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Holiday homes in Chester

Enjoy your stay and find the best Holiday homes in Chester at affordable prices

Searching for a holiday home in Chester (Vermont)? Explore a great selection of vacation homes in Chester to find the one that best fits to your needs, starting from $92.67 per night. Holiday homes offer a relaxing escape, providing a cozy retreat for vacationers seeking a home away from home.

Holiday-homes in Chester and region (30 miles)
Historic Chester House 10-30 Mins to 5 Mountains! in Chester, USA

Historic Chester House 10-30 Mins to 5 M...

Holiday home in Chester, Vermont
Historic Chester House 10-30 Mins to 5 Mountains! is set in Chester, 41 km from Mount Equinox, 26 km from Dorsey Park, as well as 27 km from Bellows F...
  • Parking
  • Pets allowed
  • Internet facilities
  • Hairdryer
  • Refrigerator

Very poor 1 Reviews 2.0

from $171.00 Show details »

Chester Home with Views about 10 Mi to Okemo Mtn Resort! in Chester, USA

Chester Home with Views about 10 Mi to O...

Holiday home in Chester, Vermont
Set 45 km from Mount Tom, 15 km from Dorsey Park and 30 km from Bellows Falls Amtrak Station, Chester Home with Views about 10 Mi to Okemo Mtn Resort!...
  • Parking
  • Internet facilities
  • Hairdryer
  • Iron
  • Refrigerator

Exceptional 1 Reviews 10.0

from $356.33 Show details »

Private Chester Home with Deck, Mins to Skiing! in Chester, USA

Private Chester Home with Deck, Mins to...

Holiday home in Chester, Vermont
Located in Chester, 48 km from Stratton Mountain and 45 km from Mount Tom, Private Chester Home with Deck, Mins to Skiing! provides accommodation with...
  • Parking

no reviews

from $358.43 Show details »

Chester Farmhouse on 100 Acres, 15 Min to Okemo! in Chester, USA

Chester Farmhouse on 100 Acres, 15 Min t...

Holiday home in Chester, Vermont
Located in Chester, 49 km from Gifford Woods State Park, 13 km from Dorsey Park and 34 km from Bellows Falls Amtrak Station, Chester Farmhouse on 100 ...
  • Parking
  • Pets allowed

no reviews

from $334.67 Show details »

Log Cabin with a View in Andover, USA

Log Cabin with a View

Holiday home in Andover near Chester, Vermont
Boasting mountain views, Log Cabin with a View provides accommodation with a garden and a balcony, around 31 km from Stratton Mountain.
  • Parking

Fabulous 1 Reviews 9.0

from $302.87 Show details »

Sherman Log House in Ludlow, USA

Sherman Log House

Holiday home in Ludlow near Chester, Vermont
Sherman Log House is situated in Ludlow, 7 km from Jackson Gore Ski Area.
  • Parking

no reviews

from $516.44 Show details »

Andover Cabin Retreat with Hot Tub and Fireplace! in Andover, USA

Andover Cabin Retreat with Hot Tub and F...

Holiday home in Andover near Chester, Vermont
Located in Andover, 40 km from Stratton Mountain, 49 km from Killington Mountain and 46 km from Gifford Woods State Park, Andover Cabin Retreat with H...
  • Parking

no reviews

from $348.33 Show details »

Vermont Mountain Farmhouse in Ludlow, USA

Vermont Mountain Farmhouse

Holiday home in Ludlow near Chester, Vermont
Vermont Mountain Farmhouse is set in Ludlow, 48 km from Stratton Mountain and 43 km from Gifford Woods State Park, in an area where skiing can be enjo...
  • Parking

no reviews

from $220.27 Show details »

Londonderry Chalet with Deck, Fire Pit and Views! in Londonderry, USA

Londonderry Chalet with Deck, Fire Pit a...

