Title: Windsor Vacation Home Rentals from CA $235: Search Top Private Vacation Homes for Rent | Expedia.ca

 

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![Cornish Windsor Covered Bridge](https://images.trvl-media.com/place/183560/cb657638-a45b-4260-96ba-18d22ff7fd4b.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Windsor Vacation Rentals

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## Check prices for these dates

In two weeks

[Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=7881&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=7881&startDate=2026-01-16&endDate=2026-01-18&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=7881&startDate=2026-02-13&endDate=2026-02-15&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=7881&startDate=2026-03-13&endDate=2026-03-15&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Browse Select Windsor Vacation Homes

![Interior](https://images.trvl-media.com/lodging/64000000/63950000/63942500/63942414/815e1d11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/64000000/63950000/63942500/63942414/5ad0db17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/64000000/63950000/63942500/63942414/af77614e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/64000000/63950000/63942500/63942414/450d67d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beautiful home offering privacy on 7 acres with private pond

West Windsor

10/10

Exceptional

(30)

"Very relaxing house, we all enjoyed the fireplaces and pellet stove and the well-equipped kitchen allowed us to cook beautiful meals. The property is gorgeous and neighbors are far away. This was the perfect place for a friends reunion/ski trip!"

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

Roy S.

CA $304

CA $709 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Windsor-Hotels-Beautiful-Home-Offering-Privacy-On-7-Acres-With-Private-Pond.h63942414.Hotel-Information)

![Comfort Townhome | Private kitchen](https://images.trvl-media.com/lodging/47000000/46990000/46981400/46981398/4cda4ab1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/47000000/46990000/46981400/46981398/5f47804a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/47000000/46990000/46981400/46981398/bf0a4dab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Comfort Townhome | Private kitchen](https://images.trvl-media.com/lodging/47000000/46990000/46981400/46981398/94f81059.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Brook Road Condo

Goshen

8.8/10

Excellent

(3)

"Convenient location, quiet and rural. Accommodations were clean and neat. Nice to have full kitchen for meal prep and snacks."

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

Margaret

CA $242

CA $404 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Goshen-Hotels-Brook-Road-Flat.h46981398.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/108000000/107610000/107603000/107602909/91d96e29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/108000000/107610000/107603000/107602909/9aa73663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, books](https://images.trvl-media.com/lodging/108000000/107610000/107603000/107602909/fbaf812d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/108000000/107610000/107603000/107602909/4f8ff888.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### @SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee

Sunapee

10/10

Exceptional

(18)

"Great home. The hosts were accessible and responded quickly to questions. Definitely will stay there again!"

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

Ellen V.

CA $254

CA $651 total

includes taxes & fees

Dec 10 - Dec 11

[](https://www.expedia.ca/Sunapee-Hotels-SunapeeSeasonsAcross-From-Dewey-Beach.h107602909.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/47000000/46560000/46559000/46558949/4a6f7251.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/47000000/46560000/46559000/46558949/50d52884.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/47000000/46560000/46559000/46558949/00acbbe3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, bed sheets](https://images.trvl-media.com/lodging/47000000/46560000/46559000/46558949/a51a1789.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Brook Road Condo

Goshen

8.8/10

Excellent

(14)

"Nice place close to the mountain!"

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

Kevin N.

CA $227

CA $437 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Goshen-Hotels-Brook-Road-Condo.h46558949.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100540000/100538400/100538389/9e5ceac5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/101000000/100540000/100538400/100538389/83d1a856.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/101000000/100540000/100538400/100538389/367a6860.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/101000000/100540000/100538400/100538389/ed1ab9f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lake Front Family Friendly Escape

Newport

10/10

Exceptional

(4)

"Great visit! The house is perfectly outfitted for a relaxing vacation. Super clean and updated. Really enjoyed the warm waters of Crescent Lake!"

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

Ann R.

CA $180

CA $527 total

includes taxes & fees

Dec 2 - Dec 3

[](https://www.expedia.ca/Newport-Hotels-Lake-Front-Family-Friendly-Escape.h100538389.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/88000000/87140000/87136000/87135975/4e6773ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/88000000/87140000/87136000/87135975/dd9dbbe8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/88000000/87140000/87136000/87135975/1f2d7230.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/88000000/87140000/87136000/87135975/cf58af9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Whimsical Room & Private Bathroom in Historic Inn

Chester Depot

8.8/10

Excellent

(9)

"After a long month of work I needed a weekend in VT to calm the nerves. This was a beautiful spot to be in, glad I was here!"

