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Check prices for these dates

In two weeks
20 Feb - 22 Feb
In two months
3 Apr - 5 Apr
In three months
1 May - 3 May
In four months
29 May - 31 May

Our top choices for Windham cottages

Exterior

3BR Cottage Parking A Peaceful Oasis on Munjoy Hill

3BR Cottage Parking A Peaceful Oasis on Munjoy Hill
Munjoy Hill
10.0 out of 10, Exceptional, (2 reviews)
"This is the best VRBO we have stayed at in the last three years of using this service. Everything was as advertised, our host was super helpful and Portland was delightful because of our great location."
United States
Greg F.
The price is €415
includes taxes & fees
9 Mar - 10 Mar
3BR Cottage Parking A Peaceful Oasis on Munjoy Hill
Exterior

4br2ba House parking A Peaceful Oasis on Munjoy Hill

4br2ba House parking A Peaceful Oasis on Munjoy Hill
Munjoy Hill
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful Cottage in a great proximity to a lot! "
United States
Joe C.
The price is €474
includes taxes & fees
10 Feb - 11 Feb
4br2ba House parking A Peaceful Oasis on Munjoy Hill
Exterior

Adorable 1 bedroom cabin only 50 ft from beach#1

Adorable 1 bedroom cabin only 50 ft from beach#1
Old Orchard Beach
10.0 out of 10, Exceptional, (3 reviews)
"The location was wonderful! The host was so communicative and kind!"
United States
Courtney W.
Adorable 1 bedroom cabin only 50 ft from beach#1
Exterior detail

Renovated 2Bd Cottage 10min walk to Beach. Pets Ok

Renovated 2Bd Cottage 10min walk to Beach. Pets Ok
Old Orchard Beach
7.2 out of 10, Good, (12 reviews)
"Was as advertised."
United States
Andrew H.
The price is €165
includes taxes & fees
9 Feb - 10 Feb
Renovated 2Bd Cottage 10min walk to Beach. Pets Ok
Exterior

Little Miss Cottages - One Bedroom Cottage

Little Miss Cottages - One Bedroom Cottage
Old Orchard Beach
10.0 out of 10, Exceptional, (2 reviews)
"Clean, very good communication with the host."
United States
Brandon F.
The price is €264
includes taxes & fees
8 Feb - 9 Feb
Little Miss Cottages - One Bedroom Cottage
Exterior

Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
Old Orchard Beach
9.8 out of 10, Exceptional, (65 reviews)
"Everything was nice & perfectly described. Great quiet neighborhood loved my stay & so did my Dogs thank you for a lovely stay"
United States
Teresa M.
The price is €204
includes taxes & fees
10 Feb - 11 Feb
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
Exterior detail

Clean cozy cottage 1 mile from beach.

Clean cozy cottage 1 mile from beach.
Old Orchard Beach
8.0 out of 10, Very good, (11 reviews)
"This house met all of our needs. It was updated and clean and has a nice little quiet enclosed back yard with a fire pit, grill and dining area. "
United States
Alyssa F.
The price is €337
includes taxes & fees
8 Feb - 9 Feb
Clean cozy cottage 1 mile from beach.
Property grounds

Cheerful 1 bedroom cottage only 50ft from beach

Cheerful 1 bedroom cottage only 50ft from beach
Old Orchard Beach
10.0 out of 10, Exceptional, (2 reviews)
"We loved the area. We loved the cottage feel. We only wished it had bigger fridge and a better cook top. Other then that it was great."
United States
Chris A.
Cheerful 1 bedroom cottage only 50ft from beach
Beach nearby

Cozy one bedroom cottage, 50 feet from the beach in OOB.

Cozy one bedroom cottage, 50 feet from the beach in OOB.
Old Orchard Beach
9.6 out of 10, Exceptional, (4 reviews)
"Great location to the beach and the pier! "
United States
Pamela C.
Cozy one bedroom cottage, 50 feet from the beach in OOB.
Exterior

Spacious 2 bedroom cabin, 50ft from the beach

Spacious 2 bedroom cabin, 50ft from the beach
Old Orchard Beach
10.0 out of 10, Exceptional, (1 review)
"The amenities were perfect and the communication was excellent!"
United States
Dawn C.
Spacious 2 bedroom cabin, 50ft from the beach
Interior

Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5

Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5
Old Orchard Beach
8.0 out of 10, Very good, (24 reviews)
"Was the perfect place to unwind. Close enough to walk to beach, restaurants and shops. Enjoyed our stay emensly!"
United States
Maria H.
The price is €185
includes taxes & fees
12 Feb - 13 Feb
Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5
Beach nearby

Attractive 1 bedroom cabin only 50 ft from beach

Attractive 1 bedroom cabin only 50 ft from beach
Old Orchard Beach
Attractive 1 bedroom cabin only 50 ft from beach
Beach nearby

beautiful 1 bedroom cabin only 50 ft from beach

beautiful 1 bedroom cabin only 50 ft from beach
Old Orchard Beach
beautiful 1 bedroom cabin only 50 ft from beach
Exterior

Large 2BD cottage 10 min to Pier & Beach Pets ok

Large 2BD cottage 10 min to Pier & Beach Pets ok
Old Orchard Beach
9.0 out of 10, Wonderful, (37 reviews)
"Wondeful place to stay while in the area. EASY walk to the beach and all that the boardwalk area has to offer. "
United States
Steven D.
The price is €184
includes taxes & fees
8 Feb - 9 Feb
Large 2BD cottage 10 min to Pier & Beach Pets ok
Exterior

Lakehouse Near N. Conway &Skiing/Pool table/Pond Access to Fish/Skate/Snowmobile

Lakehouse Near N. Conway &Skiing/Pool table/Pond Access to Fish/Skate/Snowmobile
Brownfield
10.0 out of 10, Exceptional, (3 reviews)
"Everything was great for check in, and the amenities and snacks there were a great touch! Came in handy for the couple that forgot to pack their toothbrushes! "
United States
Brian A.
The price is €258
includes taxes & fees
23 Feb - 24 Feb
Lakehouse Near N. Conway &Skiing/Pool table/Pond Access to Fish/Skate/Snowmobile
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

Tru by Hilton Portland Airport Area

Tru by Hilton Portland Airport Area

10/10 Excellent
"Clean room ,nice parking good breakfast easy to get in and out of parking lot."
Douglas 2-night trip
Posted 4 days ago
Tru by Hilton Portland Airport Area

Find out more about Windham

Windham Cottages information

Number of reviews
151
Accommodation
374 Cottages
Lowest Price
€165
Highest Price
€264

Frequently asked questions

How much do cottages in Windham cost?
Cottages in Windham range between €165 and €264 per night. These retreats offer a chance to reconnect with nature — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Windham?
Enjoy the beauty of nature in one of the 374 cottages available in Windham. To help you find your ideal stay, make use of our handy filters to search for must-have amenities or perks.
Why book your cottage in Windham with Expedia?
Expedia has some superb cottages in Windham, so start planning for an unforgettable stay on nature's doorstep. If you have a fixed budget, click on how much you want to spend and your preferred property star rating. Or, use our handy filters to search for cottages with a pool or a kitchen. We'll help you find the perfect fit whatever your plans or bank balance.
How can I find cheap cottages in Windham?
The easiest way to locate cheap cottages in Windham is with Expedia's handy filter tool. Narrow down your search by star rating, amenities and budget to land awesome rates in just a few keystrokes.
What is there to do in Windham near my cottage?
The ideal travel accessory is a well-planned to-do list. Maine Wildlife Park is a top place to kick-start your adventures in Windham.

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