Title: Chester Condo Rentals from CA $308 | Expedia.ca

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## Check prices for these dates

In two weeks

[Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=89014&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 two months

[Jun 5 - Jun 7](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jul 3 - Jul 5](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-07-03&endDate=2026-07-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 31 - Aug 2](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-07-31&endDate=2026-08-02&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Chester condo rentals

![Outdoor dining](https://images.trvl-media.com/lodging/97000000/96910000/96900500/96900410/ff1494e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/97000000/96910000/96900500/96900410/3455234a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/97000000/96910000/96900500/96900410/w1024h678x0y2-7e279cab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/97000000/96910000/96900500/96900410/w1024h680x0y3-dba94e8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Okemo | 3BR Penthouse | Slopes & Amenities Nearby

[](https://www.expedia.ca/Ludlow-Hotels-Okemo-3BR-Penthouse-Slopes-Amenities-Nearby.h96900410.Hotel-Information)

Jackson Gore Base Area

8.0/10

Very good

(1 review)

"Overall a nice stay. Unit was a bit tired and communication from VRBO/PM and onsite staff a bit problematic. "

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

Gregory Z.

CA $1,517

CA $1,872 total

includes taxes & fees

Apr 10 - Apr 11

[](https://www.expedia.ca/Ludlow-Hotels-Okemo-3BR-Penthouse-Slopes-Amenities-Nearby.h96900410.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/22000000/21710000/21708500/21708413/f68608f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/22000000/21710000/21708500/21708413/005d9ea5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, DVD player, books, video library](https://images.trvl-media.com/lodging/22000000/21710000/21708500/21708413/b47ad841.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, DVD player, books, video library](https://images.trvl-media.com/lodging/22000000/21710000/21708500/21708413/15f78921.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

[](https://www.expedia.ca/Ludlow-Hotels-Condo-With-Seasonal-Pool-Tennis-Courts-Walk-To-Ski-Trails.h21708413.Hotel-Information)

Ludlow

7.6/10

Good

(56 reviews)

"The place was very dirty. The linens were dirty, the pots/pans and all of the cooking utensils were dirty. There was a rubber band on the floor in bathroom that didn't belong to us.There was only 3 forks and a few spoons. Very little silverwear."

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

Leigh-Ellen F.

CA $74

CA $408 total

includes taxes & fees

Apr 8 - Apr 9

[](https://www.expedia.ca/Ludlow-Hotels-Condo-With-Seasonal-Pool-Tennis-Courts-Walk-To-Ski-Trails.h21708413.Hotel-Information)

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

![Exterior](https://images.trvl-media.com/lodging/22000000/21700000/21692200/21692155/e329a225.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, DVD player](https://images.trvl-media.com/lodging/22000000/21700000/21692200/21692155/5554154f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/22000000/21700000/21692200/21692155/f5aaae02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Clock Tower Base Area

9.0/10

Wonderful

(78 reviews)

"Unit was as advertised. Clean and comfortable."

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

Ralph D.

CA $104

CA $359 total

includes taxes & fees

Apr 9 - Apr 10

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

![Property grounds](https://images.trvl-media.com/lodging/73000000/72140000/72131900/72131894/455aec2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/73000000/72140000/72131900/72131894/146a8911.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, DVD player](https://images.trvl-media.com/lodging/73000000/72140000/72131900/72131894/2828ea80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, DVD player](https://images.trvl-media.com/lodging/73000000/72140000/72131900/72131894/9a087dbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

[](https://www.expedia.ca/Ludlow-Hotels-Ski-InOut-Condo-With-Patio.h72131894.Hotel-Information)

Clock Tower Base Area

9.2/10

Wonderful

(30 reviews)

"Great property, clean and close to the slope"

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

tiliger01

CA $68

CA $308 total

includes taxes & fees

Apr 12 - Apr 13

[](https://www.expedia.ca/Ludlow-Hotels-Ski-InOut-Condo-With-Patio.h72131894.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/75000000/74150000/74149800/74149788/6f090e41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/75000000/74150000/74149800/74149788/d700bf14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/75000000/74150000/74149800/74149788/dcd02e7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free internet, bed sheets](https://images.trvl-media.com/lodging/75000000/74150000/74149800/74149788/fd32c36e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Ski-In/Out Condo with Mountain Views, and Washer/Dryer

[](https://www.expedia.ca/Ludlow-Hotels-Ski-InOut-Condo-With-Electric-Fireplace.h74149788.Hotel-Information)

Ludlow

9.6/10

Exceptional

(18 reviews)

"Perfect spot to jump onto the mountain and ski. Two adults and 4 kids, and we had plenty of space for a long weekend."

