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Vacation rentals in Windham

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Top-rated vacation rentals in Windham

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Rental unit in Gorham

Cozy Private 1 Bedroom Apartment - Gorham Village

Enjoy the historical charm of one of Gorham's oldest homes. Come stay in a lovely private second floor, one bedroom apartment with private entry. Just walking distance from restaurants, the grocery store, laundromat, college campus and local trails. It offers private off-street parking for one car and it is located in the heart of Gorham village, a safe and family oriented community. Private bedroom with queen size bed and a full size futon provided. No backyard access. Full Kitchen. Full bath.

Guest suite in Bridgton

Barn on Pleasant-walk to town

Welcome to our charming loft in a peaceful neighborhood, ideal for comfort and convenience. This well maintained property provides a cozy living space. The loft features a kitchenette, a beautiful stone fireplace and a big, comfy reclining couch. Visit Bridgton this spring and summer, walking distance to Highland Lake, shops, and restaurants. Just minutes from Pleasant Mountain for hiking, 30 minutes from North Conway, and an hour from Portland a perfect central location to relax after exploring

Tiny home in Windham

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 Gorham

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!

Farm stay in Buxton

Little River Flower Farm - Cottage

Post & Beam Cottage, rustic knotty pine interior. Five miles to Gorham Center close to USM, 20 minutes to St. Josephs College on Sebago Lake, easy 30 minute drive to Portland, 12 miles to the PWM Jetport. Centrally located to many of Maine's finest breweries: Sebago Brewing, Mast Landing, Funky Bow, Nonsuch, Sea Dog, Barrel Souls, Bissell Brothers. Many local hiking trails including trails right here at our farm. Portland boasts of the finest restaurants in the state.

Guest suite in Scarborough

Beautiful, private apartment!! Great location!

Beautiful 750 square foot in-law apartment with private entrance. Full bedroom, bathroom, kitchen (including dishwasher), washer/dryer, and garage parking. Free wi-fi, cable, and Netflix included! All essentials included in addition to beach towels, chairs, table & cooler for the beach. Private patio includes a grill for use as well (weather permitting). Great location - 10 minutes to downtown Portland, 15 minutes to multiple beaches, 5 minutes to mall & restaurants.

Guest suite in South Portland

Bright Guest Studio Near Lighthouses and Beach

This bright guest studio is steps from the Greenbelt Walkway. Walk (within 10 mins) to two lighthouses, Willard beach, Bug Light Park, Scratch Bakery, Willard Scoops ice cream and a variety of restaurants. Portland is an 8 minute drive or 20 minute bike over the bridge. The space is minimal, bright and airy with windows surrounding, an elevated bed with comfy queen mattress, fully equipped kitchen, washer/dryer and cozy couch for lounging.

Guest suite in South Portland

Top of the Hill So Po In Law

Lovely In law apartment in desirable Meeting House Hill area of South Portland .We were recently the hottest real estate market in the country .Conveniently located , 10 minutes to Portland , and on the doorstep of local beaches, State parks , restaurants ,unique boutique shops ,amazing bakeries and coffee , lunch and antiquing .All you need for a home away from home . Your going to love this neighborhood !

Guest suite in Windham

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.

Guesthouse in Cumberland

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 suite in Lewiston

Sanctuary in the City

Welcome to our sanctuary in the city. Conveniently located just off the I-95, our spacious one-bedroom suite offers a queen bed, bath with cedar sauna, kitchenette, private yard with pergola, and laundry. Enjoy quick access to a range of local shops & restaurants, endless outdoor activities, and convenient access to Portland and Southern Maine’s coastal region.

Farm stay in Gray

Great Goat Get-away in Southern Maine!

This quiet and cozy house is located in the woods at the renowned Ten Apple Farm. Centrally located in Southern ME, we're just a short drive from Portland, lakes, ski areas, LL Bean and more! On the farm you can meet and interact with our herd of goats, sheep, pigs and chickens, learn to milk, collect eggs, and arrange on of our famous goat hikes!

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 Company156 locals recommend

Seacoast Adventure59 locals recommend

Sunset Ridge Golf Links3 locals recommend

Walmart Supercenter14 locals recommend

Blackstrap Hill Preserve7 locals recommend

Shaw Park6 locals recommend

Other great vacation rentals in Windham

Cottage in Windham

Cozy camp near highland lake

Rental unit in Windham

The Roost - lovely one bedroom efficiency unit

Cabin in Windham

Cozy Private Lake Getaway (Seasonal)

Home in Windham

Waterfront Gem walkable to Restaurants!

Guest suite in Standish

Steep Falls Escape, river & falls just steps away

Rental unit in Gray

Newly appointed 2 Bedroom Apartment 2nd Fl w/ deck

Cottage in Windham

Romantic waterfront cottage for two in Maine

Guest suite in Hollis

Cozy Apartment steps away from the Saco River

Quick stats about vacation rentals in Windham

Total rentals
170 properties
Wifi availability
170 properties include access to wifi
Rentals with dedicated workspaces
80 properties have a dedicated workspace
Pet-friendly rentals
50 properties allow pets
Family-friendly rentals
130 properties are a good fit for families
Total number of reviews
6.2K reviews

Frequently Asked Questions

What are the most popular amenities for Cottage Rentals in Windham?
Enhance your stay in our Cottage Rentals with the most popular amenities: over 20 homes with air conditioning, over 30 homes with wifi, over 30 homes with free parking, over 30 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 $150 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 apartment rentals in Windham have free parking?
Absolutely! We offer over 10 apartment rentals with free parking in Windham. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Windham have a kitchen?
Absolutely! We offer over 80 house rentals with a kitchen in Windham. Enjoy a tailored experience with all the comforts you desire.
Do cabin rentals in Windham have wifi?
Absolutely! We offer over 10 cabin rentals with wifi in Windham. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Windham have air conditioning?
Absolutely! We offer over 20 cottage rentals with air conditioning in Windham. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore