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Our top choices for Windham vacation homes

1. Highland Lake House - Epic Lake Views, Easy Lake Access, Fully Appointed Home!

Highland Lake House - Epic Lake Views, Easy Lake Access, Fully Appointed Home!
Windham
9.8 out of 10, Exceptional, (43 reviews)
"Beautiful location and property! "
United States
Michael S.
The price is SAR 916
SAR 2,639 total
includes taxes & fees
24 Nov - 25 Nov
Highland Lake House - Epic Lake Views, Easy Lake Access, Fully Appointed Home!

2. 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

3. New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10

New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10
North Deering
9.4 out of 10, Exceptional, (17 reviews)
"The house was perfect for our week in Portland. New, great features in the home, lovely backyard and close to everything Portland"
United States
Patrick J.
New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10

4. 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 844
SAR 994 total
includes taxes & fees
20 Nov - 21 Nov
Cozy 2-bedroom house with shared beach access to Sebago Lake

5. Cozy Family Home w/ Beach Access

Cozy Family Home w/ Beach Access
Raymond
10.0 out of 10, Exceptional, (1 review)
"Nice, clean, good location.Would Recommend!"
United States
glen l.
Cozy Family Home w/ Beach Access

6. 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
7.6 out of 10, Good, (4 reviews)
"Overall all nice stay. Thank you"
United States
Hope T.
The price is SAR 469
SAR 1,211 total
includes taxes & fees
24 Nov - 25 Nov
Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton

7. 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, (85 reviews)
"Absolutely perfect rental!Great location with an amazing view!"
United States
Mike G.
The price is SAR 2,631
SAR 3,964 total
includes taxes & fees
24 Nov - 25 Nov
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

8. 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 SAR 2,702
SAR 5,862 total
includes taxes & fees
19 Nov - 20 Nov
Family, friends, Gathering

9. Heated Game Room, Coastal Maine Cape Sleeps 10

Heated Game Room, Coastal Maine Cape Sleeps 10
Yarmouth
10.0 out of 10, Exceptional, (4 reviews)
"What a great place to stay! The home is very clean and very quiet. Our host was very responsive to any questions we had. We would book this one over and over again."
United States
Michelle T.
Heated Game Room, Coastal Maine Cape Sleeps 10

10. Quiet Spot in lovely Freeport neighborhood

Quiet Spot in lovely Freeport neighborhood
Freeport
The price is SAR 405
SAR 1,282 total
includes taxes & fees
20 Nov - 21 Nov
Quiet Spot in lovely Freeport neighborhood

11. Fully Updated Airy Historic Home in South Freeport

Fully Updated Airy Historic Home in South Freeport
Freeport
10.0 out of 10, Exceptional, (1 review)
"Great property well kept and close to everything we wanted to do"
United States
boodu
Fully Updated Airy Historic Home in South Freeport

12. 1200 sq ft ♦ West End Townhouse ♦ Walk to Old Port

1200 sq ft ♦ West End Townhouse ♦ Walk to Old Port
West End
8.6 out of 10, Excellent, (64 reviews)
"Nice place, good location and very responsive host. I would definitely stay again when in Portland."
United States
Susan d.
1200 sq ft ♦ West End Townhouse ♦ Walk to Old Port

13. Modern & Sunny East End House.

Modern & Sunny East End House.
Munjoy Hill
10.0 out of 10, Exceptional, (51 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is SAR 1,171
SAR 1,950 total
includes taxes & fees
24 Nov - 25 Nov
Modern & Sunny East End House.

14. 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, (2 reviews)
"Clean and tidy"
United States
Edward R.
The price is SAR 920
SAR 1,088 total
includes taxes & fees
20 Nov - 21 Nov
Cozy 2-bedroom Tiny Home with sauna, A/C, boat ramp access to quiet lake

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 SAR 1,344
SAR 2,395 total
includes taxes & fees
20 Nov - 21 Nov
Willard Square Family Home

16. 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, (19 reviews)
"We loved the houses and esp the hot tub!"
United States
loie H.
The price is SAR 754
SAR 2,783 total
includes taxes & fees
14 Dec - 15 Dec
Exceptional Private Lakefront Retreat | Hot Tub, Sauna, Private Dock and Floats

17. Charming West End Victorian

Charming West End Victorian
Parkside
Charming West End Victorian

18. Manor Suite,cozy newly renovated,downtown & beach

Manor Suite,cozy newly renovated,downtown & beach
Bridgton
9.2 out of 10, Wonderful, (5 reviews)
"The Manor Suite was cozy and charming. It was walking distance from restaurants and shops. I would have loved to stay longer to explore the area.I hope to stay there again if I return to Bridgton next summer."
United States
Jennifer
The price is SAR 328
SAR 591 total
includes taxes & fees
23 Nov - 24 Nov
Manor Suite,cozy newly renovated,downtown & beach

19. Old Orchard Beach Neighborhood Home

Old Orchard Beach Neighborhood Home
Old Orchard Beach
10.0 out of 10, Exceptional, (1 review)
"Excellent stay at this property. House is very nice, well furnished and clean. Location is perfect for beach time and downtown activities. We had good times and communication with host was 10/10. thank you"
United States
charles t.
The price is SAR 2,147
SAR 3,747 total
includes taxes & fees
25 Nov - 26 Nov
Old Orchard Beach Neighborhood Home

20. 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, (23 reviews)
"Great space for our needs: three generations for a graduation weekend!"
United States
Matt H.
The price is SAR 1,895
SAR 3,220 total
includes taxes & fees
20 Nov - 21 Nov
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.

Learn more about Windham

Outdoor enthusiasts flock to Dundee Park's sandy beach for swimming and picnicking on Pleasant River's shores. Windham's historic district reveals 19th-century charm, while nearby Sebago Lake State Park offers prime fishing and boating.

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

Top reviews in Windham