Search Town Houses in Chester

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$212
includes taxes & fees
18 Jan - 19 Jan 2026
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$335
includes taxes & fees
23 Dec - 24 Dec
Stone Hearth Inn and Eatery

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$290
includes taxes & fees
30 Dec - 31 Dec
Quaint Queen room at the Chester Inn

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$377
includes taxes & fees
21 Dec - 22 Dec
King & Queen Suite in Historic Inn Circa 1780

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$309
includes taxes & fees
21 Dec - 22 Dec
Whimsical Room & Private Bathroom in Historic Inn

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$856
includes taxes & fees
7 Jan - 8 Jan 2026
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$338
includes taxes & fees
4 Jan - 5 Jan 2026
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!

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$551
includes taxes & fees
7 Jan - 8 Jan 2026
Chester Farmhouse Ski Retreat near Slopes

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$1,526
includes taxes & fees
19 Dec - 20 Dec
Cozy Vermont Cabin · Mountain Views · Near 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.
The price is AU$309
includes taxes & fees
4 Jan - 5 Jan 2026
Room in Historic Inn! 20 Minutes to Okemo!

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$330
includes taxes & fees
21 Dec - 22 Dec
Honeymoon Suite with Jacuzzi Tub in Historic 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
The price is AU$149
includes taxes & fees
20 Dec - 21 Dec
The Covered Bridge Inn

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
The price is AU$252
includes taxes & fees
5 Jan - 6 Jan 2026
Best Western Springfield Hotel

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$185
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, (963)
"The room was perfect, and the food was great "
United States
Paul
The price is AU$193
includes taxes & fees
21 Dec - 22 Dec
Keene Elm City Hotel, an Ascend Collection Hotel

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, (1001)
"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$239
includes taxes & fees
21 Dec - 22 Dec
Holiday Inn Express Hotel & Suites Brattleboro by IHG

Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very good, (926)
"The room was very clean, and both staff and service were outstanding."
United States
Wonji
The price is AU$243
includes taxes & fees
24 Dec - 25 Dec
Hampton Inn Brattleboro

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$269
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn & Suites Keene

The Burrell House

The Burrell House
2.5 star property
Keene
9.6 out of 10, Exceptional, (155)
"Very helpful, kind staff"
United States
Paitris
The Burrell House

Latchis Hotel

Latchis Hotel
2.5 star property
Brattleboro
8.4 out of 10, Very good, (837)
"Great stay"
United States
Jason
The price is AU$192
includes taxes & fees
21 Dec - 22 Dec
Latchis Hotel
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 Town Houses information

Number of reviews
7,356
Accommodation
0 Town Houses
Lowest Price
AU$149
Highest Price
AU$1,526

Explore a world of travel with Expedia