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

Total vacation rentals
Explore 110 vacation rentals in Windham

Nightly prices starting at
Windham vacation rentals start at $84 CAD per night before taxes and fees

Verified guest reviews
Over 3,710 verified reviews to help you choose

Family-friendly vacation rentals
90 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
110 of Windham vacation 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.

Top Deck - Portland Property with Views!
Views, Views, Views! 2 huge decks overlooking water and city skyline. This home is adjacent to Payson’s Park – Portland’s largest park. 5-7 min ride to downtown Portland and the Old Port’s fabulous bars and restaurants. The main floor has bedroom with bath, kitchen, and living room. The upstairs has a large bedroom with bath, open room that can be used as 2nd living room or a 3rd/4th bedroom space. Sleeps 10-12. Off street parking 6-8. Large yard. Portland License #STHR-002587-2020

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.

"Good Vibes" 4 Wonderful Seasons @ Portland Home!
You will be close to everything when you stay at this centrally-located place with a pool and spacious yard! Enjoy the home and it is a quick 10 minute uber to downtown Portland to the most popular shops and restaurants. This home is located perfectly to explore greater Portland from beautiful parks/trials to the shopping outlets not far away. This is a family neighborhood and out of respect for my neighbor’s, quiet hours after 10 pm. No parties. City of Portland License #: STHR-004465-2022

*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!

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!

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.

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.

The Barnhouse with hot tub
Get away with your whole family at this peaceful home in the country. Hear the frogs chirping in the pond, birds tweeting in the treetops and watch chickens roam around. Enjoy the clear, starry nights while relaxing in the hot tub or cozying up by the fire. Centrally located between coast and mountains. Head a hour north to take the family hiking or on the slopes to enjoy the mountains. Head 40 minutes south to take in the coast and see the iconic Maine lighthouse.

Best Ski & Lake House
Spectacular, expansive, state-of-the-art log cabin—your ultimate four-season escape. Winter ski trips (just 25 minutes to Pleasant Mountain, formerly Shawnee Peak), summer fun (beaches & watersports galore), & unforgettable year-round gatherings. Chef’s kitchen with two ovens, dining for eight + bar seating, sleeps up to 12 (with 2 king beds), two living rooms, and abundant outdoor dining & lounge space, including a playground - designed to make lasting memories!

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.

Freeport Escape – LLBean | Fire Pit | 3 King | A/C
The Freeport Escape – A charming early 1900s home with modern amenities. Located in the heart of Freeport, walkable to shopping, restaurants, breweries, and the Amtrak station. Set on a private corner lot, enjoy the fire pit, porch grilling, and spacious outdoor area. Cozy up by the indoor fireplace in cooler months. Perfect for families, couples, and friends. 🛏️ 3 King Beds | Family-Friendly | ❄️ A/C | 🔥 Fire Pit | 🪵 Indoor Fireplace 📍 STRR-2022-82
Popular amenities for Windham house rentals
House rentals with a pool

OOB Oasis: 6BR Home w/ Private Pool Near Beach

Ogunquit Village 5 BDR, Heated Pool, Walk to Beach

Beach House w/ Heated Pool · Fire Pit · Kennebunk

Faith Lane with community pool

There's No Place Like Home

Moose Pond Mountain Escape

Gray Woodland Escape | Golf, Pool & Cinema

Unique Church Stay • Sebago Lake • Pool • Fire Pit
Weekly house rentals

Romantic Mirror cabin in the woods

Rustic charm close to Portland

The Modern Lakehouse

Enjoy Sunsets at Welcoming Lake Front Property

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

Lakefront | Dock + Fire Pit Near Sebago & Portland

Maine Vacation Home on the Water

cozy 3 bedroom ranch with deck and screen porch
Private house rentals

Windham Lake Retreat | Knotty Pine Cabin Fire pit

La Casita: Little Sebago Lake with hot tub!

Sebago Lake Beach Paradise

Coveside on Little Sebago

Private Beach Retreat on Sebago Lake w/ Bungalow

Lakeside Retreat | Lake Access | Grill & Fire Pit

Cozy Lakefront Cabin Near Portland

Waterfront Home w/fenced yard 15 mins to Portland
When is the best time to visit Windham?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $385 CAD | $350 CAD | $396 CAD | $385 CAD | $420 CAD | $512 CAD | $560 CAD | $539 CAD | $436 CAD | $385 CAD | $385 CAD | $353 CAD |
| 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
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- Pet-friendly rentals Windham
- Rentals with lake access Windham
- Rentals with beach access Windham
- Waterfront rentals Windham
- Rentals with a kayak Windham
- Beachfront rentals Windham
- Cottage rentals Windham
- Family-friendly rentals 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
- Short Sands Beach
- Willard Beach
- York Harbor Beach
- Scarborough Beach
- Cape Neddick Beach
- Footbridge Beach
- Pemaquid Beach
- Pemaquid Point Lighthouse
- Coastal Maine Botanical Gardens
- Cranmore Mountain Resort
- Hills Beach
- Gooch's Beach
- East End Beach
- Fortunes Rocks Beach
- Pleasant Mountain Ski Area
- Conway Scenic Railroad
- Popham Beach State Park
- Wolfe's Neck Woods State Park





