Vacation Rentals in Chester, VT
PRICE PER NIGHT
ACCOMMODATION TYPES
| Handmade 4 Bed Log Cabin | 5 Min From Skiing |
9.7
Excellent
·
Chester
·
3 br
·
Sleeps 6
·
Workspace · Mountains · Fireplace ·
From
$225/nightProperty
House · 3 Beds · 2 baths
Amenities
Mountains
Fireplace
In Unit Laundry
Furnished
Wifi
Oven
Other spaces
Workspace, Kitchen
Chester Home w/ Views ~10 Mi to Okemo Mtn Resort!
9.9
Excellent
·
Chester
·
4 br
·
Sleeps 9
·
Walk In Closets · Cable · Toiletries ·
From
$175/nightProperty
House · 4 Beds · 3 baths
Amenities
Walk In Closets
Cable
Toiletries
Assigned Parking
Ceiling Fan
Central Heat
Tv
Microwave
Other spaces
Garden, Kitchen
Charming Farmhouse in Chester
8.5
Very good
·
Chester
·
4 br
·
Sleeps 6
·
Dishwasher · Fireplace · In Unit Laundry ·
From
$299/nightProperty
House · 4 Beds · 2 baths
Amenities
Dishwasher
Fireplace
In Unit Laundry
Furnished
Wifi
Oven
Other spaces
Kitchen
Chester Home w/ Views ~10 Mi to Okemo Mtn Resort!
9.9
Excellent
·
Chester
·
4 br
·
Sleeps 9
·
High Ceilings · Ceiling Fan · Ski In Ski Out ·
From
$206/nightProperty
House · 4 Beds · 3 baths
Amenities
High Ceilings
Ceiling Fan
Ski In Ski Out
Dishwasher
Fireplace
In Unit Laundry
Furnished
Wifi
Other spaces
Kitchen
Gorgeous Log Home With Mountain Views with Hot Tub
10
Excellent
·
Chester
·
5 br
·
Sleeps 12
·
On Site Laundry · Hot Tub · Dishwasher ·
From
$550/nightProperty
House · 5 Beds · 3 baths
Amenities
On Site Laundry
Hot Tub
Dishwasher
Fireplace
In Unit Laundry
Furnished
Wifi
Oven
Other spaces
Kitchen
NEW! Andover Cabin Retreat w/ Hot Tub & Fireplace!
10
Excellent
·
Chester
·
3 br
·
Sleeps 8
·
Cable · Toiletries · Assigned Parking ·
From
$190/nightProperty
House · 3 Beds · 1 bath
Amenities
Cable
Toiletries
Assigned Parking
Central Heat
Tv
Microwave
Free Parking
Mountains
Other spaces
Garden, Balcony, Kitchen
Lovely home with hot tub, firepit, patio, full kitchen, & washer/dryer
6
Good
·
Chester
·
4 br
·
Sleeps 8
·
Hot Tub · Dishwasher · In Unit Laundry ·
From
$124/nightProperty
House · 4 Beds · 3 baths
Amenities
Hot Tub
Dishwasher
In Unit Laundry
Furnished
Oven
Swimming Pool
Other spaces
Kitchen
15 Minutes to ski Okemo - Mountain views from this magical log home on 6 acres
10
Excellent
·
Chester
·
4 br
·
Sleeps 8
·
Mountains · Air Conditioning · Dishwasher ·
From
$410/nightProperty
House · 4 Beds · 3 baths
Amenities
Mountains
Air Conditioning
Dishwasher
Fireplace
In Unit Laundry
Furnished
Wifi
Oven
Other spaces
Kitchen
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Historic Home in Vermont
10
Excellent
·
Chester
·
2 br
·
Sleeps 6
·
Workspace · Air Conditioning · Dishwasher ·
From
$223/nightProperty
House · 2 Beds · 2 baths
Amenities
Air Conditioning
Dishwasher
Fireplace
In Unit Laundry
Furnished
Wifi
Oven
Other spaces
Workspace, Kitchen
Log cabin on 25 acres bordering state forest with trails nearby.
