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Holiday homes in Chester You’ll Love

Top-Rated Chester Holiday homes for Every Budget and Style!

Looking for a holiday home in Chester (Vermont)? Browse a wide range of vacation rentals – from cozy retreats to spacious family homes – starting at just $50.00 per night. Whether you are planning a weekend getaway or a longer stay, you will find the perfect home away from home in the heart of Chester.

We found 7 Holiday-homes in Chester and the surrounding area (within 60 miles)

Country Riverside Retreat in Chester, USA

Country Riverside Retreat

Holiday home in Chester, Vermont
Country Riverside Retreat offers accommodations in Chester, 24 miles from Santas Land USA and 29 miles from Mount Ascutney.
  • Parking

no reviews

from $220.00 Show details »

House At Dream Barn Hollow in Chester, USA

House At Dream Barn Hollow

Holiday home in Chester, Vermont
House At Dream Barn Hollow offers accommodations in Chester, 26 miles from Mount Equinox and 16 miles from Dorsey Park.
  • Parking

no reviews

from $201.11 Show details »

Town & Mountain in Chester, USA

Town & Mountain

Holiday home in Chester, Vermont
Town & Mountain is located in Chester, just 29 miles from Mount Equinox and 13 miles from Dorsey Park.
  • Parking
  • Pets allowed

no reviews

from $67.00 Show details »

Peaceful Brookside Getaway about 10 Mi to Okemo Slopes! in Chester, USA

Peaceful Brookside Getaway about 10 Mi t...

Holiday home in Chester, Vermont
Peaceful Brookside Getaway about 10 Mi to Okemo Slopes! is located in Chester, just 10 miles from Dorsey Park and 20 miles from Bellows Falls Amtrak S...
  • Parking
  • Pets allowed

Exceptional 3 Reviews 9.7

from $212.43 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
Chester Home with Views about 10 Mi to Okemo Mtn Resort! offers accommodations in Chester, 28 miles from Mount Tom and 9.4 miles from Dorsey Park.
  • Parking
  • Spa and wellness centre

no reviews

from $85.00 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
Private Chester Home with Deck, Mins to Skiing! offers accommodations in Chester, 28 miles from Mount Tom and 9.1 miles from Dorsey Park.
  • Parking

no reviews

from $482.88 Show details »

Zen of the Woods Tiny Cabin in Okemo Valley in Chester, USA

Zen of the Woods Tiny Cabin in Okemo Val...

Holiday home in Chester, Vermont , 729 Clemons Road
Zen of the Woods Tiny Cabin in Okemo Valley is located in Chester, just 30 miles from Stratton Mountain and 29 miles from Mount Tom.
  • Parking

Good 1 Reviews 7.0

from $367.36 Show details »

Number of Holiday homes in Chester 7
Number of guest ratings 284
Average price per night $309.00
Lowest price per night $50,00
Highest price per night $2.198,63

Top 10 Cheapest Holiday-homes in Chester

Discover the Cheapest Holiday-homes in Chester – Ranked by Lowest Nightly Rates.

Top 10 Most Booked Holiday-homes in Chester

Check out the Most Booked Holiday-homes in Chester – Based on Guest Popularity.

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