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
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Windham vacation rentals

A modern living room with a brown leather sofa, a rustic coffee table, and a dining area with a white table and chairs.

1. Windham Lakefront: Fire Pit and Modern Comforts

Windham Lakefront: Fire Pit and Modern Comforts
Windham
9.6 out of 10, Exceptional, (4 reviews)
"It was perfect for our girls trip to Portland. Private, surrounded by woods, cozy and clean! We even saw wild turkeys and deer in the yard."
United States
Jonny D.
$796 nightly
The price is $867
Oct 28 - Oct 29
Total with taxes and fees
Windham Lakefront: Fire Pit and Modern Comforts
A dining area with a wooden table, two chairs, and a window with a view of trees.

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

Cozy 1 BR ADU | Private Access | Projector Theater
Windham
10.0 out of 10, Exceptional, (5 reviews)
"Very clean! Small space (no microwave) pet friendly and very accommodating to our travel needs!"
United States
Traci P.
$514 nightly
The price is $560
Oct 27 - Oct 28
Total with taxes and fees
Cozy 1 BR ADU | Private Access | Projector Theater
A dirt path in a park with autumn foliage.

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.
$577 nightly
The price is $629
Oct 12 - Oct 13
Total with taxes and fees
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
A dining table with two black cups and saucers, a wooden vase with flowers, and a window with white frames.

4. 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, (14 reviews)
"Excellent location, the hosts are very responsive and an absolute pleasure to work with. The home was clean, inviting and easy to check in."
United States
Bianca L.
$496 nightly
The price is $540
Oct 12 - Oct 13
Total with taxes and fees
Modern Apartment - 20 Mins to Portland, Deck, Grill & Firepit, King Bed, DogsOK
A bedroom with a large bed, white curtains, and a view through the windows.

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

Cozy 3BR | Pet Friendly | Near Portland | Parking
Westbrook
10.0 out of 10, Exceptional, (15 reviews)
"We had a great stay here. It was very clean and conveniently located."
United States
Angela B.
$443 nightly
The price is $483
Oct 12 - Oct 13
Total with taxes and fees
Cozy 3BR | Pet Friendly | Near Portland | Parking
A wooden cabin with a deck, outdoor seating, and a portable toilet in a forest.

6. 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, (16 reviews)
"Had a wonderful overnight - was perfect weekend getaway. Was great being in nature!"
United States
Alex D.
$264 nightly
The price is $288
Oct 12 - Oct 13
Total with taxes and fees
THE LILLIPAD.Off-grid A frame. Sebago lake region!
A modern kitchen with a central island, bar stools, a dining table, and a built-in oven.

7. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (125 reviews)
"Really nice room and location"
United States
Victoria
$294 nightly
The price is $314
Nov 2 - Nov 3
Total with taxes and fees
The Weldon Hotel
A spacious living area with a blue sofa, a coffee table, and a kitchen in the background.

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

New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10
North Deering
9.2 out of 10, Wonderful, (15 reviews)
"Very nice! Would stay again and would highly recommend."
United States
Peter H.
$815 nightly
The price is $824
Oct 18 - Oct 19
Total with taxes and fees
New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10
A spacious kitchen with a large island, wooden beams, and a view of the outdoors.

9. Waterfront Access with Kayaks, Private Deck and a Firepit

Waterfront Access with Kayaks, Private Deck and a Firepit
Gray
9.8 out of 10, Exceptional, (8 reviews)
"In frosty conditions the house was warm and comfortable. Jen was really responsive and welcoming, and the space was perfect."
United States
Matthew S.
$675 nightly
The price is $743
Oct 12 - Oct 13
Total with taxes and fees
Waterfront Access with Kayaks, Private Deck and a Firepit
A multi-story building with a stone facade, large windows, and a corner entrance.

10. Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (15 reviews)
"This is a very nice hotel in a great location. It’s new and wonderfully appointed. Everything about it is first class."
United States
Rick
$428 nightly
The price is $466
Nov 8 - Nov 9
Total with taxes and fees
Evalina Hotel
A living room with a sofa, armchair, and glass coffee table. There are two lamps on side tables and a window with curtains.

11. Portland 1-bedroom with enclosed porch & parking

Portland 1-bedroom with enclosed porch & parking
Deering Center
8.2 out of 10, Very good, (15 reviews)
"Easy to get to, and a great night's sleep.Want to stay in Portland but in a quiet neighborhood?-Grab this spot!"
United States
Cricket C.
$109 nightly
The price is $111
Oct 13 - Oct 14
Total with taxes and fees
Portland 1-bedroom with enclosed porch & parking
A house with a wooden front door, a stone staircase, and a porch with a wooden railing.