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

Allison T.

CA $174

CA $586 total

includes taxes & fees

Apr 8 - Apr 9

[](https://www.expedia.ca/Ludlow-Hotels-Ski-InOut-Condo-With-Electric-Fireplace.h74149788.Hotel-Information)

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

![TV, fireplace](https://images.trvl-media.com/lodging/90000000/89550000/89541000/89540910/bf43c699.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/90000000/89550000/89541000/89540910/dc8751a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/90000000/89550000/89541000/89540910/57d42e68.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

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

Stratton

8.4/10

Very good

(32 reviews)

"We loved staying at the townhome. It was a welcome place to stay while we traveled around, enjoying fall. It was very comfortable and the village amenities were great."

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

John N.

CA $99

CA $429 total

includes taxes & fees

Apr 14 - Apr 15

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

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/46000000/45710000/45709000/45708952/b0da744f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Golf](https://images.trvl-media.com/lodging/46000000/45710000/45709000/45708952/cc4de1c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/46000000/45710000/45709000/45708952/37889f48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/46000000/45710000/45709000/45708952/cb6b5625.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

[](https://www.expedia.ca/Central-Vermont-Killington-Hotels-Vrbo-Property.h45708952.Hotel-Information)

Ludlow

9.8/10

Exceptional

(107 reviews)

"Great Condo. We had plenty of space. Wendi was very responsive and even accommodated us checking in an hour early when we arrived in town. We would definitely come back. "

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

Barbara M.

CA $187

CA $394 total

includes taxes & fees

Apr 8 - Apr 9

[](https://www.expedia.ca/Central-Vermont-Killington-Hotels-Vrbo-Property.h45708952.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/49000000/48190000/48188500/48188407/6f40afa0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/49000000/48190000/48188500/48188407/ffa1709a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/49000000/48190000/48188500/48188407/32130af3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/49000000/48190000/48188500/48188407/1eaaf157.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy 3 bedroom condo 2.5 miles to Mount Snow

[](https://www.expedia.ca/Bouvet-Island-Hotels-Vrbo-Property.h48188407.Hotel-Information)

West Dover

9.2/10

Wonderful

(51 reviews)

"Great cozy apartment right next to a ski resort"

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

Mikhail S.

CA $125

CA $409 total

includes taxes & fees

Apr 14 - Apr 15

[](https://www.expedia.ca/Bouvet-Island-Hotels-Vrbo-Property.h48188407.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/102000000/101340000/101332300/101332217/195c9a91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/102000000/101340000/101332300/101332217/82a78a4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/102000000/101340000/101332300/101332217/ac902f96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/102000000/101340000/101332300/101332217/8583048f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 2nd-floor downtown Ludlow studio condo with kitchenette, streaming

[](https://www.expedia.ca/Ludlow-Hotels-2nd-Floor-Downtown-Ludlow-Studio-Condo-With-Kitchenette.h101332217.Hotel-Information)

Ludlow

8.6/10

Excellent

(4 reviews)

"Great location and convenient to all local businesses. I enjoyed it very much. Would stay here anytime and plan to again. "

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

Kevin C.

CA $132

CA $338 total

includes taxes & fees

Apr 8 - Apr 9

[](https://www.expedia.ca/Ludlow-Hotels-2nd-Floor-Downtown-Ludlow-Studio-Condo-With-Kitchenette.h101332217.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/75000000/74110000/74100100/74100040/98181c83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/75000000/74110000/74100100/74100040/74c7fd79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/75000000/74110000/74100100/74100040/98d2d233.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/75000000/74110000/74100100/74100040/76d59ca7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities

[](https://www.expedia.ca/Stratton-Hotels-Mountain-View-Condo-With-Fast-WiFi.h74100040.Hotel-Information)

Stratton

7.4/10

Good

(21 reviews)

"A great weekend. The property was clean and comfortable."

