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 Rab. I - 30 Rab. I
In two weeks
4 Rab. II - 6 Rab. II
In one month
18 Rab. II - 20 Rab. II
In two months
16 Jum. I - 18 Jum. I

Compare 131 Cottages in Windham with updated reviews, rates, and availability.

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Exterior

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

9.6 out of 10, Exceptional, (211)
"Very cute cabin with fireplace and jacuzzi. Host provided firewood - which was a nice touch. Cabin is on dead end private road so, as mentioned, very peaceful. Lots of snow so no deck access, but imagine it would be great in summer too."
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit
Interior

Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

9.8 out of 10, Exceptional, (11)
"We loved the location and home! So close to Okemo, beautiful home right on the lake. The hottub and gas fireplace were appreciated after a day of skiing. We would definitely come back again!"
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit
Charming Meadow View Cottage in heart of historic Dorset VT! Pet friendly!
Fridge, microwave, oven, stovetop

Charming Meadow View Cottage in heart of historic Dorset VT! Pet friendly!

10.0 out of 10, Exceptional, (27)
"Loved Dorset and this house was great. Very clean and living area was nice to spend time with family. Also close to skiing which we took advantage of"
Charming Meadow View Cottage in heart of historic Dorset VT! Pet friendly!
Vermont Country Cottage (Near Village)
Exterior

Vermont Country Cottage (Near Village)

9.2 out of 10, Wonderful, (10)
"This cottage reviewed very well online and pictures were very accurate too. It was secluded and far from neighbors, fire house across the street but zero activity the whole weekend. The cottage had the amenities listed. It was neat and tidy, well equipped. Very confortable. Loved the wood stove. We used that and it was wonderful. Check in/out Instructions were easy to follow. The area was beautiful, peacefu and not too far away from groceries, food or beverages. Would definitely go...
Vermont Country Cottage (Near Village)
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
TV, books

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

10.0 out of 10, Exceptional, (7)
"Great, clean, charming cottage. The hosts are amazing and communicated every detail, very hospitable. Highly recommend. "
The price is SAR 768
SAR 935 total
includes taxes & fees
24 Mar - 25 Mar
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Unique Ski cottage nestled between Mt. Snow & Stratton
Exterior

Unique Ski cottage nestled between Mt. Snow & Stratton

10.0 out of 10, Exceptional, (2)
"Sick little cabin close to snow and stratton. Quiet and good location"
Unique Ski cottage nestled between Mt. Snow & Stratton
Home with a spring-fed pond and mountain view.
Pool

Home with a spring-fed pond and mountain view.

10.0 out of 10, Exceptional, (116)
"We stayed at the guest house for 2 nights with our black lab. Jeremy’s hospitality was amazing! There were snacks and a full fridge waiting for us along with helpful guides to the area. Our dog had the best time swimming in the pond and watching the fish. It’s a very comfortable space in a stunning setting. Could not recommend more highly! "
Home with a spring-fed pond and mountain view.
This cottage is a 1 bedroom(s), 1.5 bathrooms, located in Manchester, VT.
Exterior

This cottage is a 1 bedroom(s), 1.5 bathrooms, located in Manchester, VT.

10.0 out of 10, Exceptional, (28)
"This was a great location… close to town but also close to skiing, hiking and skating."
This cottage is a 1 bedroom(s), 1.5 bathrooms, located in Manchester, VT.
Cottage in Private Village On VT-100 (5-min to Mount Snow)
Fridge, microwave, oven, stovetop

Cottage in Private Village On VT-100 (5-min to Mount Snow)

9.0 out of 10, Wonderful, (2)
"This cottage was wonderful! Great location. Great shower. Loved having a kitchen. Bed was comfortable and place was clean! The only real downfall was the couch/ seating arrangement! After a long day on mountain a nice couch or chair is where it's at! The couch was small and uncomfortable but our little family made the best of it ! Communication was always there and we were overall pleased ! "
Cottage in Private Village On VT-100 (5-min to Mount Snow)
The Cairn, 1840s Cozy Stone Cottage, Pet Friendly
Exterior

The Cairn, 1840s Cozy Stone Cottage, Pet Friendly

10.0 out of 10, Exceptional, (10)
"We started 2 nights while skiing at Okemo. It was a nice warm cozy spot to relax at the end of the day. Loved that it's a historic stone structure as well. Not to mention the covered bridge that you drive through on the way! "
The Cairn, 1840s Cozy Stone Cottage, Pet Friendly
Beautiful Vacation Cottage with a View in Newfane, Vermont, near Mt. Snow
Exterior

Beautiful Vacation Cottage with a View in Newfane, Vermont, near Mt. Snow

9.6 out of 10, Exceptional, (63)
"If you're looking to get away from it all then this is the place for you! Picturesque scenery. The nearby shops and markets were great, especially the farmers market. We would love to stay here again. "
Beautiful Vacation Cottage with a View in Newfane, Vermont, near Mt. Snow
Cottage 7min to Ski Stratton-Wood Stove,Starry Skies,Fire Pit,Views,Dogs OK
TV, fireplace, DVD player, books

Cottage 7min to Ski Stratton-Wood Stove,Starry Skies,Fire Pit,Views,Dogs OK

2.0 star property
10.0 out of 10, Exceptional, (1)
"The property was clean and neat. Very quaint and in the woods. We had a great time. Looking forward to doing it again in the near future. "
The price is SAR 300
SAR 822 total
includes taxes & fees
24 Mar - 25 Mar
Cottage 7min to Ski Stratton-Wood Stove,Starry Skies,Fire Pit,Views,Dogs OK
Charming Cavendish Cottage: All-Season Retreat for fun and relaxation!
Private kitchen

Charming Cavendish Cottage: All-Season Retreat for fun and relaxation!

