Title: Chester Vacation Rentals from CA $400: Short-Term Rentals for 2026 | Expedia.ca

[Hotels in Chester](https://expedia.ca/Chester-Hotels.d89014.Travel-Guide-Hotels)[Things to do in Chester](https://expedia.ca/Things-To-Do-In-Chester.d89014.Travel-Guide-Activities)[Chester Car Rentals](https://expedia.ca/Car-Rentals-In-Chester.d89014.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.ca/Chester.d89014.Destination-Travel-Guides)

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## Check prices for these dates

In two weeks

[Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 26 - Jun 28](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 24 - Jul 26](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-07-24&endDate=2026-07-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Chester vacation rentals

![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/125000000/124180000/124177600/124177563/c93e763c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/125000000/124180000/124177600/124177563/66b559f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/125000000/124180000/124177600/124177563/95da5fd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/125000000/124180000/124177600/124177563/f8f558ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Outdoor Adventure Hub! Family Home in West Dover

[](https://www.expedia.ca/West-Dover-Hotels-Ski.h124177563.Hotel-Information)

West Dover

CA $213

CA $725 total

includes taxes & fees

Apr 1 - Apr 2

[](https://www.expedia.ca/West-Dover-Hotels-Ski.h124177563.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/7000000/6610000/6602500/6602401/4994716e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/7000000/6610000/6602500/6602401/b907a89a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Condo, 2 Bedrooms | Balcony](https://images.trvl-media.com/lodging/7000000/6610000/6602500/6602401/c46d6757.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

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

Stratton

8.6/10

Excellent

(83 reviews)

"Nice place and great location!!!"

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

William

CA $456

CA $567 total

includes taxes & fees

Apr 21 - Apr 22

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

![Exterior](https://images.trvl-media.com/lodging/33000000/32350000/32342000/32341945/05713f89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 2 Bedrooms, Mountainside (Kettle Brook) | Private kitchen](https://images.trvl-media.com/lodging/33000000/32350000/32342000/32341945/5237275c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, individually decorated, individually furnished](https://images.trvl-media.com/lodging/33000000/32350000/32342000/32341945/66b853e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Kettle Brook Two Bedroom 1 Bath Ski In/Out | Living room](https://images.trvl-media.com/lodging/33000000/32350000/32342000/32341945/12d879f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Okemo Mountain Lodging by Vail Resorts

[](https://www.expedia.ca/Ludlow-Hotels-Okemo-Mountain-Lodging.h32341945.Hotel-Information)

Clock Tower Base Area

7.8/10

Good

(28 reviews)

"I had an amazing time with my family, I will definitely be coming back "

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

Yenifer

CA $2,084

CA $2,651 total

includes taxes & fees

Apr 2 - Apr 3

[](https://www.expedia.ca/Ludlow-Hotels-Okemo-Mountain-Lodging.h32341945.Hotel-Information)

![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/121000000/120620000/120618700/120618609/14ace880.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/121000000/120620000/120618700/120618609/0780f54b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/121000000/120620000/120618700/120618609/70217bef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/121000000/120620000/120618700/120618609/b15a729a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Outdoor Adventure Haven 14 Mi to Mount Snow Skiing

[](https://www.expedia.ca/Newfane-Hotels-Outdoor-Adventure-Haven-14-Mi-To-Mount-Snow-Skiing.h120618609.Hotel-Information)

Newfane

CA $313

CA $799 total

includes taxes & fees

Apr 5 - Apr 6

[](https://www.expedia.ca/Newfane-Hotels-Outdoor-Adventure-Haven-14-Mi-To-Mount-Snow-Skiing.h120618609.Hotel-Information)

![House (5 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/127000000/126490000/126481900/126481809/fc371b6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (5 Bedrooms) | Interior](https://images.trvl-media.com/lodging/127000000/126490000/126481900/126481809/0d8dca3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (5 Bedrooms) | Interior](https://images.trvl-media.com/lodging/127000000/126490000/126481900/126481809/09450a91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (5 Bedrooms) | Interior](https://images.trvl-media.com/lodging/127000000/126490000/126481900/126481809/9b4bc035.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxe Mountain Home w/ Chefs Kitchen & Okemo Views

[](https://www.expedia.ca/Ludlow-Hotels-Luxe-Mountain-Home-W-Chefs-Kitchen-Okemo-Views.h126481809.Hotel-Information)

