Search hotels in Chester
Enter your dates to see the latest prices and deals for Chester hotels
Filter by:
Star Rating
Review Score
Chester – 3 hotels and places to stay
See the latest prices and deals by choosing your dates.
Fullerton Inn & Restaurant
Chester
On the Village Green shopping district, this Vermont inn features free property-wide Wi-Fi, an enhanced continental breakfast, and on-site restaurant.
7.6
Scored 7.6
Good
Rated good
277 reviews
Price from$129per night
Stone Hearth Inn and Eatery
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....
8.4
Scored 8.4
Very Good
Rated very good
66 reviews
Price from$209per night
Chester Inn
Chester
Located in Chester, 25 miles from Stratton Mountain, Chester Inn has accommodations with a shared lounge, free private parking and a tennis court.
7.9
Scored 7.9
Good
Rated good
45 reviews
Price from$179per night
The Upper Pass Lodge
Londonderry (Near 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.
7.8
Scored 7.8
Good
Rated good
156 reviews
Price from$70.38per night
Best Western Springfield Hotel
Springfield (Near 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.
8.5
Scored 8.5
Very Good
Rated very good
214 reviews
Price from$179.10per night
Rodeway Inn
Bellows Falls (Near 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.
6.3
Scored 6.3
Pleasant
Rated pleasant
40 reviews
Price from$119per night
The Pointe at Castle Hill Resort & Spa
Ludlow (Vermont) (Near 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
Snowdon Chalet Motel
Londonderry (Vermont) (Near 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.
8.9
Scored 8.9
Excellent
Rated excellent
135 reviews
Price from$130per night
Main and Mountain
Ludlow (Near 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...
9.2
Scored 9.2
Wonderful
Rated wonderful
60 reviews
Price from$202.80per night
The Hartness House
Springfield (Vermont) (Near Chester)
Housed in a restored 1904 Victorian mansion that was once home to James Hartness, the Governor of Vermont, this inn is located in Springfield, Vermont.
7.8
Scored 7.8
Good
Rated good
41 reviews
Price from$187per night
What Guests Said About Chester:
- 6.0Scored 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 - 10Scored 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.
BarbaraUnited States of America - 10Scored 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.AAnonymousUnited States of America - 10Scored 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.
WendyUnited States of America - 10Scored 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.,
AdamUnited States of America - 10Scored 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.
keithUnited States of America
Explore guest reviews of hotels in Chester
- From $167.86 per night7.9Scored 7.9GoodRated good· 45 reviewsThe 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!McCabeUnited States of America
- From $140.61 per night7.6Scored 7.6GoodRated good· 277 reviewswe were traveling for a friends wedding and stayed for one night. it was beautiful, and comfortable !! It has been well maintained though some creeks when you walk but what do you expect from a 100+ year old building. we loved the veranda, it was so spacious and overlooking the little town of Chester. we didn’t take the time to eat at the resturante but man did the aromas smell amazing!! I would definitely stay here again.AAnonymousUnited States of America
- 6.0Scored 6.0PleasantRated pleasant· 13 reviewsOne 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...
StephenUnited States of America - From $167.86 per night7.9Scored 7.9GoodRated good· 45 reviewsThe property was pretty good. Good parking, easy access to rooms, comfortable, quiet, excellent location. Great bang for your buck. Tyler was great and very helpful assisting me with everything around the property. I will stay there again and will Recommend & Refer other people i know who travel through Vermont to stay at the Chester House InnKevinUnited States of America
- 8.8Scored 8.8ExcellentRated excellent· 6 reviewsI 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!
ValerieUnited States of America - From $140.61 per night7.6Scored 7.6GoodRated good· 277 reviewsHotel 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.
MalcolmUnited Kingdom - From $239.31 per night8.4Scored 8.4Very GoodRated very good· 66 reviewsThe 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.ShannonUnited States of America
- From $140.61 per night7.6Scored 7.6GoodRated good· 277 reviewsStaff 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.JJACOBUnited States of America
- 9.5Scored 9.5ExceptionalRated exceptional· 74 reviewsThe 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!TinaUnited States of America
- From $140.61 per night7.6Scored 7.6GoodRated good· 277 reviewsHotel 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.JenniferUnited States of America
- From $140.61 per night7.6Scored 7.6GoodRated good· 277 reviewsAn 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.
LindaUnited States of America - From $140.61 per night7.6Scored 7.6GoodRated good· 277 reviewsThis was a very cute bed and breakfast, the perfect stay for a quick weekend ski trip! The room was small but was only here for one night so it worked perfect. The staff was very friendly too!WaechterUnited States of America
- From $140.61 per night7.6Scored 7.6GoodRated good· 277 reviewsThe 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.
DavidCanada - From $140.61 per night7.6Scored 7.6GoodRated good· 277 reviewsGreat 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 :)JamesCanada
- From $167.86 per night7.9Scored 7.9GoodRated good· 45 reviewsThe 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.
NikolUnited States of America - From $239.31 per night8.4Scored 8.4Very GoodRated very good· 66 reviewsSuper cool historic bed and breakfast! Amazing staff! The food was great too! Love to support a small business that is ran like thisAAnonymousUnited States of America
- From $140.61 per night7.6Scored 7.6GoodRated good· 277 reviewsI loved. The warmth of fhe entire hotel. The staff was very welcoming. Dinner and cocktails were great .DeborahUnited States of America
- From $140.61 per night7.6Scored 7.6GoodRated good· 277 reviewsThe hotel is conveniently located.JocelyneUnited States of America
Research, refine, and make plans for your whole trip
Hotels with Parking in Chester
More great accommodation options for your trip.
Villas in Chester
More great accommodation options for your trip.
Vacation Rentals in Chester
More great accommodation options for your trip.