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

Joan P.

CA $185

CA $539 total

includes taxes & fees

Apr 13 - Apr 14

[](https://www.expedia.ca/Stratton-Hotels-Mountain-View-Condo-With-Fast-WiFi.h74100040.Hotel-Information)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/103000000/102350000/102344700/102344670/023207a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/103000000/102350000/102344700/102344670/378f3abe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/103000000/102350000/102344700/102344670/fb10b74e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102350000/102344700/102344670/d24ea7fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Ski Haven: 1-Bed Ski-in/out Condo, Okemo Base Area

[](https://www.expedia.ca/Ludlow-Hotels-Ski-Haven-1-Bed-Ski-Inout-Condo.h102344670.Hotel-Information)

Clock Tower Base Area

10/10

Exceptional

(13 reviews)

"Great communication, ski in/out location"

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

Robin

CA $208

CA $589 total

includes taxes & fees

Apr 8 - Apr 9

[](https://www.expedia.ca/Ludlow-Hotels-Ski-Haven-1-Bed-Ski-Inout-Condo.h102344670.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/74000000/73760000/73756200/73756146/d5e488ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/74000000/73760000/73756200/73756146/e835f3d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/74000000/73760000/73756200/73756146/fa3bb9e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/74000000/73760000/73756200/73756146/447741a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Ground Floor ski-in/out condo, full kitchen & high-speed WiFi

[](https://www.expedia.ca/Ludlow-Hotels-Ski-InSki-Out-Condo-With-Fireplace.h73756146.Hotel-Information)

Clock Tower Base Area

9.4/10

Exceptional

(27 reviews)

"Clean room and very comfortable bed. Was ready for check in sooner than expected. "

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

Wilson V.

CA $209

CA $538 total

includes taxes & fees

Apr 14 - Apr 15

[](https://www.expedia.ca/Ludlow-Hotels-Ski-InSki-Out-Condo-With-Fireplace.h73756146.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/62000000/61640000/61636400/61636331/790c70e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/62000000/61640000/61636400/61636331/4ed0f838.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, internet, bed sheets](https://images.trvl-media.com/lodging/62000000/61640000/61636400/61636331/82f89163.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/62000000/61640000/61636400/61636331/1d0d61a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street

[](https://www.expedia.ca/Ludlow-Hotels-Downtown-Condo-W-Electric-Fireplace.h61636331.Hotel-Information)

Ludlow

9.0/10

Wonderful

(25 reviews)

"Great rate for a place with all the basics!"

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

Macgregor

CA $139

CA $348 total

includes taxes & fees

Apr 14 - Apr 15

[](https://www.expedia.ca/Ludlow-Hotels-Downtown-Condo-W-Electric-Fireplace.h61636331.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/91000000/90040000/90038700/90038655/deeed4e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/91000000/90040000/90038700/90038655/ed39671f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/91000000/90040000/90038700/90038655/f304b3e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/91000000/90040000/90038700/90038655/811f5334.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo in the heart of town near skiing - less than a mile to Okemo Mountain

[](https://www.expedia.ca/Ludlow-Hotels-Light-Filled-Condo-In-The-Heart-Of-Town-Less-Than-A-Mile-To-Okemo-Mountain.h90038655.Hotel-Information)

Ludlow

9.0/10

Wonderful

(14 reviews)

"Great place!"

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

Darcie L.

CA $174

CA $419 total

includes taxes & fees

Apr 14 - Apr 15

[](https://www.expedia.ca/Ludlow-Hotels-Light-Filled-Condo-In-The-Heart-Of-Town-Less-Than-A-Mile-To-Okemo-Mountain.h90038655.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/89000000/88640000/88639400/88639305/fce63aae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fitness facility](https://images.trvl-media.com/lodging/89000000/88640000/88639400/88639305/ef38effc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/89000000/88640000/88639400/88639305/6ae09456.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/89000000/88640000/88639400/88639305/f9e6e0c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

[](https://www.expedia.ca/West-Dover-Hotels-Ski-Inski-Out-Condo-With-Deck.h88639305.Hotel-Information)

Dover

8.8/10

Excellent

(36 reviews)

"Great place with great amenities! "

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

Rachel R.

