Find Cheap Hostels in Chester

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Next weekend
Dec 26 - Dec 28
In two weeks
Jan 2 - Jan 4
In one month
Jan 16 - Jan 18
In two months
Feb 13 - Feb 15
No exact matches found, but these alternatives could be just right

Recommended hotels in Chester

Garden
Fullerton Inn

Fullerton Inn

Fullerton Inn
2.5 star property
Chester Depot
8.2 out of 10, Very Good, (402)
"Lovely stay"
United States
Christine
$129 nightly
The price is $141
Dec 16 - Dec 17
Total with taxes and fees
Fullerton Inn
Front of property
Stone Hearth Inn and Eatery

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
$223 nightly
The price is $244
Jan 3 - Jan 4, 2026
Total with taxes and fees
Stone Hearth Inn and Eatery
Terrace/patio
Room in Historic Inn! 20 Minutes to Okemo!

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.
$171 nightly
The price is $192
Dec 16 - Dec 17
Total with taxes and fees
Room in Historic Inn! 20 Minutes to Okemo!
Dining
Quaint Queen room at the Chester Inn

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
$179 nightly
The price is $200
Dec 16 - Dec 17
Total with taxes and fees
Quaint Queen room at the Chester Inn
Fridge, microwave, oven, stovetop
Cozy Vermont Cabin · Mountain Views · Near Okemo

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.
$890 nightly
The price is $997
Dec 16 - Dec 17
Total with taxes and fees
Cozy Vermont Cabin · Mountain Views · Near Okemo
Exterior
Historic 150-year-old farmhouse, Jacuzzi included

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.
$425 nightly
The price is $475
Dec 16 - Dec 17
Total with taxes and fees
Historic 150-year-old farmhouse, Jacuzzi included
Dining
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!

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
$198 nightly
The price is $222
Jan 4 - Jan 5, 2026
Total with taxes and fees
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
Interior
Whimsical Room & Private Bathroom in Historic Inn

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.
$181 nightly
The price is $203
Dec 16 - Dec 17
Total with taxes and fees
Whimsical Room & Private Bathroom in Historic Inn
Terrace/patio
Chester Farmhouse Ski Retreat near Slopes

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.
$339 nightly
The price is $380
Jan 7 - Jan 8, 2026
Total with taxes and fees
Chester Farmhouse Ski Retreat near Slopes
Interior
King & Queen Suite in Historic Inn Circa 1780

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.
$221 nightly
The price is $248
Dec 16 - Dec 17
Total with taxes and fees
King & Queen Suite in Historic Inn Circa 1780
1 bedroom, desk, iron/ironing board, free WiFi
Honeymoon Suite with Jacuzzi Tub in Historic Inn

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.
$193 nightly
The price is $216
Dec 16 - Dec 17
Total with taxes and fees
Honeymoon Suite with Jacuzzi Tub in Historic Inn
Free daily on-the-go breakfast
Holiday Inn Express Hotel & Suites Brattleboro by IHG

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
$144 nightly
The price is $158
Dec 21 - Dec 22
Total with taxes and fees
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Lobby
Comfort Inn & Suites Brattleboro I-91

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
$112 nightly
The price is $123
Dec 21 - Dec 22
Total with taxes and fees
Comfort Inn & Suites Brattleboro I-91
Indoor pool
Keene Elm City Hotel, an Ascend Collection Hotel

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, (963)
"Staff were very friendly. The pool was the perfect temperature. Would definitely stay again. "
United States
Tiffany
$118 nightly
The price is $128
Dec 18 - Dec 19
Total with taxes and fees
Keene Elm City Hotel, an Ascend Collection Hotel
Premium bedding, individually decorated, individually furnished, desk
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very Good, (1002)
"Great staff, clean room, nice breakfast"
United States
DORTHY
$129 nightly
The price is $140
Dec 21 - Dec 22
Total with taxes and fees
Best Western Plus Keene Hotel
Exterior detail
The Covered Bridge Inn

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
$79 nightly
The price is $87
Dec 22 - Dec 23
Total with taxes and fees
The Covered Bridge Inn
Exterior
Fairfield Inn & Suites by Marriott Keene Downtown

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, (758)
"Room spacious, breakfast good, poor directions to parking, snow covered disability ramp."
United States
Stephanie
$180 nightly
The price is $195
Jan 1 - Jan 2, 2026
Total with taxes and fees
Fairfield Inn & Suites by Marriott Keene Downtown
Reception
Hampton Inn & Suites Keene

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
$147 nightly
The price is $160
Dec 24 - Dec 25
Total with taxes and fees
Hampton Inn & Suites Keene
Suite, 1 King Bed, Accessible, Refrigerator & Microwave (with Sofabed) | Laptop workspace, iron/ironing board, rollaway beds, free WiFi
Best Western Springfield Hotel

Best Western Springfield Hotel

Best Western Springfield Hotel
2.5 star property
Springfield
8.8 out of 10, Excellent, (805)
"so clean and friendly it was a perfect stay!"
United States
Colette
$143 nightly
The price is $157
Dec 21 - Dec 22
Total with taxes and fees
Best Western Springfield Hotel
Exterior
The Putney Inn

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very Good, (1002)
"Nice motel. "
United States
Richard
$78 nightly
The price is $86
Dec 16 - Dec 17
Total with taxes and fees
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.
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Top Chester Hotel Reviews

The Shire Woodstock

The Shire Woodstock

10/10 Excellent
"The staff was super nice and flexible! Location was great "
Frida Nohemi 1-night trip
Posted 2 days ago
The Shire Woodstock

Find out more about Chester

Chester Hostels information

Number of reviews
8,191
Accommodation
0 Hostels
Lowest Price
$86
Highest Price
$997

Frequently asked questions

What are the best hostels in Chester?
Our customers like these accommodations in the surrounding area, and they may have reasonable prices: Woodstock Inn & Resort - 25.2 mi (40.5 km) from the heart of Chester. Guests can enjoy free breakfast, free WiFi, and free parking at this hotel. The Shire Woodstock - 25.5 mi (41 km) from the heart of Chester. Guests can enjoy free WiFi, 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 WiFi, 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 WiFi, 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 WiFi, free parking, and free bike rentals at this hotel.
When is the best time of year to stay in a hostel in Chester?
Good weather's definitely a plus when you want to venture out and explore, so here's some information about the local climate: The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Chester are January, March, November, and February, with each month seeing an average of 14 inches 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 like 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 center. Another option is Rutland, VT (RUT-Rutland Southern Vermont Regional), situated 25.4 mi (40.8 km) away.

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