8.0 out of 10, Very Good, (1)
"Beautiful house with lots of very thoughtful amenities. Very clear and easy communication from owners as well. Great location for skiing Okemo and it was a lovely place to come back to after a day on the slopes. One issue was that the listing states this is a 4 bedroom home, but in fact there are only 3. This made for a tight squeeze for 5 adults (none of whom were couples). I'm wondering if this might have been a glitch on the website. We had a great stay, but had we known it was only 3...
Charming Cavendish Cottage: All-Season Retreat for fun and relaxation!
Hike & Swim On-site: Cozy Falls Brook Cabin
House (2 Bedrooms) | Interior

Hike & Swim On-site: Cozy Falls Brook Cabin

3.0 star property
10.0 out of 10, Exceptional, (2)
"This is exactly how it’s described- perfect cozy spot- babbeling brook to keep you company while sitting on the porch - fire pit for cozy evenings and cabin inside is perfection- cozy cozy cozy!! Matt was the perfect host and readily available- hoping to return!! 15 mins from farmers markets, covered bridges, shops, food, drinks and entertainment ❤️"
Hike & Swim On-site: Cozy Falls Brook Cabin
Ski & Lake Home-Minutes from Magic, Stratton, Bromley & Okemo-Southern Vermont
Fridge, microwave, oven, stovetop

Ski & Lake Home-Minutes from Magic, Stratton, Bromley & Okemo-Southern Vermont

10.0 out of 10, Exceptional, (2)
"We had the BEST time on our short little getaway to the Vermont mountains! We are very familiar with the area but this was our first VRBO. We didn’t really know what to expect but Lizzie’s place was absolutely perfect for our family of 5 (kids ages 2,5 and 7.) The space was cleaner than clean (which is a big deal to us) and updated. It is such a cute and happy little place and we didn’t want to leave. The kids loved the bunk beds, and the rooms couldn’t have been more comfortable and well...
Ski & Lake Home-Minutes from Magic, Stratton, Bromley & Okemo-Southern Vermont
Lovely Ludlow Farmhouse ~ 1 Mi to Town & Slopes!
Microwave, oven, stovetop, cookware/dishes/utensils

Lovely Ludlow Farmhouse ~ 1 Mi to Town & Slopes!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Great place "
Lovely Ludlow Farmhouse ~ 1 Mi to Town & Slopes!
18 Mi to Skiing: Colorful Home in Springfield!
Interior

18 Mi to Skiing: Colorful Home in Springfield!

3.0 star property
18 Mi to Skiing: Colorful Home in Springfield!
Cozy Cabin Between Stratton Resort & Mount Snow
TV, fireplace

Cozy Cabin Between Stratton Resort & Mount Snow

3.0 star property
Cozy Cabin Between Stratton Resort & Mount Snow
Near Skiing & Hiking: Quiet Home in West Wardsboro
Interior

Near Skiing & Hiking: Quiet Home in West Wardsboro

3.0 star property
Near Skiing & Hiking: Quiet Home in West Wardsboro
West Dover Vacation Rental w/ Hot Tub Near Mt Snow
House (4 Bedrooms) | Interior

West Dover Vacation Rental w/ Hot Tub Near Mt Snow

3.0 star property
West Dover Vacation Rental w/ Hot Tub Near Mt Snow
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

Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.
Smart TV, fireplace, foosball, table tennis

Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.

10.0 out of 10, Exceptional, (47)
"We had a great stay at this property and every year a few families get together to spend a few days skiing and other winter activities. The house was a great layout for our group with plenty of spaces for all to sleep. Kids loved the downstairs while the adults love the game house. The property was well stocked with all needs if you forgot anything to make meal times easy. Host was great and if we had any questions they were answered right away. "
Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.
Long Trail House at Stratton Mountain Resort
Condo, 2 Bedrooms | Pool | Outdoor pool, open 10:00 AM to 10:00 PM, sun loungers

Long Trail House at Stratton Mountain Resort

3.0 star property
8.6 out of 10, Excellent, (74)
"Nice, clean room in prime location"
The price is SAR 1,294
SAR 1,608 total
includes taxes & fees
13 Apr - 14 Apr
Long Trail House at Stratton Mountain Resort
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Property grounds

Ski-in/out mountainside condo close to everything with full kitchen - tranquil

9.0 out of 10, Wonderful, (69)
"Was supposed to be first floor but had to go up lots of stairs. The place was very clean but dated. Better for young people not good for old people."
The price is SAR 315
SAR 1,026 total
includes taxes & fees
3 Apr - 4 Apr
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
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

Why book your cottage in Windham with Expedia?
Expedia has some excellent cottages in Windham, so start packing your bags for a memorable vacay close to nature. If you need to stick to a budget, choose how much you’d like to spend and the preferred star rating of your property. Or, make the most of our filters to search for cottages with a pool or free WiFi. We’ll help you find the perfect pad whatever your plans or style of travel.
How can I find cheap cottages in Windham?
Expedia is here to help you track down cheap cottages in Windham. To discover a terrific stay in a few clicks, try out our handy filter tool to tailor your search results by amenities, star rating and budget.