Holiday home in Londonderry near Chester, Vermont
Situated 33 km from Mount Equinox, 34 km from Dorsey Park and 36 km from Emerald Lake State Park, Londonderry Chalet with Deck, Fire Pit and Views! fe...
  • Parking

no reviews

from $368.33 Show details »

Magic Birch Lodge in Windham, USA

Magic Birch Lodge

Holiday home in Windham near Chester, Vermont
Located in Windham, 28 km from Stratton Mountain and 34 km from Mount Equinox, Magic Birch Lodge provides air-conditioned accommodation with a patio a...
  • Parking

Very good 3 Reviews 8.0

from $190.85 Show details »

Vermont Ski Chalet about 5 Mi to Magic Mountain in Windham, USA

Vermont Ski Chalet about 5 Mi to Magic M...

Holiday home in Windham near Chester, Vermont
Set 34 km from Mount Equinox, 35 km from Dorsey Park and 37 km from Emerald Lake State Park, Vermont Ski Chalet about 5 Mi to Magic Mountain offers ac...
  • Parking

no reviews

from $472.33 Show details »

Vermont Farm in Proctorsville, USA

Vermont Farm

Holiday home in Proctorsville near Chester, Vermont
Offering river views, a garden and free WiFi, Vermont Farm is located in Proctorsville, 47 km from Killington Mountain and 48 km from Stratton Mountai...
  • Parking

Okay 7 Reviews 6.0

from $104.00 Show details »

Little Yellow Bungalow in Cavendish, USA

Little Yellow Bungalow

Holiday home in Cavendish near Chester, Vermont
Located in Cavendish, 46 km from Killington Mountain and 48 km from Stratton Mountain, Little Yellow Bungalow provides accommodation with amenities su...
  • Parking
  • Pets allowed

Bad 1 Reviews 1.0

from $92.67 Show details »

Depot Street Condo in Proctorsville, USA

Depot Street Condo

Holiday home in Proctorsville near Chester, Vermont
Situated in Proctorsville, 46 km from Killington Mountain and 48 km from Stratton Mountain, Depot Condo & Joes Place provides accommodation with ameni...
  • Parking
  • Tea/Coffee maker
  • TV
  • Kitchenette
  • Refrigerator

no reviews

from $231.33 Show details »

Mountains View Cabin in Ludlow, USA

Mountains View Cabin

Holiday home in Ludlow near Chester, Vermont
Mountains View Cabin offers accommodation in Ludlow.
  • Parking
  • Pets allowed
  • Electric vehicle charging station
  • Tea/Coffee maker
  • Shower

Fabulous 3 Reviews 8.7

from $366.68 Show details »

Andover Retreat in Ludlow, USA

Andover Retreat

Holiday home in Ludlow near Chester, Vermont
Featuring mountain views, Andover Retreat is a holiday home around 6 km from Jackson Gore Ski Area.
  • Parking
  • Tea/Coffee maker
  • Shower
  • Bath
  • TV

Exceptional 1 Reviews 10.0

from $427.33 Show details »

Bear Hill Views in Ludlow, USA

Bear Hill Views

Holiday home in Ludlow near Chester, Vermont
Situated in Ludlow, Bear Hill Views is 5 km from Jackson Gore Ski Area.
  • Parking
  • Tea/Coffee maker
  • Shower
  • Bath
  • TV

Fabulous 9 Reviews 8.7

from $277.78 Show details »

Free in VT in Cavendish, USA

Free in VT

Holiday home in Cavendish near Chester, Vermont
Free in VT is set in Cavendish, 47 km from Gifford Woods State Park and 48 km from Pico Peak, in an area where skiing can be enjoyed.
  • Parking

no reviews

from $469.81 Show details »

Vibrant Views in Ludlow, USA

Vibrant Views

Holiday home in Ludlow near Chester, Vermont
Set in Ludlow in the Vermont region, Vibrant Views has a patio.
  • Parking

no reviews

from $442.55 Show details »

Comfy Ludlow Apartment about 3 Mi to Okemo Resort in Ludlow, USA

Comfy Ludlow Apartment about 3 Mi to Oke...

Holiday home in Ludlow near Chester, Vermont
Comfy Ludlow Apartment about 3 Mi to Okemo Resort is set in Ludlow, 45 km from Stratton Mountain, 40 km from Gifford Woods State Park, and 41 km from ...
  • Parking
  • Pets allowed

no reviews

from $446.00 Show details »

Town Farm Retreat in Ludlow, USA

Town Farm Retreat

Holiday home in Ludlow near Chester, Vermont
Set in Ludlow, 43 km from Killington Mountain, Town Farm Retreat offers accommodation with a garden, free WiFi and an ATM.
  • Parking

no reviews

from $505.32 Show details »

South Londonderry Home, Walk to Magic Mtn Ski Area in Londonderry, USA

South Londonderry Home, Walk to Magic Mt...

