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
11 Sep - 13 Sep
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Windham vacation 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 SAR 751
SAR 2,759 total
includes taxes & fees
9 Sep - 10 Sep
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 SAR 1,517
SAR 2,194 total
includes taxes & fees
5 Sep - 6 Sep
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 SAR 796
SAR 1,694 total
includes taxes & fees
21 Sep - 22 Sep
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
New and Spacious Family Home Close to Sebago Lake
Beach nearby

5. Cozy Family Home w/ Beach Access

Cozy Family Home w/ Beach Access
Raymond
Cozy Family Home w/ Beach Access
Dining

6. 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
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 SAR 845
SAR 1,052 total
includes taxes & fees
20 Sep - 21 Sep
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 SAR 469
SAR 1,289 total
includes taxes & fees
22 Sep - 23 Sep
Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton
Smart TV

9. Two Beautiful apartment

Two Beautiful apartment
Back Cove
10.0 out of 10, Exceptional, (28 reviews)
"Such an amazing property and host in an incredible location! "
United States
Devin M.
The price is SAR 4,052
SAR 5,714 total
includes taxes & fees
4 Sep - 5 Sep
Two Beautiful apartment
TV, offices

10. Fully Updated Airy Historic Home in South Freeport

Fully Updated Airy Historic Home in South Freeport
Freeport
The price is SAR 807
SAR 2,177 total
includes taxes & fees
27 Aug - 28 Aug
Fully Updated Airy Historic Home in South Freeport
Dining

11. Lakefront-Swim-Kayak-FirePit-20min to Portland

Lakefront-Swim-Kayak-FirePit-20min to Portland
Gray
9.6 out of 10, Exceptional, (16 reviews)
"We loved our stay! The house was spotless, comfortable, and exactly as described. Mornings on the water and evenings by the fire pit were perfection, and the kitchen had everything we needed. Great location and close proximity to many family-friendly activities - would absolutely come back!"
United States
Kaitlin M.
The price is SAR 1,198
SAR 2,779 total
includes taxes & fees
7 Sep - 8 Sep
Lakefront-Swim-Kayak-FirePit-20min to Portland
Exterior detail

12. 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, (79 reviews)
"Everything was very well stocked!"
United States
Sally O.
The price is SAR 3,421
SAR 5,014 total
includes taxes & fees
21 Sep - 22 Sep
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
Living area

13. Newly Remodeled Cottage with AC- Sebago Lake Area

Newly Remodeled Cottage with AC- Sebago Lake Area
Raymond
The price is SAR 1,112
SAR 1,940 total
includes taxes & fees
7 Sep - 8 Sep
Newly Remodeled Cottage with AC- Sebago Lake Area
Terrace/patio

14. 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
10.0 out of 10, Exceptional, (1 review)
"An adorable little getaway on the cutest little lake. It is quiet and peaceful."
United States
E Tyler B.
The price is SAR 845
SAR 1,052 total
includes taxes & fees
20 Sep - 21 Sep
Scenic 2-bedroom Tiny Home on the Lake with dock, boat ramp & screenhouse
TV, fireplace, offices

15. Fully Updated Lake View Home on Thomas Pond

Fully Updated Lake View Home on Thomas Pond
Casco
The price is SAR 894
SAR 2,284 total
includes taxes & fees
26 Aug - 27 Aug
Fully Updated Lake View Home on Thomas Pond
Sauna

16. 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 SAR 920
SAR 1,146 total
includes taxes & fees
21 Sep - 22 Sep
Cozy 2-bedroom Tiny Home with sauna, A/C, boat ramp access to quiet lake
Outdoor dining

17. 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 SAR 1,344
SAR 2,190 total
includes taxes & fees
1 Sep - 2 Sep
Modern & Sunny House Steps from the Promenade. Private Parking!
Exterior

18. Willard Square Family Home

Willard Square Family Home
Willard Beach
9.8 out of 10, Exceptional, (12 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 SAR 1,126
SAR 2,269 total
includes taxes & fees
30 Aug - 31 Aug
Willard Square Family Home
Interior

19. 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 and very responsive host. I would definitely stay again when in Portland."
United States
Susan d.
The price is SAR 674
SAR 1,774 total
includes taxes & fees
23 Sep - 24 Sep
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
Exterior

20. 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 SAR 1,093
SAR 3,183 total
includes taxes & fees
13 Sep - 14 Sep
Exceptional Private Lakefront Retreat | Hot Tub, Sauna, Private Dock and Floats
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

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

10/10 Excellent
"The staff was really lovely and helpful. A lovely, very well located historic property. The spa was very nice!"
Monica 1-night trip
Posted 4 hours ago
Portland Regency Hotel & Spa