A white church with a steeple and red accents, surrounded by autumn trees.

Search Vacation Homes in Windham

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Windham vacation homes

Property grounds

1. WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres

WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
Westbrook
9.6 out of 10, Exceptional, (43 reviews)
"Host was excellent, even thinking of bug spray, yoga mats, binoculars, and extra blankets. We loved our stay!"
United States
Genevieve W.
The price is ￥63,605
￥90,775 total
includes taxes & fees
Aug 2 - Aug 3
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
Interior

2. Tranquility between the Lakes & Sea

Tranquility between the Lakes & Sea
Westbrook
The price is ￥27,388
￥63,651 total
includes taxes & fees
Aug 5 - Aug 6
Tranquility between the Lakes & Sea
Smart TV, fireplace

3. Cozy 2-bedroom house with shared beach access to Sebago Lake

Cozy 2-bedroom house with shared beach access to Sebago Lake
Raymond
The price is ￥35,415
￥44,092 total
includes taxes & fees
Aug 13 - Aug 14
Cozy 2-bedroom house with shared beach access to Sebago Lake
Dining

4. Sleeps 16+ | W/D | Parking | 15 mins to Old Port

Sleeps 16+ | W/D | Parking | 15 mins to Old Port
Westbrook
Sleeps 16+ | W/D | Parking | 15 mins to Old Port
Beach

5. Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton

Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton
Buxton
6.0 out of 10, (1 review)
"Overall, value property. It's a very old home that was slightly renovated. Pros. 3 bedrooms, washer dryer, good price Cons. Smelled musty, pans not usable for cooking, small living room.Host was great with communication, and the stay was worth the price."
United States
Renee D.
The price is ￥31,952
￥68,455 total
includes taxes & fees
Aug 31 - Sep 1
Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton
TV, offices

6. Fully Updated Airy Historic Home in South Freeport

Fully Updated Airy Historic Home in South Freeport
Freeport
Fully Updated Airy Historic Home in South Freeport
Smart TV

7. Luxe 5 Bed/ 3 Bath with Game Room & AC

Luxe 5 Bed/ 3 Bath with Game Room & AC
Yarmouth
10.0 out of 10, Exceptional, (2 reviews)
"What a beautiful home! Everything about our stay was perfect. The home has everything you could possibly need and more. My family stayed for a long weekend and everyone was so happy with the accommodations. Hoping to go back!"
United States
Lisa L.
The price is ￥59,409
￥152,426 total
includes taxes & fees
Aug 3 - Aug 4
Luxe 5 Bed/ 3 Bath with Game Room & AC
TV, fireplace, offices

8. Fully Updated Lake View Home on Thomas Pond

Fully Updated Lake View Home on Thomas Pond
Casco
Fully Updated Lake View Home on Thomas Pond
Exterior

9. Willard Square Family Home

Willard Square Family Home
Willard Beach
9.8 out of 10, Exceptional, (11 reviews)
"Great location, close to Old Port. Great bakery/coffee and ice cream next door. House was clean and comfortable!"
United States
Steve S.
The price is ￥47,220
￥95,131 total
includes taxes & fees
Aug 23 - Aug 24
Willard Square Family Home
Terrace/patio

10. Scenic 2-bedroom Tiny Home on the Lake with dock, boat ramp & screenhouse

Scenic 2-bedroom Tiny Home on the Lake with dock, boat ramp & screenhouse
Casco
The price is ￥35,415
￥44,092 total
includes taxes & fees
Aug 6 - Aug 7
Scenic 2-bedroom Tiny Home on the Lake with dock, boat ramp & screenhouse
Miscellaneous

11. Cozy 2-bedroom Tiny Home with sauna, A/C, boat ramp access to quiet lake

Cozy 2-bedroom Tiny Home with sauna, A/C, boat ramp access to quiet lake
Casco
The price is ￥38,563
￥48,038 total
includes taxes & fees
Aug 5 - Aug 6
Cozy 2-bedroom Tiny Home with sauna, A/C, boat ramp access to quiet lake
Dining

