Holiday houses in Windham

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Top-rated holiday rentals in Windham

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Guest favourite

Apartment in Cumberland Mills

4.9 out of 5 average rating, 126 reviews

Private Apt in Spacious Victorian-Style House

Conveniently located in the charming Cumberland Mills neighborhood of Westbrook, this spacious one bedroom Victorian apartment offers easy access to Portland, the jetport, the highway, Rock Row, and other Westbrook attractions. Delicious eateries, local breweries, and Riverbank Park are within walking distance. This apartment comes fully furnished with a comfortable queen bed in the bedroom and a cozy twin bed in the living room. We also have a Pack 'n Play available (please bring your linens).

Top Guest favourite

Home in Windham

4.94 out of 5 average rating, 149 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.

Guest favourite

Campervan/RV in Windham

5 out of 5 average rating, 21 reviews

Tiny House Camper - Trail Access!

Nestled between Portland's fine dining and Sebago's outdoor fun, the Tiny House Camper is a great spot to explore what Southern Maine has to offer. Located with direct access to the Sebago to the Sea Trail - 28 miles of walking & biking paths. Take a dip in the Presumpscot River, play a game of corn hole, and finish the evening with some burgers on the grill and a campfire in the private backyard. **Please read "show more" section and photo captions for important notes.

Top Guest favourite

Apartment in Windham

4.99 out of 5 average rating, 147 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.

Guest favourite

Tiny home in Portland

4.96 out of 5 average rating, 492 reviews

The Garden Cabin Tiny Home

Curious about tiny homes? Love dogs, gardens, pine trees, campfires, and birds? Hate cleaning fees? Our private 128 sqft cozy cabin is for you! On the spectrum between camping and a hotel room, it's a chill place to call home while visiting Portland. Enjoy our garden while sipping a beverage from your own deck or around the campfire. Heat and A/C in the cabin. Please, no smokers, kids under 7, or guest pets. STHR-000718-2018

Top Guest favourite

Guesthouse in Windham

4.99 out of 5 average rating, 265 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.

Guest favourite

Apartment in Windham

4.93 out of 5 average rating, 15 reviews

1 Bedroom with Beach Access

Originally an 1860's barn, this space boasts high ceilings, exposed beams, and a sliding barn door. The apartment is located in a quiet, peaceful neighborhood. It includes beach access to a pond where you can swim, kayak, canoe, paddle board, and fish. This apartment is conveniently located near the many businesses in North Windham. It is 9 minutes from the I-95 exit in Gray, and 25 minutes from Portland.

Guest favourite

Guest suite in Windham

4.92 out of 5 average rating, 191 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.

Guest favourite

Cabin in Windham

4.92 out of 5 average rating, 38 reviews

Cozy Private Lake Getaway (Seasonal)

If you love the traditional camp, this place is for you! Located on Forest Lake bordering Gray, Cumberland and Windham, Maine, this cozy place is off the beaten path yet only 20-30 minutes from Portland and all it has to offer. Perfect for a couple looking for a quiet lake getaway. The one bedroom has a full size bed. The living room couch pulls out to a queen size bed for extra guests.

Guest favourite

Guesthouse in Cumberland

4.95 out of 5 average rating, 239 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.

Guest favourite

Apartment in Westbrook

4.94 out of 5 average rating, 134 reviews

Peaceful 1BR | Reading Nook | Near Portland

This bright and charming second-floor apartment is part of a beautifully renovated 1890s home in the heart of Westbrook. Just a short drive from the excitement of Portland, it’s the perfect blend of quiet comfort and city convenience. Explore nearby local shops, cafes, and riverfront trails, or head into Portland for world-class dining, galleries, and entertainment.

Guest favourite

Guest suite in Gorham

4.96 out of 5 average rating, 137 reviews

Farmhouse stay, near lakes and St. Joe's College

Charming 2 story, 2 bedroom antique farmhouse apartment within walking distance to a quaint pond. Located minutes from St. Joseph's College, Sebago Lakes region, fly-fishing on the Presumpscot River, premier mountain biking and hiking trails. 15 miles to downtown Portland’s famed restaurants, breweries, and shopping.