10
Excellent
·
Chester
·
3 br
·
Sleeps 8
·
Ceiling Fan · On Site Laundry · Outdoor Space ·
From
$328/nightProperty
Apartment · 3 Beds · 2 baths
Amenities
Ceiling Fan
On Site Laundry
Dishwasher
In Unit Laundry
Furnished
Wifi
Oven
Garage Parking
Other spaces
Kitchen
Historic Chester House 10-30 Mins to 5 Mountains!
6.7
Good
·
Chester
·
4 br
·
Sleeps 7
·
Ski In Ski Out · Fireplace · In Unit Laundry ·
From
$270/nightProperty
House · 4 Beds · 2 baths
Amenities
Ski In Ski Out
Fireplace
In Unit Laundry
Furnished
Wifi
Oven
Other spaces
Kitchen
Thistle House at Camp Wildwood
10
Excellent
·
Chester
·
1 br
·
Sleeps 2
·
Balcony · Air Conditioning · Fireplace ·
From
$215/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
Air Conditioning
Fireplace
In Unit Laundry
Furnished
Wifi
Oven
Residents Lounge
Other spaces
Balcony, Kitchen
Stone Ridge Farmhouse: secluded mountain retreat
10
Excellent
·
Chester
·
3 br
·
Sleeps 6
·
On Site Laundry · Balcony · Workspace ·
From
$293/nightProperty
House · 3 Beds · 2 baths
Amenities
On Site Laundry
Air Conditioning
Dishwasher
Fireplace
In Unit Laundry
Furnished
Wifi
Oven
Other spaces
Balcony, Workspace, Kitchen
Chester Farmhouse on 100 Acres, 15 Min to Okemo!
10
Excellent
·
Chester
·
5 br
·
Sleeps 12
·
Ceiling Fan · Central Heat · Tv ·
From
$208/nightProperty
House · 5 Beds · 2 baths
Amenities
Ceiling Fan
Central Heat
Tv
Microwave
Free Parking
Mountains
Dishwasher
Fireplace
Other spaces
Kitchen
Chester Farmhouse on 100 Acres, 15 Min to Okemo!
No reviews
·
Chester
·
5 br
·
Sleeps 12
·
Free Parking · Outdoor Space · Dishwasher ·
From
$352/nightProperty
Apartment · 5 Beds · 2 baths
Amenities
Free Parking
Dishwasher
Fireplace
In Unit Laundry
Furnished
Wifi
Oven
Other spaces
Kitchen
Historic Farmhouse in Andover Vermont
10
Excellent
·
Chester
·
11 br
·
Sleeps 24
·
Hot Tub · Workspace · Mountains ·
From
$1,400/nightProperty
House · 11 Beds · 6 baths
Amenities
Hot Tub
Mountains
Dishwasher
Fireplace
In Unit Laundry
Furnished
Wifi
Oven
Other spaces
Workspace, Kitchen
Private Chester Home w/ Deck, Mins to Skiing!
10
Excellent
·
Chester
·
3 br
·
Sleeps 8
·
Garden · Ceiling Fan · Tv ·
From
$300/nightProperty
House · 3 Beds · 3 baths
Amenities
Ceiling Fan
Tv
Microwave
Free Parking
Mountains
Dishwasher
Fireplace
Wifi
Other spaces
Garden, Kitchen
Contemporary Mountain Top House
10
Excellent
·
Chester
·
4 br
·
Sleeps 8
·
Ev Charging · Balcony · Ski In Ski Out ·
From
$424/nightProperty
House · 4 Beds · 3 baths
Amenities
Ev Charging
Ski In Ski Out
Mountains
Air Conditioning
Dishwasher
Fireplace
In Unit Laundry
Furnished
Other spaces
Balcony, Workspace, Kitchen
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
9.7
Excellent
·
Chester
·
2 br
·
Sleeps 4
·
Fireplace · Furnished · Wifi ·
From
$107/nightProperty
Apartment · 2 Beds · 1 bath
Amenities
Fireplace
Furnished
Wifi
Oven
Other spaces
Kitchen
Cheerful residential home with lots of space
10
Excellent
·
Chester
·
3 br
·
Sleeps 8
·
Air Conditioning · Dishwasher · Fireplace ·
From
$223/nightProperty
House · 3 Beds · 3 baths
Amenities
Air Conditioning
Dishwasher
Fireplace
In Unit Laundry
Furnished
Wifi
Oven
Swimming Pool
Other spaces
Kitchen
Little cabin On The Ridge
9.8
Excellent
·
Chester
·
3 br
·
Sleeps 6
·
Ski In Ski Out · Mountains · Air Conditioning ·
From
$223/nightProperty
Apartment · 3 Beds · 1 bath
Amenities
Ski In Ski Out
Mountains
Air Conditioning
Dishwasher
In Unit Laundry
Furnished
Wifi
Oven
Other spaces
Kitchen
Sage House at Camp Wildwood Vermont
No reviews
·
Chester
·
1 br
·
Sleeps 2
·
Air Conditioning · Fireplace · In Unit Laundry ·
From
$233/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
Air Conditioning
Fireplace
In Unit Laundry
Furnished
Wifi
Oven
Residents Lounge
Other spaces
Kitchen
Elegantly Appointed Ski Home in Charming Village of Chester, VT
10
Excellent
·
Chester
·
3 br
·
Sleeps 6
·
Hot Tub · Mountains · Air Conditioning ·
From
$310/nightProperty
House · 3 Beds · 1 bath
Amenities
Hot Tub
Mountains
Air Conditioning
Furnished
Wifi
Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing
8.3
Very good
·
Chester
·
3 br
·
Sleeps 8
·
Waterfront · On Site Laundry · Balcony ·
From
$119/nightProperty
House · 3 Beds · 3 baths
Amenities
Waterfront
On Site Laundry
Hot Tub
Ski In Ski Out
Mountains
Dishwasher
In Unit Laundry
Furnished
Other spaces
Balcony, Kitchen
Whimsical Room & Private Bathroom in Historic Inn
10
Excellent
·
Chester
·
1 br
·
Sleeps 3
·
Workspace · Air Conditioning · Fireplace ·
From
$165/nightProperty
House · 1 Bed · 1 bath
Amenities
Air Conditioning
Fireplace
In Unit Laundry
Furnished
Wifi
Other spaces
Workspace, Kitchen
Okemo and Magic Mountain Family Getaway
10
Excellent
·
Chester
·
4 br
·
Sleeps 14
·
On Site Laundry · Workspace · Outdoor Space ·
From
$465/nightProperty
House · 4 Beds · 4 baths
Amenities
On Site Laundry
Mountains
Air Conditioning
Dishwasher
Fireplace
In Unit Laundry
Furnished
Wifi
Other spaces
Workspace, Kitchen
Log cabin in the Smokeshire Valley area of Chester.
10
Excellent
·
Chester
·
3 br
·
Sleeps 5
·
Workspace · Outdoor Space · Mountains ·
From
$221/nightProperty
Apartment · 3 Beds · 2 baths
Amenities
Mountains
Dishwasher
In Unit Laundry
Furnished
Wifi
Oven
Other spaces
Workspace, Kitchen
Chester Farmhouse on 100 Acres, 15 Min to Okemo!
