Search Chester Hostels

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months
No exact matches found, but these alternatives could be just right

Recommended hotels in Chester

Fullerton Inn

Fullerton Inn
2.5 star property
Chester Depot
8.2 out of 10, Very good, (402)
"Lovely stay"
United States
Christine
The price is AU$211
includes taxes & fees
16 Dec - 17 Dec
Fullerton Inn

Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (107)
"Good breakfast and dinner options. Great location for hiking."
United States
Paul
The price is AU$332
includes taxes & fees
15 Dec - 16 Dec
Stone Hearth Inn and Eatery

Room in Historic Inn! 20 Minutes to Okemo!

Room in Historic Inn! 20 Minutes to Okemo!
Chester Depot
9.2 out of 10, Wonderful, (18)
"The Chester Inn was beautiful and located in downtown Chester. "
United States
Peter C.
The price is AU$291
includes taxes & fees
16 Dec - 17 Dec
Room in Historic Inn! 20 Minutes to Okemo!

Quaint Queen room at the Chester Inn

Quaint Queen room at the Chester Inn
2.0 star property
Chester Depot
10.0 out of 10, Exceptional, (1)
"This was a wonderful experience for us. The Inn and room were spotless. Very comfortable bed. We will return. The only issue was the tub/shore. Too much of a challenge for older folks. "
United States
Thomas
The price is AU$304
includes taxes & fees
15 Dec - 16 Dec
Quaint Queen room at the Chester Inn

Cozy Vermont Cabin · Mountain Views · Near Okemo

Cozy Vermont Cabin · Mountain Views · Near Okemo
Chester
10.0 out of 10, Exceptional, (3)
"We really enjoyed our stay at this home. It had everything we needed and was very comfortable. The countryside around this part of Vermont is beautiful. We found lots of great museums and restaurants. "
United States
Donald M.
The price is AU$1,514
includes taxes & fees
15 Dec - 16 Dec
Cozy Vermont Cabin · Mountain Views · Near Okemo

Historic 150-year-old farmhouse, Jacuzzi included

Historic 150-year-old farmhouse, Jacuzzi included
Chester Depot
9.8 out of 10, Exceptional, (10)
"This was a lovely inviting piece of history to stay in! The amenities were wonderful, the host very engaged with being sure we had what we needed. It is (for those who may not know Vermont) SUPER close to all sorts of hiking, tours, cute stores and great food! Our family will absolutely stay here again!"
United States
Amy S.
The price is AU$713
includes taxes & fees
15 Dec - 16 Dec
Historic 150-year-old farmhouse, Jacuzzi included

Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!

Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
Chester Depot
9.0 out of 10, Wonderful, (2)
"Property seemed well-maintained and cared for. We were only there a short time, but it was well put together. The check-in process was a little hectic, check in time was 3pm, but our room wasn't ready. The caretaker was very friendly. We only had to wait about 20 minutes. We weren't aware this property was a VRBO, and not a regular Inn. "
United States
Jacque
The price is AU$337
includes taxes & fees
4 Jan - 5 Jan 2026
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!

Whimsical Room & Private Bathroom in Historic Inn

Whimsical Room & Private Bathroom in Historic Inn
Chester Depot
8.8 out of 10, Excellent, (9)
"After a long month of work I needed a weekend in VT to calm the nerves. This was a beautiful spot to be in, glad I was here!"
United States
Paul S.
The price is AU$308
includes taxes & fees
15 Dec - 16 Dec
Whimsical Room & Private Bathroom in Historic Inn

Chester Farmhouse Ski Retreat near Slopes

Chester Farmhouse Ski Retreat near Slopes
Chester Depot
9.6 out of 10, Exceptional, (17)
"This was my second time staying at this property. Everything was great just like last year. I highly recommend it if you are staying in Chester, VT. "
United States
Lori N.
The price is AU$781
includes taxes & fees
20 Dec - 21 Dec
Chester Farmhouse Ski Retreat near Slopes

King & Queen Suite in Historic Inn Circa 1780

King & Queen Suite in Historic Inn Circa 1780
Chester Depot
9.8 out of 10, Exceptional, (16)
"Central for our needs. easy check in process. Lovely large room with comfy beds. "
United States
HIlary H.
The price is AU$376
includes taxes & fees
15 Dec - 16 Dec
King & Queen Suite in Historic Inn Circa 1780

Honeymoon Suite with Jacuzzi Tub in Historic Inn

Honeymoon Suite with Jacuzzi Tub in Historic Inn
Chester Depot
8.6 out of 10, Excellent, (7)
"Charming place, hope to go back soon."
United States
Sharon S.
The price is AU$329
includes taxes & fees
15 Dec - 16 Dec
Honeymoon Suite with Jacuzzi Tub in Historic Inn

Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG
2.5 star property
Brattleboro
8.8 out of 10, Excellent, (1000)
"Very clean room, gentlemen at the front desk were welcoming and professional and the coffee was amazing! We are frequent visitors with you; we love IHG hotels. "
United States
Belinda
The price is AU$238
includes taxes & fees
21 Dec - 22 Dec
Holiday Inn Express Hotel & Suites Brattleboro by IHG

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (740)
"Price, clean and spacious room, comfy bed."
United States
June
The price is AU$177
includes taxes & fees
21 Dec - 22 Dec
Comfort Inn & Suites Brattleboro I-91

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
2.5 star property
Keene
8.4 out of 10, Very good, (962)
"Staff were very friendly. The pool was the perfect temperature. Would definitely stay again. "
United States
Tiffany
The price is AU$187
includes taxes & fees
16 Dec - 17 Dec
Keene Elm City Hotel, an Ascend Collection Hotel

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very good, (1001)
"Great staff, clean room, nice breakfast"
United States
DORTHY
The price is AU$227
includes taxes & fees
15 Dec - 16 Dec
Best Western Plus Keene Hotel

The Covered Bridge Inn

The Covered Bridge Inn
2.5 star property
Brattleboro
7.6 out of 10, Good, (1001)
"Quiet, easy to get to right off the highway with lots of quick eats within walking distance. Staff was friendly and helpful with any requests."
United States
Zachery
The price is AU$131
includes taxes & fees
22 Dec - 23 Dec
The Covered Bridge Inn

Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown
2.5 star property
Keene
8.8 out of 10, Excellent, (756)
"Front desk pleasant and helpful Breakfast was good Room was spacious and clean Able to walk to shopping and dining. "
United States
Stephen
The price is AU$294
includes taxes & fees
1 Jan - 2 Jan 2026
Fairfield Inn & Suites by Marriott Keene Downtown

Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
2.5 star property
Keene
8.8 out of 10, Excellent, (353)
"Clean comfy nice staff "
United States
Katherine
The price is AU$240
includes taxes & fees
24 Dec - 25 Dec
Hampton Inn & Suites Keene

Best Western Springfield Hotel

Best Western Springfield Hotel
2.5 star property
Springfield
8.8 out of 10, Excellent, (804)
"so clean and friendly it was a perfect stay!"
United States
Colette
The price is AU$237
includes taxes & fees
21 Dec - 22 Dec
Best Western Springfield Hotel

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very good, (1002)
"Nice motel. "
United States
Richard
The Putney Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Chester Hotel Reviews

Find out more about Chester

Chester Hostels information

Number of reviews
8,193
Accommodation
0 Hostels
Lowest Price
AU$131
Highest Price
AU$1,514

Frequently asked questions

What are the best hostels in Chester?
Our guests like these accommodations in the surrounding area, and they may have reasonable rates: Woodstock Inn & Resort - 25.2 mi (40.5 km) from the heart of Chester. Guests can enjoy free breakfast, free Wi-Fi and free parking at this hotel. The Shire Woodstock - 25.5 mi (41 km) from the heart of Chester. Guests can enjoy free Wi-Fi, free parking and a TV in a common area at this hotel. The Equinox Golf Resort & Spa - 25 mi (40.3 km) from the heart of Chester. Guests can enjoy free Wi-Fi, free parking and an indoor pool at this hotel. Kimpton Taconic Hotel by IHG - 24.9 mi (40 km) from the heart of Chester. You can take advantage of free breakfast, free Wi-Fi and free parking at this hotel. Pointe at Castle Hill Resort - 8.8 mi (14.1 km) from the heart of Chester. You can take advantage of free Wi-Fi, free parking and free bike hire at this hotel.
When is the best time of year to stay in a hostel in Chester?
The weather is important when you're discovering new places, so here are some stats about the seasons: The hottest months are usually July and August, with an average temperature of 18°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Chester are January, March, November and February, with each month seeing an average of 35 cm of snowfall.
What is there to see and do in Chester?
Overall, Chester is known for its skiing, coffee shops and mountain views. Major attractions include Stratton Mountain Resort. Get out into nature with places such as Lowell Lake State Park, Buttermilk Falls and Lake Rescue. Cultural attractions include Grafton Historical Society, Weston Playhouse and Bellows Falls Opera House.
What's the best way to get to and around Chester while staying at a hostel?
Keep this information about transit options in and around Chester on hand to make the most of your stay: You can fly into the nearest airport, which is Springfield, VT (VSF-Hartness State), located 6.6 mi (10.7 km) away from the city centre. Another option is Rutland, VT (RUT-Rutland Southern Vermont Regional), located 25.4 mi (40.8 km) away.

Explore a world of travel with Expedia