Search for vacation rentals in Windham.

Whether it's vacation home rentals, apartments, condos, or cabins/cottages, we have you covered -- search for rental properties in the entire Windham area to find the perfect spot for your vacay.

Cottage Rd

Cottage Rd

Windham, ME
$3,500
Vacation Rentals, Unknown
Cozy lakefront cottage on Highland Lake- 3bd/1.5 bath house with a large yard and an amazing sandy beach, great for kayaking, swimming or just relaxing and watching the sunset on your own lakefront......

111 Cottage Rd

111 Cottage Rd

Windham, ME
$3,700
Vacation Rentals, Unknown
Cozy lakefront cottage on Highland Lake- 3bd/1.5 bath house with a large yard and an amazing sandy beach, great for kayaking, swimming or just relaxing and watching the sunset on your own lakefront......

0 Southside Dr

0 Southside Dr

Windham, ME
$2,900
Vacation Rentals, Unknown
You will love coming home to this sun filled 3 bedroom house complete with shiplap accents and modern farmhouse feel. This home has been completely renovated and offers bright kitchen, open concept......

190 Mount Hunger Shore Rd

190 Mount Hunger Shore Rd

Windham, ME
$1,950
Vacation Rentals, Unknown
**AVAILABLE 9/1/2024-5/30/2025** Fully furnished 3 bedroom, 2 bath cape with heated unfinished walk out basement. Open floor plan with hardwood floors in Kitchen, dining, living room. Carpet in......

Vista Dr

Vista Dr

Windham, ME
$5,500
Vacation Rentals, Unknown
Lake front rental available for yearly or short term lease starting May 1st. All utilities included, electric, water, internet, and heating (heat pumps also provide AC), comes fully furnished as......

Keene Rd

Keene Rd

Windham, ME
$3,000
Vacation Rentals, Unknown
Three Bedroom home with end of the road privacy on 20 acres. No neighbors in sight. Plenty of room for gardens and animals. Huge South facing windows floods the space with sunlight. Heated by......

Forbes Ln

Forbes Ln

Windham, ME
$3,500
Vacation Rentals, Unknown
Immaculate Single family house with 3 bedrooms/2 bathrooms/ 2 car garage, plus bonus room downstairs, located on a safe well established residential neighborhood. Good credit required, criminal......

392 Roosevelt Trl

392 Roosevelt Trl

Windham, ME
$1,750
Vacation Rentals, Unknown
Cozy 1 bed 1 bath home located off 302 offering convenient travel to major towns and destination areas such as Portland, Windham, Westbrook, Sebago Lakes, Falmouth and more. More privacy than an......

Nelson Ln

Nelson Ln

Windham, ME
$3,000
Vacation Rentals, Unknown
Summer Camp on Little Sebago Lake , that we rent some weeks during the summer months, has available time this year. The camp is nestled among old, tall pine trees, and has its own PRIVATE GRADUAL,......

59 Forbes Ln

59 Forbes Ln

Windham, ME
$1,700
Vacation Rentals, Unknown
**6 Months lease** Jan-July 2024 1 bedrooms 1 bathroom in-law apartment for rent in a quiet neighborhood. Private entrance. Furnished. Ready to move in. a double size bed. Washer & dryer in unit.......

22 Montgomery Rd

22 Montgomery Rd

Windham, ME
$1,180
Vacation Rentals, Unknown
Private room in a shared house with ample sunshine and view of the babbling brook. Fully equiped kitchen, free parking, washer & dryer, and garden space. 15-20 minutes from Portland. There are......

1 Doris Ave

1 Doris Ave

Windham, ME
$2,800
Vacation Rentals, Unknown
Completely renovated three bedroom one and a half bath private home. New kitchen, new appliances, new bathrooms, new floors, new composite decking, new hot water heater, new windows, washer, and......

14 Sabbady Point Rd

14 Sabbady Point Rd

Windham, ME
$2,200
Vacation Rentals, Unknown
2 bedroom, 2 full bath w/ 2 car detached garage. Stainless steel appliances, w/d hookup, large private deck, public water and paved driveway. Close to downtown North Windham yet feels miles away on......

River Rd

River Rd

Windham, ME
$1,200
Vacation Rentals, Unknown
Private room, spacious A-frame, sunny and airy located on the second floor with views of woods and farm. Room has hardwood floors and is recently painted. Recently renovated bathrooms and recently......

15 Curtis Dr

15 Curtis Dr

Windham, ME
$2,145
Vacation Rentals, Unknown
Single-Family Home in Great Location Windham - Westbrook Sunny, easy to heat, three-bedroom home in established neighborhood off River Road in Windham. Bonus rooms in the basement. Close to......

120 Anglers Rd

120 Anglers Rd

Windham, ME
$2,400
Vacation Rentals, Unknown
Lovely modern lakefront home available for rent from December 1 - May 17. Fully renovated, fully furnished home. Driveway plowed after each storm at no additional cost. 2 minutes to North Windham,......

Curtis Dr

Curtis Dr

Windham, ME
$2,145
Vacation Rentals, Unknown
Single-Family Home in Great Location Windham - Westbrook Sunny, easy to heat, three-bedroom home in established neighborhood off River Road in Windham. Bonus rooms in the basement. Close to......

4 Sundowner Hill Rd

4 Sundowner Hill Rd

Windham, ME
$4,500
Vacation Rentals, Unknown
Two Year Old Charming Farmhouse-Style Colonial for Rent in Windham, Maine! Welcome to your dream home in the quickly growing town of Windham, Maine! This large 2544 square foot farmhouse-style......

