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

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Windham holiday homes

TV, offices

1. Windham Lakefront: Fire Pit and Modern Comforts

Windham Lakefront: Fire Pit and Modern Comforts
Windham
10.0 out of 10, Exceptional, (2 reviews)
"This is an exceptional property. It was quiet and comfortable, and we all slept well. The location was ideal for our plans and the host answered every question promptly.I highly recommend this rental, and I plan to return."
United States
Richard G.
The price is £581
includes taxes & fees
19 Aug - 20 Aug
Windham Lakefront: Fire Pit and Modern Comforts
Property grounds

2. 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 £427
includes taxes & fees
17 Aug - 18 Aug
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
Interior

3. Tranquility between the Lakes & Sea

Tranquility between the Lakes & Sea
Westbrook
The price is £309
includes taxes & fees
8 Sept - 9 Sept
Tranquility between the Lakes & Sea
Dining

4. New and Spacious Family Home Close to Sebago Lake

New and Spacious Family Home Close to Sebago Lake
Standish
The price is £744
includes taxes & fees
17 Aug - 18 Aug
New and Spacious Family Home Close to Sebago Lake
Dining

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

Sleeps 16+ | W/D | Parking | 15 mins to Old Port
Westbrook
The price is £824
includes taxes & fees
3 Sept - 4 Sept
Sleeps 16+ | W/D | Parking | 15 mins to Old Port
Beach nearby

6. Cozy Family Home w/ Beach Access

Cozy Family Home w/ Beach Access
Raymond
The price is £406
includes taxes & fees
17 Aug - 18 Aug
Cozy Family Home w/ Beach Access
Smart TV, fireplace

7. 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 £210
includes taxes & fees
23 Aug - 24 Aug
Cozy 2-bedroom house with shared beach access to Sebago Lake
Beach

8. 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 £254
includes taxes & fees
9 Sept - 10 Sept
Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton
Exterior detail

9. Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
East Deering
10.0 out of 10, Exceptional, (78 reviews)
"Everything was very well stocked!"
United States
Sally O.
The price is £943
includes taxes & fees
9 Sept - 10 Sept
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
Exterior

10. 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 £438
includes taxes & fees
23 Aug - 24 Aug
Willard Square Family Home
Terrace/patio

11. 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 £210
includes taxes & fees
30 Aug - 31 Aug
Scenic 2-bedroom Tiny Home on the Lake with dock, boat ramp & screenhouse
Coffee/tea maker, fridge, microwave, oven

12. 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
10.0 out of 10, Exceptional, (1 review)
"Very nice stay thank you. Lots if local things to do nearby."
United States
Bob P.
The price is £229
includes taxes & fees
27 Aug - 28 Aug
Cozy 2-bedroom Tiny Home with sauna, A/C, boat ramp access to quiet lake
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)
"Overall amazing experience! Property is beautifully maintained. Perfectly located, within walking distance from bakeries, pubs, and restraunts. Host was responsive and helpful."
United States
Jacqui B.
The price is £426
includes taxes & fees
1 Sept - 2 Sept
Modern & Sunny House Steps from the Promenade. Private Parking!
Interior

14. 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.
The price is £324
includes taxes & fees
3 Sept - 4 Sept
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
Interior

15. 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 £643
includes taxes & fees
24 Aug - 25 Aug
Pastoral Tranquil Walkable to Trails Dining Shopping Secure Bike Boat Storage
Living area

16. SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11

SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11
Ligonia
10.0 out of 10, Exceptional, (2 reviews)
"Incredibly welcoming house! Very nicely furnished and prepared for guests. Couldn’t be more grateful for the thoughtfulness and accessibility to the property. We kept saying how impressed we were with how many towels were available! A lot of small details were paid attention to by the host! Thank you so much!"
United States
Patrick S.
The price is £779
includes taxes & fees
26 Aug - 27 Aug
SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11
Beach nearby

17. 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 £905
includes taxes & fees
25 Aug - 26 Aug
Beachwood Cottage by Bayley Vacation Rentals
House, 5 Bedrooms | Private kitchen | Coffee/tea maker, fridge, oven, electric kettle

18. Gray Woodland Escape Golf, Pool & Cinema 5 Bedroom Home

Gray Woodland Escape Golf, Pool & Cinema 5 Bedroom Home
3.5 star property
Gray
The price is £1,006
includes taxes & fees
8 Sept - 9 Sept
Gray Woodland Escape Golf, Pool & Cinema 5 Bedroom Home
Exterior

19. Exceptional Private Lakefront Retreat | Hot Tub, Sauna, Private Dock and Floats

Exceptional Private Lakefront Retreat | Hot Tub, Sauna, Private Dock and Floats
Casco
9.8 out of 10, Exceptional, (15 reviews)
"Our stay at this vacation home was wonderful! We had the best time relaxing and enjoying the fall weather. The property manager was responsive and helpful upon check in and check out. We will most definitely be staying there again!"
United States
Michie K.
The price is £691
includes taxes & fees
13 Sept - 14 Sept
Exceptional Private Lakefront Retreat | Hot Tub, Sauna, Private Dock and Floats
Dining

20. ANY BIG PARTY!!!!

ANY BIG PARTY!!!!
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 £1,202
includes taxes & fees
27 Aug - 28 Aug
ANY BIG PARTY!!!!
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.
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Top Windham Hotel Reviews

Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

10/10 Excellent
"The Fireside Inn was an enjoyable stay for my family. We loved the heated outdoor pool. Parking was very convenient. The location was central to many areas. Staff were friendly and helpful. We would stay here again."
Eileen 3-night trip
Posted 8 hours ago
Fireside Inn & Suites Portland

Find out more about Windham

Windham Holiday Homes information

Number of reviews
264
Accommodation
958 Holiday Homes
Lowest Price
£210
Highest Price
£1,202