Vacation Rentals in Chester, VT
PRICE PER NIGHT
ACCOMMODATION TYPES
Top-Rated Vacation Rentals in Chester, VT
Book a vacation rental in Chester that has the highest visitor rating. Here are 6 of the best vacation rentals in Chester.
Private Chester Home w/ Deck, Mins to Skiing!
10
Excellent
·
Chester
·
3 br
·
Sleeps 8
·
Oven · Wifi · Mountains ·
From
$300/nightProperty
House · 3 Beds · 3 baths
Amenities
Oven
Wifi
Mountains
Microwave
Fireplace
Ceiling Fan
Assigned Parking
Dishwasher
Other spaces
Kitchen, Garden
Andover Cabin Retreat w/ Hot Tub & Fireplace!
10
Excellent
·
Chester
·
3 br
·
Sleeps 8
·
Balcony · Central Heat · Mountains ·
From
$190/nightProperty
House · 3 Beds · 1 bath
Amenities
Central Heat
Mountains
Air Conditioning
Tv
Fireplace
Cable
Toiletries
Wifi
Other spaces
Balcony, Kitchen, Garden
Private Chester Home w/ Deck, Mins to Skiing!
10
Excellent
·
Chester
·
3 br
·
Sleeps 8
·
High Ceilings · Dishwasher · Furnished ·
From
$327/nightProperty
House · 3 Beds · 3 baths
Amenities
High Ceilings
Dishwasher
Furnished
On Site Laundry
Ski In Ski Out
Wifi
Oven
Fireplace
Other spaces
Kitchen
Price drop
Work, Ski, Relax - Big Restored 1860s Farmhouse
10
Excellent
·
Chester
·
5 br
·
Sleeps 12
·
Mountains · Workspace · Wifi ·
From
$933/nightProperty
House · 5 Beds · 4 baths
Amenities
Mountains
Wifi
Furnished
Dishwasher
Fitness Center
Oven
On Site Laundry
Other spaces
Workspace, Kitchen
UNIQUE/HISTORIC STAY IN AN 1874 ERA SCHOOLHOUSE!!
10
Excellent
·
Chester
·
4 br
·
Sleeps 10
·
Kitchen · Air Conditioning · Wifi ·
From
$550/nightProperty
House · 4 Beds · 2 baths
Amenities
Air Conditioning
Wifi
Mountains
Swimming Pool
Oven
Fireplace
Furnished
On Site Laundry
Other spaces
Kitchen, Balcony
Chester Farmhouse on 100 Acres, 15 Min to Okemo!
10
Excellent
·
Chester
·
4 br
·
Sleeps 8
·
Outdoor Space · Dishwasher · Residents Lounge ·
From
$246/nightProperty
House · 4 Beds · 2 baths
Amenities
Dishwasher
Residents Lounge
Oven
Furnished
Fireplace
Air Conditioning
On Site Laundry
Ski In Ski Out
Other spaces
Kitchen
Our Recommended Vacation Rentals in Chester, VT
We analyzed vacation rentals in Chester from many property providers including but not limited to VRBO, Booking.com, Evolve, Blueground and more. We're providing our top recommended offers on the best vacation rentals in Chester to help you find a deal for your next trip.
Price drop
Chester Farmhouse on 100 Acres, 15 Min to Okemo!
No rating
·
Chester
·
4 br
·
Sleeps 8
·
Wifi · Free Parking · In Unit Laundry ·
From
$352/nightProperty
Apartment · 4 Beds · 2 baths
Amenities
Wifi
Free Parking
In Unit Laundry
Furnished
Fireplace
Dishwasher
Oven
Other spaces
Kitchen
Chester Home about 12 Mi to Magic Mountain Ski Area
No rating
·
Chester
·
4 br
·
Sleeps 8
·
Free Parking · Kitchen · Workspace ·
From
$368/nightProperty
Apartment · 4 Beds · 2 baths
Amenities
Free Parking
Oven
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen, Workspace
Chester Farmhouse on 100 Acres, 15 Min to Okemo!
9.7
Excellent
·
Chester
·
4 br
·
Sleeps 8
·
Mountains · Dishwasher · Wifi ·
From
$208/nightProperty
House · 4 Beds · 2 baths
Amenities
Mountains
Dishwasher
Wifi
Microwave
Assigned Parking
Fireplace
Tv
Oven
Other spaces
Kitchen
Budget-Friendly Vacation Rentals in Chester, VT
Traveling on a budget? We've got you covered. Find a great deal on a vacation rental in Chester starting at $110. Use the price filter at the top of the page to search for more specific prices.
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
10
Excellent
·
Chester
·
2 br
·
Sleeps 4
·
Kitchen · Fireplace · Oven ·
From
$110/nightProperty
Apartment · 2 Beds · 1 bath
Amenities
Fireplace
Oven
Wifi
Furnished
Other spaces
Kitchen
Historic Chester House 10-30 Mins to 5 Mountains!