1023 River Rd

1023 River Rd

Windham, ME
$2,700
Vacation Rentals, Unknown
Close to Sebago Lake!! Also close to Route 302 and all major grocery stores, shopping, pharmacies, gyms, beaches & ocean, public transportation in the Windham area. The home for rent has had many......

161 Cottage Rd

161 Cottage Rd

Windham, ME
$2,150
Vacation Rentals, Unknown
Fully furnished winter rental: This delightful "Maine CAMP" cottage will be your home with an unparalleled view of sunset over the width of Highland Lake. Beautiful shady trees and afternoon......

34 Snowy Ridge Rd

34 Snowy Ridge Rd

Windham, ME
$2,325
Vacation Rentals, Unknown
Fully furnished all-inclusive corporate rental surrounded by nature. Roomy remodeled manufactured home 3/4 mile up a well-maintained private dirt road. Private, cozy, bright 2 BR, 2 full BA,......

21 Lakeside Dr

21 Lakeside Dr

Windham, ME
$2,800
Vacation Rentals, Unknown
Fully furnished winter/spring rental on Forest Lake, includes all utilities / cable / internet. Close to I95 / Portland. Newly renovated cozy 2 bedroom house with fully stocked kitchen and bedding,......

7 Moss Rd

7 Moss Rd

Windham, ME
$3,000
Vacation Rentals, Unknown
Available for rent starting December 1,2023. Well maintained 3 bedroom, 2 bathroom home on a very quiet 1.19 acre corner lot down a private road in Windham. The kitchen, featuring a new dishwasher......

67F Cottage Rd

67F Cottage Rd

Windham, ME
$3,200
Vacation Rentals, Unknown
New Lake house (built in 2020) on Highland Lake. Lakefront with water access, swimming, canoeing and fishing. The home is equipped with all kitchen amenities, 2 bedrooms, 400 mbs WiFi and dedicated......

319 Falmouth Rd

319 Falmouth Rd

Windham, ME
$1,850
Vacation Rentals, Unknown
Vintage mobile home with addition on a large wooded lot. Convenient, quiet location close to Portland. Zillow applications for this property are preferred....

92 Brown Cove Rd

92 Brown Cove Rd

Windham, ME
$3,000
Vacation Rentals, Unknown
**Seasonal Winter Rental ** Gorgeous lakefront home on Little Sebago. Fully furnished 6 bedroom, 4 bath. Lower level recreation room. In-unit laundry. Beautiful views of the lake. Perfect spot to......

27 Brentwood Rd

27 Brentwood Rd

Windham, ME
$3,250
Vacation Rentals, Unknown
Beautiful 150 feet of lake view very cozy 900 ft. 2 bedroom 1 bathroom with bunk bed and sofa couch also a king bed in the master bedroom. Has Gas Fireplace also heat pump for AC and heat. Fully......

399 Pope Rd

399 Pope Rd

Windham, ME
$3,000
Vacation Rentals, Unknown
Great split level home with 2 bedrooms, 1 bathroom, kitchen, dining room and living room upstairs, and an in-law apartment with a smaller kitchen, bathroom and 1.5 bedrooms and a living room......

30 Belvedere Dr

30 Belvedere Dr

Windham, ME
$3,600
Vacation Rentals, Unknown
New construction unfurnished 3 bedroom, 2.5 bathroom, 1-car garage house in Windham built in August 2021 for $3,600/month. $50 off each month if paid at least three days before rent is due on the......

39 Brentwood Rd

39 Brentwood Rd

Windham, ME
$2,100
Vacation Rentals, Unknown
SHORT TERM/WINTER RENTAL Winter rental available Oct 9 until mid May (will consider shorter term) Fully furnished Includes all utilities (electric, Wi-Fi, heat, water & snow removal) 2 queen beds......

551 Gray Rd

551 Gray Rd

Windham, ME
$2,000
Vacation Rentals, Unknown
This house is 20 minutes from Portland and 5 minutes from North Windham in a country setting. It is a well maintained two bedroom ranch with an attached garage. Hardwood floors throughout,......

172 Mount Hunger Shore Rd

172 Mount Hunger Shore Rd

Windham, ME
$1,300
Vacation Rentals, Unknown
Plenty of room to spread out in this spacious home with wall of windows facing Little Sebago. Vaulted ceiling with exposed beams in open concept living / dining area, and cozy little reading nook.......

74 Basin Rd

74 Basin Rd

Windham, ME
$1,650
Vacation Rentals, Unknown
Fully furnished school-year rental located in friendly neighborhood on Sebago Lake Basin. House is just a few miles from Windham shopping areas and schools. An association sandy beach is steps......

9 Kennard Rd

9 Kennard Rd

Windham, ME
$2,500
Vacation Rentals, Unknown
Comfortable 2-bedroom, 1-bathroom home located in a quiet neighborhood on Sebago Lake, just a 6-minute drive from the conveniences of North Windham and Saint Joseph's College. Two levels are fully......

483 Gray Rd

483 Gray Rd

Windham, ME
$1,600
Vacation Rentals, Unknown
If you are looking for a cute space in a convenient location- this place is for you! $1600 a month includes water, sewer and parking. Tenants will pay electric and cable. No pets or smoking on......

74 Lakeside Dr

74 Lakeside Dr

Windham, ME
$2,200
Vacation Rentals, Unknown
This beautiful ranch-style home on the Windham side of peaceful Forest Lake is located on a generous lot with plenty of space for outdoor enjoyment, lake views and right-across-the-road access to......

253 Smith Rd

253 Smith Rd

Windham, ME
$2,200
Vacation Rentals, Unknown
Picturesque Lake Front Furnished Winter Rental (Little Sebago Lake- Windham) Rent includes Wireless Internet, Electric utilities, Microwave, Washer and Dryer. Oil not included. Available September......

Windham, ME

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