Title: Chester Vacation Rentals from CA $263: Short-Term Rentals for 2025 | Expedia.ca

 

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# Chester Vacation Rentals

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## Check prices for these dates

Tonight

[Nov 5 - Nov 6](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-11-05&endDate=2025-11-06&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Nov 6 - Nov 7](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-11-06&endDate=2025-11-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-11-14&endDate=2025-11-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Vacation Rentals in Chester

![Interior](https://images.trvl-media.com/lodging/89000000/88940000/88933400/88933370/b26aecc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/89000000/88940000/88933400/88933370/1abb18c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/89000000/88940000/88933400/88933370/e84b9d61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/89000000/88940000/88933400/88933370/9868dcd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area

Chester

10/10

Exceptional

(23)

"Peaceful vacation"

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

Naga Veerendra G.

[](https://www.expedia.ca/Chester-Hotels-Luxury-Glamping-Cabin-Close-To-Hiking-And-15-Minutes-From-Ski-Area.h88933370.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/22000000/21440000/21432600/21432554/6ca4befa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/22000000/21440000/21432600/21432554/3d510c69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/22000000/21440000/21432600/21432554/383f0611.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![48-inch flat-screen TV with cable channels, TV, fireplace](https://images.trvl-media.com/lodging/22000000/21440000/21432600/21432554/8b7c60dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Killington

9.0/10

Wonderful

(53)

"Absolutely perfect! Very nice location. Quiet and cozy little townhome. Short drive to Bear Mountain and Killington Ski Resort. Amazing area with plenty of awesome views."

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

David

[](https://www.expedia.ca/Killington-Hotels-Ski-In-Out-Spruce-Glen-Townhomes-On-Great-Eastern-Trail.h21432554.Hotel-Information)

![Condo, 2 Bedrooms | Pool](https://images.trvl-media.com/lodging/7000000/6610000/6602500/6602401/31db03a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Snow and ski sports](https://images.trvl-media.com/lodging/7000000/6610000/6602500/6602401/1e2b3992.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Yoga](https://images.trvl-media.com/lodging/7000000/6610000/6602500/6602401/cfa3a228.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/7000000/6610000/6602500/6602401/a16eeef9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Long Trail House at Stratton Mountain Resort

Stratton

8.6/10

Excellent

(76)

"Nice, clean room in prime location"

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

Kristin

CA $466

CA $580 total

includes taxes & fees

Nov 11 - Nov 12

[](https://www.expedia.ca/Stratton-Hotels-Long-Trail-House-At-Stratton-Mountain-Resort.h6602401.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/32000000/31140000/31137700/31137653/dd998d3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/32000000/31140000/31137700/31137653/70722da7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/32000000/31140000/31137700/31137653/a5bdbf23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/32000000/31140000/31137700/31137653/c707b887.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo

Ludlow

9.8/10

Exceptional

(127)

"Enjoyed our stay immensely"

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

jim m.

[](https://www.expedia.ca/Ludlow-Hotels-Traveling-With-Kids-Check-This-Secluded-Update-3-Bedroom-Home-Close-To-Okemo.h31137653.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/22000000/21700000/21692200/21692155/7f99722e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, DVD player](https://images.trvl-media.com/lodging/22000000/21700000/21692200/21692155/57672945.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/22000000/21700000/21692200/21692155/ce1e5a47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/22000000/21700000/21692200/21692155/3d411f82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Clock Tower Base Area

9.0/10

Wonderful

(73)

"It was a perfect location and had everything we needed for a great stay."

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

Danna K.

CA $106

CA $357 total

includes taxes & fees

Nov 10 - Nov 11

[](https://www.expedia.ca/Ludlow-Hotels-Ski-Inout-Mountainside-Condo-Close-To-Everything-With-Full-Kitchen-Tranquil.h21692155.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/92000000/91760000/91754400/91754323/c7361572.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/92000000/91760000/91754400/91754323/49345747.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91760000/91754400/91754323/1ae59db8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, table tennis, books](https://images.trvl-media.com/lodging/92000000/91760000/91754400/91754323/dd3af0de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Winhall

9.8/10

Exceptional

(29)

"Family ski weekend. Our stay was very comfortable. Communication with host was phenomenal, always prompt and courteous Location is nice , very close to the ski resorts "

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

Virginia A.