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

Paul S.

CA $140

CA $235 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Chester-Hotels-Whimsical-Room-Private-Bathroom-In-Historic-Inn.h87135975.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/61000000/60670000/60662500/60662471/aff31f77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/61000000/60670000/60662500/60662471/67f97b9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/61000000/60670000/60662500/60662471/2a3d5154.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/61000000/60670000/60662500/60662471/9636317e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chic Farmhouse Decor | Deck w/View

Sunapee

10/10

Exceptional

(51)

"The house was cozy, peaceful and convenient to skiing. "

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

Megan D.

CA $279

CA $601 total

includes taxes & fees

Nov 22 - Nov 23

[](https://www.expedia.ca/Sunapee-Hotels-Chic-Farmhouse-Decor-Deck-Wview.h60662471.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101900000/101895700/101895664/8d25e78c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/102000000/101900000/101895700/101895664/9d2d9170.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/102000000/101900000/101895700/101895664/85ba9de7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/102000000/101900000/101895700/101895664/ac990b4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Carol - 10 minutes to Okemo & Newly Renovated

Cavendish

10/10

Exceptional

(6)

"Check in and check out were incredibly easy, house decor was eclectic upscale, beds were super comfortable. Thank you Chris! Would definitely stay here again"

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

Esther K.

CA $220

CA $415 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Cavendish-Hotels-The-Carol-Styled-And-Freshly-Renovated-Stay10-Minutes-To-Okemo.h101895664.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78350000/78342500/78342432/0a51ad2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/79000000/78350000/78342500/78342432/4a020446.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/79000000/78350000/78342500/78342432/f922de49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/79000000/78350000/78342500/78342432/17915502.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

Bridgewater

9.6/10

Exceptional

(17)

"Very nice home! Plenty of room for everyone and a short drive to the mountain! Perfect "

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

Gerri B.

CA $192

CA $691 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Bridgewater-Corners-Hotels-NEW-Blueberry-Hill-Escape-Pet-Friendly-King-Bed-Fire-Pit-Grill.h78342432.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119100000/119097900/119097860/ea91e459.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119100000/119097900/119097860/a40db391.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/120000000/119100000/119097900/119097860/2fbac199.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/120000000/119100000/119097900/119097860/906f227a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury Condo Tucked in the Heart of Killington

Killington

8.0/10

Very good

(1)

"The condo was in a beautiful location but was rather isolated from grocery and dining options. Our host was good at communicating however we received a message about the fireplace not being available to us a day before we came and we got there in the dark with no lights on. The condo itself could not really be called "luxury" as it was dated and lacked some basics like soap in the bathroom, a towel hook in the 1/2 bath, kleenex, cracked dishes, etc. Liked that it was near a waterfall and hiking...

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

Dean

CA $167

CA $455 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Killington-Hotels-Luxury-Condo-Tucked-In-The-Heart-Of-Killington.h119097860.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/99000000/98550000/98541400/98541375/bb2d115e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/99000000/98550000/98541400/98541375/cba45686.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/99000000/98550000/98541400/98541375/154d7e92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/99000000/98550000/98541400/98541375/35e53179.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming Cavendish Guesthouse

Cavendish

9.8/10

Exceptional

(7)

"Just as described with Everything we needed. Very comfy and roomy. Loved the private feeling and backyard. Would highly recommend to anyone wanting to stay in this area of Vermont."

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

deborah m.

CA $221

CA $389 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Cavendish-Hotels-Cozy-Cavendish-Bunk-Minutes-To-Okemo.h98541375.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/61000000/60670000/60662500/60662486/4c9c72c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/61000000/60670000/60662500/60662486/83f26aff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/61000000/60670000/60662500/60662486/5ab266ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/61000000/60670000/60662500/60662486/9ac7a10c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Unique Treehouse Near Mt Sunapee – No Cleaning Fee

Newbury

10/10

Exceptional

(26)

"Great stay. Had a wonderful time."

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

Chris P.

CA $330

CA $624 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Newbury-Hotels-Luxurious-Two-Story-Treehouse-Minutes-From-Skiing-Peaceful.h60662486.Hotel-Information)

![Indoor pool, a heated pool](https://images.trvl-media.com/lodging/101000000/100830000/100822600/100822513/3523e734.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/101000000/100830000/100822600/100822513/df0eafeb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100830000/100822600/100822513/6c93e544.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/101000000/100830000/100822600/100822513/0bf9adcf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bearmont- Pool, HotTub, Fireplace

The Woods

10/10

Exceptional

(6)

"Great location and a great place. Felt right at home"

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

Tyler B.

