
House holiday rentals in Windham
Find and book unique houses on Airbnb
Quick stats about house rentals in Windham

Total holiday rentals
Explore 90 holiday rentals in Windham

Nightly prices starting at
Windham holiday rentals start at €53 per night before taxes and fees

Verified guest reviews
Over 2,930 verified reviews to help you choose

Family-friendly holiday rentals
80 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
90 of Windham holiday rentals include wifi 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 house rentals in Windham
Guests agree: these houses are highly rated for location, cleanliness and more.

Amazing Bay View Home with Hot Tub
This enchanting 2-bedroom home is a coastal dream come true! Luxurious and well-appointed, Casco Bay House sleeps up to six, provides a five-star stay, offers all of the comforts of home AND a relaxing hot tub spa. With stunning views of the water, the house also has easy access to dining, shopping, and sightseeing in Portland's lively Old Port district (just 5 minutes away). Whether you seek quiet tranquility or want to hit the town, this waterside house is the perfect home away from home!

Cozy Maine Cottage • Near Jetport & Coast
Cozy Cottage Retreat w/ Loft near Portland Welcome to your Maine escape. Reno barn offers a warm, cottage-inspired atmosphere with character, an open loft, and inviting spaces for rest and connection. Located mins from the airport and within walking distance to Allagash Brewing Company and other local favorites. A quick drive to downtown Portland, beaches, lighthouses, and live music. End your evenings on the private back deck — wine in hand, stars overhead, and nothing but quiet around you.

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.

*1MMview*Bar,Hot Tub,3mins2Pleasant Mnt, Pool tab.
This special, completely renovated place can host your family gathering or group of friends in an inviting setting. This unique house with a private bar, spa, and a pool table will satisfy all your vacation needs! Located close to everything, but absolutely quite and private 20 acres property! It is situated on a ridge with a spectacular mountain view. Our house offers comfort & entertainment. The property will give you the full vacation in the woods experience. This is just what you need!

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.

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!

Maine Lakes Region house (private hot tub)
Cozy new construction, Chalet style, year-round house, on 9 wooded acres. Lots of Privacy, Short drive to Ski slopes, snowmobile trails, hiking, or beautiful lake to swim, or kayak. Gage beach a 10-minute drive. Close to great hiking, Also Shawni peak and Sunday River. Great restaurants, Mt Washington, NH shopping outlets. Full Desk / office, 200 mb of streaming. Wi-Fi, Netflix via ROKU, Canines only, NO CATS, NO EXCEPTIONS. Portable generator in the event of a power failure provided.

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!

Higgins Beach *New* Beach Home & Private Offices
Custom designed contemporary at the beach. Perfect for a relaxing getaway, visiting family and friends or working remotely. Chef's kitchen w/ high end appliances, granite countertops, enclosed porch grill area. 3 bedrooms and 2 private offices Huge windows and amazing views from all of the rooms highlight the natural beauty of high tides, sun rises and sun sets. Wonderful beachfront walks and beautiful surroundings inside and out. Easy proximity to Portland's Old Port.

New and Spacious Family Home Close to Sebago Lake
Full of light and thoughtful touches, this giant five bedroom home is perfect for your Sebago Lake getaway. Spend your evenings relaxing or entertaining on the spacious deck and days on the water. Perfect for family fun and couples' retreats, this home is a fantastic home base to explore the Sebago Lake Region. Enjoy a fully air conditioned home with mini splits in every room. Bedrooms include 4 King, 1 Full, and 5 Twin beds. Bathrooms include 2 walk in showers and one bathtub.

Beautiful Home In Gorham Maine
Well appointed, bright and sunny apartment for two people in a quiet neighborhood. Large private back yard, formal gardens and pond, elevated deck, well stocked kitchen. 25 mins. to downtown Portland and the seacoast area. Minutes to local nature trails, swimming, kayaking, dining, supermarket & bakeries. ** NO PROFILE/REVIEWS? please provide a little info about whose coming, ie, name/age/occupation, reason of visit, etc, and any other info you wish to provide. Thank you!

The LOTUS welcomes you, stay a while
The Lotus is your zen home away from home. Enjoy peace and tranquility on your private back deck, the amazing salt water hot tub (exclusively use) new sauna, heated seasonal outdoor shower, deep bathtub (showering is tricky for people taller then 5'5)with bluetooth speaker.Comfortable king size bed with European bedding and a single fold out foam mattress on the 1st floor, that was just finished as another relax area, with 70" TV, record player, hammock & hanging chair.
Popular amenities for house rentals in Windham
House rentals with a pool

Faith Lane with community pool

Bubbles & Pines - Pool, HotTub, Lg Deck, ME Coast

The Lodge at Hidden Pines

Unique Church Accommodation • Sebago Lake • Pool • Fire Pit

Ski Chalet|Ping-Pong|Fire Pit|5 min -> Slopes

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

There's No Place Like Home

River Access|Gas stove|Min to N. Conway, Attitash
Weekly house rentals

Maine Vacation Home on the Water

cozy 3 bedroom ranch with deck and screen porch

Enjoy Sunsets at Welcoming Lake Front Property

Lakefront, Dock, Kayaks, & SUPs-Windham Wind Down

Lakeside Modern Retreat

Serene Modern Lakefront Escape l 20 min Portland

Coveside on Little Sebago

Windham Lake Retreat | Knotty Pine Cabin Fire pit
Private house rentals

The Lazy Hummingbird - Little Sebago Home w/ Sauna

The Lake House

Private Beach Retreat on Sebago Lake w/ Bungalow

Lakehouse on Highland Lake

Golden Hour Getaway- A Sebago Stay in the Basin

Cozy Lakefront Cabin Near Portland

Cozy Lakefront Cabin-Private Dock-Kayaks-Firepit

Arthur's Place • Sebago Lakefront • Near Windham
When is the best time to visit Windham?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €241 | €219 | €248 | €207 | €241 | €297 | €351 | €338 | €274 | €241 | €241 | €221 |
| 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 |
Destinations to explore
- New York City Holiday rentals
- Montreal Holiday rentals
- Boston Holiday rentals
- Québec City Holiday rentals
- Jersey City Holiday rentals
- Newark Holiday rentals
- Portland Holiday rentals
- Mont-Tremblant Holiday rentals
- Providence Holiday rentals
- Newport Holiday rentals
- York County Holiday rentals
- Cambridge Holiday rentals
- Beachfront rentals Windham
- Cottage rentals Windham
- Family-friendly rentals Windham
- Pet-friendly rentals Windham
- Rentals with beach access Windham
- Rentals with lake access Windham
- Rentals with a firepit Windham
- Rentals with a fireplace Windham
- Rentals with a patio Windham
- Rentals with outdoor seating Windham
- Waterfront rentals Windham
- Rentals with a kayak Windham
- Rentals with a washing machine and dryer Windham
- House rentals Cumberland County
- House rentals Maine
- House rentals United States
- Sebago Lake
- Ogunquit Beach
- Wells Beach
- Story Land
- Long Sands Beach
- Popham Beach, Phippsburg
- Willard Beach
- York Harbor Beach
- Short Sands Beach
- Scarborough Beach
- Pemaquid Beach
- Footbridge Beach
- Pemaquid Point Lighthouse
- East End Beach
- Cape Neddick Beach
- Coastal Maine Botanical Gardens
- Gooch's Beach
- Popham Beach State Park
- Cranmore Mountain Resort
- King Pine Ski Area
- Hills Beach
- Conway Scenic Railroad
- Wolfe's Neck Woods State Park
- Crescent Beach State Park