CA $270

CA $885 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/Bondville-Hotels-Stratton-ChaletbrBeautiful-Pet-Friendly-Chalet-With-Hot-Tub.h91754323.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/13000000/12530000/12522700/12522689/64a51502.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Condo, 2 Bedrooms, Mountainside (Winter Place, plus Loft) | Living room](https://images.trvl-media.com/lodging/13000000/12530000/12522700/12522689/f29c7f91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Condo, 2 Bedrooms, Mountainside (Winter Place, plus Loft) | Private kitchen](https://images.trvl-media.com/lodging/13000000/12530000/12522700/12522689/459fe6c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Winter Place Two Bedroom plus Loft Ski In/Out](https://images.trvl-media.com/lodging/13000000/12530000/12522700/12522689/6a064e37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Winterplace at Okemo

Clock Tower Base Area

8.8/10

Excellent

(25)

"I think it needs some wall touch ups and new shower liners , other than that is was a pleasant stay. "

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

Jocelin

[](https://www.expedia.ca/Ludlow-Hotels-Winterplace-At-Okemo.h12522689.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/120000000/119530000/119523200/119523119/9724b081.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119530000/119523200/119523119/6814c3b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119530000/119523200/119523119/1ac33e5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/120000000/119530000/119523200/119523119/3a8306d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC

Townshend

10/10

Exceptional

(4)

"Had a great time . Excellent communication Very clean .Would definitely stay there again. "

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

Chris R.

[](https://www.expedia.ca/Townshend-Hotels-Luxurious.h119523119.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/112000000/112000000/111998700/111998634/40d77b74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/112000000/112000000/111998700/111998634/1c9d2743.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Gift shop](https://images.trvl-media.com/lodging/112000000/112000000/111998700/111998634/e74cd874.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/112000000/112000000/111998700/111998634/b701e9e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Owl's Nest Treehouse

Alstead

10/10

Exceptional

(11)

"Great place . Would highly recommend it.!"

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

Peter G.

CA $388

CA $479 total

includes taxes & fees

Nov 11 - Nov 12

[](https://www.expedia.ca/Alstead-Hotels-Owls-Nest-Treehouse.h111998634.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/28000000/27120000/27117200/27117112/62670e78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/28000000/27120000/27117200/27117112/becbfa0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/28000000/27120000/27117200/27117112/306e8880.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Books, stereo](https://images.trvl-media.com/lodging/28000000/27120000/27117200/27117112/04dd28e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Grafton

9.6/10

Exceptional

(166)

"Very nice and clean cabin, not too far from small towns, decently supplied for expected conveniences, charming area - a small stream nearby provides a pleasant background noise. "

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

Philip

CA $239

CA $505 total

includes taxes & fees

Nov 11 - Nov 12

[](https://www.expedia.ca/Grafton-Hotels-Charming-Fully-Renovated-One-Room-Schoolhouse-On-22-Acres.h27117112.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/31000000/30750000/30746800/30746800/159b0e50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/31000000/30750000/30746800/30746800/de0df7de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/31000000/30750000/30746800/30746800/cc3848ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/31000000/30750000/30746800/30746800/1c5742b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Winhall

9.6/10

Exceptional

(239)

"What a wonderful place to stay! My boyfriend and I too advantage of the beautiful deck and had coffee and dinner on it every day. We also used the charcoal grill to cook dinner and the wood stove outside, for a beautiful outside dining expereince! We would love to come back again!"

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

Katherine B.

[](https://www.expedia.ca/Bondville-Hotels-Beautiful-Honeymoon-Cottage-Close-To-Manchester-Vermont-Manchester-Center.h30746800.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/73000000/72140000/72131900/72131806/5c4d09d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/73000000/72140000/72131900/72131806/f6b88b6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/73000000/72140000/72131900/72131806/7ff65ad2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, DVD player](https://images.trvl-media.com/lodging/73000000/72140000/72131900/72131806/c05c5eaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

Ludlow

8.0/10

Very good

(41)

"This Vrbo has been housing people since the 1960's, and we're so glad to be a part of this place's history It is truly a timeless home within a beautiful area with great outdoor activites, generous people and good food (we recommend The Hatchery). Both showers (the top floor shower and the middle floor) did have a leak, but our hosts responded quickly to our concerns and addressed them within a timely manner :) "

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

John Q.

[](https://www.expedia.ca/Ludlow-Hotels-Classic-Ski-Home-With-Hot-Tub.h72131806.Hotel-Information)

![3 bedrooms, internet, bed sheets](https://images.trvl-media.com/lodging/72000000/71550000/71546900/71546851/5fc6b5db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, DVD player, table tennis, books](https://images.trvl-media.com/lodging/72000000/71550000/71546900/71546851/8f7be5d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/72000000/71550000/71546900/71546851/8c416ff5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71550000/71546900/71546851/01bfc43c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing

Andover

9.0/10

Wonderful

(29)

"The property was beautiful with a gorgeous view. The cleanliness of the house was less than expected. Cobwebs, stained bedspread, dirty cabinets, and handprints all over the loft windows gave the impression that it hadn't been thoroughly cleaned in a while. There were also several lightbulbs that were burned out on arrival. If it were cleaned up properly, it would be a great place to stay."

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

Stephen T.

[](https://www.expedia.ca/Ludlow-Hotels-Secluded-Cabin-W-Private-Hot-Tub.h71546851.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/108000000/107560000/107553700/107553693/dc9c0b14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107560000/107553700/107553693/77508c6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/108000000/107560000/107553700/107553693/0cc7bf4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107560000/107553700/107553693/20d51d16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!

Londonderry

8.6/10

Excellent

(8)

"My husband and I stayed at the treehouse cabin for two nights. It was so adorable and had so many fun amenities from the hot tub, to the fire place and record player. They even had snow shoes for us to borrow and we were able to use them and had a fun morning snow shoeing. Easy check in, and just a nice clean fun place to stay."

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

Meghan C.

CA $463

CA $799 total

includes taxes & fees

Nov 6 - Nov 7

[](https://www.expedia.ca/Londonderry-Hotels-Treehouse-Lifted-Up-Over-A-Stocked-Trout-Pond-Up-In-The-Beautiful-Birch-Trees.h107553693.Hotel-Information)

![Smart TV, fireplace, DVD player, table tennis](https://images.trvl-media.com/lodging/34000000/33710000/33710000/33709968/429008d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/34000000/33710000/33710000/33709968/dc95f952.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33710000/33710000/33709968/de6e43f0.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/34000000/33710000/33710000/33709968/2de9f2fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beautiful Custom Built Timber Frame Home, Sleeps 11

Wilmington

10/10

Exceptional

(108)

"The house is beautiful and has a gorgeous view, especially at night of the stars. Michael was super responsive with a couple of questions we had on logistics and supplies to bring. We would highly recommend staying there and will probably book again in the future."

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

Jeff L.

[](https://www.expedia.ca/Wilmington-Hotels-Beautiful-Custom-Built-Timber-Frame-Home.h33709968.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/111000000/110900000/110896100/110896001/w1114h746x0y9-9e33c846.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110900000/110896100/110896001/w1179h807x0y0-78265303.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110900000/110896100/110896001/7749ca9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/111000000/110900000/110896100/110896001/f164c130.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

Dover

10/10

Exceptional

(9)

"This place is somehow better than it looks online. It is truly spectacular. And incredibly easy ski in ski out. Ski in is right to the door and ski out is about 10 foot walk to the magic carpet in the backyard. Tina of room. First class appliances. Tons of parking. We had a big group. Also two great places to hang out upstairs in the great room then the kids needed up hanging out a lot on the main floor. Checking in was a piece of cake and Todd was very responsive if we needed anything. Can’t...

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

Marc G.

[](https://www.expedia.ca/West-Dover-Hotels-Brand-New-Listing-True-Ski-In-Ski-Out-With-Private-Hot-Tub-Fire-Pit.h110896001.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/97000000/96390000/96381300/96381283/09218223.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/97000000/96390000/96381300/96381283/99e2bd8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi](https://images.trvl-media.com/lodging/97000000/96390000/96381300/96381283/w2439h1625x0y0-7dca8401.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fitness facility](https://images.trvl-media.com/lodging/97000000/96390000/96381300/96381283/9974e428.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Treehouse at Wise Pines- SoBo

Woodstock

9.8/10

Exceptional

(24)

"The treehouse is super comfortable and spacious and the lodge was very cozy with everything you need! Breakfast was great too :)"

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Victoria M.

CA $211

CA $263 total

includes taxes & fees

Nov 8 - Nov 9

[](https://www.expedia.ca/Treehouse-At-Wise-Pines-SoBo.h96381283.Hotel-Information)

![TV, fireplace](https://images.trvl-media.com/lodging/90000000/89550000/89541000/89540910/73348812.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, internet, bed sheets](https://images.trvl-media.com/lodging/90000000/89550000/89541000/89540910/7cb29799.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89550000/89541000/89540910/916d5cf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/90000000/89550000/89541000/89540910/f8d749ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lovely ski-in/out condo steps from ski lift with trails and amazing views

Stratton

8.4/10

Very good

(26)

"Great location close to lift. Condo is clean and well appointed."

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

Grace Ann B.

CA $100

CA $391 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/Stratton-Hotels-Lovely-Ski-Inout-Condo-Steps-From-Ski-Lift-With-Trails-And-Amazing-Views.h89540910.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/19000000/18960000/18956500/18956475/f1210b7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/19000000/18960000/18956500/18956475/f08a0feb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/19000000/18960000/18956500/18956475/a5d04bfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/19000000/18960000/18956500/18956475/fc012403.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury Renovated Mount Snow Chalet with Upscale Amenities– Sleeps 12!

West Dover Vermont

9.6/10

Exceptional

(26)

"Perfect location to walk to slopes. The host was phenomenal! Very responsive and helpful. Can’t wait to stay again soon!"

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

R B.

[](https://www.expedia.ca/West-Dover-Hotels-Beautifully-Renovated-Mount-Snow-Luxury-Chalet-Sleeps-12.h18956475.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107910000/107901400/107901330/de12cb70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107910000/107901400/107901330/9b9c05f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107910000/107901400/107901330/4be6bdff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/108000000/107910000/107901400/107901330/9577aab1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy 2-bedroom cabin near Mount Snow 3 min drive

Dover

9.6/10

Exceptional

(9)

"Great cabin! Perfect for our family of 4 and our dog! Very close to mount snow and walking distance to great restaurants! "

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

Lisa R.

[](https://www.expedia.ca/West-Dover-Hotels-Dream-Wood-Log-Cabin-With-A-Fire-Place-15-Miles-From-The-Chairlifts.h107901330.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=2025-11-19&endDate=2025-11-20&regionId=89014&adults=2&sort=RECOMMENDED&openPlayBack=true)

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## Top Chester Hotel Reviews

![The Shire Woodstock](//images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/3700fd69_y.jpg)

### The Shire Woodstock

10/10 Excellent

"Everything was awesome! Great view and very clean. Just what we were looking for. Very easy check in and out"

[](https://expedia.ca/Woodstock-Hotels-The-Shire-Woodstock.h10453651.Hotel-Information)

![Best Western Plus Keene Hotel](//images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-984046b8_y.jpg)

### Best Western Plus Keene Hotel

10/10 Excellent

"Front desk woman excellent "

[](https://expedia.ca/Keene-Hotels-Best-Western-Plus-Keene-Hotel.h15916.Hotel-Information)

![Holiday Inn Club Vacations Mount Ascutney Resort by IHG](//images.trvl-media.com/lodging/1000000/430000/425200/425171/fead325a_y.jpg)

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

10/10 Excellent

"We loved this hotel as everything was very clean. The staff was very friendly and helpful. They provided us with information as to other areas or places we could go with our family. They were very informative. And they do provide just about everything you need."

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

![Hampton Inn and Suites Manchester](//images.trvl-media.com/lodging/19000000/18190000/18188900/18188804/5bd509a3_y.jpg)

### Hampton Inn and Suites Manchester

10/10 Excellent

"Excellent. Most folks were friendly and would smile. Front desk seemed to being having some rough days. :( But still a great stay. "

[](https://expedia.ca/Bennington-Hotels-Hampton-Inn-And-Suites-Manchester.h18188804.Hotel-Information)

![Woodstock Inn & Resort](//images.trvl-media.com/lodging/1000000/30000/25700/25690/6bca8eff_y.jpg)

### Woodstock Inn & Resort

10/10 Excellent

"The staff were so welcoming and friendly! When we got engaged they all cheered for us and were so sweet!"

[](https://expedia.ca/Woodstock-Hotels-Woodstock-Inn-Resort.h25690.Hotel-Information)

![Latchis Hotel](//images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/9faca473_y.jpg)

### Latchis Hotel

10/10 Excellent

"Friendly staff. Unique stay. "

[](https://expedia.ca/Brattleboro-Hotels-Latchis-Hotel.h1367207.Hotel-Information)

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

### The Jackson

10/10 Excellent

"The owner and staff were great. Whole experience was very good. Highly recommend "

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

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

### Pointe at Castle Hill Resort

10/10 Excellent

"We had a great experience at Resort and the room was clean and very nice. "

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

![Jackson Gore Village](//images.trvl-media.com/lodging/3000000/2420000/2417100/2417009/7193c148_y.jpg)

### Jackson Gore Village

10/10 Excellent

"Great swimming pools.. Also enjoyed the hot chocolate at the complimentary wending machine.. Rooms were cosy too.."

[](https://expedia.ca/Ludlow-Hotels-Jackson-Gore-Village.h2417009.Hotel-Information)

## Find out more about Chester

**Everything you need to know about** **Chester** **vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chester vacation rental for you. At Expedia, you can take your pick from [private vacation homes](https://www.expedia.ca/aa/PrivateVacationHomes), [apartments](https://www.expedia.ca/aa/Apartments), cottages, [cabins](https://www.expedia.ca/aa/Cabins), villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

**Chester vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Chester. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chester vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chester vacation rentals we have selected for you start as low as CA $263 per night. Entering your travel dates in the search wizard you might find even better deals!

**How to find incredible deals on Chester rentals**

At Expedia, we put the best Chester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chester vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

## Explore a world of travel with Expedia

-   Trending destinations on Expedia.ca
-   All accommodation types in Chester

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-   [Vacation Homes in Chester](https://expedia.ca/Chester-Private-Vacation-Homes.d89014-aaPrivateVacationHomes.Travel-Guide-Accommodation)
-   [Condo Rentals in Chester](https://expedia.ca/Chester-Condos.d89014-aaCondos.Travel-Guide-Accommodation)
-   [Apartments in Chester](https://expedia.ca/Chester-Apartments.d89014-aaApartments.Travel-Guide-Accommodation)
-   [Cottages in Chester](https://expedia.ca/Chester-Cottages.d89014-aaCottages.Travel-Guide-Accommodation)
-   [Cabin Rentals in Chester](https://expedia.ca/Chester-Cabins.d89014-aaCabins.Travel-Guide-Accommodation)
-   [Chalets in Chester](https://expedia.ca/Chester-Chalets.d89014-aaChalets.Travel-Guide-Accommodation)
-   [B&B in Chester](https://expedia.ca/Chester-Bed-And-Breakfast.d89014-aaBedAndBreakfast.Travel-Guide-Accommodation)
-   [Resorts in Chester](https://expedia.ca/Chester-Resort-Hotels.d89014-aaResortHotels.Travel-Guide-Accommodation)
-   [Farmstay in Chester](https://expedia.ca/Chester-Agritourism.d89014-aaAgritourism.Travel-Guide-Accommodation)
-   [Motels in Chester](https://expedia.ca/Chester-Motels.d89014-aaMotels.Travel-Guide-Accommodation)
-   [Aparthotels in Chester](https://expedia.ca/Chester-Apart-Hotels.d89014-aaApartHotels.Travel-Guide-Accommodation)
-   [Guest Houses in Chester](https://expedia.ca/Chester-Guest-Houses.d89014-aaGuestHouses.Travel-Guide-Accommodation)
-   [Inns in Chester](https://expedia.ca/Chester-Inns.d89014-aaInns.Travel-Guide-Accommodation)
-   [Lodges in Chester](https://expedia.ca/Chester-Lodges.d89014-aaLodges.Travel-Guide-Accommodation)
-   [Villas in Chester](https://expedia.ca/Chester-Villas.d89014-aaVillas.Travel-Guide-Accommodation)
-   [RV Parks in Chester](https://expedia.ca/Chester-RV-Parks.d89014-aaRVParks.Travel-Guide-Accommodation)

## Frequently asked questions

### Are there vacation rentals in Chester?

> Yes, there are vacation rentals in Chester near DaVallia Art & Accents, or you can select a more remote option if you want a relaxing stay. The ski slopes and shops are just a few reasons why tourists like Chester. While you're in the area, grab a bite or have a drink at the coffeehouses and restaurants.

### What are some of the best vacation rentals in Chester?

> [Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo](https://www.expedia.ca/Ludlow-Hotels-Traveling-With-Kids-Check-This-Secluded-Update-3-Bedroom-Home-Close-To-Okemo.h31137653.Hotel-Information): This vacation home rental near Chester is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

### How many vacation rentals will I find in Chester?

> Choose from 33 Expedia vacation rentals in Chester for a memorable vacation.

### What’s there to see and do in Chester?

> DaVallia Art & Accents and Bonnie's Bundles Dolls are a couple of family-friendly sights. Grafton Historical Society and Vermont Country Store are a couple of places you'll find in the larger area.

### What’s a vacation rental in Chester like?

> Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Chester. Vacation rentals offer extras such as WiFi and washers and dryers to help you enjoy your stay. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from shared hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for family trips or small group gatherings.

![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg)

## Go further with the Expedia app

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Scan the QR code with your device camera and download our app

![QR code to download the app](data:image/png;base64,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)