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Check prices for these dates

In two weeks
Jun 26 - Jun 28
In two months
Aug 7 - Aug 9
In three months
Sep 4 - Sep 6
In four months
Oct 2 - Oct 4

Our top choices for Windham cottages

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, (12 reviews)
"Ani was very friendly and communicative and the place was comfortable and inviting. We had a great stay!"
United States
Cristina Q.
$755 nightly
The price is $823
Jun 28 - Jun 29
Total with taxes and fees
4br2ba House parking A Peaceful Oasis on Munjoy Hill
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, (72 reviews)
"Place was great and fenced in backyard for our dog. "
United States
Billy N.
$237 nightly
The price is $259
Jun 15 - Jun 16
Total with taxes and fees
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
Exterior

Little Miss Cottages - One Bedroom Cottage

Little Miss Cottages - One Bedroom Cottage
Old Orchard Beach
8.8 out of 10, Excellent, (5 reviews)
"Clean, very good communication with the host."
United States
Brandon F.
$367 nightly
The price is $400
Jun 15 - Jun 16
Total with taxes and fees
Little Miss Cottages - One Bedroom Cottage
Exterior

Nautical View

Nautical View
Old Orchard Beach
10.0 out of 10, Exceptional, (19 reviews)
"Beautiful place!"
United States
Louise P.
$977 nightly
The price is $1,057
Jun 23 - Jun 24
Total with taxes and fees
Nautical View
Exterior

Cottages by the Sea #1 by Bayley Vacation Rentals

Cottages by the Sea #1 by Bayley Vacation Rentals
Surfside
10.0 out of 10, Exceptional, (7 reviews)
"Clean place, had everything we needed, and can’t beat the location. Will definitely be back."
United States
Matthew J.
$1,347 nightly
The price is $1,459
Jul 13 - Jul 14
Total with taxes and fees
Cottages by the Sea #1 by Bayley Vacation Rentals
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, (5 reviews)
"It was the perfect little place to stay for our anniversary!"
United States
Haley W.
$318 nightly
The price is $347
Jun 15 - Jun 16
Total with taxes and fees
Adorable 1 bedroom cabin only 50 ft from beach#1
2 bedrooms, iron/ironing board, free WiFi, bed sheets

Renovated 2Bd Cottage 10min walk to Beach.

Renovated 2Bd Cottage 10min walk to Beach.
Old Orchard Beach
7.2 out of 10, Good, (12 reviews)
"Was as advertised."
United States
Andrew H.
$376 nightly
The price is $380
Jun 15 - Jun 16
Total with taxes and fees
Renovated 2Bd Cottage 10min walk to Beach.
Exterior

Soothing 2-bedroom cottage with Sauna in Old Orchard Beach

Soothing 2-bedroom cottage with Sauna in Old Orchard Beach
Old Orchard Beach
$332 nightly
The price is $362
Jun 23 - Jun 24
Total with taxes and fees
Soothing 2-bedroom cottage with Sauna in Old Orchard 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.
$371 nightly
The price is $404
Jun 16 - Jun 17
Total with taxes and fees
Cozy one bedroom cottage, 50 feet from the beach in OOB.
Beach nearby

Attractive 1 bedroom cabin only 50 ft from beach

Attractive 1 bedroom cabin only 50 ft from beach
Old Orchard Beach
10.0 out of 10, Exceptional, (1 review)
"It was very close to the beach but I would not call it beach view. Having said that it was only a very short walk, 5 minutes. The cabin was perfect for two people and two mid sized dogs. Very clean and well supplied. Will most certainly book again."
United States
Nichole B.
$299 nightly
The price is $326
Jun 15 - Jun 16
Total with taxes and fees
Attractive 1 bedroom cabin only 50 ft from beach
Exterior

Little Miss Cottages - Two Bedroom Cottage Suite - 9

Little Miss Cottages - Two Bedroom Cottage Suite - 9
Old Orchard Beach
$431 nightly
The price is $470
Jun 17 - Jun 18
Total with taxes and fees
Little Miss Cottages - Two Bedroom Cottage Suite - 9
Property grounds

Cheerful 1 bedroom cottage only 50ft from beach

Cheerful 1 bedroom cottage only 50ft from beach
Old Orchard Beach
9.6 out of 10, Exceptional, (4 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.
$307 nightly
The price is $335
Jun 15 - Jun 16
Total with taxes and fees
Cheerful 1 bedroom cottage only 50ft from beach
Interior

Large 2BD cottage 10 min to Pier & Beach Sleeps 6

Large 2BD cottage 10 min to Pier & Beach Sleeps 6
Old Orchard Beach
9.0 out of 10, Wonderful, (40 reviews)
"The location and the space is great!!"
United States
Anonymous traveler
$412 nightly
The price is $416
Jun 15 - Jun 16
Total with taxes and fees
Large 2BD cottage 10 min to Pier & Beach Sleeps 6
Beach nearby

beautiful 1 bedroom cabin only 50 ft from beach

beautiful 1 bedroom cabin only 50 ft from beach
Old Orchard Beach
$306 nightly
The price is $334
Jun 15 - Jun 16
Total with taxes and fees
beautiful 1 bedroom cabin only 50 ft from beach
Beach

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

Updated 2 BD cottage. 10 min walk to Pier & Beach
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.
$352 nightly
The price is $355
Jun 15 - Jun 16
Total with taxes and fees
Updated 2 BD cottage. 10 min walk to Pier & Beach
Exterior

Spacious 2 bedroom cabin, 50ft from the beach

Spacious 2 bedroom cabin, 50ft from the beach
Old Orchard Beach
8.0 out of 10, Very Good, (2 reviews)
"The amenities were perfect and the communication was excellent!"
United States
Dawn C.
$709 nightly
The price is $773
Jun 28 - Jun 29
Total with taxes and fees
Spacious 2 bedroom cabin, 50ft from the beach
Exterior

Attractive 1 bedroom cabin only 50 ft from beach

Attractive 1 bedroom cabin only 50 ft from beach
Old Orchard Beach
$498 nightly
The price is $543
Jun 21 - Jun 22
Total with taxes and fees
Attractive 1 bedroom cabin only 50 ft from beach
Outdoor dining

Sebago Waterfront-Large Private Lot, Dock, Screened Porch, Grill. Pets Allowed

Sebago Waterfront-Large Private Lot, Dock, Screened Porch, Grill. Pets Allowed
SEBAGO
Sebago Waterfront-Large Private Lot, Dock, Screened Porch, Grill. Pets Allowed
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

Clarion Pointe South Portland

Clarion Pointe South Portland

8/10 Good
"Our stay was good!"
Kristina 1-night trip
Posted 2 hours ago
Clarion Pointe South Portland

Find out more about Windham

Windham Cottages information

Number of reviews
198
Accommodation
427 Cottages
Lowest Price
$259
Highest Price
$1,459

Frequently asked questions

How much do cottages in Windham cost?
Cottages in Windham range between $259 and $1,459 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 427 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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