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

Windham Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Windham vacation rentals

Dining

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.
$492 nightly
The price is $536
Sep 15 - Sep 16
Total with taxes and fees
Cozy 1 BR ADU | Private Access | Projector Theater
TV, offices

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.
$675 nightly
The price is $736
Sep 9 - Sep 10
Total with taxes and fees
Windham Lakefront: Fire Pit and Modern Comforts
Property grounds

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.
$536 nightly
The price is $584
Aug 26 - Aug 27
Total with taxes and fees
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
3 bedrooms, premium bedding, iron/ironing board, travel crib

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.
$438 nightly
The price is $477
Sep 1 - Sep 2
Total with taxes and fees
Cozy 3BR | Pet Friendly | Near Portland | Parking
Dining

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.
$474 nightly
The price is $516
Aug 30 - Aug 31
Total with taxes and fees
Modern Apartment - 20 Mins to Portland, Deck, Grill & Firepit, King Bed, DogsOK
Terrace/patio

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)
$189 nightly
The price is $206
Sep 1 - Sep 2
Total with taxes and fees
Sebago Lake studio-style condo with enclosed sunroom and sunset views
Outdoor dining

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.
$268 nightly
The price is $292
Aug 26 - Aug 27
Total with taxes and fees
THE LILLIPAD.Off-grid A frame. Sebago lake region!
Interior

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
$300 nightly
The price is $327
Sep 1 - Sep 2
Total with taxes and fees
Sunny Spot with Private Parking.
Honeymoon Studio | Egyptian cotton sheets, premium bedding, down comforters, bed sheets

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
$422 nightly
The price is $460
Sep 7 - Sep 8
Total with taxes and fees
Fortland Island Campground
Outdoor dining

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.
$368 nightly
The price is $401
Sep 1 - Sep 2
Total with taxes and fees
Peaceful & minutes from the Old Port with private parking
Property grounds

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.
$365 nightly
The price is $398
Sep 8 - Sep 9
Total with taxes and fees
Modern cabin w/ full bath & kitchenette - 03
Exterior

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.
$571 nightly
The price is $604
Aug 30 - Aug 31
Total with taxes and fees
Willard Square Family Home
Smart TV

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.
$292 nightly
The price is $318
Sep 19 - Sep 20
Total with taxes and fees
Pine Point Beach private, quaint, charming studio.
Exterior detail

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
$368 nightly
The price is $401
Aug 30 - Aug 31
Total with taxes and fees
Adorable Portland getaway on the Eastern Promenade
Exterior detail

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.
$1,203 nightly
The price is $1,311
Sep 14 - Sep 15
Total with taxes and fees
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
Property grounds

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.
$384 nightly
The price is $418
Aug 26 - Aug 27
Total with taxes and fees
Modern dome w/ full bath + spa access - 04
Interior

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, (26 reviews)
"Great place! We would definitely return if we were in the area."
United States
Preston
$306 nightly
The price is $334
Sep 17 - Sep 18
Total with taxes and fees
Charming Studio apartment with WiFi, AC in welcoming Portland
Dining

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.
$679 nightly
The price is $740
Sep 7 - Sep 8
Total with taxes and fees
Lakefront-Swim-Kayak-FirePit-20min to Portland
Beach nearby

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, (70 reviews)
"Beautiful place, perfect location! "
United States
Melissa M.
$533 nightly
The price is $580
Aug 26 - Aug 27
Total with taxes and fees
Arlie`s Digs! - One Block To Willard Beach!
Exterior

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.
$429 nightly
The price is $468
Aug 30 - Aug 31
Total with taxes and fees
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

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

10/10 Excellent
"The staff was really lovely and helpful. A lovely, very well located historic property. The spa was very nice!"
Monica 1-night trip
Posted 7 hours ago
Portland Regency Hotel & Spa

Find out more about Windham

Everything you need to know about Windham vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windham vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windham vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windham vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windham. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Windham in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $179 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windham rentals

At Expedia, we put the best Windham vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windham rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windham vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windham. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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.