9.6
Excellent
·
Chester
·
5 br
·
Sleeps 12
·
Ski In Ski Out · Outdoor Space · Air Conditioning ·
From
$237/nightProperty
House · 5 Beds · 2 baths
Amenities
Ski In Ski Out
Air Conditioning
Dishwasher
Fireplace
In Unit Laundry
Furnished
Oven
Residents Lounge
Other spaces
Kitchen
Perfect for School Break or ski weekends. Luxury stone farmhouse - lots of room
10
Excellent
·
Chester
·
7 br
·
Sleeps 16
·
Pool · Ski In Ski Out · Workspace ·
From
$667/nightProperty
House · 7 Beds · 3 baths
Amenities
Pool
Ski In Ski Out
Air Conditioning
Dishwasher
Fireplace
In Unit Laundry
Furnished
Wifi
Other spaces
Workspace, Kitchen
Ski Okemo - Spacious, Family Friendly Chalet
10
Excellent
·
Chester
·
4 br
·
Sleeps 10
·
Outdoor Space · Mountains · Dishwasher ·
From
$355/nightProperty
Apartment · 4 Beds · 2 baths
Amenities
Mountains
Dishwasher
Fireplace
In Unit Laundry
Furnished
Wifi
Oven
Other spaces
Kitchen
"Everything VT" Getaway Centrally Located: Ski, Shop, Golf, Hike, Relax
9.8
Excellent
·
Chester
·
2 br
·
Sleeps 6
·
Balcony · Workspace · Outdoor Space ·
From
$273/nightProperty
House · 2 Beds · 2 baths
Amenities
Mountains
Air Conditioning
Dishwasher
Fireplace
In Unit Laundry
Furnished
Wifi
Oven
Other spaces
Balcony, Workspace, Kitchen
1868 CARRIAGE HOUSE-QUAINT + COZY -PERFECT ESCAPE-20 MIN TO OKEMO!
9.4
Excellent
·
Chester
·
3 br
·
Sleeps 6
·
Pool · On Site Laundry · Hot Tub ·
From
$195/nightProperty
Apartment · 3 Beds · 1 bath
Amenities
Pool
On Site Laundry
Hot Tub
Ski In Ski Out
Air Conditioning
In Unit Laundry
Furnished
Wifi
Other spaces
Workspace, Kitchen
Amazing Custom Home on 40+ Acres
No reviews
·
Chester
·
5 br
·
Sleeps 12
·
Dishwasher · In Unit Laundry · Furnished ·
From
$500/nightProperty
House · 5 Beds · 6 baths
Amenities
Dishwasher
In Unit Laundry
Furnished
Oven
Fitness Center
Other spaces
Kitchen
Hawks Mountain Farm, full apartment on a working farm.
9.5
Excellent
·
Chester
·
1 br
·
Sleeps 2
·
Workspace · Mountains · Air Conditioning ·
From
$128/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
Mountains
Air Conditioning
Dishwasher
In Unit Laundry
Furnished
Wifi
Oven
Other spaces
Workspace, Kitchen
SPACIOUS VICTORIAN FARMHOUSE- 20 MIN TO OKEMO
9.8
Excellent
·
Chester
·
4 br
·
Sleeps 8
·
Hardwood Floor · Pool · Hot Tub ·
From
$270/nightProperty
House · 4 Beds · 3 baths
Amenities
Hardwood Floor
Pool
Hot Tub
Ski In Ski Out
Air Conditioning
Dishwasher
Fireplace
In Unit Laundry
Other spaces
Workspace, Kitchen
NEW! Modern Chester Escape
10
Excellent
·
Chester
·
3 br
·
Sleeps 9
·
Walk In Closets · Toiletries · Assigned Parking ·
From
$575/nightProperty
House · 3 Beds · 2 baths
Amenities
Walk In Closets
Toiletries
Assigned Parking
Central Heat
Tv
Microwave
Free Parking
Dishwasher
Other spaces
Garden, Kitchen
Historic Chester House 10-30 Mins to 5 Mountains!
8
Very good
·
Chester
·
4 br
·
Sleeps 7
·
Assigned Parking · Garden · Central Heat ·
From
$140/nightProperty
House · 4 Beds · 2 baths
Amenities
Assigned Parking
Central Heat
Tv
Microwave
Free Parking
Fireplace
Wifi
Oven
Other spaces
Garden, Kitchen
Picturesque VT Farmhouse on 12 Acres, near 4 major ski areas and VSF Horse Show
10
Excellent
·
Chester
·
3 br
·
Sleeps 9
·
On Site Laundry · Workspace · Mountains ·
From
$506/nightProperty
House · 3 Beds · 2 baths
Amenities
On Site Laundry
Mountains
Air Conditioning
Dishwasher
Fireplace
In Unit Laundry
Furnished
Wifi
Other spaces
Workspace, Kitchen
Vermont Country Home
10
Excellent
·
Chester
·
4 br
·
Sleeps 8
·
Hot Tub · Outdoor Space · Mountains ·
From
$275/nightProperty
House · 4 Beds · 2 baths
Amenities
Hot Tub
Mountains
Dishwasher
In Unit Laundry
Furnished
Wifi
Oven
Garage Parking
Other spaces
Kitchen
Private Chester Home with Deck, Mins to Skiing!
