Minimap with link to location map
Filters
Price
Rating
Distance from Center
Rating (according to Stars)
Facilities

Check availability






Holiday homes in Chester (Page 4)

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)
Timeless Red Sox Retreat with Scenic Mountain Views! in Putney, USA

Timeless Red Sox Retreat with Scenic Mou...

Holiday home in Putney near Chester, Vermont
Situated in Putney, 7.2 km from Santa s Land, 13 km from Bellows Falls Amtrak Station and 35 km from Fort Dummer State Park, Timeless Red Sox Retreat ...
  • Parking
  • Sauna
  • Internet facilities
  • Iron
  • Refrigerator

no reviews

from $458.67 Show details »

The Strattonwald Burrow in Strattonwald, USA

The Strattonwald Burrow

Holiday home in Strattonwald near Chester, Vermont
The Strattonwald Burrow is located in Strattonwald, 5.2 km from Stratton Mountain, and provides a balcony, garden, and free WiFi.
  • Parking
  • Pets allowed

no reviews

from $344.00 Show details »

Mountain Oasis - Endless Amenities! in Jamaica, USA

Mountain Oasis - Endless Amenities!

Holiday home in Jamaica near Chester, Vermont , 1 Benson Fuller Drive
Boasting garden views, Mountain Oasis - Endless Amenities! provides accommodation with a garden, a terrace and a bar, around 2.8 km from Stratton Moun...
  • Parking
  • Pets allowed
  • Bar
  • Sauna
  • Family rooms

Exceptional 1 Reviews 10.0

from $274.55 Show details »

Lakefront Paradise Near Okemo and Killington in Mount Holly, USA

Lakefront Paradise Near Okemo and Killin...

Holiday home in Mount Holly near Chester, Vermont
Located 32 km from Gifford Woods State Park, 33 km from Pico Peak and 38 km from Mount Tom, Lakefront Paradise Near Okemo and Killington provides acco...
  • Parking

no reviews

from $479.67 Show details »

The Pond House in Plymouth, USA

The Pond House

Holiday home in Plymouth near Chester, Vermont
Located in Plymouth, within 29 km of Killington Mountain and 25 km of Gifford Woods State Park, The Pond House offers accommodation with free WiFi, ai...
  • Parking

Exceptional 5 Reviews 9.8

from $317.69 Show details »

Ski Bearadise in Stratton Acres, USA

Ski Bearadise

Holiday home in Stratton Acres near Chester, Vermont
Set in Stratton Acres, 2.5 km from Stratton Mountain, 23 km from Mount Equinox and 26 km from Emerald Lake State Park, Ski Bearadise offers accommodat...
  • Parking

no reviews

from $363.67 Show details »

375 Hawk Spur in Plymouth, USA

375 Hawk Spur

Holiday home in Plymouth near Chester, Vermont
375 Hawk Spur is located in Plymouth, 26 km from Gifford Woods State Park and 27 km from Pico Peak, in an area where skiing can be enjoyed.
  • Parking

no reviews

from $303.07 Show details »

Stratton Hollow House in Forest Farms, USA

Stratton Hollow House

Holiday home in Forest Farms near Chester, Vermont
Boasting a hot tub, Stratton Hollow House is situated in Forest Farms.
  • Parking

no reviews

from $425.67 Show details »

Delightful Seclusion in Stratton, USA

Delightful Seclusion

Holiday home in Stratton near Chester, Vermont
Situated in Stratton, 3.2 km from Stratton Mountain, 23 km from Mount Equinox and 26 km from Emerald Lake State Park, Delightful Seclusion features ac...
  • Parking
  • Pets allowed

Very good 2 Reviews 8.0

from $399.67 Show details »

Casita Bacon in Vermont Ventures, USA

Casita Bacon

Holiday home in Vermont Ventures near Chester, Vermont
Located in Vermont Ventures, within 7.1 km of Stratton Mountain and 17 km of Mount Equinox, Casita Bacon offers accommodation with free WiFi, air cond...
  • Parking
  • Sauna

no reviews

from $486.01 Show details »

Upscale VT Getaway by Slopes, Lakes and Trails! in Plymouth, USA

Upscale VT Getaway by Slopes, Lakes and...

Holiday home in Plymouth near Chester, Vermont
Located in Plymouth, 28 km from Killington Mountain, 25 km from Gifford Woods State Park and 26 km from Pico Peak, Upscale VT Getaway by Slopes, Lakes...
  • Parking
  • Pets allowed
  • Sauna

Fabulous 1 Reviews 9.0

from $351.67 Show details »

Stylish Mountain Home Near Ski, Golf and Manchester! in Bondville, USA

Stylish Mountain Home Near Ski, Golf and...

Holiday home in Bondville near Chester, Vermont
Boasting a hot tub, Stylish Mountain Home Near Ski, Golf and Manchester! is situated in Bondville.
  • Parking
  • Pets allowed

no reviews

from $368.33 Show details »

Beautiful Winter Escape on Bromley Mountain! in Peru, USA

Beautiful Winter Escape on Bromley Mount...

