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

Holiday Homes in Windham

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Windham holiday homes

Living area

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.
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 NZ$982
includes taxes & fees
6 Sept - 7 Sept
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
Property grounds

3. Serenity between the lakes and seashore

Serenity between the lakes and seashore
Westbrook
9.8 out of 10, Exceptional, (30 reviews)
"This is my second stay at this property and we have a third stay booked in the fall. Everything was perfect from ease of checking in and communication with the host to fully stocked kitchen and cleanliness. Highly recommend "
United States
Joanne N.
The price is NZ$504
includes taxes & fees
7 Sept - 8 Sept
Serenity between the lakes and seashore
Interior

4. Tranquility between the Lakes & Sea

Tranquility between the Lakes & Sea
Westbrook
The price is NZ$546
includes taxes & fees
8 Sept - 9 Sept
Tranquility between the Lakes & Sea
Dining

5. New and Spacious Family Home Close to Sebago Lake

New and Spacious Family Home Close to Sebago Lake
Standish
The price is NZ$1,518
includes taxes & fees
7 Sept - 8 Sept
New and Spacious Family Home Close to Sebago Lake
Living area

6. 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 NZ$467
includes taxes & fees
17 Sept - 18 Sept
Cozy 2-bedroom house with shared beach access to Sebago Lake
Beach

7. Cozy Family Home w/ Beach Access

Cozy Family Home w/ Beach Access
Raymond
The price is NZ$852
includes taxes & fees
8 Sept - 9 Sept
Cozy Family Home w/ Beach Access
Living area

8. Fully Updated Airy Historic Home in South Freeport

Fully Updated Airy Historic Home in South Freeport
Freeport
The price is NZ$823
includes taxes & fees
7 Sept - 8 Sept
Fully Updated Airy Historic Home in South Freeport
Living area

9. 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.
Luxe 5 Bed/ 3 Bath with Game Room & AC
Dining

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

Lakefront-Swim-Kayak-FirePit-20min to Portland
Gray
9.6 out of 10, Exceptional, (16 reviews)
"Loved the space and location. We had a beautiful time with friends!"
United States
Lydia T.
The price is NZ$1,051
includes taxes & fees
7 Sept - 8 Sept
Lakefront-Swim-Kayak-FirePit-20min to Portland
Exterior detail

11. 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, (80 reviews)
"Everything was very well stocked!"
United States
Sally O.
The price is NZ$2,250
includes taxes & fees
30 Sept - 1 Oct
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
Beach

12. 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 NZ$582
includes taxes & fees
6 Oct - 7 Oct
Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton
Outdoor dining

13. The Globe House on Munjoy Hill - Walk to Breweries

The Globe House on Munjoy Hill - Walk to Breweries
Munjoy Hill
10.0 out of 10, Exceptional, (105 reviews)
"Everything was as advertised; great accommodations!"
United States
Richard D.
The price is NZ$980
includes taxes & fees
15 Sept - 16 Sept
The Globe House on Munjoy Hill - Walk to Breweries
Private kitchen

14. Quiet Spot in lovely Freeport desert pines neighborhood

Quiet Spot in lovely Freeport desert pines neighborhood
Freeport
The price is NZ$690
includes taxes & fees
14 Sept - 15 Sept
Quiet Spot in lovely Freeport desert pines neighborhood
Exterior

15. 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, (16 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 NZ$1,306
includes taxes & fees
8 Sept - 9 Sept
Exceptional Private Lakefront Retreat | Hot Tub, Sauna, Private Dock and Floats
Private kitchen

16. Newly Remodeled Cottage with AC- Sebago Lake Area

Newly Remodeled Cottage with AC- Sebago Lake Area
Raymond
The price is NZ$842
includes taxes & fees
13 Sept - 14 Sept
Newly Remodeled Cottage with AC- Sebago Lake Area
Living area

17. Fully Updated Lake View Home on Thomas Pond

Fully Updated Lake View Home on Thomas Pond
Casco
The price is NZ$928
includes taxes & fees
8 Sept - 9 Sept
Fully Updated Lake View Home on Thomas Pond
Interior

18. 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 NZ$670
includes taxes & fees
20 Sept - 21 Sept
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
Exterior

19. 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 NZ$1,198
includes taxes & fees
14 Sept - 15 Sept
Willard Square Family Home
Living area

20. Huge New Townhome 10mins from the Beach

Huge New Townhome 10mins from the Beach
Saco
9.0 out of 10, Wonderful, (2 reviews)
"The location was very convenient. Easy drive to downtown Saco and Biddeford. As well as very quick access to the highway so Portland and other points are easy to get to. Ample parking."
United States
Ellen L.
The price is NZ$915
includes taxes & fees
7 Sept - 8 Sept
Huge New Townhome 10mins from the Beach
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

Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG

10/10 Excellent
"I love this hotel it was close to everything on the town and it was affordable I will stay there again ."
Carlos 1-night trip
Posted 1 hour ago
Holiday Inn Portland-By the Bay by IHG

Find out more about Windham

Windham Holiday Homes information

Number of reviews
370
Accommodation
923 Holiday Homes
Lowest Price
NZ$467
Highest Price
NZ$2,250