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Vacation rentals in Windham

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Top-rated vacation rentals in Windham

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

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Tiny home in Windham

4.98 out of 5 average rating, 139 reviews

Private riverside retreat

Private tiny house situated on the Pleasant river in Windham Maine surrounded by woods and nature! River is stocked with brook trout and lots of bass. Canoes are available for guest use to explore the river. The camp is located behind the main property ~500ft down a dirt road. 4X4 is recommended or you can park at the main house and it's a 3 minute walk. House is very comfortable with modern amenities. Running hot water, electricity, smart TV, wifi , firepit, outdoor shower, king sized bed.

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.

Rental unit in Gray

4.94 out of 5 average rating, 121 reviews

Two bedroom duplex across st from crystal lake

Relax, have fun, spend quality time with friends and family right here at our quiet little place. Two bedrooms, three beds, one pull out couch, we can accommodate up to six guests. We have walking trails, firepit, and a barbecue area. The house sits across the street from crystal lake, with a boat launch 3/4 mile down the road with a parking area. An easy 20-minute drive to Portland. Supermarket, gas station, and restaurant less than five minutes away and ten minutes from Gray exit to 95.

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.

Cabin in South Berwick

5 out of 5 average rating, 126 reviews

Romantic A-Frame cabin in the woods

Modern cabin tucked privately in the forest. Loaded with modern amenities make it perfect for a romantic getaway. Unwind in the hot tub looking up at the sky full of stars. Take a Sauna while being surrounded by nature all around. Relax by the fire pit. Located in the majestic forest of mount agamenticus, the extensive trail system is off our road. Short drive to the Ogunquit/ york beaches, outlets at Kittery and near Portsmouth, Dover and Portland restaurant scenes.

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.

Cottage in Portland

4.89 out of 5 average rating, 534 reviews

Cozy & Quiet Modern Cottage

Modern studio cottage designed and maintained with sustainability and eco-friendliness in mind, located in a quiet Portland neighborhood only a 7-10 minute drive (and $10 Uber/Lyft ride) from downtown Portland, the Old Port, and all local visitor attractions. The cottage is a mile down the road from the Allagash Brewing complex and is within walking distance (.5 mi) of the restaurants and bars at Morrill's Corner. This is an LBGTQIA- and BIPOC-friendly space.

Guesthouse in Windham

4.99 out of 5 average rating, 251 reviews

Cottage on Black Brook Preserve

This charming cottage is thoughtfully furnished, it's your home away from home! Clean and cozy, one bedroom with queen size bed and full kitchen. Sit in front of the gas fireplace or on your own private deck overlooking the 105 acres of Black Brook Preserve. Take a hike, snowshoe or cross-country ski right outside your door. We now have new sofa, bed, refrigerator, stove, as well as shower and bathroom flooring.

Home in Westbrook

4.89 out of 5 average rating, 507 reviews

Reno Barn w/ a lot of Charm! Breweries & Airport

** Cozy Renovated Barn w/ artist loft ** Minutes from airport and within walking distance to the Allagash Brewing Company & other breweries. Lots of hiking trails along the Presumpscot River. Short drive to downtown Portland, restaurants, music venues, beaches, lighthouses and nightlife. Barn is located in a quiet area ~ relax on the back deck with a glass of wine star gazing. Come check us out!!

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.

Cabin in Lovell

4.96 out of 5 average rating, 306 reviews

Secluded, cozy cabin nestled in the Maine woods

Kick back and relax in this calm, stylish space with a semi-remote cabin experience while keeping the gentle daily living comforts. Right at the edge of the White Mountain National Forest in one direction and in the other direction, a short five minute drive to Kezar Lake this secluded cabin has it all for the nature lover in you! Close to local favorite trailheads for hiking and mountain biking.

Guesthouse in Cumberland

4.96 out of 5 average rating, 201 reviews

Cottage Under a Crabapple Tree

Steps from extensive nature trails and wildflower meadows, this quaint studio cottage is nestled conveniently between the restaurants and breweries of Portland, the outlet shopping of Freeport, and miles and miles of rocky coastline. Perfect for a quiet Maine getaway, lodging near Cumberland fairgrounds and other local attractions, or a visit to family and friends in the area.

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Popular amenities for Windham vacation rentals

Free parking on premises

Air conditioning

Stay near Windham's top sights

Allagash Brewing Company155 locals recommend

Seacoast Adventure59 locals recommend

Bob's Seafood43 locals recommend

Good Life Market39 locals recommend

Bull Jagger Brewing Company38 locals recommend

Smitty's Cinema Windham25 locals recommend

Other great vacation rentals in Windham

Cottage in Windham

4.91 out of 5 average rating, 85 reviews

Tranquil waterfront cottage

Guest suite in Raymond

4.83 out of 5 average rating, 47 reviews

Lil' Sebago Unit

Home in Windham

5 out of 5 average rating, 22 reviews

Maine Vacation Home on the Water

Home in Gray

4.97 out of 5 average rating, 62 reviews

cozy 3 bedroom ranch with deck and screen porch

Home in Naples

4.99 out of 5 average rating, 92 reviews

LUX Designer Private Waterfront

Home in Windham

4.92 out of 5 average rating, 26 reviews

Lakehouse on Highland Lake

Vacation home in Windham

5 out of 5 average rating, 63 reviews

Sebago Lakehouse: Hot Tub and Private Beach Access

Cabin in Kennebunk

4.98 out of 5 average rating, 85 reviews

HotTub/5min to K-port, Pet friendly, @anchorunwind

Quick stats about vacation rentals in Windham

Total rentals
170 properties
Nightly prices starting at
$60 before taxes and fees
Total number of reviews
7K reviews
Family-friendly rentals
120 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with dedicated workspaces
80 properties have a dedicated workspace

Frequently Asked Questions

What are the most popular amenities for House Rentals in Windham?
Enhance your stay in our House Rentals with the most popular amenities: over 80 homes with free parking, over 60 homes with air conditioning, over 80 homes with wifi, over 80 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.
How much does it cost to stay in cabin rentals in Windham?
Experience the best of Windham with our cabin rentals, starting at about $140 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there vacation rentals with a dedicated workspace in Windham?
Yes! Work meets play with ease at over 80 vacation rentals in Windham featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Windham?
Four-legged friends are welcome in Windham. Choose from more than 50 vacation rentals for guests traveling with pets.
Do cottage rentals in Windham have free parking?
Absolutely! We offer over 40 cottage rentals with free parking in Windham. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Windham have a kitchen?
Absolutely! We offer over 40 cottage rentals with a kitchen in Windham. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Windham have wifi?
Absolutely! We offer over 30 cottage rentals with wifi in Windham. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Windham have air conditioning?
Absolutely! We offer over 60 house rentals with air conditioning in Windham. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore