See all properties

Chester Inn

Top rated by guests
Chester Inn Inn in Chester
Chester Inn Inn in Chester
Chester Inn Inn in Chester
Chester Inn Inn in Chester
Chester Inn Inn in Chester
review stars
8.4Excellent
(129 Ratings)
"The Chester Inn paid attention to details and was extremely clean. Not crazy about the memory foam mattress but??? Oh well"
Verified guest
Don't miss out! Price and availability may change
8.4 / 10.0
Excellent(129 Ratings)

Inn in Chester, VT

2 guests · 1 bedroom · 1 bath

Reasons to book

Guests love it hereGuests give this property a top rating
Well priced for this locationPriced under area average
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

About this inn

Located in Chester, 24 miles from Stratton Mountain, Chester Inn has accommodations with a shared lounge, free private parking and a tennis court.

Amenities at Chester Inn

Free WiFi/internet
Free Parking
Air conditioning
Non-smoking
Heating
Kitchen
WiFi/Internet
Hot tub/Jacuzzi
Shared living spaces
Ski in/Ski out
Family friendly
Contactless check-in/out
Fire alarm
Fire extinguisher
Tennis court
Cleaning products

Map of Chester, VT

city location on map

Nearby attractions

Montshire Museum of Science
33.5 mi
Quechee Gorge Bridge
27.5 mi
Saint-Gaudens National Historical Site
19.7 mi
Marsh-Billings-Rockefeller National Historical Park
25.7 mi

Available Rooms

Ratings and reviews

8.4 / 10.0
Excellent(129 Ratings)
100% verified reviews
10.0 / 10.0Outstanding·Mar 2026
The Chester Inn paid attention to details and was extremely clean. Not crazy about the memory foam mattress but??? Oh well
10.0 / 10.0Outstanding·Mar 2026
Took me back to the 1800s. Felt cozy and vintage. Jacuzzi and fireplace was a hit.
Nothing.
10.0 / 10.0Outstanding·Feb 2026
easy parking and nice house
walls very thin
5.0 / 10.0·Feb 2026
Convenient location, clean, comfortable bed.
Noisy, bathroom door sticking, jacuzzi out of order, drafty.
$$$$
booking logo

FAQs

Does this property follow enhanced cleaning procedures?

Yes, this inn has implemented enhanced cleaning procedures and processes to keep you healthy and safe.

Is parking included with this inn?

Parking is not specified as an available amenity at Chester Inn. For more information, we encourage you to contact the property about where to park.

Is there a pool at this inn?

We didn’t find pool listed as an amenity for this inn. It may be worth double checking if a pool is important for your stay.

Is Chester Inn pet friendly?

Unfortunately, this inn is not pet-friendly. Try searching again and filter for "Pets Allowed"

What amenities are available at Chester Inn?

We found 16 amenities for this rental. This includes free wifi/internet, free parking, air conditioning, non-smoking, and heating.

Explore similar stays in Chester

Explore all stays
You can save with One Key
9.2 / 10.0
Outstanding(20 Ratings)
Room in Historic Inn! 20 Minutes to Okemo!
Bed and Breakfast
 in Chester
3 guests · 1 bedroom · 1 bath

Business stays, family stays, couples stay, getaway vacation, and rental in Chester at Room in Historic Inn! 20 Minutes to Okemo! for $152 for your next trip.

vrbo logo
View deal
9.6 / 10.0
Outstanding(68 Ratings)
Franklyn Farm Inn
Bed and Breakfast
 in Chester
3star
2 guests · 1 bedroom · 1 bath
Free WiFi/internet · Air conditioning · Shared living spaces

Experience the best of Chester with this Bed and Breakfast available for $153. This property is equipped with amenities including Free Parking, Garden and Non-smoking, and more.

booking logo
View deal
10.0 / 10.0
Outstanding(3 Ratings)
Spacious 5-bedroom cabin in charming Chester
Cabin
 in Chester
10 guests · 5 bedrooms · 2 baths

This Cabin in Chester, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

expedia logo
View deal
Hike, Ski & Unwind: Cabin w/ Deck in Chester!
House
 in Chester
6 guests · 3 bedrooms · 1 bath
Free WiFi/internet · Air conditioning · TV

When traveling to Chester, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $135 per night.

evolve logo
View deal
8.4 / 10.0
Excellent(7 Ratings)
Honeymoon Suite with Jacuzzi Tub in Historic Inn
Bed and Breakfast
 in Chester
3 guests · 1 bedroom · 1 bath

Enjoy the best of Chester in our Bed and Breakfast, Honeymoon Suite with Jacuzzi Tub in Historic Inn. A stunning property with amenities including Family friendly, and more.

vrbo logo
View deal
2.0 / 10.0
(1 Rating)
Hike, Ski & Unwind: Cabin w/ Deck in Chester!
Cottage
 in Chester
2 guests

Looking to create some memories in Chester? Look no further than our Cottage, Hike, Ski & Unwind: Cabin w/ Deck in Chester!. Enjoy top-rated amenities including Non-smoking, and more.

hotelscom logo
View deal
You can save with One Key
9.0 / 10.0
Outstanding(2 Ratings)
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
Bed and Breakfast
 in Chester
3 guests · 1 bedroom · 1 bath

Soak up the beauty of Chester in our Bed and Breakfast, Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo! . With a range of amenities such as Family friendly, you'll feel right at home.

vrbo logo
View deal
10.0 / 10.0
Outstanding(27 Ratings)
Log Cabin Retreat - Chester, VT 25 Acres + State Forest Access
Cabin
 in Chester
8 guests · 3 bedrooms · 2 baths
Free WiFi/internet · TV · Coffee/tea maker

Experience vacation in Chester with our Cabin, Log Cabin Retreat - Chester, VT 25 Acres + State Forest Access. Enjoy amenities such as Dryer, WiFi/Internet and Kitchen, and more.

expedia logo
View deal
9.8 / 10.0
Outstanding(16 Ratings)
King & Queen Suite in Historic Inn Circa 1780
Bed and Breakfast
 in Chester
6 guests · 1 bedroom · 1 bath
WiFi/Internet · Air conditioning · TV

This inviting Bed and Breakfast in Chester can fit your needs for many types of vacations, at $204 per night.

vrbo logo
View deal
10.0 / 10.0
Outstanding(3 Ratings)
Ski Vermont! Amazing Vermont Farmhouse, perfect for getaways!
Farm Stay
 in Chester
8 guests · 4 bedrooms · 2 baths

Enjoy the best of Chester in our Farm Stay, Ski Vermont! Amazing Vermont Farmhouse, perfect for getaways! . A stunning property with amenities including Pets allowed, Family friendly and Non-smoking, and more.

vrbo logo
View deal
10.0 / 10.0
Outstanding(3 Ratings)
Spacious 5-bedroom cabin in charming Chester
Cabin
 in Chester
10 guests · 5 bedrooms · 2 baths

Looking to create some memories in Chester? Look no further than our Cabin, Spacious 5-bedroom cabin in charming Chester. Enjoy top-rated amenities including Pets allowed, Family friendly and Non-smoking, and more.

vrbo logo
View deal
6.0 / 10.0
Average(1 Rating)
Hike, Ski and Unwind Cabin with Deck in Chester!
Cabin
 in Chester
6 guests · 3 bedrooms · 1 bath
Free WiFi/internet

Looking for a Cabin in Chester, this Cabin for $193 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

booking logo
View deal
2.0 / 10.0
(1 Rating)
Hike, Ski & Unwind: Cabin w/ Deck in Chester!
Cottage
 in Chester
2 guests

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Chester, at $224 per night for your next great vacation.

expedia logo
View deal
10.0 / 10.0
Outstanding(240 Ratings)
Vermont Hillside Cottage w/Great View - Pet Friendly, Fee Required
House
 in Chester
4 guests · 2 bedrooms · 1 bath

This House for $140 in Chester, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

vrbo logo
View deal
10.0 / 10.0
Outstanding(27 Ratings)
Log Cabin Retreat - Chester, VT 25 Acres + State Forest Access
Cabin
 in Chester
8 guests · 3 bedrooms · 2 baths
Free WiFi/internet · TV · Coffee/tea maker

Indulge in a peaceful retreat at Log Cabin Retreat - Chester, VT 25 Acres + State Forest Access, our elegant Cabin in Chester. Enjoy amenities including Dryer, WiFi/Internet and Kitchen, and more.

