Skip to main content

Filter by:


Star Rating

Review Score

Chester – 3 hotels and places to stay
See the latest prices and deals by choosing your dates.
Stone Hearth Inn and Eatery, hotel in Chester

Stone Hearth Inn and Eatery offers accommodations in Chester, 24 miles from Stratton Mountain and 28 miles from Mount Equinox. Private parking is available on site at this recently renovated property....

Vicky was great she was very attentive and hospitable to us . The breakfast was great, a farm to table expericne that included fresh baked bread, pastries and local roasted coffee.
8.4
Scored 8.4
Very Good
Rated very good
66 reviews
Price from$209per night
Chester Inn, hotel in Chester

Located in Chester, 25 miles from Stratton Mountain, Chester Inn has accommodations with a shared lounge, free private parking and a tennis court.

Breakfast was not included. Location was great. I could walk to many stores and restaurants.
8.0
Scored 8.0
Very Good
Rated very good
46 reviews
Price from$179per night
Fullerton Inn & Restaurant, hotel in Chester

On the Village Green shopping district, this Vermont inn features free property-wide Wi-Fi, an enhanced continental breakfast, and on-site restaurant.

No Hot water for Tea at Breakfast. No one present to ask for some. The Hotel needs update.
7.6
Scored 7.6
Good
Rated good
277 reviews
Price from$129per night
The Upper Pass Lodge, hotel in Chester

Located in Londonderry, 14 miles from Stratton Mountain, The Upper Pass Lodge has accommodations with a seasonal outdoor swimming pool, free private parking, a garden and a shared lounge.

It was clean
7.8
Scored 7.8
Good
Rated good
157 reviews
Price from$70.38per night
Best Western Springfield Hotel, hotel in Chester

Directly off highway I-91 and a short drive from many leisure activities and Okemo Mountain, this Springfield, Vermont hotel offers a free daily hot breakfast and an on-site game room.

Immaculately clean, easy to access, great staff, very friendly and professional
8.5
Scored 8.5
Very Good
Rated very good
213 reviews
Price from$179.10per night
Rodeway Inn, hotel in Chester

This hotel is located along the Connecticut River, a 5 minutes’ drive from Bellow Falls. The inn features a seasonal outdoor pool, free Wi-Fi and a refrigerator in every room.

Price and location
6.3
Scored 6.3
Pleasant
Rated pleasant
40 reviews
Price from$99per night
The Pointe at Castle Hill Resort & Spa, hotel in Chester

In the Green Mountains of Vermont, this resort has a full service spa and health club, as well as an on-site restaurant. Skiing at Okemo Mountain is just 4 miles away.

8.2
Scored 8.2
Very Good
Rated very good
251 reviews
Price from$169per night
Main and Mountain, hotel in Chester

Located in Ludlow, within 25 miles of Killington Peak and 27 miles of Stratton Mountain, Main and Mountain has accommodations with a bar and free WiFi throughout the property as well as free private...

Location, nice rustic farmhouse style room decor, keyless entry, ample sized fridge, plenty of hooks & hangars for clothes & gear, wonderful bath products, great to have a sound machine for sleeping!
9.2
Scored 9.2
Wonderful
Rated wonderful
60 reviews
Price from$202.80per night
The Governor's Inn, hotel in Chester

The Governor's Inn is located in Ludlow, within walking distance of quaint village shops and restaurants. The property has an on-site restaurant, a concierge service and a shared TV lounge.

Spent a lovely weekend here with my son. The home is charming and the owners, Holgar and Rose, are warm, welcoming and helpful. Always available and always responsive. The breakfast is phenomenal, too! Looking forward to coming back.
9.7
Scored 9.7
Exceptional
Rated exceptional
98 reviews
Price from$175per night
Snowdon Chalet Motel, hotel in Chester

Within 19 mi of 4 different ski resorts, this Londonderry motel is set in Vermont, off Route 11, just 6.2 mi from Green Mountain National Forest. WiFi is provided free of charge.

I thought the room was very well done
8.9
Scored 8.9
Excellent
Rated excellent
135 reviews
Price from$130per night
See all hotels in and around Chester
Subscribe to receive premium deals

Prices drop the second you sign up!

