Title: Windsor County Cottages from CA $303 | Expedia.ca

[Windsor County Hotels](https://expedia.ca/Destinations-In-Windsor-County.d553248635976432508.Hotel-Destinations)[Vacation Rentals in Windsor County](https://expedia.ca/Destinations-In-Windsor-County.d553248635976432508.Vacation-Rental-Destinations)[Windsor County Car Rentals](https://expedia.ca/Destinations-In-Windsor-County.d553248635976432508.Car-Rental-Destinations)[Windsor County Vacations](https://expedia.ca/Windsor-County.d553248635976432508.Destination-Travel-Guides)

![](https://images.trvl-media.com/place/3000459649/24ffd150-771e-42f6-8fd9-a3002aef691c.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Rachel Samanyi

![](https://images.trvl-media.com/place/3000459649/24ffd150-771e-42f6-8fd9-a3002aef691c.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 26 - Jun 28](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 24 - Jul 26](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2026-07-24&endDate=2026-07-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Top Cities in Windsor County

![](https://images.trvl-media.com/place/3000459649/7d354301-07a8-4d26-bfd8-54320ed05c30.jpg?impolicy=fcrop&w=384&h=216&q=medium)

#### White River Junction

[](https://expedia.ca/White-River-Junction-Cottages.d6294-aaCottages.Travel-Guide-Accommodation)

![](https://images.trvl-media.com/place/10868/c2d6773f-8f3f-4c1a-b710-f2f2bceab647.jpg?impolicy=fcrop&w=384&h=216&q=medium)

#### Woodstock

[](https://expedia.ca/Woodstock-Cottages.d10868-aaCottages.Travel-Guide-Accommodation)

![](https://images.trvl-media.com/place/8496/505d08ac-b11f-4f25-a539-2958ea0722b2.jpg?impolicy=fcrop&w=384&h=216&q=medium)

#### Ludlow

[](https://expedia.ca/Ludlow-Cottages.d8496-aaCottages.Travel-Guide-Accommodation)

![](https://images.trvl-media.com/place/9580/a3d99a95-3156-473d-99ae-f796cac4afe4.jpg?impolicy=fcrop&w=384&h=216&q=medium)

#### Quechee

[](https://expedia.ca/Quechee-Cottages.d9580-aaCottages.Travel-Guide-Accommodation)

![A small village on the edge of a peninsula with trees and houses reflecting in the calm bay water, Prince Edward Island, Canada](https://images.trvl-media.com/place/6023399/d2b7795d-f2ec-496f-8ad6-83ab36f98f0b.jpg?impolicy=fcrop&w=384&h=216&q=medium)

#### Cavendish

[](https://expedia.ca/Cavendish-Cottages.d6023399-aaCottages.Travel-Guide-Accommodation)

![Paine Mountain](https://images.trvl-media.com/place/184063/fd3e4c3f-7b8d-43ea-be6c-7ecb5c63234e.jpg?impolicy=fcrop&w=384&h=216&q=medium)

#### Norwich

[](https://expedia.ca/Norwich-Cottages.d184063-aaCottages.Travel-Guide-Accommodation)

## Our top choices for Windsor County cottages

![Exterior](https://images.trvl-media.com/lodging/117000000/116350000/116341300/116341257/4ccd0baf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/117000000/116350000/116341300/116341257/5afbd4d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116350000/116341300/116341257/18611595.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116350000/116341300/116341257/da57711b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Addie's Place: A Quiet and Quirky Guesthouse

[](https://www.expedia.ca/Wilder-Hotels-Addies-Place-A-Quiet-And-Quirky-Private-Guesthouse.h116341257.Hotel-Information)

Hartford

10/10

Exceptional

(9 reviews)

"Perfect size and location! "

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

Lyn H.

CA $167

CA $303 total

includes taxes & fees

Apr 26 - Apr 27

[](https://www.expedia.ca/Wilder-Hotels-Addies-Place-A-Quiet-And-Quirky-Private-Guesthouse.h116341257.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/21000000/20160000/20157600/20157543/bda1c661.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/21000000/20160000/20157600/20157543/573416c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/21000000/20160000/20157600/20157543/054b855d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/21000000/20160000/20157600/20157543/811848ec_edited_9b37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Woodstock Village Carriage House

[](https://www.expedia.ca/Woodstock-Hotels-Woodstock-Village-Carriage-House.h20157543.Hotel-Information)

Woodstock

9.6/10

Exceptional

(108 reviews)

"Clean, friendly host, quiet. Perfect location to everything in town"

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

Mia M.

