
Vacation rentals with a kayak in Windham
Find and book unique kayak rentals on Airbnb
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.

Tranquil waterfront cottage
A private clean tranquil cottage, dock, parking, deck, grill, hammock, kitchen & all amenities, bathroom, 2 bedrooms, sleeps 5, futon, WIFI, cable, bidet, washer & dryer, granite outdoor table, kayaks, paddle boards, floats, fire pit and fireplace. Minutes from great restaurants, bars, hiking trails, and shopping. The most amazing sunsets. 30 minutes from Portland. Winter rentals as well. 40 min. from Shawnee Peek, 1 mile from Seacoast tubing. This place is privately yours. Smoke free please!
Outdoor spacesLocationNearby

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.
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1 Bedroom with Beach Access
This beautifully converted 1860s carriage house loft blends historic charm with modern comfort. Tall vaulted ceilings showcase the exposed beams of the original timber framing, while a sliding barn door adds rustic character to the space. Nestled in a tranquil neighborhood, the apartment offers beach access to our neighborhood's pond—perfect for swimming or kayaking on sunny days. Conveniently located near North Windham businesses, 9 minutes from I-95 in Gray and 25 minutes from Portland.
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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.
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Beautiful lake-side home close to Portland Maine
A peaceful & charming renovated old home with private dock on Highland Lake, Falmouth Maine, 20 mins from Portland. *Contact us for longer winter availability! **June/July/Aug, Sat-Sat 7 day min Enjoy beautiful sunsets, canoeing, kayaking, paddle-boarding or fishing on the lake. Or take a short drive to downtown Portland, visit Old Port restaurants & bars, local breweries, Freeport outlet shopping, ski resorts, hiking and walking trails, golf courses, indoor/outdoor cinemas, and more!
LocationOutdoor spacesSleep quality

StreamSide Getaway- HOT TUB / AC/ Wi-Fi
The Streamside Getaway offers a luxurious glamping experience in a new solar and wind-powered Geodome. Equipped with custom furniture, new hot tub,luxury appliances, free high speed wifi, AC/Heat Unit and modern bathroom and kitchen facilities, guests can enjoy a homely and comfortable stay in nature. A glamping site built in 2022 offers a contactless check-in process with a custom key code. Additionally, we have added archery, axe throwing, and kayaks to enhance your outdoor activity!
Outdoor spacesValueTV

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!
ValueLocationSleep quality

Lakefront, Dock, Kayaks, & SUPs-Windham Wind Down
Welcome to Windham Wind Down, your peaceful getaway in Windham, Maine! As you step into this charming lake house, you’ll be greeted by beautiful views and the fresh scent of the surrounding pines. Whether you're here for adventure or relaxation, this home provides everything you need for an unforgettable stay including private lake access. Spend your days kayaking, paddle boarding, or fishing on the lake off of the private dock, and unwind by the fire pit in the evening.
LocationValueHospitality

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.
ValueOutdoor spacesParks

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.
LocationValueCheck-in

Waterfront, Wood stove & Private beach, Solo Stove
Welcome to the Luna Lake House, your very own lakefront retreat! Just 2 hrs from Boston and 1 hour from Portland, this is the perfect getaway. You get the entire house to yourself! This 1,810 sq ft house has 100 ft of private waterfront, a wood burning stove, private dock (June-October) and outdoor bonfire pit for your enjoyment. With incredible sunset views and it’s amazing location, you will make lasting memories in this one of a kind experience.
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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!
ValueOutdoor spacesQuiet
Popular amenities for Windham kayak rentals
House rentals with a kayak

Mirror Pond Cottage
Outdoor spacesLocationDecor

The Loons' Nest: Lakefront oasis w/ hottub
LocationOutdoor spacesWalkability

Kayak to the Causeway-50s cottage with modern vibe
Outdoor spacesValueCheckout

Golden Hour Getaway- A Sebago Stay in the Basin
Outdoor spacesLocationQuiet

Lakehouse on Highland Lake
LocationOutdoor spacesAccuracy

Serene Modern Lakefront Escape l 20 min Portland
LocationOutdoor spacesGetting around

Lakefront | Dock + Fire Pit Near Sebago & Portland
Outdoor spacesLocationCheck-in

Sunset & Lake View, Theater, HTub, Xbox, Mini Golf
Outdoor spacesLocationCondition
Cottage rentals with a kayak

Gorgeous Romantic Lakefront Getaway
Outdoor spacesLocationNearby

Rising Tide Times - quintessential Maine cottage
ValueLocationCondition

Thompson Lake, No Cleaning Fee Pine Point Cottage,
ValueLocationSleep quality

Coastal Waterfront Cottage in West Bath
Outdoor spacesValueNearby

Cozy Waterfront Cottage w/ Private Dock & Kayaks
ValueLocationQuiet

Cozy waterfront home on Merrymeeting Bay.
LocationOutdoor spacesWalkability

Charming Designer Cottage on Marsh
ValueLocationKitchen

The Loon's Nest Cottage
LocationOutdoor spacesLayout
Cabin rentals with a kayak

Sunday River & Lake Chalet, 2 Kitchens, Hot Tub
ValueOutdoor spacesAccuracy

Idyllic Lakeside Cabin Winter Getaway
Outdoor spacesValueWalkability

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

The Conscious Cabin | Getaways + Retreats
Outdoor spacesLocationSleep quality

Private cabin with lake access, hot tub & firepit!
ValueOutdoor spacesGrill

Bear Cabin
Outdoor spacesLocationWifi

Barrett’s Cabin-Lakes Region-Private Trails
Outdoor spacesValueCheck-in

Private Lakefront Cabin in Woods near Sunday River
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When is the best time to visit Windham?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 918 | ﺩ.ﺇ 1,102 | ﺩ.ﺇ 1,039 | ﺩ.ﺇ 966 | ﺩ.ﺇ 1,061 | ﺩ.ﺇ 1,172 | ﺩ.ﺇ 1,414 | ﺩ.ﺇ 1,421 | ﺩ.ﺇ 1,102 | ﺩ.ﺇ 1,047 | ﺩ.ﺇ 1,135 | ﺩ.ﺇ 1,061 |
| Avg. temp | -6°C | -4°C | 1°C | 6°C | 12°C | 18°C | 21°C | 20°C | 16°C | 10°C | 4°C | -2°C |
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- Sebago Lake
- Ogunquit Beach
- Wells Beach
- Story Land
- Long Sands Beach
- Popham Beach, Phippsburg
- Short Sands Beach
- Willard Beach
- York Harbor Beach
- Scarborough Beach
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- Fortunes Rocks Beach
- Conway Scenic Railroad
- Popham Beach State Park
- Pleasant Mountain Ski Area
- Wolfe's Neck Woods State Park





