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

A dining area with a wooden table, two chairs, and a window with a view of trees.

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 ￥23,864
￥85,317 total
includes taxes & fees
Sep 15 - Sep 16
Cozy 1 BR ADU | Private Access | Projector Theater
A modern living room with a brown leather sofa, a rustic coffee table, and a dining area with a white table and chairs.

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 ￥30,386
￥115,143 total
includes taxes & fees
Sep 9 - Sep 10
Windham Lakefront: Fire Pit and Modern Comforts
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 ￥64,288
￥92,964 total
includes taxes & fees
Aug 28 - Aug 29
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
A bedroom with a large bed, white curtains, and a view through the windows.

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 ￥29,113
￥75,952 total
includes taxes & fees
Sep 1 - Sep 2
Cozy 3BR | Pet Friendly | Near Portland | Parking
A dining table with two black cups and saucers, a wooden vase with flowers, and a window with white frames.

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, (14 reviews)
"Fantastic property. Hosts were very communicative. Amazing stay. Great location! Thank you so much!"
United States
Laurie A.
The price is ￥41,957
￥90,503 total
includes taxes & fees
Aug 30 - Aug 31
Modern Apartment - 20 Mins to Portland, Deck, Grill & Firepit, King Bed, DogsOK
A lakeside deck with outdoor seating and a dock extending into the water.

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 ￥21,477
￥32,774 total
includes taxes & fees
Sep 7 - Sep 8
Sebago Lake studio-style condo with enclosed sunroom and sunset views
A wooden cabin with a deck, outdoor seating, and a portable toilet in a forest.

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, (15 reviews)
"Had a wonderful overnight - was perfect weekend getaway. Was great being in nature!"
United States
Alex D.
The price is ￥37,227
￥46,473 total
includes taxes & fees
Aug 27 - Aug 28
THE LILLIPAD.Off-grid A frame. Sebago lake region!
A modern kitchen with a wooden countertop, a glass coffee table, and a built-in shelf with kitchenware.

8. Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
10.0 out of 10, Exceptional, (32 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 ￥31,341
￥52,023 total
includes taxes & fees
Sep 1 - Sep 2
Sunny Spot with Private Parking.
A yurt with a bed, a desk, and a view of the outdoors.

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 ￥42,771
￥72,650 total
includes taxes & fees
Sep 7 - Sep 8
Fortland Island Campground
A building with a sign for "The Send Brewing Co." and a logo featuring a stylized tree.

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 ￥39,295
￥63,814 total
includes taxes & fees
Sep 1 - Sep 2
Peaceful & minutes from the Old Port with private parking
A cabin with two chairs facing a fire pit, surrounded by trees.

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 ￥36,941
￥60,555 total
includes taxes & fees
Sep 8 - Sep 9
Modern cabin w/ full bath & kitchenette - 03
A building named Willard Square with a storefront and a red vehicle parked outside.

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 ￥47,727
￥96,152 total
includes taxes & fees
Aug 30 - Aug 31
Willard Square Family Home
A modern living room with a sofa, a coffee table, a TV, and a window with blinds.

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 ￥27,860
￥50,670 total
includes taxes & fees
Sep 19 - Sep 20
Pine Point Beach private, quaint, charming studio.
A street lined with buildings, one with a red door and a sign that reads "MINATO".

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 ￥42,477
￥63,814 total
includes taxes & fees
Aug 30 - Aug 31
Adorable Portland getaway on the Eastern Promenade
A house with a wooden front door, a stone staircase, and a porch with a wooden railing.

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 ￥142,226
￥208,609 total
includes taxes & fees
Sep 14 - Sep 15
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
A geodesic dome structure in a forest setting with a visible interior space.

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 ￥40,234
￥66,571 total
includes taxes & fees
Sep 1 - Sep 2
Modern dome w/ full bath + spa access - 04
A kitchen with a wooden countertop, a black kettle, a vase with flowers, and a small wire basket.

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
Charming Studio apartment with WiFi, AC in welcoming Portland
A dining area with a table and chairs, large windows with a view of trees and water, and a candle on the table.

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 ￥50,750
￥117,744 total
includes taxes & fees
Sep 7 - Sep 8
Lakefront-Swim-Kayak-FirePit-20min to Portland
A beach with a wooden chair and a small building in the background.

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.
The price is ￥53,779
￥101,624 total
includes taxes & fees
Aug 30 - Aug 31
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 ￥47,727
￥74,392 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

Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

10/10 Excellent
"I had a wonderful stay. I received an upgraded room which was very nice. I even enjoyed the pool."
Pamela 3-night trip
Posted 2 hours ago
Fireside Inn & Suites 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
  • Use the map to find apartments and other holiday homes in the Windham neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Windham while they last

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?

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.