6
Good
·
Chester
·
4 br
·
Sleeps 7
·
Fireplace · Tv · Kitchen ·
From
$140/nightProperty
House · 4 Beds · 2 baths
Amenities
Fireplace
Tv
Oven
Wifi
Assigned Parking
Central Heat
Microwave
Other spaces
Kitchen, Garden
Vermont Hillside Cottage w/Great View - Pet Friendly
10
Excellent
·
Chester
·
2 br
·
Sleeps 6
·
Waterfront · Oven · In Unit Laundry ·
From
$145/nightProperty
House · 2 Beds · 1 bath
Amenities
Waterfront
Oven
In Unit Laundry
Mountains
Wheelchair Accessible
Fireplace
Air Conditioning
Furnished
Other spaces
Kitchen
Historic Chester House 10-30 Mins to 5 Mountains!
No rating
·
Chester
·
4 br
·
Sleeps 7
·
Kitchen · Wifi · Free Parking ·
From
$171/nightProperty
Apartment · 4 Beds · 2 baths
Amenities
Wifi
Free Parking
Furnished
Fireplace
Oven
Other spaces
Kitchen
Price drop
Chester Home w/ Views ~10 Mi to Okemo Mtn Resort!
9.9
Excellent
·
Chester
·
4 br
·
Sleeps 9
·
Fireplace · Kitchen · Garden ·
From
$175/nightProperty
House · 4 Beds · 3 baths
Amenities
Fireplace
Wifi
Tv
Toiletries
Central Heat
Mountains
Walk In Closets
Ceiling Fan
Other spaces
Kitchen, Garden, Workspace
Price drop
Historic Chester House 10-30 Mins to 5 Mountains!
10
Excellent
·
Chester
·
4 br
·
Sleeps 7
·
On Site Laundry · Kitchen · Fireplace ·
From
$181/nightProperty
House · 4 Beds · 2 baths
Amenities
On Site Laundry
Fireplace
Wifi
Oven
Ski In Ski Out
Furnished
Other spaces
Kitchen
Vacation Rentals With A Pool in Chester, VT
Want to relax by the pool? Book one of these Chester vacation rentals with a pool.
Price drop
Luxury stone farmhouse - lots of room! Perfect for long ski weekends -Sleeps 16
10
Excellent
·
Chester
·
7 br
·
Sleeps 16
·
Swimming Pool · Pool · Oven ·
From
$606/nightProperty
House · 7 Beds · 3 baths
Amenities
Swimming Pool
Pool
Oven
Ski In Ski Out
Fireplace
Air Conditioning
Furnished
Dishwasher
Other spaces
Kitchen, Workspace
Price drop
SPACIOUS VICTORIAN FARMHOUSE- 20 MIN TO OKEMO
10
Excellent
·
Chester
·
4 br
·
Sleeps 8
·
Ski In Ski Out · Wifi · On Site Laundry ·
From
$240/nightProperty
House · 4 Beds · 3 baths
Amenities
Ski In Ski Out
Wifi
On Site Laundry
Furnished
Air Conditioning
Swimming Pool
Storage
Dishwasher
Other spaces
Kitchen, Workspace
1868 CARRIAGE HOUSE-QUAINT + COZY -PERFECT ESCAPE-20 MIN TO OKEMO!
10
Excellent
·
Chester
·
3 br
·
Sleeps 6
·
Fitness Center · On Site Laundry · Furnished ·
From
$199/nightProperty
Apartment · 3 Beds · 1 bath
Amenities
Fitness Center
On Site Laundry
Furnished
Hot Tub
Air Conditioning
Wifi
Swimming Pool
Ski In Ski Out
Other spaces
Kitchen, Workspace
Family-Friendly Vacation Rentals in Chester, VT
Heading to Chester for your next family vacation? Check out these family-friendly vacation rentals, which have more bedrooms and more space for you and your loved ones. Use the filters at the top of the page to narrow your search and find what you need.
This tiny house is a 1 bedroom(s), 1 bathrooms, located in Chester, VT.
10
Excellent
·
Chester
·
1 br
·
Sleeps 2
·
Oven · On Site Laundry · Outdoor Space ·
From
$225/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
Oven
On Site Laundry
Furnished
Fireplace
Wifi
Waterfront
Residents Lounge
Air Conditioning
Other spaces
Kitchen
This tiny house is a 1 bedroom(s), 1 bathrooms, located in Chester, VT.
No rating
·
Chester
·
1 br
·
Sleeps 2
·
Residents Lounge · Outdoor Space · Oven ·
From
$227/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
Residents Lounge
Oven
Fireplace
Air Conditioning
On Site Laundry
Furnished
Wifi
Other spaces
Kitchen
Whimsical Room & Private Bathroom in Historic Inn
10
Excellent
·
Chester
·
1 br
·
Sleeps 3
·
In Unit Laundry · Furnished · Fireplace ·
From
$245/nightProperty
House · 1 Bed · 1 bath
Amenities
In Unit Laundry
Furnished
Fireplace
Wifi
Air Conditioning
Other spaces
Workspace, Kitchen
Expand your search criteria to see more vacation rentals near Chester.
Updated: September 26, 2023
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