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

Windham Vacation Rentals

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Our top choices for Windham vacation rentals

1. Cozy 1 BR ADU | Private Access | Projector Theater

Cozy 1 BR ADU | Private Access | Projector Theater
Windham
10.0 out of 10, Exceptional, (4 reviews)
"Spotlessly clean, very comfortable bed. Quietly watched a deer just a few feet from me outside the property. Very peaceful."
United States
Anne T.
The price is CA $184
CA $706 total
includes taxes & fees
Sep 15 - Sep 16
Cozy 1 BR ADU | Private Access | Projector Theater

2. 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 CA $277
CA $1,005 total
includes taxes & fees
Sep 9 - Sep 10
Windham Lakefront: Fire Pit and Modern Comforts

3. 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 CA $556
CA $801 total
includes taxes & fees
Aug 25 - Aug 26
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres

4. Cozy 3BR | Pet Friendly | Near Portland | Parking

Cozy 3BR | Pet Friendly | Near Portland | Parking
Westbrook
10.0 out of 10, Exceptional, (14 reviews)
"We had a great stay here. It was very clean and conveniently located."
United States
Angela B.
The price is CA $271
CA $678 total
includes taxes & fees
Aug 30 - Aug 31
Cozy 3BR | Pet Friendly | Near Portland | Parking

5. Modern Apartment - 20 Mins to Portland, Deck, Grill & Firepit, King Bed, DogsOK

Modern Apartment - 20 Mins to Portland, Deck, Grill & Firepit, King Bed, DogsOK
Westbrook
10.0 out of 10, Exceptional, (13 reviews)
"Fantastic property. Hosts were very communicative. Amazing stay. Great location! Thank you so much!"
United States
Laurie A.
The price is CA $309
CA $713 total
includes taxes & fees
Aug 25 - Aug 26
Modern Apartment - 20 Mins to Portland, Deck, Grill & Firepit, King Bed, DogsOK

6. Sebago Lake studio-style condo with enclosed sunroom and sunset views

Sebago Lake studio-style condo with enclosed sunroom and sunset views
Standish
9.0 out of 10, Wonderful, (12 reviews)
The price is CA $186
CA $279 total
includes taxes & fees
Aug 26 - Aug 27
Sebago Lake studio-style condo with enclosed sunroom and sunset views

7. THE LILLIPAD.Off-grid A frame. Sebago lake region!

THE LILLIPAD.Off-grid A frame. Sebago lake region!
Standish
9.8 out of 10, Exceptional, (14 reviews)
"Had a wonderful overnight - was perfect weekend getaway. Was great being in nature!"
United States
Alex D.
The price is CA $322
CA $397 total
includes taxes & fees
Aug 25 - Aug 26
THE LILLIPAD.Off-grid A frame. Sebago lake region!

8. Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
10.0 out of 10, Exceptional, (31 reviews)
"Cute property.. also really suitable for long stay as the amenities were complete and near groceries and some restaurants and cafes.. convenient!"
United States
Giana
The price is CA $271
CA $442 total
includes taxes & fees
Sep 1 - Sep 2
Sunny Spot with Private Parking.

9. Fortland Island Campground

Fortland Island Campground
1.0 star property
Portland
10.0 out of 10, Exceptional, (3 reviews)
"It was very quiet and liked the experience of staying in a camp like setting."
United States
leela srinivas
The price is CA $387
CA $647 total
includes taxes & fees
Aug 25 - Aug 26
Fortland Island Campground

10. Peaceful & minutes from the Old Port with private parking

Peaceful & minutes from the Old Port with private parking
Knightville
9.8 out of 10, Exceptional, (12 reviews)
"Cute, convenient spot!"
United States
Kelly S.
The price is CA $340
CA $547 total
includes taxes & fees
Sep 1 - Sep 2
Peaceful & minutes from the Old Port with private parking

