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Compare 264 Cottages in Windham with updated reviews, rates, and availability.

Sensational House on Sebago Lake, Raymond, ME
Exterior

Sensational House on Sebago Lake, Raymond, ME

9.8 out of 10, Exceptional, (43)
"Great property located on an amazing lake sebago great amenities."
Sensational House on Sebago Lake, Raymond, ME
Updated Cottage - Steps to Pine Point Beach!
Living area

Updated Cottage - Steps to Pine Point Beach!

10.0 out of 10, Exceptional, (12)
"Loved the location and proximity to the ocean. The cottage was meticulously clean and had everything we needed for our stay. Highly recommend! "
Updated Cottage - Steps to Pine Point Beach!
Great Location! 5 min Walk to Beach/Pier-Cottage Sleeps 6;12 w/back unit
Open concept Living/Dining/Kitchen

Great Location! 5 min Walk to Beach/Pier-Cottage Sleeps 6;12 w/back unit

9.8 out of 10, Exceptional, (49)
"Convenient to all that Old Orchard Beach has to offer. Great communication and offerings of beach chairs and beach towels. Wonderful time. Definitely recommend."
Great Location! 5 min Walk to Beach/Pier-Cottage Sleeps 6;12 w/back unit
Great Location! Walk to Beach/Pier in 5 minutes-Cottage Sleeps 6;12 w/front unit
Living area

Great Location! Walk to Beach/Pier in 5 minutes-Cottage Sleeps 6;12 w/front unit

9.8 out of 10, Exceptional, (48)
"the location was perfect. Close enough to walk to everything, but far enough to not be noisy from the crowds. The place was very clean and had all of the amenities we needed. I would 100% stay here again. The property manager was easy to contact and answered every question or concern in a very quick manner and was very kind. Highly recommend this property"
Great Location! Walk to Beach/Pier in 5 minutes-Cottage Sleeps 6;12 w/front unit
Family-friendly Bridgton Home, Steps to Lake!
Exterior

Family-friendly Bridgton Home, Steps to Lake!

3.0 star property
Family-friendly Bridgton Home, Steps to Lake!
Little Miss Cottages
Exterior

Little Miss Cottages

2.5 star property
8.4 out of 10, Very Good, (82)
"We stayed because they accept pets. Good place the 24/7 laundry was useable but not everything working"
Little Miss Cottages
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
THE GILLS GROUP has two additional cottages available for larger groups

PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room

10.0 out of 10, Exceptional, (99)
"This property is stunning, and the view is spectacular. If this were my house, I’d never leave! We had a fabulous time. "
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
Cottages by the Sea #1 | Private Beach | Steps to Sand | Bayley Vacation Rentals
Path to the beach

Cottages by the Sea #1 | Private Beach | Steps to Sand | Bayley Vacation Rentals

10.0 out of 10, Exceptional, (6)
"We had a wonderful stay - myself, my husband and my 6,4, and 2 year old children all enjoyed our time at the beach. We could have done without the harassment of the old lady from cottage 4 (owner perhaps?) telling us to get out at 10am. We were packing the car at 10:02 and trying to get the kids in - we were not in the cottage anymore everything was out. We left the property 10:11am. Her nagging and threats of charging extra were completely unnecessary. It was too bad to have to leave on...
Cottages by the Sea #1 | Private Beach | Steps to Sand | Bayley Vacation Rentals
Charming 3BR, 1.5BA beachfront cottage with multi-level decks

Charming 3BR, 1.5BA beachfront cottage with multi-level decks

9.2 out of 10, Wonderful, (31)
"Wonderful "
Charming 3BR, 1.5BA beachfront cottage with multi-level decks
Private Contemporary Artist's Tree House on two acres with perennial gardens.
The floating two story private addition extends into the apple trees.

Private Contemporary Artist's Tree House on two acres with perennial gardens.

10.0 out of 10, Exceptional, (31)
"Very homey, very clean, comfortable bed. All we needed during our stay was procedez. The host was extremely responsive and courteous. We will like to visit again and I would stay here again."
Private Contemporary Artist's Tree House on two acres with perennial gardens.
Lakefront camp with cozy cottage-style interior and board games - kayaks welcome

Lakefront camp with cozy cottage-style interior and board games - kayaks welcome

9.6 out of 10, Exceptional, (15)
"We had a great stay at this cozy camp, thoroughly enjoyed spending time by the water and relaxing. Lots to do in the area but not a bad drive to Portland either. We wish the bedrooms had an extra lamp each- very dark! But that is a minor complaint. Hope to Iretun next year!"
Lakefront camp with cozy cottage-style interior and board games - kayaks welcome
The Wee White Cottage on Tripp Lake in Poland, Maine.
Living area

The Wee White Cottage on Tripp Lake in Poland, Maine.

