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Holiday homes in Chester (Page 6)

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)
Spacious Home Near Bromley Mountain Ski Resort! in Manchester Center, USA

Spacious Home Near Bromley Mountain Ski...

Holiday home in Manchester Center near Chester, Vermont
Within 26 km of Stratton Mountain and 44 km of Bennington Battle Monument, Spacious Home 9 Mi to Bromley Mountain Ski Resort! offers free WiFi and a g...
  • Parking
  • Pets allowed

no reviews

from $271.00 Show details »

Wooded Wonder in West Dover, USA

Wooded Wonder

Holiday home in West Dover near Chester, Vermont
Situated in West Dover, 34 km from Stratton Mountain, 50 km from Bennington Battle Monument and 48 km from Bennington Museum, Wooded Wonder features a...
  • Parking

no reviews

from $339.02 Show details »

Valley View: Forest Edge 189 in Dover, USA

Valley View: Forest Edge 189

Holiday home in Dover near Chester, Vermont
Valley View: Forest Edge 189 is situated in Dover, 44 km from Adams.
  • Parking
  • Pets allowed
  • Tea/Coffee maker
  • TV
  • Telephone

Pleasant 4 Reviews 6.2

from $165.33 Show details »

Nostalgic Vermont Escape in Manchester Center in Manchester Center, USA

Nostalgic Vermont Escape in Manchester C...

Holiday home in Manchester Center near Chester, Vermont
Located 44 km from Bennington Battle Monument, 4 km from Mount Equinox and 41 km from Bennington College, Nostalgic Vermont Escape in Manchester Cente...
  • Parking
  • Pets allowed

Very good 2 Reviews 8.5

from $321.00 Show details »

Brook Road Condo in Goshen, USA

Brook Road Condo

Holiday home in Goshen near Chester, Vermont
Set 27 km from Lake Sunapee Golf Course, 44 km from Mount Ascutney and 48 km from Bellows Falls Amtrak Station, Brook Road Condo offers accommodation ...
  • Parking
  • Family rooms
  • Tea/Coffee maker
  • Shower
  • Bath

Very good 5 Reviews 8.0

from $172.00 Show details »

Dover Home 7 Mi to Mount Snow Grand Summit Resort in Dover, USA

Dover Home 7 Mi to Mount Snow Grand Summ...

Holiday home in Dover near Chester, Vermont
Featuring a spa bath, Dover Home 7 Mi to Mount Snow Grand Summit Resort is located in Dover.
  • Parking
  • Internet facilities
  • Hairdryer
  • Spa bath
  • Refrigerator

no reviews

from $412.00 Show details »

Brookside Hideaway, Brook Road Inn in Goshen, USA

Brookside Hideaway, Brook Road Inn

Holiday home in Goshen near Chester, Vermont
Brookside Hideaway, Brook Road Inn is set in Goshen, 27 km from Lake Sunapee Golf Course, 44 km from Mount Ascutney, as well as 48 km from Bellows Fal...
  • Parking
  • Family rooms

Superb 2 Reviews 9.5

from $256.33 Show details »

Brook Road Inn in Goshen, USA

Brook Road Inn

Holiday home in Goshen near Chester, Vermont
Situated 27 km from Lake Sunapee Golf Course in Goshen, Brook Road Inn features accommodation with air conditioning and free WiFi.
  • Parking
  • Shower
  • Air conditioning
  • Hairdryer
  • Iron

Good 77 Reviews 8.0

from $111.00 Show details »

Beautiful Six Bedroom in the Middle of Manchester in Manchester, USA

Beautiful Six Bedroom in the Middle of M...

Holiday home in Manchester near Chester, Vermont , 83 High Hill Road
Featuring a garden, a restaurant, and a bar, Beautiful Six Bedroom in the Middle of Manchester offers accommodation in Manchester with free WiFi and m...
  • Parking
  • Restaurant
  • Pets allowed
  • Bar
  • Fitness centre

no reviews

from $441.75 Show details »

Brook Road Cabin in Goshen, USA

Brook Road Cabin

Holiday home in Goshen near Chester, Vermont
Located 27 km from Lake Sunapee Golf Course, 44 km from Mount Ascutney and 49 km from Bellows Falls Amtrak Station, Brook Road Cabin provides accommod...
  • Parking
  • Tea/Coffee maker
  • Shower
  • TV
  • Hairdryer

Good 19 Reviews 7.3

from $172.00 Show details »

Brook Road Cabin in Goshen, USA

Brook Road Cabin

Lodge in Goshen near Chester, Vermont
Situated 27 km from Lake Sunapee Golf Course, 44 km from Mount Ascutney and 49 km from Bellows Falls Amtrak Station, Brook Road Cabin features accommo...
  • Parking
  • Family rooms
  • Tea/Coffee maker
  • Shower
  • TV

Very good 2 Reviews 8.0

from $172.00 Show details »

Farmhouse Mountain Escape about 1 Mile to Mount Snow! in Dover, USA

Farmhouse Mountain Escape about 1 Mile t...