Holiday home in Londonderry near Chester, Vermont
Located 28 km from Mount Equinox, 29 km from Dorsey Park and 31 km from Emerald Lake State Park, South Londonderry Home, Walk to Magic Mtn Ski Area pr...
  • Parking

no reviews

from $265.00 Show details »

Special Serenity in Londonderry, USA

Special Serenity

Holiday home in Londonderry near Chester, Vermont
Special Serenity is situated in Londonderry, 29 km from Mount Equinox, 22 km from Dorsey Park, as well as 32 km from Emerald Lake State Park.
  • Parking
  • Pets allowed

Passable 2 Reviews 5.0

from $456.77 Show details »

Ludlow Home - Under 3 Miles to Okemo Mtn Resort! in Ludlow, USA

Ludlow Home - Under 3 Miles to Okemo Mtn...

Holiday home in Ludlow near Chester, Vermont
Situated 45 km from Stratton Mountain, 40 km from Gifford Woods State Park and 41 km from Pico Peak, Ludlow Home - Under 3 Miles to Okemo Mtn Resort! ...
  • Parking
  • Hairdryer
  • Iron
  • Refrigerator
  • DVD player

no reviews

from $336.00 Show details »

South Hill Lodge in Ludlow, USA

South Hill Lodge

Holiday home in Ludlow near Chester, Vermont
Offering mountain views, South Hill Lodge is an accommodation set in Ludlow, 43 km from Stratton Mountain and 39 km from Gifford Woods State Park.
  • Parking
  • Tea/Coffee maker
  • Shower
  • Bath
  • TV

no reviews

from $172.00 Show details »

Number of Holiday homes in Chester 147
Number of guest ratings 481
Average price per night $435.30
Lowest price per night $92.67
Highest price per night $1.863.00

Most popular Holiday-homes in Chester

The most popular Holiday-homes in Chester based on average guest rating (Top 10).

Cheapest Holiday-homes in Chester

The cheapest Holiday-homes in Chester based on room rate per night (Top 10).

Most booked Holiday-homes in Chester

The most booked Holiday-homes in Chester based on popularity with guests (Top 10).

Holiday homes in Chester (Vermont), comfortable and familiar

Staying in a holiday or vacation home in Chester can be a great alternative to a hotel or resort. They can range from small cottages to luxurious villas, and are often located in popular tourist destinations such as beaches or mountains. One of the main benefits is the privacy and flexibility that comes with having your own space. Unlike a hotel room, a holiday home provides you with a living area, kitchen, and sometimes even outdoor space, allowing you to cook your own meals, relax in comfort, and enjoy the company of your friends or family without the interruptions of other guests.

Holiday homes often offer more space than a hotel room. This can be particularly useful for families or groups of friends traveling together, who may need more than one room or want to avoid the cramped feeling of a single hotel room. They can also provide a more authentic travel experience, allowing guests to immerse themselves in the local culture and lifestyle. This can be particularly appealing for those who prefer to stay in quieter, residential areas away from the hustle and bustle of tourist hotspots.

Find the best Holiday home in Chester for your needs

Holiday homes should offer a comfortable and enjoyable stay, providing all the necessary amenities and conveniences to make your vacation experience memorable. At a minimum, your holiday home in Chester should offer a clean and well-maintained living space with comfortable furnishings, adequate lighting, and climate control.

In addition to basic amenities such as a fully equipped kitchen, comfortable bedding, and clean linens and towels, holiday homes should also offer modern conveniences such as Wi-Fi, cable or streaming TV, and laundry facilities. A private outdoor space, such as a balcony or terrace, can also add to the overall enjoyment. They can also offer additional features such as a swimming pool, hot tub, or outdoor grill. Location is also important, for example, close to popular tourist attractions, restaurants and shopping areas.

Accommodation data and pictures provided by Booking.com