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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! "
Michael S.
The price is SAR 856
SAR 2,570 total
includes taxes & fees
1 Dec - 2 Dec
2. New and Spacious Family Home Close to Sebago Lake
New and Spacious Family Home Close to Sebago LakeStandish
3. Cozy 2-bedroom house with shared beach access to Sebago Lake
Cozy 2-bedroom house with shared beach access to Sebago LakeRaymond
4. Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton
Center of Everything Southern Maine… 3-bedroom house, huge yard in BuxtonBuxton
7.6 out of 10, Good, (4 reviews)
"Overall all nice stay. Thank you"
Hope T.
5. Newly Renovated Luxury House with Game Room
Newly Renovated Luxury House with Game RoomYarmouth
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."
Michelle T.
6. 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 PortEast Deering
10.0 out of 10, Exceptional, (85 reviews)
"Absolutely perfect rental!Great location with an amazing view!"
Mike G.
7. Family, friends, Gathering
Family, friends, GatheringStandish
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."
Logan R.
The price is SAR 2,703
SAR 5,863 total
includes taxes & fees
19 Nov - 20 Nov
9. 1200 sq ft ♦ West End Townhouse ♦ Walk to Old Port
1200 sq ft ♦ West End Townhouse ♦ Walk to Old PortWest 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."
Susan d.
10. Fully Updated Airy Historic Home in South Freeport
Fully Updated Airy Historic Home in South FreeportFreeport
10.0 out of 10, Exceptional, (1 review)
"Great property well kept and close to everything we wanted to do"
boodu
The price is SAR 537
SAR 1,731 total
includes taxes & fees
11 Nov - 12 Nov
11. 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! "
stacey p.
12. Newly Remodeled Cottage with AC- Sebago Lake Area
Newly Remodeled Cottage with AC- Sebago Lake AreaRaymond
13. Chic 3-bedroom house in Munjoy Hill with off-street parking.
Chic 3-bedroom house in Munjoy Hill with off-street parking.Munjoy Hill
10.0 out of 10, Exceptional, (10 reviews)
"Wow, wow, wow! My family and I all agree that this has been the best rental home we have ever stayed in. The interior design is so chic, we were truly wowed by the attention to detail in this place. The beds and pillows are also extremely comfy, we all had a great two nights of sleep here. The location of this place is phenomenal, it neighbors the Portland Observatory, many bars/cafes, and is a short walk down to the eastern promenade. We will absolutely stay here again the next time we’re in...
Maris P.
14. Willard Square Family Home
Willard Square Family HomeWillard Beach
9.8 out of 10, Exceptional, (13 reviews)
"Thoroughly enjoyed this house! "
David W.
15. 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 lakeCasco
10.0 out of 10, Exceptional, (2 reviews)
"Clean and tidy"
Edward R.
The price is SAR 920
SAR 1,039 total
includes taxes & fees
18 Nov - 19 Nov
16. Exceptional Private Lakefront Retreat | Hot Tub, Sauna, Private Dock and Floats
Exceptional Private Lakefront Retreat | Hot Tub, Sauna, Private Dock and FloatsCasco
9.8 out of 10, Exceptional, (19 reviews)
"We loved the houses and esp the hot tub!"
loie H.
The price is SAR 755
SAR 2,824 total
includes taxes & fees
10 Nov - 11 Nov
18. The Barnhouse with hot tub
The Barnhouse with hot tubNew 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! "
Jen V.
19. LUX Designer Private Waterfront Crooked River SEBAGO - GLASS WALLS - Huge Yard
LUX Designer Private Waterfront Crooked River SEBAGO - GLASS WALLS - Huge YardNaples
9.8 out of 10, Exceptional, (9 reviews)
"Fantastic home! We had a great time here and look forward to booking again."
Gina P.
The price is SAR 1,774
SAR 2,768 total
includes taxes & fees
15 Nov - 16 Nov
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!"
Matt H.
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.
