Title: Windham Cottages from CA $345 | Expedia.ca

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## Check prices for these dates

In two weeks

[Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=6150553&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=6150553&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=6150553&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[May 22 - May 24](https://www.expedia.ca/Hotel-Search?regionId=6150553&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Windham cottages

![TV, books](https://images.trvl-media.com/lodging/69000000/68720000/68712000/68711922/8f769c56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, WiFi](https://images.trvl-media.com/lodging/69000000/68720000/68712000/68711922/8d64a97b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/69000000/68720000/68712000/68711922/d16d9700.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, WiFi](https://images.trvl-media.com/lodging/69000000/68720000/68712000/68711922/4c6a2082.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Walpole-Hotels-Cozy-Farm-Cottage-On-Gorgeous-Landscape.h68711922.Hotel-Information)

Walpole

10/10

Exceptional

(8 reviews)

"Beautiful cozy cottage. Very clean. Wonderful host."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Gloria A.

CA $279

CA $345 total

includes taxes & fees

Feb 2 - Feb 3

[](https://www.expedia.ca/Walpole-Hotels-Cozy-Farm-Cottage-On-Gorgeous-Landscape.h68711922.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/120000000/119140000/119130500/119130417/171ffbfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119140000/119130500/119130417/82ebadba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, DVD player](https://images.trvl-media.com/lodging/120000000/119140000/119130500/119130417/6b5c4803.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, DVD player](https://images.trvl-media.com/lodging/120000000/119140000/119130500/119130417/aa44f0f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Terrific 3-bedroom cottage with AC in charming Cavendish

[](https://www.expedia.ca/Cavendish-Hotels-Terrific-3-Bedroom-Cottage-With-AC-In-Charming-Cavendish.h119130417.Hotel-Information)

Cavendish

CA $306

CA $828 total

includes taxes & fees

Feb 4 - Feb 5

[](https://www.expedia.ca/Cavendish-Hotels-Terrific-3-Bedroom-Cottage-With-AC-In-Charming-Cavendish.h119130417.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-02-15&endDate=2026-02-16&regionId=6150553&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Aparthotels

[](https://www.expedia.ca/Hotel-Search?destination=Windham%2C+Vermont%2C+United+States+of+America&regionId=6150553&latLong=43.173435%2C-72.72345&adults=2&startDate=2026-05-02&d1=2026-05-02&endDate=2026-05-05&d2=2026-05-05&lodging=APART_HOTEL)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Windham%2C+Vermont%2C+United+States+of+America&regionId=6150553&latLong=43.173435%2C-72.72345&adults=2&startDate=2026-05-02&d1=2026-05-02&endDate=2026-05-05&d2=2026-05-05&lodging=APARTMENT)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Windham%2C+Vermont%2C+United+States+of+America&regionId=6150553&latLong=43.173435%2C-72.72345&adults=2&startDate=2026-05-02&d1=2026-05-02&endDate=2026-05-05&d2=2026-05-05&lodging=VACATION_HOME)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Windham%2C+Vermont%2C+United+States+of+America&regionId=6150553&latLong=43.173435%2C-72.72345&adults=2&startDate=2026-05-02&d1=2026-05-02&endDate=2026-05-05&d2=2026-05-05&lodging=CONDO)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Windham%2C+Vermont%2C+United+States+of+America&regionId=6150553&latLong=43.173435%2C-72.72345&adults=2&startDate=2026-05-02&d1=2026-05-02&endDate=2026-05-05&d2=2026-05-05&lodging=VILLA)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Windham%2C+Vermont%2C+United+States+of+America&regionId=6150553&latLong=43.173435%2C-72.72345&adults=2&startDate=2026-05-02&d1=2026-05-02&endDate=2026-05-05&d2=2026-05-05&lodging=COTTAGE)

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Windham%2C+Vermont%2C+United+States+of+America&regionId=6150553&latLong=43.173435%2C-72.72345&adults=2&startDate=2026-05-02&d1=2026-05-02&endDate=2026-05-05&d2=2026-05-05&lodging=CABIN)

Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Windham%2C+Vermont%2C+United+States+of+America&regionId=6150553&latLong=43.173435%2C-72.72345&adults=2&startDate=2026-05-02&d1=2026-05-02&endDate=2026-05-05&d2=2026-05-05&lodging=CHALET)

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## Top Windham Hotel Reviews

![Pointe at Castle Hill Resort](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/6a80e6c5_y.jpg)

### Pointe at Castle Hill Resort

10/10 Excellent

"Friendly staff, clean rooms. "

[](https://expedia.ca/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.Hotel-Information)

![Chalet 239](https://images.trvl-media.com/lodging/102000000/101290000/101284000/101283909/c6beb381_y.jpg)

### Chalet 239

10/10 Excellent

"Chalet 239 was awesome and completely unexpected! It's an old motel that was recently renovated and has a country charm with new decor and amenities. Everything was clean, new and beautiful. Max was excellent in keeping in touch. I will definitely stay there again! "

[](https://expedia.ca/West-Dover-Hotels-Chalet-239.h101283909.Hotel-Information)

![The Manchester View](https://images.trvl-media.com/lodging/7000000/6850000/6846700/6846625/b534a8c8_y.jpg)

### The Manchester View

10/10 Excellent

"The MV was perfect for a getaway to the southern greens for snow. Place was clean, great water pressure, and heat. Had to upgrade my room and it wasn't a problem. Looking forward to coming back. "

[](https://expedia.ca/Bennington-Hotels-The-Manchester-View.h6846625.Hotel-Information)

![The Putney Inn](https://images.trvl-media.com/lodging/2000000/1820000/1810900/1810866/43775dcc_y.jpg)

### The Putney Inn

10/10 Excellent

"Staff and room were great, even let me check in at 1:30am after getting stuck in the recent storm. The room was spotless and comfortable. "

[](https://expedia.ca/Putney-Hotels-The-Putney-Inn.h1810866.Hotel-Information)

![Big Bears Lodge](https://images.trvl-media.com/lodging/17000000/16430000/16427600/16427587/5147c108_y.jpg)

### Big Bears Lodge

10/10 Excellent

"Yes "

[](https://expedia.ca/West-Dover-Hotels-Big-Bears-Lodge.h16427587.Hotel-Information)

![The Black Bear Lodge at Stratton Mountain Resort](https://images.trvl-media.com/lodging/1000000/810000/800800/800765/ac6aa3fb_y.jpg)

### The Black Bear Lodge at Stratton Mountain Resort

10/10 Excellent

"Amazing staff. Comfortable beds. Clean room. Phenomenal breakfast "

[](https://expedia.ca/Stratton-Hotels-The-Black-Bear-Lodge-At-Stratton-Mountain-Resort.h800765.Hotel-Information)

![The Equinox Golf Resort & Spa](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/0d30b96a_y.jpg)

### The Equinox Golf Resort & Spa

10/10 Excellent

"We have been staying at the Equinox for over 35 yrs. Love the whole scene and vibe. Love the pool and hot tub. Love the big real wood fireplace. "

[](https://expedia.ca/Bennington-Hotels-The-Equinox-Golf-Resort-Spa.h2759006.Hotel-Information)

![Aspen At Manchester](https://images.trvl-media.com/lodging/11000000/10260000/10254500/10254459/6f88107a_y.jpg)

### Aspen At Manchester

10/10 Excellent

"Very nice room! "

[](https://expedia.ca/Bennington-Hotels-Aspen-At-Manchester.h10254459.Hotel-Information)

![Bromley View Inn](https://images.trvl-media.com/lodging/2000000/1510000/1503000/1502963/85d1c6cb_y.jpg)

### Bromley View Inn

10/10 Excellent

"Easy check in, comfortable room, will definitely return."

[](https://expedia.ca/Bennington-Hotels-Bromley-View-Inn.h1502963.Hotel-Information)

## Find out more about Windham

## Windham Cottages information

| Number of reviews | 8            |
| ----------------- | ------------ |
| Accommodation     | 143 Cottages |
| Lowest Price      | CA $345      |
| Highest Price     | CA $828      |

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