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

Windham Vacation Rentals

Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Windham vacation rentals

TV, offices

1. 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.
$685 nightly
The price is $747
Aug 19 - Aug 20
Total with taxes and fees
Windham Lakefront: Fire Pit and Modern Comforts
Property grounds

2. 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 16 - Aug 17
Total with taxes and fees
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
3 bedrooms, premium bedding, iron/ironing board, travel crib

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

Cozy 3BR | Pet Friendly | Near Portland | Parking
Westbrook
10.0 out of 10, Exceptional, (13 reviews)
"We had a great stay here. It was very clean and conveniently located."
United States
Angela B.
$454 nightly
The price is $495
Aug 24 - Aug 25
Total with taxes and fees
Cozy 3BR | Pet Friendly | Near Portland | Parking
Outdoor dining

4. Sebago Lake Cottage on Raymond Cape

Sebago Lake Cottage on Raymond Cape
Raymond
10.0 out of 10, Exceptional, (51 reviews)
"Beautiful location and wonderful hosts. Made us feel right at home."
United States
Donna
$181 nightly
The price is $191
Sep 8 - Sep 9
Total with taxes and fees
Sebago Lake Cottage on Raymond Cape
Outdoor dining

5. 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 16 - Aug 17
Total with taxes and fees
THE LILLIPAD.Off-grid A frame. Sebago lake region!
Interior

6. 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.
Outdoor dining

7. 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, (11 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
1 bedroom, WiFi, bed sheets

8. Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.2 out of 10, Very Good, (14 reviews)
"A perfectly decent place to stay, plenty of restaurants and bars within reasonable walking distance. Neighborhood is a bit rough, as the listing mentioned, but no problems while I was there. Response time on questions to the host could be better."
Canada
Brian
$178 nightly
The price is $180
Aug 18 - Aug 19
Total with taxes and fees
Studio Apartment near downtown Walkable!
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
$466 nightly
The price is $508
Sep 7 - Sep 8
Total with taxes and fees
Fortland Island Campground
Exterior detail

10. 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, (78 reviews)
"Everything was very well stocked!"
United States
Sally O.
$1,194 nightly
The price is $1,301
Sep 9 - Sep 10
Total with taxes and fees
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
Interior

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

Charming Studio apartment with WiFi, AC in welcoming Portland
Munjoy Hill
9.6 out of 10, Exceptional, (24 reviews)
"Great place! We would definitely return if we were in the area."
United States
Preston
$305 nightly
The price is $332
Sep 6 - Sep 7
Total with taxes and fees
Charming Studio apartment with WiFi, AC in welcoming Portland
Property grounds

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

Modern cabin w/ full bath & kitchenette - 03
Freeport
10.0 out of 10, Exceptional, (7 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.
$414 nightly
The price is $451
Sep 8 - Sep 9
Total with taxes and fees
Modern cabin w/ full bath & kitchenette - 03
Property grounds

13. Spacious and Contemporary Condo in the Heart of Portland - Close to Beach

Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
East Bayside
8.8 out of 10, Excellent, (38 reviews)
"Overall a pleasing stay."
United States
Mallory D.
$432 nightly
The price is $470
Aug 25 - Aug 26
Total with taxes and fees
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
Dining

14. Elegant condo - walk to Portland's best restaurants & Old Port

Elegant condo - walk to Portland's best restaurants & Old Port
East Bayside
9.2 out of 10, Wonderful, (82 reviews)
"I had a wonderful week at this perfect place. Met my expectations and way more. So walkable all over Portland. I will be back. Thank you so very much."
United States
Margaret H.
$468 nightly
The price is $510
Aug 25 - Aug 26
Total with taxes and fees
Elegant condo - walk to Portland's best restaurants & Old Port
Smart TV

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

Pine Point Beach private, quaint, charming studio.
Blue Point
10.0 out of 10, Exceptional, (39 reviews)
"Absolutely wonderful little place to stay in Scarborough! "
United States
Eric S.
$320 nightly
The price is $349
Sep 1 - Sep 2
Total with taxes and fees
Pine Point Beach private, quaint, charming studio.
Exterior detail

16. Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (140 reviews)
"Owner was so accommodating!"
United States
Kiernan
$288 nightly
The price is $314
Sep 15 - Sep 16
Total with taxes and fees
Adorable Portland getaway on the Eastern Promenade
Exterior

17. Willard Square Family Home

Willard Square Family Home
Willard Beach
9.8 out of 10, Exceptional, (11 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 23 - Aug 24
Total with taxes and fees
Willard Square Family Home
Beach nearby, sun loungers, beach towels

18. Charming Pine Point OOB Beach Cottage Tiny House, Steps away from the beach

Charming Pine Point OOB Beach Cottage Tiny House, Steps away from the beach
Grand Beach
9.8 out of 10, Exceptional, (54 reviews)
"Stay was good. It was clean well decorated and equipped with everything you need"
United States
Tom K.
$292 nightly
The price is $318
Sep 7 - Sep 8
Total with taxes and fees
Charming Pine Point OOB Beach Cottage Tiny House, Steps away from the beach
Exterior detail

19. Glorious getaway on Portland's Eastern Promenade.

Glorious getaway on Portland's Eastern Promenade.
Munjoy Hill
9.8 out of 10, Exceptional, (183 reviews)
"Wonderful experience with exceptional hosts!"
United States
Cynthia
$431 nightly
The price is $470
Sep 1 - Sep 2
Total with taxes and fees
Glorious getaway on Portland's Eastern Promenade.
Smart TV

20. Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower
Parkside
9.2 out of 10, Wonderful, (29 reviews)
"Apartment was as described. Clean, walking distort downtown and parks. Enjoyed stay. Easy communication with host. "
United States
James R.
$298 nightly
The price is $325
Aug 17 - Aug 18
Total with taxes and fees
Beautiful 1st Floor Apartment & Amazing Shower
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

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

10/10 Excellent
"Pretty close to the airport and about a 15 minute drive to downtown Portland. It looks like it was built fairly recently. Clean and well maintained. Staff members are efficient, courteous and very helpful. Breakfast was standard bland hotel buffet, you know, yogurt, a few fruits, cereal, sliced bread, bagels, eggs and a self-serve waffle maker. Overall nothing particularly memorable, but nothing to complain about either. Quite good for an airport hotel."
Burcin 3-night trip
Posted 7 hours ago
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

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 $180 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?

New Listing. 2BR+Bonus Sleeping Room in OOB. Walk to Beach & Amusement Park.: This vacation home rental near Windham is located near the beach and offers a patio, air-conditioning, and laundry facilities to help you feel perfectly comfortable in your new surroundings.

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.