pads in bloom greet us each day. It is a natural water landscape.

4.93 out of 5 average rating, 184 reviews
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

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 Lakeside Tavern, or Bob's Seafood for a fish taco! This is a piece of paradise on sweet Pettingill Pond in the heart of Windham.

4.95 out of 5 average rating, 205 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

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.

4.99 out of 5 average rating, 510 reviews

Popular amenities for Windham kayak rentals

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a kayak

Top guest favorite
The lakefront property is nestled among trees, showcasing a charming house with large windows and a deck. A private dock extends into the calm water, providing space for seating. A sandy beach area leads to the water's edge, creating a serene natural setting.
Home in Limerick

Waterfront, Wood stove & Private beach, Solo Stove

5.0 out of 5 average rating, 142 reviews
Top guest favorite
Home in Limerick

Lakefront Getaway

4.93 out of 5 average rating, 150 reviews
Top guest favorite
Home in Wakefield

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

4.98 out of 5 average rating, 210 reviews
Guest favorite
Home in Auburn

The Loons' Nest: Lakefront oasis w/ hottub

4.9 out of 5 average rating, 125 reviews
Guest favorite
A serene view of a lake at sunset is presented, showcasing soft hues of orange, pink, and purple reflected on the water. Silhouettes of trees line the shore, while the calm surface creates gentle ripples, inviting relaxation and contemplation.
Home in Manchester

Lakeside retreat on quiet cove on Cobbessee Lake!

4.84 out of 5 average rating, 115 reviews
Guest favorite
Home in Falmouth

Highland Lake Cottage/Waterfront/Dock/Kayaks

5.0 out of 5 average rating, 7 reviews
Top guest favorite
A spacious backyard features a firepit surrounded by six blue Adirondack chairs, creating a cozy gathering area. The well-maintained lawn is bordered by trees, and the home is visible in the background with warm lighting illuminating its deck and windows.
Home in Windham

Maine Vacation Home on the Water

5.0 out of 5 average rating, 67 reviews
Top guest favorite
A circular fire pit is surrounded by several black Adirondack chairs, set on a lush green lawn. The tranquil surface of the lake reflects the blue sky and fluffy clouds, while trees in varying shades of green line the opposite shore.
Home in Windham

Lakefront | Dock + Fire Pit Near Sebago & Portland

4.98 out of 5 average rating, 40 reviews

Cottage rentals with a kayak

Guest favorite
The exterior of the house is visible, featuring a light grey façade with multiple windows allowing natural light inside. A wooden deck is seen on the left, surrounded by trees. A patio area with stone accents is also present, offering potential for outdoor gatherings.
Cottage in Standish

Peaceful Lakeside Maine Retreat

4.92 out of 5 average rating, 139 reviews
Guest favorite
A cozy cottage exterior is depicted, featuring white siding and a green roof. A screened-in porch with comfortable seating is prominently displayed, along with a wooden entrance staircase. The surrounding area includes natural vegetation and a pathway made from red bricks, providing a welcoming access point.
Cottage in Standish

The Loon's Nest Cottage

4.96 out of 5 average rating, 107 reviews
Top guest favorite
Cottage in Buxton

Peaceful Cottage on Maine Flower Farm

4.97 out of 5 average rating, 187 reviews
Top guest favorite
A cozy cottage is nestled among trees by the beach, featuring a sandy shoreline and stacks of kayaks nearby. A serene dock extends into the water at sunset, offering tranquil views. Inside, a modern kitchen with stainless steel appliances and ample counter space invites home-cooked meals.
Cottage in Sebago

Recently renovated waterfront! Cedar Side Cottage

4.99 out of 5 average rating, 114 reviews
Guest favorite
Cottage in Lyman

Cozy Waterfront Cottage w/ Private Dock & Kayaks

4.83 out of 5 average rating, 121 reviews
Guest favorite
An aerial view captures a serene point surrounded by calm water, with lush green trees lining the rocky shore. The rocky outcrop extends into the water, providing direct access to the tidal area. The tranquil setting highlights the natural beauty of the landscape.
Cottage in Harpswell

