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

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Our top choices for Windham vacation homes

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 AED 1,616
AED 2,182 total
includes taxes & fees
27 Sep - 28 Sep
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres

2. Tranquility between the Lakes & Sea

Tranquility between the Lakes & Sea
Westbrook
The price is AED 420
AED 1,139 total
includes taxes & fees
29 Sep - 30 Sep
Tranquility between the Lakes & Sea

3. New and Spacious Family Home Close to Sebago Lake

New and Spacious Family Home Close to Sebago Lake
Standish
The price is AED 1,014
AED 3,147 total
includes taxes & fees
28 Sep - 29 Sep
New and Spacious Family Home Close to Sebago Lake

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

Sleeps 16+ | W/D | Parking | 15 mins to Old Port
Westbrook
10.0 out of 10, Exceptional, (1 review)
"This place was excellent, very clean, and the check-in/checkout process was very easy. The unit is broken into 3 distinct apartments with the upstairs being a one bedroom suite. However, all of the units are accessible to each other through stairs so it's convenient for staying connected while also having some separate space."
United States
damean s.
The price is AED 1,429
AED 3,331 total
includes taxes & fees
6 Oct - 7 Oct
Sleeps 16+ | W/D | Parking | 15 mins to Old Port

5. Cozy Family Home w/ Beach Access

Cozy Family Home w/ Beach Access
Raymond
The price is AED 533
AED 1,641 total
includes taxes & fees
28 Sep - 29 Sep
Cozy Family Home w/ Beach Access

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 AED 826
AED 981 total
includes taxes & fees
5 Oct - 6 Oct
Cozy 2-bedroom house with shared beach access to Sebago Lake

7. 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
8.0 out of 10, Very good, (2 reviews)
"Place was clean and cozy. Big yard for games and a fire pit for s’mores. Based on previous review I brought pots/pans but didn’t need them. Everything was available. Stove is gas and I was not familiar with using one so that was the only “challenge”We had a ball and the place was perfect for us!!"
United States
Anonymous traveler
The price is AED 459
AED 1,181 total
includes taxes & fees
27 Sep - 28 Sep
Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton

8. Quiet Spot in lovely Freeport neighborhood

Quiet Spot in lovely Freeport neighborhood
Freeport
The price is AED 440
AED 1,307 total
includes taxes & fees
11 Oct - 12 Oct
Quiet Spot in lovely Freeport neighborhood

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, (81 reviews)
"Everything was very well stocked!"
United States
Sally O.
The price is AED 2,562
AED 3,853 total
includes taxes & fees
28 Sep - 29 Sep
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

10. 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, (3 reviews)
"The property was beautifully decorated, cleaned to perfection, and a great size home for our family trip. Thank you Mike and Kate!"
United States
Gina H.
The price is AED 1,512
AED 3,502 total
includes taxes & fees
28 Sep - 29 Sep
Luxe 5 Bed/ 3 Bath with Game Room & AC

11. Modern & Sunny House Steps from the Promenade.

Modern & Sunny House Steps from the Promenade.
Munjoy Hill
10.0 out of 10, Exceptional, (44 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is AED 1,118
AED 1,767 total
includes taxes & fees
27 Sep - 28 Sep
Modern & Sunny House Steps from the Promenade.

12. Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland

Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland
Scarborough
10.0 out of 10, Exceptional, (17 reviews)
"Great stay. Alexa was a great host. Having garaged parking and the indoor pool/hot tub was perfect for our stay that coincided with a snow. Would definitely stay here again next winter."
United States
Stuart R.
The price is AED 1,157
AED 2,398 total
includes taxes & fees
1 Oct - 2 Oct
Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland

13. Fully Updated Lake View Home on Thomas Pond

Fully Updated Lake View Home on Thomas Pond
Casco
The price is AED 525
AED 1,674 total
includes taxes & fees
28 Sep - 29 Sep
Fully Updated Lake View Home on Thomas Pond

14. 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 AED 863
AED 2,732 total
includes taxes & fees
27 Oct - 28 Oct
Exceptional Private Lakefront Retreat | Hot Tub, Sauna, Private Dock and Floats

15. Willard Square Family Home

Willard Square Family Home
Willard Beach
9.8 out of 10, Exceptional, (13 reviews)
"Thoroughly enjoyed this house! "
United States
David W.
The price is AED 1,102
AED 2,096 total
includes taxes & fees
14 Oct - 15 Oct
Willard Square Family Home

16. 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, (108 reviews)
"Everything was as advertised; great accommodations!"
United States
Richard D.
The price is AED 1,363
AED 2,294 total
includes taxes & fees
6 Oct - 7 Oct
The Globe House on Munjoy Hill - Walk to Breweries

17. 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 AED 575
AED 1,848 total
includes taxes & fees
27 Oct - 28 Oct
Huge New Townhome 10mins from the Beach

18. The Barnhouse with hot tub

The Barnhouse with hot tub
New Gloucester
9.8 out of 10, Exceptional, (10 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 AED 694
AED 1,237 total
includes taxes & fees
27 Sep - 28 Sep
The Barnhouse with hot tub

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 AED 417
AED 1,343 total
includes taxes & fees
19 Oct - 20 Oct
1200 sq ft ♦ West End Townhouse ♦ Perfect Location

20. Newly Remodeled Cottage with AC- Sebago Lake Area

Newly Remodeled Cottage with AC- Sebago Lake Area
Raymond
The price is AED 1,088
AED 1,770 total
includes taxes & fees
27 Sep - 28 Sep
Newly Remodeled Cottage with AC- Sebago Lake Area
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