[](https://www.expedia.ca/Woodstock-Hotels-Woodstock-Village-Carriage-House.h20157543.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/99000000/98630000/98624200/98624120/11fec3a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/99000000/98630000/98624200/98624120/1487350e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/99000000/98630000/98624200/98624120/29447a6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, books](https://images.trvl-media.com/lodging/99000000/98630000/98624200/98624120/3c384a91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Ludlow-Hotels-Renovated-Lakefront-Cottage-With-Deep-Water-Dock.h98624120.Hotel-Information)

Ludlow

9.4/10

Exceptional

(22 reviews)

"Excellent location! Nicely renovated with great views of the lake. It could be a little hard to find in the dark on your first time there. There was a small issue with there, not being some towels in one of the bathrooms, but they did bring some by. Very nice place highly recommend!"

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

Bruce B.

[](https://www.expedia.ca/Ludlow-Hotels-Renovated-Lakefront-Cottage-With-Deep-Water-Dock.h98624120.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/101000000/100810000/100807000/100806959/d3456560.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/101000000/100810000/100807000/100806959/e38d428d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/101000000/100810000/100807000/100806959/cf09c2e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100810000/100807000/100806959/428535e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy cottage on the river, minutes from skiing, horse events, and so much more!

[](https://www.expedia.ca/Reading-Hotels-Cozy-Cottage-On-The-River.h100806959.Hotel-Information)

Reading

9.6/10

Exceptional

(15 reviews)

"We loved the place and will stay again"

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

Michelle

[](https://www.expedia.ca/Reading-Hotels-Cozy-Cottage-On-The-River.h100806959.Hotel-Information)

![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/99000000/98560000/98555400/98555376/2cd953a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/99000000/98560000/98555400/98555376/a2fe346b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/99000000/98560000/98555400/98555376/82047e63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/99000000/98560000/98555400/98555376/8127252b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury Vermont Vacation Rental: Private Hot Tub!

[](https://www.expedia.ca/Brownsville-Hotels-Luxury-Vermont-Vacation-Rental-Private-Hot-Tub.h98555376.Hotel-Information)

Brownsville

[](https://www.expedia.ca/Brownsville-Hotels-Luxury-Vermont-Vacation-Rental-Private-Hot-Tub.h98555376.Hotel-Information)

![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/119000000/118050000/118040400/118040302/8d3a3825.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/119000000/118050000/118040400/118040302/8eaccf48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/119000000/118050000/118040400/118040302/b22d25e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (4 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/119000000/118050000/118040400/118040302/9175b2aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 8 Mi to Okemo Mountain Resort: Mtn-view Retreat!

[](https://www.expedia.ca/Ludlow-Hotels-8-Mi-To-Okemo-Mountain-Resort-Mtn-View-Retreat.h118040302.Hotel-Information)

Ludlow

10/10

Exceptional

(1 review)

"Everything was as advertised we had an ice storm and a nice guy came and salted stairs and driveway bright an early , the only issue we has was the inside steps going to the upstairs bedroom were very slippery but otherwise great stay "

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

JIM

[](https://www.expedia.ca/Ludlow-Hotels-8-Mi-To-Okemo-Mountain-Resort-Mtn-View-Retreat.h118040302.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/35000000/34330000/34329400/34329330/469c25b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hair dryer, towels, soap, toilet paper](https://images.trvl-media.com/lodging/35000000/34330000/34329400/34329330/bc28e3c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/35000000/34330000/34329400/34329330/5a13e6da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/35000000/34330000/34329400/34329330/2d5fd428.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Historic Hilltop Cottage with Mount Ascutney View

[](https://www.expedia.ca/Windsor-Hotels-Cozy-Historic-Hilltop-Cottage-With-Mount-Ascutney-View.h34329330.Hotel-Information)

West Windsor

9.6/10

Exceptional

(84 reviews)

"Beautiful country! Very laid back atmosphere!Easy to check in and out. Great experience!"

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

Paul H.

