Search Cottages in Windham

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Compare 284 Cottages in Windham with updated reviews, rates, and availability.

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
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!
The Renaissance - Majestic Sebago Lake panorama
Exterior

The Renaissance - Majestic Sebago Lake panorama

9.2 out of 10, Wonderful, (11)
"This house was close to Portland in a nice, quiet neighborhood. It had plenty of space for me, my wife, and four kids. I love the care the owners take to make sure we have the comforts of home. It's fully stocked up with towels, toilet paper, kitchen cookware, you name it. They also took the time to label all of the light switches so you know how to turn everything one. We were very happy with our stay and highly recommend. The home itself was nice, but the care the owners took to make...
The Renaissance - Majestic Sebago Lake panorama
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, (49)
"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
The Great Escape - Picturesque Sebago Lake
Backyard

The Great Escape - Picturesque Sebago Lake

9.8 out of 10, Exceptional, (44)
"Property was perfect for our stay."
The Great Escape - Picturesque Sebago Lake
Nautical View | Luxury Oceanside Cottage | Steps to Beach | Bayley Vacation Rentals
The exterior of your vacation rental

Nautical View | Luxury Oceanside Cottage | Steps to Beach | Bayley Vacation Rentals

10.0 out of 10, Exceptional, (17)
"Great property! Very close to the beach. The place was spotless and easy to find. Checking in was a breeze too. The only thing I would say was that it was very tight with 2 boys and a giant husband but the closet system thing that they have was very well thought out. "
Nautical View | Luxury Oceanside Cottage | Steps to Beach | Bayley Vacation Rentals
Cottages by the Sea #1 | Private Beach | Steps to Sand | Bayley Vacation Rentals
Outside of cottage | Steps to the sand

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
Bright Beach Cottage, Waterviews, Dog Ok, Honeymoon, Weddings
Dining area with sweeping water views of our inner harbor "The Pool"

Bright Beach Cottage, Waterviews, Dog Ok, Honeymoon, Weddings

9.6 out of 10, Exceptional, (44)
"I absolutely loved staying at Sarah's cottage! It perfectly embodies quintessential coastal Maine style, with gorgeous views, breathtaking sunsets, and the beach right across the street. You can even hear the soothing sound of the ocean at night! I had never been to Biddeford Pool before, and I’m so happy I found this listing. I fell in love with both the town and this charming home. Sarah was incredibly responsive and accommodating throughout my stay. I definitely plan on returning!"
Bright Beach Cottage, Waterviews, Dog Ok, Honeymoon, Weddings
Sea Bisquit Cottage by the Ocean
Living area

Sea Bisquit Cottage by the Ocean

9.4 out of 10, Exceptional, (10)
"fine"
Sea Bisquit Cottage by the Ocean
Airy beach cottage steps away from Pine Point Beach!
Exterior

Airy beach cottage steps away from Pine Point Beach!

9.8 out of 10, Exceptional, (22)
"Pine Point Beach is a beautiful beach and the location of the house was very convenient and worked well for our family. The outdoor space at the home could use some updating and additional seating. The lack of dressers and space to put clothing was a challenge for our family. "
Airy beach cottage steps away from Pine Point Beach!
The Outlet House, Comfortable Cottage
Interior

The Outlet House, Comfortable Cottage

9.8 out of 10, Exceptional, (38)
"This is a perfect haven for a couple, or a small group of family or friends. Everything is as nice as it's presented here at VRBO. Clean, spacious, and well-appointed. Owner was very responsive and quickly addressed a minor heating issue and it was resolved. Highly recommended!"
The Outlet House, Comfortable Cottage
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
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.
PRIVATE OCEANFRONT RETREAT - enjoy the peace and quiet of an historic Maine home
The view from the front door at The Gills cottage. THE GILLS GROUP

PRIVATE OCEANFRONT RETREAT - enjoy the peace and quiet of an historic Maine home

9.6 out of 10, Exceptional, (61)
"Dating from 1918, vacationing in this cottage was a quiet visual delight. The view from the front porch, overlooking the evergreen trees and blueberry bushes, out to the ever-changing ocean will stay in my mind throughout the year. The house itself is much the way it has always been, simple, rustic and quiet; off the beaten path, a retreat with few conveniences, a great place to look and contemplate, to read and draw. For us, it was perfect."
PRIVATE OCEANFRONT RETREAT - enjoy the peace and quiet of an historic Maine home
Beachfront Sebago Cottage w/ Deck + Grill!
Sebago Vacation Rental | 1BR | 1BA | 600 Sq Ft | Step-Free Access

Beachfront Sebago Cottage w/ Deck + Grill!

9.4 out of 10, Exceptional, (18)
"Minimum amenities; window a/c was dirty, box fan was dirty...got a bit warm but could not use these items. Kuerig coffee maker would be nice, ironing board was also dusty. I believe a deep clean is needed. However, outside was comfortable and the lake view was awesome."
Beachfront Sebago Cottage w/ Deck + Grill!
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
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
SLEEPS 15 WITH A PRIVATE SANDY BEACH ON LONG LAKE.

SLEEPS 15 WITH A PRIVATE SANDY BEACH ON LONG LAKE.

SLEEPS 15 WITH A PRIVATE SANDY BEACH ON LONG LAKE.
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
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.
Don't see what you're looking for?
See all available properties in Windham
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Windham

Lakefront House
Miscellaneous

Lakefront House

10.0 out of 10, Exceptional, (23)
"The house was clean and welcoming. The hosts were quick to respond to questions. It would be remarkable in the warm months, so you could enjoy the lake! "
The price is AED 588
AED 2,678 total
includes taxes & fees
24 Feb - 25 Feb
Lakefront House
The Weldon Hotel
Front of property

The Weldon Hotel

4.0 star property
9.4 out of 10, Exceptional, (36)
"Overall, the stay was great. The lower-level suite was a bit noisy, as we were at ground level; however, I would highly recommend staying here if you are looking for full amenities and a short commute to everything in downtown Portland. "
The price is AED 534
AED 582 total
includes taxes & fees
6 Mar - 7 Mar
The Weldon Hotel
Lakefront House with Private Sandy Beach
Exterior

Lakefront House with Private Sandy Beach

9.8 out of 10, Exceptional, (26)
"I would have given this property 5 stars except for the sketchy kitchen equipment. When traveling with pets it is often difficult to go out to eat. Therefore we made three meals a day and wished for 1)a toaster oven 2)electric kettle and 3) more hot pads, kitchen towels, and spatulas"
Lakefront House with Private Sandy Beach
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 and 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 284 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.