CA $160

CA $671 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Killington-Hotels-Bearmont-Pool.h100822513.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/42000000/41900000/41897300/41897267/9d83dbe7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/42000000/41900000/41897300/41897267/a60117a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, books](https://images.trvl-media.com/lodging/42000000/41900000/41897300/41897267/0d7d95c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/42000000/41900000/41897300/41897267/7febc41c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

Mt Holly

9.8/10

Exceptional

(36)

"Wonderful cabin, well stocked, host was attentive and quick to address any questions."

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

Eyal O.

CA $222

CA $728 total

includes taxes & fees

Nov 22 - Nov 23

[](https://www.expedia.ca/Mount-Holly-Hotels-Charming-Family-Ski-Chalet-Less-Than-5-Minutes-Drive-To-OkemoJackson-Gore.h41897267.Hotel-Information)

![Golf](https://images.trvl-media.com/lodging/102000000/101250000/101243900/101243826/c685e8e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, books](https://images.trvl-media.com/lodging/102000000/101250000/101243900/101243826/2dd85cca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/102000000/101250000/101243900/101243826/7f264063.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/102000000/101250000/101243900/101243826/400bb017.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### TheGrizz! Shuttle on/off!

Killington

10/10

Exceptional

(4)

"Place was overall great and just as advertised. Beds were awesome including the Murphy bed. Thanks for a wonderful weekend! I would definitely stay again. "

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

Angela S.

CA $158

CA $623 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Killington-Hotels-TheGrizz-Bike-And-Ski-Shuttle-On-Off-By-Golf.h101243826.Hotel-Information)

![House, 3 Bedrooms | Interior](https://images.trvl-media.com/lodging/91000000/90030000/90027900/90027836/4f7b2683.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House, 3 Bedrooms | Property grounds](https://images.trvl-media.com/lodging/91000000/90030000/90027900/90027836/7c3cc5a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House, 3 Bedrooms | View from property](https://images.trvl-media.com/lodging/91000000/90030000/90027900/90027836/3189f3ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House, 3 Bedrooms | Lobby](https://images.trvl-media.com/lodging/91000000/90030000/90027900/90027836/48c9dac0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Left Duplex Home Directly Across From Pico Mountain, Close To Killington. 3 Bedroom Home

Killington

CA $246

CA $870 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Killington-Hotels-Left-Duplex-Home-Directly-Across-From-Pico-Mountain.h90027836.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100510000/100501900/100501897/c9400bbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/101000000/100510000/100501900/100501897/f1b12770.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/101000000/100510000/100501900/100501897/acc10e06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/101000000/100510000/100501900/100501897/743b417c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### CozyDen-Location, Fireplace, Ski Off/Shuttle On!

Killington

10/10

Exceptional

(1)

"Very quiet and private feeling even though it is in a condo like setting. Very clean, and had all the conveniences we needed (A/C, coffee maker, full kitchen appliances). And so kind and personal to leave some souvenirs of the area. We felt very comfortable when every we finished our day of sightseeing to come back to our home away from home. "

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

denise k.

CA $132

CA $406 total

includes taxes & fees

Nov 25 - Nov 26

[](https://www.expedia.ca/Killington-Hotels-CozyDen-AC.h100501897.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90700000/90693000/90692944/602db30e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/91000000/90700000/90693000/90692944/c184f626.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/91000000/90700000/90693000/90692944/25803efa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/91000000/90700000/90693000/90692944/fd584ad3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Mountain Stay | Skiing | Hiking | Sleeps 8

Bridgewater

9.6/10

Exceptional

(7)

"My family enjoyed this house and there was plenty of space for sleeping and for the kids to play. Conveniently located for skiing at Killington."

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

Owen C.

CA $290

CA $791 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Bridgewater-Hotels-Bridgewater-Inn-2-King-Beds-Game-Room-Skiing.h90692944.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/102000000/101480000/101473400/101473310/9fc41d82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101480000/101473400/101473310/dffaa55c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/102000000/101480000/101473400/101473310/fb8c05d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/102000000/101480000/101473400/101473310/578d98e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chester Farmhouse Ski Retreat near Slopes

Chester Depot

9.6/10

Exceptional

(16)

"This was my second time staying at this property. Everything was great just like last year. I highly recommend it if you are staying in Chester, VT. "

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

Lori N.