9.8 out of 10, Exceptional, (69)
"the cottage was lovely. open air plan.. surprisingly quiet but we were there during the week. well off the beaten track so we were very happy with it"
The Wee White Cottage on Tripp Lake in Poland, Maine.
Charming cottage short walk to beach!
1

Charming cottage short walk to beach!

9.4 out of 10, Exceptional, (26)
"We had a great time on our recent stay here. short walk to the beach, quiet neighborhood. This home was fully stocked with all the amenities and truly felt like our home away from home. Check in/out was seamless and there was great communication the the host. If we ever plan to travel to the area again, we would definately stay here once more. "
Charming cottage short walk to beach!
Lakefront cabin with shared firepit & access to Sebago Lake

Lakefront cabin with shared firepit & access to Sebago Lake

8.0 out of 10, Very Good, (10)
"very nice!"
Lakefront cabin with shared firepit & access to Sebago Lake
Classic Maine Beach Cottage **** Fabulous location!
Vibrant active local boating community

Classic Maine Beach Cottage **** Fabulous location!

9.2 out of 10, Wonderful, (24)
"Comfortable cottage with plenty of room. Very pleasant living space. We found it very convenient to the things we like to do, places we like to go. We would certainly come back"
The price is SAR 1,220
SAR 2,202 total
includes taxes & fees
2 Dec - 3 Dec
Classic Maine Beach Cottage **** Fabulous location!
Updated Long Island Maine Cottage
Interior

Updated Long Island Maine Cottage

10.0 out of 10, Exceptional, (4)
"We really enjoyed our stay at Chaz' Long Island house. It is open and airy and maintains its 100 year old charm even as it's been updated. It sits in a great, grassy yard with plenty of bright light and has a terrific, large deck on the front. The golf cart ride to all beaches is short and lovely!"
Updated Long Island Maine Cottage
The Outlet House, Comfortable Cottage
Interior

The Outlet House, Comfortable Cottage

9.8 out of 10, Exceptional, (35)
"Nice clean quiet place but close to a lot of things."
The Outlet House, Comfortable Cottage
As much "an experience" as shelter, Kinsale delights everyone of all ages.

As much "an experience" as shelter, Kinsale delights everyone of all ages.

9.2 out of 10, Wonderful, (13)
"Fantastic !!!"
As much "an experience" as shelter, Kinsale delights everyone of all ages.
Quaint Retro Ash Cove Cottage
Room

Quaint Retro Ash Cove Cottage

9.6 out of 10, Exceptional, (15)
"a 12 on a 1=10 scale. Real Maine...void of pretense and dreaded pandemic migrants...wonderful folks own the property. "
Quaint Retro Ash Cove Cottage
Cozy countryside cottage located on Crooked river in Naples Maine.
Property grounds

Cozy countryside cottage located on Crooked river in Naples Maine.

10.0 out of 10, Exceptional, (10)
"Had everything we needed. Stream would be very nice if we had come during warmer weather. Next time!"
Cozy countryside cottage located on Crooked river in Naples Maine.
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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Other property types in Windham

Charming lakefront cottage with a dock, WiFi, & washer/dryer - dogs welcome

Charming lakefront cottage with a dock, WiFi, & washer/dryer - dogs welcome

8.6 out of 10, Excellent, (35)
"We would absolutely book this house again. Super peaceful location. Loons in the morning were a stellar start to each day. "
Charming lakefront cottage with a dock, WiFi, & washer/dryer - dogs welcome
Beachfront Luxury Grand Victorian Condo (Primetime View directly down the pier)
Beach

Beachfront Luxury Grand Victorian Condo (Primetime View directly down the pier)

9.8 out of 10, Exceptional, (115)
"Very relaxing getaway."
Beachfront Luxury Grand Victorian Condo (Primetime View directly down the pier)
Sensational House on Sebago Lake, Raymond, ME
Exterior

Sensational House on Sebago Lake, Raymond, ME

9.8 out of 10, Exceptional, (43)
"Great property located on an amazing lake sebago great amenities."
Sensational House on Sebago Lake, Raymond, ME
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.

Frequently asked questions

How much do cottages in Windham cost?
Cottages in Windham range between SAR 1,220 and SAR 1,220 per night. These retreats offer a chance to touch base 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?
Pack your suitcases and pick from 264 cottages in Windham. Thinking about a place where you can reconnect with nature? Expedia can help you find your ideal getaway in a few simple clicks.
Why book your cottage in Windham with Expedia?
Booking a cottage in Windham is as easy as working out your travel dates and picking your ideal place for outdoor fun and relaxation. From high-end retreats to budget-friendly stays and cottages that come with perks like a pool, Expedia has something for all traveler tastes. As for terrific deals? We’ve got you covered!
How can I find cheap cottages in Windham?
Expedia can help you easily track down cheap cottages in Windham. To find a fantastic stay in a few clicks, use our convenient filter tool to tailor your search results by star rating, amenities and budget.