12. 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, (82 reviews)
"Everything was very well stocked!"
United States
Sally O.
$1,020 nightly
The price is $1,111
Oct 12 - Oct 13
Total with taxes and fees
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
A cozy living room with a dark gray sofa, two pillows with text, a wooden coffee table, and a ceiling fan.

13. Cozy 2-bedroom house with shared beach access to Sebago Lake

Cozy 2-bedroom house with shared beach access to Sebago Lake
Raymond
$254 nightly
The price is $277
Oct 18 - Oct 19
Total with taxes and fees
Cozy 2-bedroom house with shared beach access to Sebago Lake
A building with a brick facade, large windows, and a covered outdoor seating area.

14. Spacious 3 BR in Portland's Libbytown!

Spacious 3 BR in Portland's Libbytown!
Portland
9.4 out of 10, Exceptional, (62 reviews)
"Nice host, great location & property."
United States
Brittney C.
$453 nightly
The price is $494
Oct 12 - Oct 13
Total with taxes and fees
Spacious 3 BR in Portland's Libbytown!
A kitchen with a wooden countertop, a black kettle, a vase with flowers, and a small wire basket.

15. Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland

Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland
Munjoy Hill
9.6 out of 10, Exceptional, (31 reviews)
"Had a wonderful stay. Very clean and great location."
United States
Aimee S.
$212 nightly
The price is $231
Nov 1 - Nov 2
Total with taxes and fees
Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland
A street lined with buildings, one with a red door and a sign that reads "MINATO".

16. Glorious getaway on Portland's Eastern Promenade.

Glorious getaway on Portland's Eastern Promenade.
Munjoy Hill
9.8 out of 10, Exceptional, (188 reviews)
"The property is well equipped for a long weekend. Parking was convenient. The location offered a quiet place to stay just minutes from Portland’s bustling commercial corridors. Will definitely look to book again on our next visit."
United States
William
$428 nightly
The price is $467
Oct 14 - Oct 15
Total with taxes and fees
Glorious getaway on Portland's Eastern Promenade.
Exterior

17. 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, (114 reviews)
"Fantastic host, fantastic place, fantastic location. 30 second walk out to a massive green lawned park overlooking the water. Easy stroll downtown. Dan was a very friendly, welcoming, and accommodating host. We had a great stay and would return again."
United States
Ryan S.
$426 nightly
The price is $464
Oct 13 - Oct 14
Total with taxes and fees
Ocean View East End Studio in a Historic Victorian
A modern kitchen with a wooden countertop, a glass coffee table, and a built-in shelf with kitchenware.

18. Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
9.8 out of 10, Exceptional, (36 reviews)
"This is a perfect location. 6 minutes from downtown Portland. Secure, Clean and Jen was a Perfect and attentive host. It is a hidden Gem!"
United States
Irish D.
$264 nightly
The price is $288
Oct 12 - Oct 13
Total with taxes and fees
Sunny Spot with Private Parking.
A street lined with buildings, one with a red door and a sign that reads "MINATO".

19. Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (153 reviews)
"Owner was so accommodating!"
United States
Kiernan
$253 nightly
The price is $276
Oct 20 - Oct 21
Total with taxes and fees
Adorable Portland getaway on the Eastern Promenade
A modern living room with a wooden dining table, chairs, a TV, and a bookshelf.

20. East end. Walk to food, beer and downtown fun.

East end. Walk to food, beer and downtown fun.
Munjoy Hill
9.8 out of 10, Exceptional, (47 reviews)
"Very comfortable and stocked well. Lacked for nothing and able to walk to most places. Host checked in which was very nice. Enjoyed Portland."
United States
sheila g.
$334 nightly
The price is $356
Oct 25 - Oct 26
Total with taxes and fees
East end. Walk to food, beer and downtown fun.
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

Spark by Hilton Portland Airport Maine Mall

Spark by Hilton Portland Airport Maine Mall

10/10 Excellent
"Perfect for a stay before an early flight. Helpful staff, clean room."
Julie 1-night trip
Posted 2 hours ago
Spark by Hilton Portland Airport Maine Mall

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 $147 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?

The Perfect Beach Escape: Cozy 4-Bedroom Retreat: This vacation home rental near Windham is located on the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 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 37 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.