Vacation rentals in Windham

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Top-rated vacation rentals in Windham

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Guest favourite

Home in Windham

5 out of 5 average rating, 11 reviews

New Listing! Pool, Hot tub & Lakes! Mins to Sebago

This spacious home is nestled min.from stunning Jordan Bay/Sebago L. Private in-ground pool, fire pit, &an open-concept offers perfect blend of comfort and style for families & groups. Ideal for holiday gatherings, summer reunions, or just a relaxing escape. Oversized windows will make you feel as though you are in the treetops. 4-7min drive to beaches, restaurants, and shopping. 30min from Portland. 15-30min to trails(hike/ski), ferry, & historic landmarks. Perfect all year-round. Pets welcome!

Top guest favourite

Cottage in Windham

5 out of 5 average rating, 86 reviews

Romantic waterfront cottage for two in Maine

This private cottage on Collins Pond in Windham, Maine is the ideal spot for a couple to enjoy a relaxing getaway together. The cottage features one bedroom, full kitchen and modern bath. Two kayaks, canoe and paddleboat are included, so guests can explore the pond or fish. Soothing water views, stone hearth and outdoor dining add charm to the deck. Accessed by steep stone stairs, not ideal for guests with limited mobility or children. Please no pets, parties or smoking. 3 day min. stay.

Top guest favourite

Home in Windham

4.94 out of 5 average rating, 151 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

Home in Windham

4.96 out of 5 average rating, 51 reviews

Modern Chic Home in Windham

Kick back and relax in this new calm, stylish space. Centrally located close to Sebago Lake, Portland’s Old Port, coastal Maine beaches, Mountains, St Joseph’s College, famous breweries, Freeport & more! Enjoy this chic 2 bedroom home that is private yet minutes to all the excitement the Lake’s Region has to offer. You’ll enjoy everything this fully equipped home has to offer making your stay worry free. This cozy home is perfect for weekend stays or couples vacations!

Top guest favourite

Apartment in Windham

4.99 out of 5 average rating, 150 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

Cottage in Gray

4.91 out of 5 average rating, 213 reviews

Sunset Haven - Little Sebago Lake

Sunset Haven is a beautiful 3BR, 1.5 bath year round lakeside cottage on Little Sebago Lake in Gray, Maine. It boasts a private beach and water frontage in the heart of Maine's Sebago Lakes Region. Located only about half an hour max from Portland, Maine and the Atlantic coastline, approximately an hour or less from Shawnee Peak and the Sunday River Ski areas, 40 minutes from Oxford Casino, this area is truly a great destination for four season recreation.

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

4.94 out of 5 average rating, 17 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, 193 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, 39 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

Guest suite in Gorham

4.96 out of 5 average rating, 138 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.