CA $99

CA $432 total

includes taxes & fees

Apr 12 - Apr 13

[](https://www.expedia.ca/West-Dover-Hotels-Ski-Inski-Out-Condo-With-Deck.h88639305.Hotel-Information)

![Sauna](https://images.trvl-media.com/lodging/71000000/70020000/70012000/70011996/6dd344f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/71000000/70020000/70012000/70011996/18a6c891.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fitness facility](https://images.trvl-media.com/lodging/71000000/70020000/70012000/70011996/c5876dff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/71000000/70020000/70012000/70011996/2105ec50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Magic Mountain Trailside Condo - Ski In / Ski Out

[](https://www.expedia.ca/Londonderry-Hotels-Magic-Mountain-Trailside-Condo-Ski-In-Ski-Out.h70011996.Hotel-Information)

Londonderry

9.8/10

Exceptional

(14 reviews)

"Nice and we enjoyed our stay"

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

Gretchen H.

CA $174

CA $440 total

includes taxes & fees

Apr 15 - Apr 16

[](https://www.expedia.ca/Londonderry-Hotels-Magic-Mountain-Trailside-Condo-Ski-In-Ski-Out.h70011996.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/112000000/111560000/111559500/111559426/ef2b1d4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/112000000/111560000/111559500/111559426/64ebd344.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/112000000/111560000/111559500/111559426/a98c1bae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/112000000/111560000/111559500/111559426/bcf7cf4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Trailside Village #1: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals

[](https://www.expedia.ca/Killington-Hotels-Trailside-Village-1-Slopeside-1BR-W-Hot-Tub-And-Sauna-Ski-InOut-With-Discounted-Lift-Tickets.h111559426.Hotel-Information)

Killington

9.4/10

Exceptional

(58 reviews)

"Wonderful location…"

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

David C.

CA $271

CA $796 total

includes taxes & fees

Apr 8 - Apr 9

[](https://www.expedia.ca/Killington-Hotels-Trailside-Village-1-Slopeside-1BR-W-Hot-Tub-And-Sauna-Ski-InOut-With-Discounted-Lift-Tickets.h111559426.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/89000000/88310000/88304400/88304398/922d40ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/89000000/88310000/88304400/88304398/2ec0429d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![A heated pool](https://images.trvl-media.com/lodging/89000000/88310000/88304400/88304398/4830e6d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/89000000/88310000/88304400/88304398/2018eac6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stratton Mtn Studio | Renovated | Walk to Lifts

[](https://www.expedia.ca/Stratton-Hotels-Stratton-Studio-Newly-Renovated-Walk-To-Lifts.h88304398.Hotel-Information)

Stratton Mountain

10/10

Exceptional

(31 reviews)

"Great location."

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

Jeffrey

CA $237

CA $574 total

includes taxes & fees

Apr 9 - Apr 10

[](https://www.expedia.ca/Stratton-Hotels-Stratton-Studio-Newly-Renovated-Walk-To-Lifts.h88304398.Hotel-Information)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/68000000/67680000/67676900/67676844/12b9c5fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fitness facility](https://images.trvl-media.com/lodging/68000000/67680000/67676900/67676844/0636cbc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/68000000/67680000/67676900/67676844/ccde78f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/68000000/67680000/67676900/67676844/w1024h676x0y46-4a569c47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

[](https://www.expedia.ca/Cavendish-Hotels-Beautiful-Condominium-At-Castle-Hill-Resort.h67676844.Hotel-Information)

Cavendish

10/10

Exceptional

(23 reviews)

"Amazing place! "

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

Tara

CA $417

CA $754 total

includes taxes & fees

Apr 11 - Apr 12

[](https://www.expedia.ca/Cavendish-Hotels-Beautiful-Condominium-At-Castle-Hill-Resort.h67676844.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/73000000/72140000/72131700/72131664/a283578c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/73000000/72140000/72131700/72131664/1dab8185.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/73000000/72140000/72131700/72131664/5c70d1ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/73000000/72140000/72131700/72131664/dae29296.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck

[](https://www.expedia.ca/Plymouth-Hotels-Hawk-Mountain-Retreat-Near-Okemo-With-Fireplace.h72131664.Hotel-Information)

Plymouth

9.8/10

Exceptional

(24 reviews)

"The Nest at Hawk Ledges was a perfect summer getaway. The home provides comfort in a tranquil setting while being close enough to many summer adventures. We enjoyed relaxing in the bright, open home after taking many day trips to explore the area. What a gem!"