[](https://www.expedia.ca/Windsor-Hotels-Cozy-Historic-Hilltop-Cottage-With-Mount-Ascutney-View.h34329330.Hotel-Information)

![House (5 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/95000000/94330000/94322000/94321966/c1e4cd90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (5 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94330000/94322000/94321966/e8f607a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/95000000/94330000/94322000/94321966/d884b500.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (5 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94330000/94322000/94321966/28858758.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chester Farmhouse on 100 Acres, 15 Min to Okemo!

[](https://www.expedia.ca/Chester-Hotels-Chester-Farmhouse-On-100-Acres.h94321966.Hotel-Information)

Chester

[](https://www.expedia.ca/Chester-Hotels-Chester-Farmhouse-On-100-Acres.h94321966.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)

![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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119140000/119130500/119130417/f1003380.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)

### 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

10/10

Exceptional

(1 review)

"House was perfect! Well appointed with everything you need. Beds very comfortable and very clean. Host was very responsive and was there if you needed anything. Will definitely stay again. "

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

Stephen S.

CA $312

CA $841 total

includes taxes & fees

Apr 14 - Apr 15

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

![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/109000000/108320000/108315900/108315854/c41cfe05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/109000000/108320000/108315900/108315854/915d9041.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (2 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/109000000/108320000/108315900/108315854/4070a40e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/109000000/108320000/108315900/108315854/7eac386e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Peaceful Brookside Getaway \~10 Mi to Okemo Slopes!

[](https://www.expedia.ca/Chester-Hotels-Peaceful-Brookside-Getaway-10-Mi-To-Okemo-Slopes.h108315854.Hotel-Information)

Chester

10/10

Exceptional

(2 reviews)

"The property was lovely, peaceful, and quiet, surrounded by trees on a quiet country drive. It was the perfect weekend getaway and we really enjoyed sitting on the porch and out under the string lights, watching the sun go down through the trees. The house itself is lovely, cozy, and comfortable. Our hosts were very sweet, everything was very thoughtfully laid out and clean and easy to access. We also loved meeting the goats, Ozzy and Coco, and the chickens! This was such a pleasant stay, I...

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

Angela

[](https://www.expedia.ca/Chester-Hotels-Peaceful-Brookside-Getaway-10-Mi-To-Okemo-Slopes.h108315854.Hotel-Information)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/114000000/113570000/113569600/113569511/b3e4761f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/114000000/113570000/113569600/113569511/82f1c1b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/114000000/113570000/113569600/113569511/03930d40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/114000000/113570000/113569600/113569511/39cf355a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hike, Ski & Unwind: Cabin w/ Deck in Chester!

[](https://www.expedia.ca/Chester-Hotels-Hike.h113569511.Hotel-Information)

Chester

2.0/10

(1 review)

[](https://www.expedia.ca/Chester-Hotels-Hike.h113569511.Hotel-Information)

![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/124000000/123200000/123195900/123195896/03e81b65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/124000000/123200000/123195900/123195896/67dbaa15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/124000000/123200000/123195900/123195896/5527f0c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/124000000/123200000/123195900/123195896/383c827a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Ludlow Ski Cabin 2 Mi to Ski Parking

[](https://www.expedia.ca/Ludlow-Hotels-Mtn-View-Lake-Pauline-Cabin-3-Mi-To-Okemo-Resort.h123195896.Hotel-Information)

Ludlow

[](https://www.expedia.ca/Ludlow-Hotels-Mtn-View-Lake-Pauline-Cabin-3-Mi-To-Okemo-Resort.h123195896.Hotel-Information)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93550000/93545900/93545845/bfe3aab1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93550000/93545900/93545845/9e5f9958.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93550000/93545900/93545845/47c3c64d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93550000/93545900/93545845/16584d92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Killington Area Escape w/ Deck, Views & Hot Tub!

[](https://www.expedia.ca/Stockbridge-Hotels-Killington-Area-Escape-W-Deck-Private-Hot-Tub.h93545845.Hotel-Information)

Stockbridge

[](https://www.expedia.ca/Stockbridge-Hotels-Killington-Area-Escape-W-Deck-Private-Hot-Tub.h93545845.Hotel-Information)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/101000000/100010000/100000700/100000677/ff7a99a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/101000000/100010000/100000700/100000677/f8c095aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/101000000/100010000/100000700/100000677/3e6c56a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/101000000/100010000/100000700/100000677/b94f2668.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Weston Vacation Rental - Close to Ski Resorts!

