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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Windham cottages

House (2 Bedrooms) | Interior

Hiking Trails On-site: Cozy Falls Brook Cabin

Hiking Trails On-site: Cozy Falls Brook Cabin
3.0 star property
Brattleboro
10.0 out of 10, Exceptional, (2 reviews)
"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 ❤️"
United States
sarah
$377 nightly
The price is $411
Aug 5 - Aug 6
Total with taxes and fees
Hiking Trails On-site: Cozy Falls Brook Cabin
Terrace/patio

Spectacular Cottage with Swimming Pool and Foosball in Stratton, Vermont

Spectacular Cottage with Swimming Pool and Foosball in Stratton, Vermont
Stratton
$437 nightly
The price is $493
Jul 19 - Jul 20
Total with taxes and fees
Spectacular Cottage with Swimming Pool and Foosball in Stratton, Vermont
Exterior

Terrific 3-bedroom cottage with AC in charming Cavendish

Terrific 3-bedroom cottage with AC in charming Cavendish
Cavendish
10.0 out of 10, Exceptional, (2 reviews)
"Such a beautiful place and we loved the area. It was our first trip to Vermont. "
United States
Mark G.
$543 nightly
The price is $608
Jul 26 - Jul 27
Total with taxes and fees
Terrific 3-bedroom cottage with AC in charming Cavendish
TV, books

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

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Walpole
9.6 out of 10, Exceptional, (9 reviews)
"Easy hand's off check in and great communication with the host. The cottage itself was lovely - my friends and I were in town for a wedding and it was the perfect accommodations! Would definitely stay here again! "
United States
Frances D.
$297 nightly
The price is $322
Jul 19 - Jul 20
Total with taxes and fees
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Outdoor dining

Awesome Cottage with Fireplace and Swimming Pool in Sunderland, Vermont

Awesome Cottage with Fireplace and Swimming Pool in Sunderland, Vermont
Sunderland
$936 nightly
The price is $1,049
Jul 21 - Jul 22
Total with taxes and fees
Awesome Cottage with Fireplace and Swimming Pool in Sunderland, Vermont
House (2 Bedrooms) | Interior

Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit

Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
3.0 star property
Ludlow
$406 nightly
The price is $447
Jul 19 - Jul 20
Total with taxes and fees
Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
House (4 Bedrooms) | Interior

3 Mi to Mount Snow: Spacious West Dover Home

3 Mi to Mount Snow: Spacious West Dover Home
3.0 star property
West Dover
$594 nightly
The price is $653
Jul 19 - Jul 20
Total with taxes and fees
3 Mi to Mount Snow: Spacious West Dover Home
House (5 Bedrooms) | Interior

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
3.0 star property
Ludlow
$1,679 nightly
The price is $1,847
Jul 19 - Jul 20
Total with taxes and fees
Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
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

Hampton Inn Brattleboro

Hampton Inn Brattleboro

10/10 Excellent
"Clean, comfortable and fairly priced."
Cynthia 1-night trip
Posted 2 days ago
Hampton Inn Brattleboro

Find out more about Windham

Windham Cottages information

Number of reviews
11
Accommodation
155 Cottages
Lowest Price
$322
Highest Price
$1,847

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