Holiday home in Dover near Chester, Vermont
Situated in Dover, 26 km from Stratton Mountain, 48 km from Mount Equinox and 50 km from Bennington Museum, Farmhouse Mountain Escape about 1 Mile to ...
  • Parking
  • Fitness centre
  • Swimming pool
  • Swimming Pool
  • Internet facilities

no reviews

from $480.33 Show details »

Timber Creek #98 in Dover, USA

Timber Creek #98

Holiday home in Dover near Chester, Vermont
Set in Dover, 26 km from Stratton Mountain, Timber Creek #98 offers accommodation with a shared lounge, free WiFi and an ATM.
  • Parking
  • Pets allowed
  • Sauna
  • Fitness centre
  • Outdoor pool

no reviews

from $228.40 Show details »

Mandy's Mountain Chalet in Dover, USA

Mandy's Mountain Chalet

Holiday home in Dover near Chester, Vermont , 15 Mandys Road
Set in Dover, 38 km from Stratton Mountain, Mandys Mountain Chalet offers accommodation with a shared lounge, free WiFi and a shared kitchen.
  • Parking
  • Family rooms

no reviews

from $246.87 Show details »

Hartland Hideaway in Hartland, USA

Hartland Hideaway

Holiday home in Hartland near Chester, Vermont
Located in Hartland, 46 km from Killington Mountain and 11 km from Mount Tom, Hartland Hideaway provides accommodation with amenities such as free WiF...
  • Parking

no reviews

from $135.33 Show details »

Ski on ski off, conveniently located, 2 bedroom condo with beautiful views, access to indoor pool Sunrise B3 in Killington, USA

Ski on ski off, conveniently located, 2...

Holiday home in Killington near Chester, Vermont , 49 East Glade Road
Sunrise Village East Glade B3 offers accommodation in Killington.
  • Parking
  • Indoor pool
  • Swimming pool
  • Swimming Pool
  • Bath

Very good 2 Reviews 8.5

from $350.75 Show details »

Ski on ski off, beautiful views, 2 bedroom condo with access to indoor pool, Sunrise C5 in Killington, USA

Ski on ski off, beautiful views, 2 bedro...

Holiday home in Killington near Chester, Vermont
Sunrise Village East Glade C5 offers accommodation in Killington.
  • Parking
  • Indoor pool
  • Swimming pool
  • Swimming Pool
  • Bath

Passable 6 Reviews 5.3

from $336.40 Show details »

Make this beautiful property your family vacation home while in Killington B301 in Killington, USA

Make this beautiful property your family...

Holiday home in Killington near Chester, Vermont , 283 Sunrise Road
Set in Killington and only 6.3 km from Killington Mountain, Make this beautiful property your family vacation home while in Killington B301 offers acc...
  • Parking
  • Fitness centre
  • Indoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $405.69 Show details »

Spacious Dover Home with Sauna Less Than 5 Miles to Ski! in Dover, USA

Spacious Dover Home with Sauna Less Than...

Holiday home in Dover near Chester, Vermont
Situated in Dover, 32 km from Stratton Mountain and 48 km from Bennington Battle Monument, Spacious Dover Home with Sauna Less Than 5 Miles to Ski! pr...
  • Parking
  • Sauna

Exceptional 2 Reviews 10.0

from $459.00 Show details »

Sunrise Glade in Killington, USA

Sunrise Glade

Holiday home in Killington near Chester, Vermont
Sunrise Glade offers accommodation in Killington.
  • Parking
  • Sauna
  • Fitness centre
  • Outdoor pool
  • Swimming pool

Good 5 Reviews 7.6

from $248.89 Show details »

Sunrise: West Glade-J2 in Killington, USA

Sunrise: West Glade-J2

Holiday home in Killington near Chester, Vermont
Located in Killington, Sunrise: West Glade-J2 is 2.9 km from Killington Mountain.
  • Pets allowed
  • Sauna
  • Fitness centre
  • Indoor pool
  • Outdoor pool

Pleasant 8 Reviews 6.9

from $235.10 Show details »

Ski In/Out Trailside Townhome in Killington, USA

Ski In/Out Trailside Townhome

Holiday home in Killington near Chester, Vermont , 81 Timberline South Unit K5
Located in Killington, just 6.7 km from Killington Mountain, Ski In/Out Trailside Townhome provides accommodation with a seasonal outdoor swimming poo...
  • Parking
  • Bar
  • Sauna
  • Fitness centre
  • Family rooms

Fabulous 31 Reviews 8.8

from $217.77 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