Vacation Homes in Chester, VT

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Top Vacation Homes in Chester

4 Season Secluded Lakefront Home near Ski Mountains

4 Season Secluded Lakefront Home near Ski Mountains

Mt Holly VT
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This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Cozy 3br cabin 5 minutes (1.5 miles) from Okemo Mountain Base

Cozy 3br cabin 5 minutes (1.5 miles) from Okemo Mountain Base

Ludlow VT
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This vacation home includes a garden and laundry facilities. A free bus station shuttle is offered as well.
Kitchen
Washer
Beautifully Remodeled VT Mountain Oasis with Stratton Views and private Hot Tub

Beautifully Remodeled VT Mountain Oasis with Stratton Views and private Hot Tub

2 out of 5
Peru VT
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This vacation home features an outdoor pool and a gym. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. A hot tub and barbecue grills are also provided.
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

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

Ludlow VT
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A hot tub is featured at this vacation home, along with laundry facilities.
Rustic home with a private hot tub, fireplace, cable, & washer/dryer

Rustic home with a private hot tub, fireplace, cable, & washer/dryer

Plymouth VT
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A hot tub is featured at this vacation home, along with laundry facilities and barbecue grills.
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo

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

Ludlow VT
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This vacation home features a garden, laundry facilities, and barbecue grills. There's fun for all ages with a playground and an arcade/game room.
Kitchen
Washer
500ft across the street to Carnitha. Gromet to main lift or take Moover to Base

500ft across the street to Carnitha. Gromet to main lift or take Moover to Base

Dover VT
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This vacation home features ski-in/ski-out access, a garden, and laundry facilities. Barbecue grills are provided for your convenience.
Kitchen
Washer
Newly Renovated Cottage, Hot Tub, Fire place, 5min to Killington Ski Gondola

Newly Renovated Cottage, Hot Tub, Fire place, 5min to Killington Ski Gondola

Bridgewater Corners VT
$441 nightly
The price is $494 total per night
$494 total
Dec 22 - Dec 23
Total with taxes and fees
A hot tub is featured at this vacation home, along with laundry facilities and barbecue grills.
Ski in Ski out Condo! Pool access

Ski in Ski out Condo! Pool access

Stratton VT
$481 nightly
The price is $544 total per night
$544 total
Dec 2 - Dec 3
Total with taxes and fees
Ski-in/ski-out access and a hot tub are featured at this smoke-free vacation home. Laundry facilities are provided for your convenience.
Mountain View Manor - Expansive Views, Hot Tub, Hiking & Nearby Lakes!

Mountain View Manor - Expansive Views, Hot Tub, Hiking & Nearby Lakes!

Ludlow VT
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Ski-in/ski-out access and a hot tub are featured at this smoke-free vacation home. A garden, laundry facilities, and barbecue grills are also on offer.
Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Winhall VT
$606 nightly
The price is $680 total per night
$680 total
Dec 3 - Dec 4
Total with taxes and fees
A hot tub is featured at this vacation home, along with free WiFi in public areas and a garden. Families will appreciate the arcade/game room and onsite laundry facilities. Barbecue grills are provided for your convenience.
Beautiful Custom Built Timber Frame Home, Sleeps 11

Beautiful Custom Built Timber Frame Home, Sleeps 11

Wilmington VT
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A hot tub is featured at this vacation home, along with a garden and laundry facilities. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site.
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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.

Top hotels in Chester

Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

4519 Main St Manchester Center VT
$127 nightly
The price is $140 total per night from Dec 7 to Dec 8
$140 total
Dec 7 - Dec 8
Total with taxes and fees
9.6/10 Exceptional! (1,000 reviews)

Find the Best Vacation Homes in Chester

Why book a vacation home in Chester?

Vacation homes in Chester make for a different travel experience. Your holiday home will allow you to feel at home during your visit. You’ll usually have more space, more privacy, and extra amenities not typically included with hotel stays.

How much is a vacation home in Chester?

Private Chester rental homes range between $124 - $680 per night. Prices change based on seasonal demand, travel dates, property location, capacity, amenities, etc.

What are the cancellation and flexibility options on Travelocity?

To cancel your vacation home, you must reach out to the individual property manager. Their contact details are available in your itinerary. For more information, head over to our customer service portal. Use the ‘free cancellation’ or ‘reserve now, pay later’ filters to find the most flexible options for your bookings.

What amenities should I look out for in a vacation home?

There are some exciting amenities available in Chester vacation home rentals. You might look for Chester rental houses with a private pool or free Wi-Fi. Some popular amenities also include a private hot tub, air-conditioning, laundry facilities, and a games room. 

Vacation rentals in Chester offer other accommodations that may interest you. Some have resort-like amenities such as a fitness center, bar/lounge, or swimming pool.

When is the best time to rent a vacation home in Chester?

You’ll typically get cheaper rates when staying during the off-season, . Prices are usually at their lowest for stays in . are the most popular months to visit.

Why book a vacation home with Travelocity?

Travel smart with Travelocity. Search over 1 million properties worldwide and access an incredible selection of holiday homes in Chester. Our members save 10% or more on select hotels, and if you find a lower price, we’ll match it with our Price Match Guarantee. Get started finding Chester hotels and vacation homes that best suit your stay. We also have deals for flights, and Chester car rentals. You’ll save even more when you bundle your items into a Chester vacation package!

How many vacation homes are available to book in Chester?

There are 949 rental homes in Chester. Enter your travel dates to check availability.

How do I find the best price for a vacation home in Chester?

Private vacation homes vary in price, and we’ll help you get the best deal possible. Use the map feature to compare rental house prices in different neighborhoods. Also, try adjusting your dates to compare nightly rates within a similar timeframe.

Chester Vacation Homes essential information

Accommodation
949 Vacation Homes
Lowest Price
$124
Highest Price
$680
Popular accommodation
4 Season Secluded Lakefront Home near Ski Mountains , Cozy 3br cabin 5 minutes (1.5 miles) from Okemo Mountain Base, Beautifully Remodeled VT Mountain Oasis with Stratton Views and private Hot Tub, Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable, Rustic home with a private hot tub, fireplace, cable, & washer/dryer, Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo, 500ft across the street to Carnitha. Gromet to main lift or take Moover to Base, Newly Renovated Cottage, Hot Tub, Fire place, 5min to Killington Ski Gondola, Ski in Ski out Condo! Pool access, Mountain View Manor - Expansive Views, Hot Tub, Hiking & Nearby Lakes!, Your Vermont Mountain Haven Pet Friendly home with Hot tub!, Beautiful Custom Built Timber Frame Home, Sleeps 11

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