Rising Tide Times - quintessential Maine cottage

4.88 out of 5 average rating, 136 reviews
Superhost
A view from water level shows a bright blue kayak in the foreground, with a forest of tall green trees surrounding a cabin in the background. The cabin features multiple windows that reflect the natural light and scenery.
Cottage in Parsonsfield

RiverPine Retreat - Clean & Bright Waterfront Home

4.84 out of 5 average rating, 196 reviews
Top guest favorite
A modern two-story home is set amidst a wooded area, featuring a spacious outdoor seating arrangement with a picnic table and various chairs. A fire pit and grill are present, with the soft glow of twilight highlighting the inviting exterior.
Cottage in Acton

Eclectic Lakefront Cottage on Great East Lake

4.99 out of 5 average rating, 187 reviews

Cabin rentals with a kayak

Top guest favorite
A log cabin surrounded by trees is situated near the shoreline of the Ossipee River. A wooden deck extends from the cabin, and a red tandem kayak is positioned on a small dock, creating an inviting space for outdoor activities.
Cabin in Parsonsfield

Riverfront cabin between Portland & White Mtns.

4.96 out of 5 average rating, 285 reviews
Top guest favorite
A warm and inviting living area showcases a stone fireplace framed by soft lighting. Two plush armchairs are positioned near a wooden coffee table. A cozy sofa adorned with a colorful blanket complements the wooden beams and walls, creating a tranquil atmosphere.
Cabin in Conway

The Conscious Cabin | Getaways + Retreats

4.96 out of 5 average rating, 201 reviews
Top guest favorite
The entrance of a green cabin is framed by snow-covered ground and trees, with a glimpse of a lake visible in the background. A grill is positioned near the steps, and ski equipment leans against the wall, hinting at winter activities.
Cabin in Raymond

Idyllic Lakeside Cabin Winter Getaway

4.96 out of 5 average rating, 222 reviews
Superhost
A hot tub bubbles gently, surrounded by towering trees and a serene view of Moose Pond. The water reflects the clear blue sky and is framed by a tranquil landscape, creating a peaceful atmosphere for relaxation.
Cabin in Bridgton

Waterfront,Hot tub,Private dock,Freshly renovated

4.82 out of 5 average rating, 192 reviews
Top guest favorite
Cabin in Denmark

Barrett’s Cabin-Lakes Region-Private Trails

4.96 out of 5 average rating, 232 reviews
Guest favorite
A spacious living area is adorned with warm wooden paneling and large windows that overlook the natural surroundings. Comfortable seating includes a large sectional sofa and a dark coffee table, complemented by lamps that provide soft lighting. A television is positioned on a media unit against the wall.
Cabin in Denmark

Cabin w/ Lake Access, Hot Tub, Kayaks, + Firepit!

4.96 out of 5 average rating, 188 reviews
Guest favorite
A spacious outdoor patio is surrounded by a stone path and colorful garden beds. Multiple lounge chairs are arranged around a stone fire pit, creating a cozy gathering space. Large windows offer views of the surrounding trees and provide natural light to the cabin.
Cabin in Madison

Bear Cabin

4.9 out of 5 average rating, 181 reviews
Top guest favorite
Cabin in Greenwood

Sun&Fun on the Pond! Swim, Fish, Kayak, Paddle

4.95 out of 5 average rating, 279 reviews

When is the best time to visit Windham?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ 918ﺩ.ﺇ 1,102ﺩ.ﺇ 1,039ﺩ.ﺇ 966ﺩ.ﺇ 1,061ﺩ.ﺇ 1,172ﺩ.ﺇ 1,414ﺩ.ﺇ 1,421ﺩ.ﺇ 1,102ﺩ.ﺇ 1,047ﺩ.ﺇ 1,135ﺩ.ﺇ 1,061
Avg. temp-6°C-4°C1°C6°C12°C18°C21°C20°C16°C10°C4°C-2°C

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