Vacation rentals in Windham

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Top-rated vacation rentals in Windham

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Guest favorite

Apartment in Gorham

4.96 out of 5 average rating, 194 reviews

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.

Jun 3 – 10

R2,859 ZAR per night

Guest favorite

Guest suite in New Gloucester

4.98 out of 5 average rating, 171 reviews

Peaceful Lakeside Suite w/Firepit and Kayaks

Open the double doors of your suite for direct access to a beautiful Maine lake. With a private entrance, the open concept apartment is in the walk-out basement of our log-cabin style home. Includes a kitchenette, private bathroom, enclosed unheated porch, large flat screen TV with DirecTV, washer & dryer. A patio with firepit is available (except when snow-covered). You may swim and use our kayaks and other boats, in season, at your own risk. Nice views. Quiet and peaceful. Enjoy star-gazing.

May 2 – 9

R1,936 ZAR per night

Guest favorite

Tiny home in Windham

4.98 out of 5 average rating, 132 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.

Dec 30 – Jan 6

R3,323 ZAR per night

Guest favorite

Guest suite in Portland

4.95 out of 5 average rating, 111 reviews

Sunflower Retreat in North Back Cove

The Sunflower Retreat is a private, self-contained, peaceful hideaway. Located in the back half of an adorable 1920's home, this BnB space has everything you could need. A driveway leads you around to the back of the house, where a stone walkway guides you to your own private patio and entrance. A comfortable queen bed, kitchenette, full bathroom, closet, dining nook, black-out curtains, eatery, and television are included. Free street parking. Located in close proximity of many things!

Sep 12 – 19

R2,227 ZAR per night

Guest favorite

Cabin in Raymond

4.93 out of 5 average rating, 144 reviews

Rustic, cozy cabin on Sebago Lake. A hidden gem.

Step out of the screened in patio to lakeside relaxation. Dive into crystal waters, snorkel or float with a cool beverage. Kayak or canoe out to Turtle Cove and enjoy the wildlife in this natural waterway teeming with birds to include our resident Blue Heron, ducks, geese, and loons who make this place their home. We have the fortune of bald eagle pairs in several tall pines. Turtles sunning on doting rocks and lily pads in bloom greet us each day. It is a natural water landscape.

Oct 7 – 14

R3,519 ZAR per night

Guest favorite

Home in Gorham

4.99 out of 5 average rating, 138 reviews

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!

Dec 29 – Jan 5

R3,360 ZAR per night

Guest favorite

Farm stay in Buxton

4.96 out of 5 average rating, 202 reviews

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.

Nov 14 – 21

R2,888 ZAR per night

Guest favorite

Farm stay in Gray

4.88 out of 5 average rating, 240 reviews

The Retreat at Crystal Lake Farm

This getaway features two spacious bedrooms plus an upstairs bedroom loft, sleeping up to 6 with ease. The large bathroom is accessed by both the master bedroom and living room and features on-site laundry. For guests who love to cook the kitchen is fully equipped and the deck is a perfect place to relax in the summer and enjoy the view. In colder seasons guests are encouraged to cozy up by the wood-burning stove or use the outdoor BARREL SAUNA.

Jul 10 – 17

R3,360 ZAR per night

Guest favorite

Guesthouse in Windham

5.0 out of 5 average rating, 217 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.

Jul 10 – 17

R2,425 ZAR per night

Superhost

Home in Windham

4.89 out of 5 average rating, 132 reviews

Cozy cottage near Sebago Lake

Cozy & adorable house (cottage) close to Sebago Lake. Backyard with fire pit. Great for those who like boating, swimming, fishing, skiing, snowmobiling. You are close to everything; Sebago Lake State Parks, several areas to launch a boat or visit one of the area beaches (house does not have lake access but plenty of access nearby). Less than 2 miles from grocery stores & restaurants/bars. Sorry no pets!l

Aug 19 – 26

R4,091 ZAR per night

Guest favorite

Guest suite in Windham

4.92 out of 5 average rating, 151 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.

Jun 13 – 20

R2,207 ZAR per night

Guest favorite

Cabin in Lovell

4.98 out of 5 average rating, 253 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.

Jul 20 – 27

R2,179 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Windham vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Windham's top sights

Seacoast Adventure59 locals recommend

Walmart Supercenter14 locals recommend

Bob's Seafood43 locals recommend

Pat's Pizza23 locals recommend

Applebee's Grill + Bar4 locals recommend

Smitty's Cinema Windham25 locals recommend

Other great vacation rentals in Windham

Guest favorite

Cabin in Windham

5.0 out of 5 average rating, 14 reviews

Cozy Private Lake Getaway (Seasonal)

Jul 12 – 17

R3,693 ZAR per night

Guest favorite

Home in Windham

4.95 out of 5 average rating, 63 reviews

Waterfront Gem walkable to Restaurants!

Nov 26 – Dec 3

R4,204 ZAR per night

Guest favorite

Apartment in Gray

4.96 out of 5 average rating, 26 reviews

A lovely 2 Bedroom Apt 1st FL w/ backyard and deck

Apr 23 – 30

R2,190 ZAR per night

Superhost

Cottage in Windham

4.9 out of 5 average rating, 10 reviews

Relaxing 2 bed cottage on Little Sebago Lake

Apr 29 – May 6

R4,418 ZAR per night

Guest favorite

Guest suite in Standish

4.92 out of 5 average rating, 87 reviews

Steep Falls Escape, river & falls just steps away

Aug 25 – Sep 1

R2,490 ZAR per night

Guest favorite

Guest suite in Gorham

4.98 out of 5 average rating, 99 reviews

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

Aug 25 – Sep 1

R3,482 ZAR per night

Guest favorite

Cottage in Windham

5.0 out of 5 average rating, 65 reviews

Romantic waterfront cottage for two in Maine

Aug 1 – 8

R5,835 ZAR per night

Guest favorite

Cottage in Windham

4.89 out of 5 average rating, 62 reviews

Covered Bridge Cottage - Maine woods and river

Nov 10 – 17

R3,571 ZAR per night

Show all

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 Cabin Rentals in Windham?
Enhance your stay in our Cabin Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with free parking, over 10 homes with a kitchen, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
How much does it cost to stay in apartment rentals in Windham?
Experience the best of Windham with our apartment rentals, starting at about $120 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 30 cottage rentals with free parking in Windham. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Windham have a kitchen?
Absolutely! We offer over 10 apartment rentals with a kitchen in Windham. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Windham have wifi?
Absolutely! We offer over 80 house rentals with wifi in Windham. Enjoy a tailored experience with all the comforts you desire.
Do cabin rentals in Windham have air conditioning?
Absolutely! We offer over 10 cabin rentals with air conditioning in Windham. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Windham

Top-rated vacation rentals in Windham

Vacation rentals for every style

Houses

Cottages

Hotels

Popular amenities for Windham vacation rentals

Stay near Windham's top sights

Other great vacation rentals in Windham

Cabin in Windham

Home in Windham

Apartment in Gray

Cottage in Windham

Guest suite in Standish

Guest suite in Gorham

Cottage in Windham

Cottage in Windham

Quick stats about vacation rentals in Windham

Total rentals

Wifi availability

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

What are the most popular amenities for Cabin Rentals in Windham?

How much does it cost to stay in apartment rentals in Windham?

Are there vacation rentals with a dedicated workspace in Windham?

Are there pet-friendly vacation rentals in Windham?

Do cottage rentals in Windham have free parking?

Do apartment rentals in Windham have a kitchen?

Do house rentals in Windham have wifi?

Do cabin rentals in Windham have air conditioning?

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