CA $210

CA $491 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Chester-Hotels-Charming-Chester-Farmhouse-Peaceful-And-Close-To-Everything.h101473310.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/112000000/111420000/111411200/111411190/5e2fb8ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/112000000/111420000/111411200/111411190/90789a76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/112000000/111420000/111411200/111411190/5200e83b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/112000000/111420000/111411200/111411190/0326abbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Peaceful oasis, stunning views, less than 10 mins from Woodstock Village

Pomfret

10/10

Exceptional

(3)

"Enjoyed the cleanliness and the convenience of being close to Woodstock, and not too far from Stowe."

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

Dee Dee H.

CA $211

CA $535 total

includes taxes & fees

Dec 11 - Dec 12

[](https://www.expedia.ca/South-Pomfret-Hotels-Peaceful-Oasis.h111411190.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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## Top Windsor Hotel Reviews

![Align Inn Vermont](https://images.trvl-media.com/lodging/1000000/10000/1200/1108/996cad8e_y.jpg)

### Align Inn Vermont

10/10 Excellent

"Room was fine. Staff available. "

[](https://expedia.ca/Quechee-Hotels-Quality-Inn-At-Quechee-Gorge.h1108.Hotel-Information)

![On The River Inn](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/fa7b6946_y.jpg)

### On The River Inn

10/10 Excellent

"Hands down one of the best places I have ever stayed. Beautiful view, great room and very cozy no matter where you were in the inn."

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

![Super 8 by Wyndham White River Junction](https://images.trvl-media.com/lodging/1000000/900000/897900/897894/bbecedb2_y.jpg)

### Super 8 by Wyndham White River Junction

10/10 Excellent

"The room was a very nice, felt safe. Enjoyed the fun small talk with the women at the front desk. Also felt its a good location as well. "

[](https://expedia.ca/White-River-Junction-Hotels-Super-8-By-Wyndham-White-River-Junction.h897894.Hotel-Information)

![Hampton Inn White River Junction](https://images.trvl-media.com/lodging/1000000/80000/79300/79224/e21b1496_y.jpg)

### Hampton Inn White River Junction

10/10 Excellent

"Very friendly staff Nice work area "

[](https://expedia.ca/White-River-Junction-Hotels-Hampton-Inn-White-River-Junction.h79224.Hotel-Information)

![Hanover Inn Dartmouth](https://images.trvl-media.com/lodging/4000000/3980000/3974400/3974306/1703a489_y.jpg)

### Hanover Inn Dartmouth

10/10 Excellent

"Perfect when visiting Dartmouth. Location, cozyness, seamless check-in & check-out, spotless rooms."

[](https://expedia.ca/Lebanon-Hotels-Hanover-Inn-Dartmouth.h3974306.Hotel-Information)

![Fireside Inn & Suites West Lebanon](https://images.trvl-media.com/lodging/1000000/20000/12300/12300/adb27d13_y.jpg)

### Fireside Inn & Suites West Lebanon

10/10 Excellent

"Well kept rooms"

[](https://expedia.ca/Lebanon-Hotels-Fireside-Inn-Suites-West-Lebanon.h12300.Hotel-Information)

![The Jackson ](https://images.trvl-media.com/lodging/1000000/190000/181400/181337/f642c888_y.jpg)

### The Jackson

10/10 Excellent

"The room was as clean as could be and everyone we met was very friendly. "

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

![Hotel Coolidge](https://images.trvl-media.com/lodging/2000000/1110000/1100200/1100199/w2880h2170x0y0-a69a5404_y.jpg)

### Hotel Coolidge

10/10 Excellent

"Easy check-in, friendly staff, old-timey New England atmosphere, free coffee in lobby 24/7 to guests with fire place "

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

![The Mountain Inn at Killington](https://images.trvl-media.com/lodging/1000000/980000/975400/975389/29356441_y.jpg)

### The Mountain Inn at Killington

10/10 Excellent

"We stay here all the time and have no reason to choose anywhere else! Great prices, clean rooms and nice staff. On top of that, the distillery on site makes it so you don't have to leave your hotel at night and drive! Would recommend to anyone who is taking a trip to Killington!"

[](https://expedia.ca/Killington-Hotels-The-Mountain-Inn-At-Killington.h975389.Hotel-Information)

## Find out more about Windsor

## Windsor Vacation Homes information

| Number of reviews | 182 |
| --- | --- |
| Accommodation | 772 Vacation Homes |
| Lowest Price | CA $235 |
| Highest Price | CA $870 |

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