[](https://www.expedia.ca/Weston-Hotels-Weston-Vacation-Rental-Close-To-Ski-Resorts.h100000677.Hotel-Information)

Weston

[](https://www.expedia.ca/Weston-Hotels-Weston-Vacation-Rental-Close-To-Ski-Resorts.h100000677.Hotel-Information)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/105000000/104960000/104954000/104953935/226bf513.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/105000000/104960000/104954000/104953935/20f55bb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/105000000/104960000/104954000/104953935/30de5ba0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/105000000/104960000/104954000/104953935/472e026b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lovely Ludlow Farmhouse \~ 1 Mi to Town & Slopes!

[](https://www.expedia.ca/Ludlow-Hotels-Lovely-Ludlow-Farmhouse-1-Mi-To-Town-Slopes.h104953935.Hotel-Information)

Ludlow

10/10

Exceptional

(1 review)

"Great place "

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

Mauro

[](https://www.expedia.ca/Ludlow-Hotels-Lovely-Ludlow-Farmhouse-1-Mi-To-Town-Slopes.h104953935.Hotel-Information)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93590000/93587000/93586992/555e634a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93590000/93587000/93586992/614501c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93590000/93587000/93586992/916ccf71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93590000/93587000/93586992/bde1feef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Inviting Vermont Home On Mount Ascutney!

[](https://www.expedia.ca/Brownsville-Hotels-Inviting-Vermont-Cabin-On-Mount-Ascutney.h93586992.Hotel-Information)

Brownsville

[](https://www.expedia.ca/Brownsville-Hotels-Inviting-Vermont-Cabin-On-Mount-Ascutney.h93586992.Hotel-Information)

![House (6 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94360000/94353200/94353127/6deb0bff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (6 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94360000/94353200/94353127/7c229706.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (6 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94360000/94353200/94353127/e45bf1e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (6 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94360000/94353200/94353127/2b2e34bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Picture-perfect Vermont Mtn Cabin w/ Hot Tub!

[](https://www.expedia.ca/Bridgewater-Corners-Hotels-Picture-Perfect-Vermont-Mtn-Cabin-W-Hot-Tub.h94353127.Hotel-Information)

Bridgewater Corners

[](https://www.expedia.ca/Bridgewater-Corners-Hotels-Picture-Perfect-Vermont-Mtn-Cabin-W-Hot-Tub.h94353127.Hotel-Information)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/111000000/110930000/110920400/110920350/4717ae92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/111000000/110930000/110920400/110920350/93825cef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/111000000/110930000/110920400/110920350/ab774371.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/111000000/110930000/110920400/110920350/3b1a5bfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 18 Mi to Skiing: Colorful Home in Springfield!

[](https://www.expedia.ca/Springfield-Hotels-18-Mi-To-Skiing-Colorful-Home-In-Springfield.h110920350.Hotel-Information)

Springfield

[](https://www.expedia.ca/Springfield-Hotels-18-Mi-To-Skiing-Colorful-Home-In-Springfield.h110920350.Hotel-Information)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94330000/94327900/94327824/1a409653.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94330000/94327900/94327824/340b2a48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94330000/94327900/94327824/9ecd508e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94330000/94327900/94327824/338a6acd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Private Chester Home w/ Deck, Mins to Skiing!

[](https://www.expedia.ca/Chester-Hotels-Private-Chester-Home-W-Deck.h94327824.Hotel-Information)

Chester

[](https://www.expedia.ca/Chester-Hotels-Private-Chester-Home-W-Deck.h94327824.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/77000000/76860000/76855900/76855859/8df9a704.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/77000000/76860000/76855900/76855859/6d64ba8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/77000000/76860000/76855900/76855859/4ca5a9a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/77000000/76860000/76855900/76855859/af57ac2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 4bdrm Cottage central to year round fun w/fireplace

[](https://www.expedia.ca/Weston-Hotels-4bdrm-Cottage-Central-To-Year-Round-Fun-Wfireplace.h76855859.Hotel-Information)

Weston

[](https://www.expedia.ca/Weston-Hotels-4bdrm-Cottage-Central-To-Year-Round-Fun-Wfireplace.h76855859.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.

