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Holiday homes in Chester (Page 2)

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)
The Foxhole in Ludlow, USA

The Foxhole

Holiday home in Ludlow near Chester, Vermont
Situated in Ludlow, 43 km from Killington Mountain, The Foxhole features accommodation with a garden, free WiFi and an ATM.
  • Parking

no reviews

from $223.71 Show details »

Green Mountain Riverside Retreat in Weston, USA

Green Mountain Riverside Retreat

Holiday home in Weston near Chester, Vermont
Set in Weston, 28 km from Stratton Mountain, Green Mountain Riverside Retreat offers accommodation with a garden, free WiFi and an ATM.
  • Parking

Superb 10 Reviews 9.5

from $178.18 Show details »

Casa Okemo in Ludlow, USA

Casa Okemo

Holiday home in Ludlow near Chester, Vermont
Set in Ludlow in the Vermont region, Casa Okemo has a patio.
  • Parking
  • Pets allowed
  • Tea/Coffee maker
  • Internet facilities
  • Shower

no reviews

from $359.18 Show details »

Brookhaven Condos in Ludlow, USA

Brookhaven Condos

Holiday home in Ludlow near Chester, Vermont
Located 42 km from Killington Mountain and 44 km from Stratton Mountain, Brookhaven Condos provides accommodation in Ludlow.
  • Parking
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Good 14 Reviews 7.7

from $317.88 Show details »

Butte Bliss in Ludlow, USA

Butte Bliss

Holiday home in Ludlow near Chester, Vermont
Situated 43 km from Stratton Mountain, 38 km from Gifford Woods State Park and 39 km from Pico Peak, Butte Bliss features accommodation located in Lud...
  • Parking

Bad 1 Reviews 1.0

from $156.67 Show details »

Present on Pleasant in Ludlow, USA

Present on Pleasant

Holiday home in Ludlow near Chester, Vermont
Within 41 km of Killington Mountain and 43 km of Stratton Mountain, Present on Pleasant provides free WiFi and a garden.
  • Parking

no reviews

from $242.71 Show details »

Ludlow Hideout in Ludlow, USA

Ludlow Hideout

Holiday home in Ludlow near Chester, Vermont
Situated 42 km from Stratton Mountain, 38 km from Gifford Woods State Park and 39 km from Pico Peak, Ludlow Hideout features accommodation located in ...
  • Parking

Fabulous 4 Reviews 9.0

from $305.04 Show details »

Downtown Ludlow Home in Ludlow, USA

Downtown Ludlow Home

Holiday home in Ludlow near Chester, Vermont
Offering mountain views, Downtown Ludlow Home is an accommodation set in Ludlow, 43 km from Stratton Mountain and 37 km from Gifford Woods State Park.
  • Parking

no reviews

from $236.00 Show details »

Small Town Charm in Ludlow, USA

Small Town Charm

Holiday home in Ludlow near Chester, Vermont
Set in Ludlow, 40 km from Killington Mountain, 42 km from Stratton Mountain and 37 km from Gifford Woods State Park, Small Town Charm offers accommoda...
  • Parking

no reviews

from $288.33 Show details »

The Fun House - Downstairs in Ludlow, USA

The Fun House - Downstairs

Holiday home in Ludlow near Chester, Vermont
Situated in Ludlow, 42 km from Killington Mountain, The Fun House - Downstairs features accommodation with a garden, free WiFi and an ATM.
  • Parking

Exceptional 1 Reviews 10.0

from $263.67 Show details »

The Fun House - Upstairs in Ludlow, USA

The Fun House - Upstairs

Holiday home in Ludlow near Chester, Vermont
Set in Ludlow, 42 km from Killington Mountain, The Fun House - Upstairs offers accommodation with a garden, free WiFi and an ATM.
  • Parking

no reviews

from $213.67 Show details »

Ludlow Escape in Ludlow, USA

Ludlow Escape

Holiday home in Ludlow near Chester, Vermont
Ludlow Escape features accommodation situated in Ludlow, 40 km from Killington Mountain and 43 km from Stratton Mountain.
  • Parking

Very good 30 Reviews 8.0

from $119.86 Show details »

Cozy in Cavendish in Cavendish, USA

Cozy in Cavendish

Holiday home in Cavendish near Chester, Vermont
Featuring a hot tub, Cozy in Cavendish is set in Cavendish.
  • Parking
  • Tea/Coffee maker
  • Shower
  • Bath
  • TV

no reviews

from $367.08 Show details »

Londonderry Retreat about 3 Mi to Lowell Lake! in Londonderry, USA

Londonderry Retreat about 3 Mi to Lowell...

