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 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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.
The price is ￥41,246
￥137,607 total
includes taxes & fees
Oct 28 - Oct 29
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.
The price is ￥21,099
￥88,118 total
includes taxes & fees
Oct 28 - Oct 29
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.
The price is ￥69,817
￥99,790 total
includes taxes & fees
Oct 14 - Oct 15
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.
The price is ￥36,979
￥83,710 total
includes taxes & fees
Oct 18 - Oct 19
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.
The price is ￥27,921
￥77,986 total
includes taxes & fees
Oct 15 - Oct 16
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.
The price is ￥37,045
￥45,556 total
includes taxes & fees
Oct 20 - Oct 21
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
The price is ￥30,961
￥45,621 total
includes taxes & fees
Nov 2 - Nov 3
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.
The price is ￥66,787
￥128,874 total
includes taxes & fees
Oct 18 - Oct 19
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.
The price is ￥26,810
￥119,637 total
includes taxes & fees
Nov 2 - Nov 3
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
The price is ￥47,532
￥75,606 total
includes taxes & fees
Nov 10 - Nov 11
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.
The price is ￥14,159
￥17,617 total
includes taxes & fees
Oct 14 - Oct 15
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)
"Very nice houseLots of roomKitchen well appointed"
United States
george f.
The price is ￥122,946
￥191,593 total
includes taxes & fees
Oct 19 - Oct 20
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
The price is ￥35,694
￥43,921 total
includes taxes & fees
Oct 18 - Oct 19
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.
The price is ￥47,335
￥78,169 total
includes taxes & fees
Oct 14 - Oct 15
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
9.4 out of 10, Exceptional, (32 reviews)
"Had a wonderful stay. Very clean and great location."
United States
Aimee S.
The price is ￥19,830
￥36,486 total
includes taxes & fees
Nov 1 - Nov 2
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, (189 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
The price is ￥40,049
￥65,268 total
includes taxes & fees
Oct 14 - Oct 15
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.
The price is ￥47,592
￥73,663 total
includes taxes & fees
Oct 14 - Oct 15
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, (37 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.
The price is ￥31,187
￥51,767 total
includes taxes & fees
Oct 26 - Oct 27
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
The price is ￥28,021
￥45,728 total
includes taxes & fees
Oct 28 - Oct 29
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.
The price is ￥33,648
￥58,534 total
includes taxes & fees
Oct 25 - Oct 26
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

DoubleTree by Hilton Hotel Portland

DoubleTree by Hilton Hotel Portland

8/10 Good
"Location is next to a shopping center on the decline and across the street from a busy Starbucks. There was an overnight delivery truck left running outside our window that kept us awake. The bed was softer that we prefer and we woke up with a backache. Pool is much smaller than the pictures make it look. Breakfast was very good."
Laura 1-night trip
Posted 1 hour ago
DoubleTree by Hilton Hotel Portland

Find out more about Windham

Search for holiday rentals in Windham on Expedia! You can easily find your home rentals, villas, holiday apartments in Windham using one of the methods below:

  • View our selection of featured holiday rentals in Windham
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Look no further and take a look at our great range of rental properties in Windham!

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.