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

Ben N.

CA $257

CA $971 total

includes taxes & fees

Apr 20 - Apr 21

[](https://www.expedia.ca/Plymouth-Hotels-Hawk-Mountain-Retreat-Near-Okemo-With-Fireplace.h72131664.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=2026-04-21&endDate=2026-04-22&regionId=89014&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Cabins

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Private vacation homes

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Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America&regionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-07-05&d1=2026-07-05&endDate=2026-07-08&d2=2026-07-08&lodging=COTTAGE)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America&regionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-07-05&d1=2026-07-05&endDate=2026-07-08&d2=2026-07-08&lodging=CONDO)

Aparthotels

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America&regionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-07-05&d1=2026-07-05&endDate=2026-07-08&d2=2026-07-08&lodging=APART_HOTEL)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America&regionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-07-05&d1=2026-07-05&endDate=2026-07-08&d2=2026-07-08&lodging=APARTMENT)

Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America&regionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-07-05&d1=2026-07-05&endDate=2026-07-08&d2=2026-07-08&lodging=CHALET)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America&regionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-07-05&d1=2026-07-05&endDate=2026-07-08&d2=2026-07-08&lodging=VILLA)

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## Top Chester Hotel Reviews

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

### On The River Inn

8/10 Good

"Everything was cool except the rude woman bartending at the 506 bistro"

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

![Colonial Motel And Spa](https://images.trvl-media.com/lodging/2000000/1080000/1070800/1070729/05f7e3bc_y.jpg)

### Colonial Motel And Spa

10/10 Excellent

"Older motel style not fancy. Good hot tub in pool area. Ok for overnight on a budget. "

[](https://expedia.ca/Brattleboro-Hotels-Colonial-Motel-And-Spa.h1070729.Hotel-Information)

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

### Hampton Inn and Suites Manchester

10/10 Excellent

"Great breakfast and excellent location."

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

![Best Western Plus Keene Hotel](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-4a5edcca_y.jpg)

### Best Western Plus Keene Hotel

10/10 Excellent

"Nice place"

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

![Woodstock Inn & Resort](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/fd07b171_y.jpg)

### Woodstock Inn & Resort

10/10 Excellent

"Always an Amazing time when we stay here. Property well maintained, staff is super friendly and the food here is above and beyond. Did I mention I got married here 👍👍"

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

![Hideaway Inn Mt. Snow](https://images.trvl-media.com/lodging/123000000/122980000/122978200/122978111/c5bdc83b_y.jpg)

### Hideaway Inn Mt. Snow

10/10 Excellent

"Stayed in February for easy access to skiing at Mount Snow. Hideaway Inn is 2 minutes from Mount Snow and a confortable place to stay. Basic accomodations in winter but you have everything you need in a room. Beverages in common area and helpfull staff. Very pleasant check in and check out. Overall, great experience and will stay again."

[](https://expedia.ca/West-Dover-Hotels-Hideaway-Inn-Mt-Snow.h122978111.Hotel-Information)

![The Palmer House Resort, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/7000000/6030000/6028500/6028480/4412313e_y.jpg)

### The Palmer House Resort, an Ascend Collection Hotel

10/10 Excellent

"it's all good"

[](https://expedia.ca/Bennington-Hotels-The-Palmer-House-Resort.h6028480.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)

![Aspen At Manchester](https://images.trvl-media.com/lodging/11000000/10260000/10254500/10254459/cbf700aa_y.jpg)

### Aspen At Manchester

10/10 Excellent

"Excellent location, v"

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

## Find out more about Chester

## Chester Condo Rentals information

| Number of reviews | 402               |
| ----------------- | ----------------- |
| Accommodation     | 494 Condo Rentals |
| Lowest Price      | CA $308           |
| Highest Price     | CA $1,872         |

## Frequently asked questions

### How much do condos in Chester cost?

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