Ludlow

CA $1,364

CA $2,198 total

includes taxes & fees

May 1 - May 2

[](https://www.expedia.ca/Ludlow-Hotels-Luxe-Mountain-Home-W-Chefs-Kitchen-Okemo-Views.h126481809.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=2026-04-14&endDate=2026-04-15&regionId=89014&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Cabins

[](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=2026-06-29&d1=2026-06-29&endDate=2026-07-02&d2=2026-07-02&lodging=CABIN)

Private vacation homes

[](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=2026-06-29&d1=2026-06-29&endDate=2026-07-02&d2=2026-07-02&lodging=VACATION_HOME)

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=2026-06-29&d1=2026-06-29&endDate=2026-07-02&d2=2026-07-02&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=2026-06-29&d1=2026-06-29&endDate=2026-07-02&d2=2026-07-02&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=2026-06-29&d1=2026-06-29&endDate=2026-07-02&d2=2026-07-02&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=2026-06-29&d1=2026-06-29&endDate=2026-07-02&d2=2026-07-02&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=2026-06-29&d1=2026-06-29&endDate=2026-07-02&d2=2026-07-02&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=2026-06-29&d1=2026-06-29&endDate=2026-07-02&d2=2026-07-02&lodging=VILLA)

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## Top Chester Hotel Reviews

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

### Pointe at Castle Hill Resort

8/10 Good

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

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

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

### On The River Inn

10/10 Excellent

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

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

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

### Colonial Motel And Spa

4/10 Poor

"Plenty of parking Clean - no bugs Goes downhill from there. Front desk people were polite but far from friendly. Major renovations need to be done before I will come back. Windows did not lock, which my husband discovered as we were getting ready for bed. He decided that they were too small for anyone to crawl through, but not a comforting feeling. Pool - closes at 5pm on Sunday - we arrived at 5:10 😳 Hot tub - closed for cleaning on Monday until 1pm, but check out is at 11am So I have no idea what the condition is of either, but I cannot imagine that they are in great shape. I should have known that 2 pools and a hot tub for that price was too good to be true "

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

![The Equinox Golf Resort & Spa](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/fddf0cb9_y.jpg)

### The Equinox Golf Resort & Spa

10/10 Excellent

"We love the Equinox. We usually stay here during ski season. Always looking forward to rest after a long day of ski. Amenities are amazing, the restaurant and bar are great to eat and hangout. "

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

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

### Aspen At Manchester

10/10 Excellent

"Clean room. Shops nearby"

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

"Great place, nice restaurant next door."

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

![Stone Hearth Inn and Eatery](https://images.trvl-media.com/lodging/88000000/87490000/87486300/87486236/52ce2be1_y.jpg)

### Stone Hearth Inn and Eatery

8/10 Good

"Fantastic breakfast in this quaint inn. Right in the road so very easy to find. Wonderful meal in the attached restaurant. Friendly staff. Easy parking."

[](https://expedia.ca/Chester-Hotels-Stone-Hearth-Inn-And-Eatery.h87486236.Hotel-Information)

![The Covered Bridge Inn](https://images.trvl-media.com/lodging/28000000/27670000/27661400/27661353/10a69b41_y.jpg)

### The Covered Bridge Inn

4/10 Poor

"The rrooms were clean, shower was great. Hallways dark, parking lot not to much lighting. There is no breakfast just coffee."

[](https://expedia.ca/Brattleboro-Hotels-The-Covered-Bridge-Inn.h27661353.Hotel-Information)

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

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

10/10 Excellent

"courteous staff, great property."

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

## Find out more about Chester

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Chester. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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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)
- [Villas in Chester ](https://expedia.ca/Chester-Villas.d89014-aaVillas.Travel-Guide-Accommodation)
- [Guest Houses in Chester ](https://expedia.ca/Chester-Guest-Houses.d89014-aaGuestHouses.Travel-Guide-Accommodation)
- [Lodges in Chester ](https://expedia.ca/Chester-Lodges.d89014-aaLodges.Travel-Guide-Accommodation)
- [Inns in Chester ](https://expedia.ca/Chester-Inns.d89014-aaInns.Travel-Guide-Accommodation)
- [RV Parks in Chester ](https://expedia.ca/Chester-RV-Parks.d89014-aaRVParks.Travel-Guide-Accommodation)

## Frequently asked questions

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