Holiday home in Peru near Chester, Vermont
Within 17 km of Stratton Mountain and 12 km of Mount Equinox, Home near Stratton Mountain, Manchester and Bromley! features free WiFi and a garden.
  • Parking
  • Pets allowed
  • Internet facilities
  • Hairdryer
  • Iron

Fabulous 1 Reviews 9.0

from $391.33 Show details »

Rivendell Home at Hawk Mountain in Plymouth, USA

Rivendell Home at Hawk Mountain

Holiday home in Plymouth near Chester, Vermont
Situated in Plymouth, 30 km from Killington Mountain and 27 km from Gifford Woods State Park, Rivendell Home at Hawk Mountain offers free WiFi and air...
  • Parking
  • Pets allowed

no reviews

from $483.00 Show details »

Jamaica Escape about 2 Mi to Stratton Mountain! in Jamaica, USA

Jamaica Escape about 2 Mi to Stratton Mo...

Holiday home in Jamaica near Chester, Vermont
Jamaica Escape about 2 Mi to Stratton Mountain! is situated in Jamaica, 25 km from Mount Equinox, 28 km from Emerald Lake State Park, and 29 km from M...
  • Parking
  • Pets allowed

no reviews

from $427.00 Show details »

Stratton Mountain Home with View - 2 Mi to Ski Lift! in Stratton, USA

Stratton Mountain Home with View - 2 Mi...

Holiday home in Stratton near Chester, Vermont
Situated 25 km from Mount Equinox, 28 km from Emerald Lake State Park and 29 km from Mount Snow Resort, Stratton Mountain Home with View - 2 Mi to Ski...
  • Parking

Exceptional 6 Reviews 9.8

from $211.00 Show details »

Sunny Mountainside Chalet in Plymouth, USA

Sunny Mountainside Chalet

Holiday home in Plymouth near Chester, Vermont
Situated in Plymouth, 29 km from Killington Mountain and 26 km from Gifford Woods State Park, Sunny Mountainside Chalet offers free WiFi, a garden and...
  • Parking
  • Pets allowed
  • Sauna

no reviews

from $485.67 Show details »

Plymouth Hideaway in Plymouth, USA

Plymouth Hideaway

Holiday home in Plymouth near Chester, Vermont
Situated in Plymouth, 29 km from Killington Mountain, Plymouth Hideaway features accommodation with a garden, free WiFi and an ATM.
  • Parking
  • Pets allowed
  • Sauna

Very good 2 Reviews 8.5

from $216.00 Show details »

1477 Salt Ash Road in Plymouth, USA

1477 Salt Ash Road

Holiday home in Plymouth near Chester, Vermont
1477 Salt Ash Road is set in Plymouth, 27 km from Gifford Woods State Park and 29 km from Pico Peak, in an area where skiing can be enjoyed.
  • Parking
  • Sauna

Superb 3 Reviews 9.0

from $320.85 Show details »

Mount Holly Home in Mount Holly, USA

Mount Holly Home

Holiday home in Mount Holly near Chester, Vermont
Mount Holly Home is set in Mount Holly, 48 km from Killington Mountain, 49 km from Stratton Mountain, as well as 41 km from Pico Peak.
  • Parking
  • Tea/Coffee maker
  • Shower
  • Bath
  • TV

Fabulous 1 Reviews 9.0

from $386.05 Show details »

Northern Comfort in Plymouth, USA

Northern Comfort

Holiday home in Plymouth near Chester, Vermont
Offering free WiFi and river views, Northern Comfort is an accommodation located in Plymouth.
  • Parking
  • Sauna

no reviews

from $440.67 Show details »

Stratton Hideway in Stratton, USA

Stratton Hideway

Holiday home in Stratton near Chester, Vermont
Featuring a sauna, Stratton Hideway is located in Stratton.
  • Parking
  • Sauna
  • Outdoor pool
  • Electric vehicle charging station
  • Swimming pool

no reviews

from $409.00 Show details »

Wardsboro Family Escape in Wardsboro, USA

Wardsboro Family Escape

Holiday home in Wardsboro near Chester, Vermont
Featuring a hot tub, Wardsboro Family Escape is situated in Wardsboro.
  • Parking
  • Pets allowed
  • Tea/Coffee maker
  • Internet facilities
  • Shower

Good 4 Reviews 7.7

from $360.36 Show details »

Long Trail House Condos in Stratton, USA

Long Trail House Condos

Holiday home in Stratton near Chester, Vermont
Set 3.3 km from Stratton Mountain and 25 km from Mount Equinox, Long Trail House Condos offers accommodation in Stratton.
  • Parking
  • Sauna
  • Fitness centre
  • Outdoor pool
  • Swimming pool

Pleasant 22 Reviews 6.4

from $361.88 Show details »

Mountain Reach 46 in Stratton, USA

Mountain Reach 46

Holiday home in Stratton near Chester, Vermont
Mountain Reach 46 is set in Stratton, 25 km from Mount Equinox and 28 km from Emerald Lake State Park, in an area where skiing can be enjoyed.
  • Parking

Good 4 Reviews 7.5

from $267.11 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