What Guests Said About Chester:

  • 6.0
    Scored 6.0

    Chester seemed like a nice historic town with a laid back...

    Chester seemed like a nice historic town with a laid back approach to life. We did not visit any other sites there because we had a wedding up the road. I would probably not stay at the Inn again due to no tv, no air conditioning and no elevator.
    Jennifer
  • 10
    Scored 10

    Good walking town, nice green with picnic tables.

    Good walking town, nice green with picnic tables. They have a self guided tour of the historic buildings and a well-maintained cemetery. There is a large antique store, bakery, ice rink and scenic train ride in the immediate area. The stone house village is a short drive and a must see to appreciate. The town has a nice pub within walking distance of the Inns and a tavern about one mile down the street. There are also two great restaurants within a 10 minute drive and skiing with 25 minutes.
    Barbara
    United States of America
  • 10
    Scored 10

    This is the epitome of a charming New England Village, with...

    This is the epitome of a charming New England Village, with just the right amount of little shops and not touristy, and places to eat. Easy access to skiing and hiking trails and more tourist destinations, if you like.
    A
    Anonymous
    United States of America
  • 10
    Scored 10

    It was a cute little town with just enough shopping which...

    It was a cute little town with just enough shopping which didn't interfere with relaxing. Also, easy to get to other towns if you were inclined to. The Free Range restaurant was very good for dinner, as well as the Scottish pub. Also, the Fullerton Inn had a very nice lunch. Very reasonable.
    Wendy
    United States of America
  • 10
    Scored 10

    Chester is the perfect little New England town with great...

    Chester is the perfect little New England town with great places to stay, eat, and shop right in town. It is also located in easy driving distance to many area places of interest, hiking, skiing, snowmobiling, fall foliage viewing, etc.,
    Adam
    United States of America
  • 10
    Scored 10

    Chester, VT is a beautiful town with very friendly residents...

    Chester, VT is a beautiful town with very friendly residents. We stayed in Chester and explored Vermont, New Hampshire and Maine. Our stay was the 2nd week of October, the weather and fall foliage were amazing. Restaurant selections are somewhat limited. We tried The Fullerton Inn as it was advertised as fine dining and were NOT IMPRESSED.
    keith
    United States of America