No reviews
·
Chester
·
3 br
·
Sleeps 8
·
Free Parking · Dishwasher · Fireplace ·
From
$353/nightProperty
Apartment · 3 Beds · 3 baths
Amenities
Free Parking
Dishwasher
Fireplace
In Unit Laundry
Furnished
Wifi
Oven
Other spaces
Kitchen
Work, Ski, Relax - Big Restored 1860s Farmhouse
10
Excellent
·
Chester
·
5 br
·
Sleeps 12
·
Workspace · Dishwasher · In Unit Laundry ·
From
$933/nightProperty
House · 5 Beds · 4 baths
Amenities
Dishwasher
In Unit Laundry
Furnished
Wifi
Oven
Fitness Center
Other spaces
Workspace, Kitchen
UNIQUE/HISTORIC STAY IN AN 1874 ERA SCHOOLHOUSE!!
10
Excellent
·
Chester
·
4 br
·
Sleeps 10
·
Balcony · Fireplace · In Unit Laundry ·
From
$709/nightProperty
House · 4 Beds · 2 baths
Amenities
Fireplace
In Unit Laundry
Furnished
Wifi
Oven
Swimming Pool
Other spaces
Balcony, Kitchen
1830's Recently Renovated Rustic Farmhouse, Windham Vermont
10
Excellent
·
Chester
·
3 br
·
Sleeps 8
·
Dishwasher · Fireplace · In Unit Laundry ·
From
$260/nightProperty
House · 3 Beds · 3 baths
Amenities
Dishwasher
Fireplace
In Unit Laundry
Furnished
Wifi
Oven
Other spaces
Kitchen
Private Chester Home w/ Deck, Mins to Skiing!
10
Excellent
·
Chester
·
3 br
·
Sleeps 8
·
High Ceilings · Ceiling Fan · Dishwasher ·
From
$325/nightProperty
House · 3 Beds · 3 baths
Amenities
High Ceilings
Ceiling Fan
Dishwasher
Fireplace
In Unit Laundry
Furnished
Wifi
Oven
Other spaces
Kitchen
Spacious 1-level ranch, mtn. views, htd. flrs , fire pit, 10 mi. to Okemo!
9.9
Excellent
·
Chester
·
3 br
·
Sleeps 8
·
Workspace · Outdoor Space · Air Conditioning ·
From
$467/nightProperty
House · 3 Beds · 2 baths
Amenities
Air Conditioning
Dishwasher
Fireplace
In Unit Laundry
Furnished
Wifi
Oven
Garage Parking
Other spaces
Workspace, Kitchen
Historic VT Grist Mill on the Williams River
10
Excellent
·
Chester
·
6 br
·
Sleeps 12
·
Balcony · Workspace · Outdoor Space ·
From
$940/nightProperty
House · 6 Beds · 3 baths
Amenities
Air Conditioning
Dishwasher
Fireplace
In Unit Laundry
Furnished
Wifi
Oven
Other spaces
Balcony, Workspace, Kitchen
Indoor Hot Tub Room/10 Miles to Okemo
No reviews
·
Chester
·
5 br
·
Sleeps 8
·
Fitness Center · Deck · Outdoor Space ·
From
$705/nightProperty
House · 5 Beds · 5 baths
Amenities
Fitness Center
Air Conditioning
Dishwasher
Fireplace
In Unit Laundry
Furnished
Wifi
Oven
Other spaces
Deck, Kitchen
NEW! Modern Chester Escape
10
Excellent
·
Chester
·
3 br
·
Sleeps 9
·
Central Heat · On Site Laundry · Dishwasher ·
From
$621/nightProperty
House · 3 Beds · 2 baths
Amenities
Central Heat
On Site Laundry
Dishwasher
Fireplace
In Unit Laundry
Furnished
Wifi
Oven
Other spaces
Kitchen
Historic Chester House 10-30 Mins to 5 Mountains!