Holiday home in Londonderry near Chester, Vermont
Featuring a hot tub, Londonderry Retreat about 3 Mi to Lowell Lake! is set in Londonderry.
  • Parking
  • Pets allowed

no reviews

from $419.33 Show details »

The "Okemo House" at Trailside in Ludlow, USA

The "Okemo House" at Trailside

Holiday home in Ludlow near Chester, Vermont , 239 Trailside Road
Located in Ludlow and across the street from Okemos Sunshine Chairlift with direct ski trail access, this property includes free WiFi.
  • Parking
  • Fitness centre
  • Family rooms
  • Indoor pool
  • Swimming pool

Exceptional 1 Reviews 10.0

from $319.00 Show details »

The "Okemo House" at Clocktower in Ludlow, USA

The "Okemo House" at Clocktower

Chalet in Ludlow near Chester, Vermont , 152 Upper Crossroad
Featuring mountain views, The "Okemo House" at Clocktower offers accommodation with a balcony and a coffee machine, around 44 km from Stratton Mountai...
  • Parking
  • Family rooms

no reviews

from $378.43 Show details »

230 Ghia Farm Road in Ludlow, USA

230 Ghia Farm Road

Holiday home in Ludlow near Chester, Vermont
230 Ghia Farm Road is located in Ludlow, 45 km from Stratton Mountain and 39 km from Gifford Woods State Park, in an area where skiing can be enjoyed.

no reviews

from $287.92 Show details »

Award-Winning Log Cabin, Top 5 in New England! in Londonderry, USA

Award-Winning Log Cabin, Top 5 in New En...

Holiday home in Londonderry near Chester, Vermont
Located 16 km from Stratton Mountain, 24 km from Mount Equinox and 26 km from Dorsey Park, Award-Winning Log Cabin, Top 5 in New England! provides acc...
  • Parking
  • Pets allowed
  • Internet facilities
  • Hairdryer
  • Refrigerator

no reviews

from $287.33 Show details »

Kettle Brook A in Ludlow, USA

Kettle Brook A

Holiday home in Ludlow near Chester, Vermont
Located in Ludlow, Kettle Brook A provides mountain views and free WiFi, 42 km from Killington Mountain and 45 km from Stratton Mountain.
  • Parking

Fabulous 1 Reviews 9.0

from $174.21 Show details »

Kettle Brook G in Ludlow, USA

Kettle Brook G

Holiday home in Ludlow near Chester, Vermont
Located in Ludlow, 42 km from Killington Mountain and 45 km from Stratton Mountain, Kettle Brook G provides mountain views and free WiFi.
  • Parking

Fabulous 3 Reviews 8.7

from $231.45 Show details »

Hygge House in Londonderry, USA

Hygge House

Holiday home in Londonderry near Chester, Vermont
Located in Londonderry, 13 km from Stratton Mountain, Hygge House provides accommodation with a garden, free WiFi and an ATM.
  • Parking

no reviews

from $169.33 Show details »

Cozy Cabin in the Woods in Londonderry, USA

Cozy Cabin in the Woods

Holiday home in Londonderry near Chester, Vermont
Set in Londonderry, 14 km from Stratton Mountain, Cozy Cabin in the Woods offers accommodation with a garden, free WiFi and an ATM.
  • Parking
  • Pets allowed

no reviews

from $412.91 Show details »

Tranquility in Londonderry, USA

Tranquility

Holiday home in Londonderry near Chester, Vermont
Located in Londonderry in the Vermont region, Tranquility features a balcony.
  • Parking

no reviews

from $190.00 Show details »

Sherwood Forest in Londonderry, USA

Sherwood Forest

Holiday home in Londonderry near Chester, Vermont
Sherwood Forest is located in Londonderry, 21 km from Mount Equinox and 24 km from Emerald Lake State Park, in an area where skiing can be enjoyed.
  • Parking

Okay 4 Reviews 5.7

from $162.86 Show details »

Misty Mountain Retreat in Ludlow, USA

Misty Mountain Retreat

Holiday home in Ludlow near Chester, Vermont
Located in Ludlow, 37 km from Killington Mountain, Misty Mountain Retreat provides accommodation with a garden, free WiFi and an ATM.
  • Parking

Exceptional 1 Reviews 10.0

from $287.54 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