Explore guest reviews of hotels in Chester

  • From $255.06 per night
    8.0
    Scored 8.0
    Very Good
    Rated very good
     · 46 reviews
    The owners were very accommodating and very easy to contact. We travelled to visit and care for family nearby. The owners reprogrammed the exterior lighting timer for us to sleep earlier and they let us move rooms for another guest bed, at the end of our stay. The kitchen use, dining area, lounge space and front porch made our stay feel like home away from home. All of the other guests were considerate and quiet and the cleaning on the property was first rate. We will stay here again!
    McCabe
    United States of America
  • 6.0
    Scored 6.0
    Pleasant
    Rated pleasant
     · 13 reviews
    One mile from Chester village, this met the minimal requirements (or I would have rated it a "1" - there was a bed, a place to sit, there was a glaring ceiling light and a lamp, there was a bathroom (with hot water for the shower) ... not worth the price, and certainly NOTHING LIKE the romantic Vermont getaway at an old tavern any couple would have dreamt about ... Motel 6 would have been a nicer space...
    Stephen
    United States of America
  • 8.8
    Scored 8.8
    Excellent
    Rated excellent
     · 6 reviews
    I thoroughly enjoyed my stay at the The Chester House. The innkeeper provided a delicious breakfast each morning and shared his knowledge of places to go. It is conveniently located to serve as home base for day trips. I enjoyed a break on the front porch and watching life go by. We felt safe and at home. I’m planning another stay!
    Valerie
    United States of America
  • From $140.61 per night
    7.6
    Scored 7.6
    Good
    Rated good
     · 277 reviews
    Hotel was well placed for our tour of New England. Lovely, big entrance area with comfortable seating and imposing fireplace. Restaurant served very good food from an extensive menu with very pleasant staff. Breakfast was reasonably good if you were not too late (see below). Hotel was easy to find with good parking directly outside.
    Malcolm
    United Kingdom
  • From $239.31 per night
    8.4
    Scored 8.4
    Very Good
    Rated very good
     · 66 reviews
    The inn was very clean and quaint. There was hot chocolate and cookies upon our arrival and a delicious hot breakfast made to order each morning. We stayed on the top floor, which had 4 twin beds- all with comfortable linens and comforters. There was also plenty of room to move around and a spacious closet for our suitcases.
    Shannon
    United States of America
  • From $140.61 per night
    7.6
    Scored 7.6
    Good
    Rated good
     · 277 reviews
    Staff was super nice. They upgraded my room for no extra charge and gave me bag to wrap my luggage in when I checked out, since it was raining and I was traveling by motorcycle. The location was also perfect to be able to see the main drag in Chester on foot. Many local beer options on tap in the restaurant onsite.
    J
    JACOB
    United States of America
  • 9.5
    Scored 9.5
    Exceptional
    Rated exceptional
     · 74 reviews
    The inn is very charming, the staff ensures that you get the Vermont hospitality experience with hot tea and baked goods ready, the fire burning and inn dog to welcome you! I highly recommend this family run inn to everyone who visits the Chester Area!
    Tina
    United States of America
  • From $140.61 per night
    7.6
    Scored 7.6
    Good
    Rated good
     · 277 reviews
    Hotel manager was very personable. I booked through Booking.com for 2 nights however the hotel only had 1 night available so the billing was a bit complicated but the manager was very nice aviary resolving it. On-site restaurant was very convenient.
    Jennifer
    United States of America
  • From $255.06 per night
    8.0
    Scored 8.0
    Very Good
    Rated very good
     · 46 reviews
    Chester is a charming, small New England town, and Chester Inn faces the village green. The Inn has a welcoming, colonial ambience, but with modern amenities. The room was clean and comfortable, and the common rooms had a nice, homey feel.
    D
    David
    United States of America
  • From $140.61 per night
    7.6
    Scored 7.6
    Good
    Rated good
     · 277 reviews
    The Fullerton is a classic 19th century hotel in the middle of charming Chester, close to the many attractions of the town and the region. A bonus for electric vehicle owners is the proximity of FREE charging stations around the corner,
    John
    United States of America
  • From $140.61 per night
    7.6
    Scored 7.6
    Good
    Rated good
     · 277 reviews
    An old-style hotel and helpful and friendly staff. Generous breakfast spread.. l would have liked to have tried the restaurant for dinner but train arrival in Bellows Falls did not allow.
    Linda
    United States of America
  • From $140.61 per night
    7.6
    Scored 7.6
    Good
    Rated good
     · 277 reviews
    The traditional style hotel is centrally located in the quiet little town. The staff were very nice, and helpful. I enjoyed my evening meal in the restaurant. I would stay there again.
    David
    Canada
  • From $140.61 per night
    7.6
    Scored 7.6
    Good
    Rated good
     · 277 reviews
    Great location in the centre of town. Breakfast was very good and the staff were warm, welcoming and very helpful. We will for sure stay here again next time we visit Chester :)
    James
    Canada
  • From $255.06 per night
    8.0
    Scored 8.0
    Very Good
    Rated very good
     · 46 reviews
    The town of Chester was really cute. The room was very clean. The coffee bar in the kitchen was well stocked and and there was a nice room to play games or do puzzles.
    Nikol
    United States of America
  • From $239.31 per night
    8.4
    Scored 8.4
    Very Good
    Rated very good
     · 66 reviews
    Super cool historic bed and breakfast! Amazing staff! The food was great too! Love to support a small business that is ran like this
    A
    Anonymous
    United States of America
  • From $140.61 per night
    7.6
    Scored 7.6
    Good
    Rated good
     · 277 reviews
    No Hot water for Tea at Breakfast. No one present to ask for some. The Hotel needs update.
    M
    Melba
    United States of America
  • From $140.61 per night
    7.6
    Scored 7.6
    Good
    Rated good
     · 277 reviews
    Charming, old-fashioned hotel with wonderful food available.
    Virginia
    United States of America
  • From $140.61 per night
    7.6
    Scored 7.6
    Good
    Rated good
     · 277 reviews
    The hotel is conveniently located.
    Jocelyne
    United States of America