2
Poor
·
Chester
·
4 br
·
Sleeps 7
·
Free Parking · Fireplace · Furnished ·
From
$171/nightProperty
Apartment · 4 Beds · 2 baths
Amenities
Free Parking
Fireplace
Furnished
Wifi
Oven
Other spaces
Kitchen
Vermont Hillside Cottage w/Great View - Pet Friendly
9.9
Excellent
·
Chester
·
2 br
·
Sleeps 6
·
Outdoor Space · Air Conditioning · Fireplace ·
From
$132/nightProperty
House · 2 Beds · 1 bath
Amenities
Air Conditioning
Fireplace
In Unit Laundry
Furnished
Wifi
Oven
Wheelchair Accessible
Other spaces
Kitchen
Showing 1 - 50 of 56 results
Updated: March 25, 2023
Learn about vacation rentals in
Chester
Explore 56 vacation rentals near Chester, Vermont. Whether you’re a tourist or on a staycation, there’s plenty of things to do and restaurants to try around the city. If you’re looking to take a trip to Chester, you can see photos of Chester vacation rentals, view amenities and features, browse by specific property types, and more. Use our interactive map to find Chester vacation rentals in specific areas. Whether you’re looking for a Chester staycation, weekend getaway, or a long vacation, we’ve got you covered. Use the date filters at the top to select your travel dates and view availability. The lowest vacation rental price in Chester is $107 per night and the highest price is $1,400 per night.
3 of the vacation rentals near Chester are
apartments or condos. The average bathroom count for this property type is 1. The median price for these vacation
units is $215 per night. There are
currently 2 vacation units under this
price. 46 of the vacation rentals near Chester are houses.
The average bathroom count for a vacation house near Chester is
3. The average price for vacation houses near Chester is $390 per night. There are 28 vacation homes under this price. The most common
amenities for vacation rentals near Chester are: furnished, kitchen, and oven. To find vacation properties that might be a good option for large groups or families, use our filters for bedroom count, bathroom count and more.
1 bed rentals
5 available
2 bed rentals
4 available
3 bed rentals
20 available
4+ bed rentals
27 available
Getting around Chester
Walking
3/10
Fewer daily needs are within walking distance (unless you’re up for a challenge).
Car
10/10
Commuting is easy with multiple accessible routes and plenty of parking.
Points of interest in Chester
Groceries
3/10
At least one grocery store within a 30-minute walk
Shopping
2/10
Few or no shops within walking distance
Cafes
3/10
Few or no cafés within walking distance
Restaurants
4/10
Some restaurants within walking distance
Nightlife
3/10
Few or no bars within walking distance
Vacation Rentals in Chester, VT FAQ
How many vacation rentals in Chester are available?
There are currently 56 vacation rentals in Chester available. Our vacation rentals in Chester include nightly rentals, weekend rentals, weekly rentals, and monthly rentals.
Are there any pet friendly vacation rentals in Chester?
Yes, right now there are 24 pet friendly vacation rentals in Chester. A pet friendly vacation rental in Chester means a rental home that is dog friendly or cat friendly. Some pet friendly homes may accommodate other types of pets, as well. Contact the listing agent for any pet related inquiries.
Are there any vacation rentals in Chester with a pool?
Yes there are vacation rentals with a pool available in Chester, VT. View more detailed vacation spots on Vacations by Zumper.
Are there any vacation rentals in Chester with internet access?
As of March 25, 2023, there are vacation rentals with internet access available in Chester, Vermont. Check out more enjoyable destinations on Vacations by Zumper.
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