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## Find vacation rentals that suit your style

Cabins

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Aparthotels

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Private vacation homes

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Condos

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Apartments

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Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Windsor+County%2C+Vermont%2C+United+States+of+America&regionId=553248635976432508&latLong=43.624765%2C-72.518979&adults=2&startDate=2026-07-01&d1=2026-07-01&endDate=2026-07-04&d2=2026-07-04&lodging=CHALET)

Villas

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## Top Windsor County Hotel Reviews

![Best Western Springfield Hotel](https://images.trvl-media.com/lodging/1000000/20000/17800/17753/d8a154ae_y.jpg)

### Best Western Springfield Hotel

8/10 Good

"Breakfast had lot of options Room was good Always stay there"

[](https://expedia.ca/Springfield-Hotels-Best-Western-Springfield-Hotel.h17753.Hotel-Information)

![Fullerton Inn](https://images.trvl-media.com/lodging/16000000/15850000/15845400/15845368/662925ab_y.jpg)

### Fullerton Inn

8/10 Good

"The staff were so friendly and helpful...made us feel very welcome. There was no television in our room, which was no problem...just wish we had known in advance. Then we could have brought a good book or crossword puzzle!"

[](https://expedia.ca/Chester-Hotels-Fullerton-Inn.h15845368.Hotel-Information)

![The Jackson ](https://images.trvl-media.com/lodging/1000000/190000/181400/181337/6aabd3c1_y.jpg)

### The Jackson 

10/10 Excellent

"Yes, breakfast was delicious with a good amount of options for all."

[](https://expedia.ca/Woodstock-Hotels-The-Jackson-House-Inn.h181337.Hotel-Information)

![Hotel Coolidge](https://images.trvl-media.com/lodging/2000000/1110000/1100200/1100199/2db4f9a7_y.jpg)

### Hotel Coolidge

8/10 Good

"Room was nice and clean, staff was lovely and parking was okay. "

[](https://expedia.ca/White-River-Junction-Hotels-Hotel-Coolidge.h1100199.Hotel-Information)

![Pointe at Castle Hill Resort](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/b9b1ed95_y.jpg)

### Pointe at Castle Hill Resort

8/10 Good

"Have stayed here many times. Close to town and Okemo. Very convenient."

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

![On The River Inn](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/8d6bfa64_y.jpg)

### On The River Inn

10/10 Excellent

"I recommend it nice rooms and area around the property. Convenient for skiing. "

[](https://expedia.ca/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information)

![Sleep Woodstock Motel](https://images.trvl-media.com/lodging/10000000/9660000/9658900/9658860/9d3fcb33_y.jpg)

### Sleep Woodstock Motel

8/10 Good

"A good stay, comfortable beds, nice bathroom, keurig didn’t work, dog poop not picked up across the driveway, but a good alternative near an expensive town. Great to allow dogs, just clear some dog owners not so great. Overall, very good."

[](https://expedia.ca/Woodstock-Hotels-Sleep-Woodstock-Motel.h9658860.Hotel-Information)

![Holiday Inn Club Vacations Mount Ascutney Resort by IHG](https://images.trvl-media.com/lodging/1000000/430000/425200/425171/06298210_y.jpg)

### Holiday Inn Club Vacations Mount Ascutney Resort by IHG

10/10 Excellent

"courteous staff, great property."

[](https://expedia.ca/Brownsville-Hotels-Holiday-Inn-Club-Vacations-Mount-Ascutney-Resort.h425171.Hotel-Information)

![The Quechee Inn at Marshland Farm](https://images.trvl-media.com/lodging/2000000/1930000/1924800/1924710/c8372335_y.jpg)

### The Quechee Inn at Marshland Farm

8/10 Good

"It was a nice place. Staff was very kind and helpful. "

[](https://expedia.ca/Quechee-Hotels-The-Quechee-Inn-At-Marshland-Farm.h1924710.Hotel-Information)

## Find out more about Windsor County

## Windsor County Cottages information

| Number of reviews | 133         |
| ----------------- | ----------- |
| Accommodation     | 52 Cottages |
| Lowest Price      | CA $303     |
| Highest Price     | CA $841     |

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- [Billings Farm and Museum ](https://www.expedia.ca/Billings-Farm-And-Museum-Woodstock.d6175222.Vacation-Attraction)
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