11. Modern cabin w/ full bath & kitchenette - 03

Modern cabin w/ full bath & kitchenette - 03
Freeport
10.0 out of 10, Exceptional, (8 reviews)
"Easy check in process. More than clean, it looked brand new. Overall a great stay. Kitchen was well stocked with plates, utensils, and cookware. "
United States
Michael H.
The price is CA $338
CA $544 total
includes taxes & fees
Sep 8 - Sep 9
Modern cabin w/ full bath & kitchenette - 03

12. 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 CA $413
CA $829 total
includes taxes & fees
Aug 30 - Aug 31
Willard Square Family Home

13. Pine Point Beach private, quaint, charming studio.

Pine Point Beach private, quaint, charming studio.
Blue Point
10.0 out of 10, Exceptional, (40 reviews)
"Absolutely wonderful little place to stay in Scarborough! "
United States
Eric S.
The price is CA $241
CA $433 total
includes taxes & fees
Sep 19 - Sep 20
Pine Point Beach private, quaint, charming studio.

14. Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (143 reviews)
"Owner was so accommodating!"
United States
Kiernan
The price is CA $367
CA $550 total
includes taxes & fees
Aug 26 - Aug 27
Adorable Portland getaway on the Eastern Promenade

15. 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 CA $1,230
CA $1,803 total
includes taxes & fees
Sep 14 - Sep 15
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

16. Modern dome w/ full bath + spa access - 04

Modern dome w/ full bath + spa access - 04
Freeport
10.0 out of 10, Exceptional, (5 reviews)
"Pet friendly and the experience is just amazing. Thank you for having us! "
United States
Rene B.
The price is CA $395
CA $629 total
includes taxes & fees
Sep 2 - Sep 3
Modern dome w/ full bath + spa access - 04

17. Charming Studio apartment with WiFi, AC in welcoming Portland

Charming Studio apartment with WiFi, AC in welcoming Portland
Munjoy Hill
9.4 out of 10, Exceptional, (25 reviews)
"Great place! We would definitely return if we were in the area."
United States
Preston
The price is CA $286
CA $456 total
includes taxes & fees
Sep 17 - Sep 18
Charming Studio apartment with WiFi, AC in welcoming Portland

18. 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 CA $439
CA $1,018 total
includes taxes & fees
Sep 7 - Sep 8
Lakefront-Swim-Kayak-FirePit-20min to Portland

19. Arlie`s Digs! - One Block To Willard Beach!

Arlie`s Digs! - One Block To Willard Beach!
Willard Beach
10.0 out of 10, Exceptional, (69 reviews)
"Beautiful place, perfect location! "
United States
Melissa M.
The price is CA $406
CA $802 total
includes taxes & fees
Aug 25 - Aug 26
Arlie`s Digs! - One Block To Willard Beach!

20. Ocean View East End Studio in a Historic Victorian

Ocean View East End Studio in a Historic Victorian
Portland
9.8 out of 10, Exceptional, (110 reviews)
"Lovely view and accessibility to the Old Port area. Enjoyed our relaxing stay! Thanks Dan! "
United States
David E.
The price is CA $413
CA $640 total
includes taxes & fees
Aug 30 - Aug 31
Ocean View East End Studio in a Historic Victorian
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

Find out more about Windham

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Windham. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Windham?

Yes, we offer vacation rentals in Windham near Seacoast Adventure, or you can go with a more remote option if you're looking for extra privacy while you relax. Visitors to Windham speak positively about the lakeside and restaurants in this destination. Make sure you have time to check out the shopping and coffeehouses during your trip.

What are some of the best vacation rentals in Windham?

Spacious Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach: This vacation home rental near Windham is located on the beach and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Windham?

Expedia has 36 vacation rentals for your stay in Windham.

What can I see and do in Windham?

Little Sebago Lake and Sebago Lake are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Seacoast Adventure. Other places in town to visit include Sebago Lake Basin and Forest Lake.

What are vacation rentals like in Windham?

Vacation rentals are privately owned accommodations you can book for a couple days or more in Windham. Vacation rentals provide amenities such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from public hotel elevators and busy reception areas while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for a family getaway.