12. Family, friends, Gathering

Family, friends, Gathering
Standish
8.0 out of 10, Very Good, (2 reviews)
"Beautiful property, spacious, plenty of beds and super easy to get to the lake. Owner was very responsive throughout the process."
United States
Logan R.
The price is ￥113,328
￥258,722 total
includes taxes & fees
Aug 6 - Aug 7
Family, friends, Gathering
Outdoor dining

13. Modern & Sunny House Steps from the Promenade. Private Parking!

Modern & Sunny House Steps from the Promenade. Private Parking!
Munjoy Hill
10.0 out of 10, Exceptional, (42 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is ￥56,349
￥91,788 total
includes taxes & fees
Sep 1 - Sep 2
Modern & Sunny House Steps from the Promenade. Private Parking!
Terrace/patio

14. Cozy Maine Camp on Private Peninsula

Cozy Maine Camp on Private Peninsula
Raymond
The price is ￥60,206
￥111,433 total
includes taxes & fees
Aug 9 - Aug 10
Cozy Maine Camp on Private Peninsula
Beach nearby

15. Beachwood Cottage by Bayley Vacation Rentals

Beachwood Cottage by Bayley Vacation Rentals
Grand Beach
9.8 out of 10, Exceptional, (15 reviews)
"Great place Location was excellent and there are many activities nearby. The beach was just across the street! "
United States
Douglas K.
The price is ￥59,733
￥198,884 total
includes taxes & fees
Aug 25 - Aug 26
Beachwood Cottage by Bayley Vacation Rentals
Interior

16. Pastoral Tranquil Walkable to Trails Dining Shopping Secure Bike Boat Storage

Pastoral Tranquil Walkable to Trails Dining Shopping Secure Bike Boat Storage
Cape Elizabeth
10.0 out of 10, Exceptional, (6 reviews)
"The host was welcoming and it was an easy and smooth check in and check out process. Place was a great spot for my friends and I during our stay for a pond hockey tournament."
United States
Kerry W.
The price is ￥94,440
￥166,591 total
includes taxes & fees
Aug 12 - Aug 13
Pastoral Tranquil Walkable to Trails Dining Shopping Secure Bike Boat Storage
Interior

17. 1200 sq ft ♦ West End Townhouse ♦ Perfect Location

1200 sq ft ♦ West End Townhouse ♦ Perfect Location
West End
8.4 out of 10, Very Good, (61 reviews)
"Nice place. Good location."
United States
Rob M.
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
Microwave, oven, stovetop, dishwasher

18. The Barnhouse with hot tub

The Barnhouse with hot tub
New Gloucester
9.8 out of 10, Exceptional, (9 reviews)
"This was the perfect spot for my friends and I who were attending a wedding down the road! Great location, lovely property and very clear instructions from the hosts! "
United States
Jen V.
The price is ￥31,008
￥57,475 total
includes taxes & fees
Aug 24 - Aug 25
The Barnhouse with hot tub
Interior

19. Spacious 4-bedroom house located in the heart of Portland, ME.

Spacious 4-bedroom house located in the heart of Portland, ME.
Munjoy Hill
10.0 out of 10, Exceptional, (15 reviews)
"Great place great location. "
United States
Chris f.
The price is ￥116,791
￥189,581 total
includes taxes & fees
Aug 3 - Aug 4
Spacious 4-bedroom house located in the heart of Portland, ME.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windham Hotel Reviews

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

10/10 Excellent
"Great stay! Definitely will stay there again"
Russ 1-night trip
Posted less than an hour ago
La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

Find out more about Windham

Windham Vacation Homes information

Number of reviews
15,621
Accommodation
923 Vacation Homes
Lowest Price
￥16,456
Highest Price
￥39,953