vrbo logo
View deal
You can save with One Key
Hike, Ski & Unwind: Cabin w/ Deck in Chester!
Cabin
 in Chester
6 guests · 3 bedrooms · 1 bath
WiFi/Internet · Air conditioning · TV

The best choice in Chester for Cabin, for $178 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

vrbo logo
View deal
9.8 / 10.0
Outstanding(73 Ratings)
Log Cabin - Cozy, Quaint & Scenic and Ready for Your Enjoyment!
Cabin
 in Chester
5 guests · 1 bedroom · 1 bath
WiFi/Internet · Air conditioning · Pool

Are you ready to indulge in a relaxing getaway? Our Cabin in Chester has everything you need for a rejuvenating stay. Treat yourself to Log Cabin - Cozy, Quaint & Scenic and Ready for Your Enjoyment!'s exceptional amenities, such as Air conditioning, Balcony/Terrace and WiFi/Internet.

expedia logo
View deal
10.0 / 10.0
Outstanding(26 Ratings)
Chester Farmhouse on 100 Acres, 15 Min to Okemo!
House
 in Chester
10 guests · 5 bedrooms · 2 baths
Free WiFi/internet · Air conditioning · TV

Indulge in a peaceful retreat at Chester Farmhouse on 100 Acres, 15 Min to Okemo!, our elegant House in Chester. Enjoy amenities including Pets allowed, Dryer and Mountain view, and more.

evolve logo
View deal
Chester Farmhouse on 100 Acres, 15 Min to Okemo!
Cottage
 in Chester
2 guests
Free WiFi/internet · Air conditioning · TV

This attractive Cottage in Chester, $282 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

hotelscom logo
View deal
You can save with One Key
9.7 / 10.0
Outstanding(73 Ratings)
Log Cabin - Cozy, Quaint & Scenic and Ready for Your Enjoyment!
Cabin
 in Chester
5 guests · 1 bedroom · 1 bath
WiFi/Internet · Air conditioning · Pool

The best choice in Chester for Cabin, for $289 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

vrbo logo
View deal
9.8 / 10.0
Outstanding(24 Ratings)
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
Cabin
 in Chester
4 guests · 2 bedrooms
Free WiFi/internet · Coffee/tea maker · Refridgerator

Are you ready to indulge in a relaxing getaway? Our Cabin in Chester has everything you need for a rejuvenating stay. Treat yourself to Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area's exceptional amenities, such as Fireplace, WiFi/Internet and Kitchen.

vrbo logo
View deal
9.6 / 10.0
Outstanding(51 Ratings)
Chester Farmhouse on 100 Acres, 15 Min to Okemo!
House
 in Chester
10 guests · 5 bedrooms · 2 baths
WiFi/Internet · Air conditioning · TV

This attractive House in Chester, $331 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

vrbo logo
View deal
Chester Farmhouse on 100 Acres, 15 Min to Okemo!
House
 in Chester
10 guests · 5 bedrooms · 2 baths
Free WiFi/internet

Soak up the beauty of Chester in our House, Chester Farmhouse on 100 Acres, 15 Min to Okemo!. With a range of amenities such as Free Parking, Pets allowed and Non-smoking, you'll feel right at home.

booking logo
View deal
10.0 / 10.0
Outstanding(24 Ratings)
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
Cabin
 in Chester
4 guests · 2 bedrooms
Free WiFi/internet · Coffee/tea maker · Refridgerator

Looking to create some memories in Chester? Look no further than our Cabin, Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area. Enjoy top-rated amenities including Fireplace, WiFi/Internet and Kitchen, and more.

expedia logo
View deal
You can save with One Key
10.0 / 10.0
Outstanding(10 Ratings)
Amazing Custom Home on 40+ Acres
House
 in Chester
12 guests · 5 bedrooms · 6 baths
WiFi/Internet · TV · Coffee/tea maker

When traveling to Chester, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $510 per night.

vrbo logo
View deal
10.0 / 10.0
Outstanding(7 Ratings)
Renovated ski house near Okemo and Stratton
House
 in Chester
8 guests · 3 bedrooms · 2 baths
WiFi/Internet · TV · Refridgerator

Looking to create some memories in Chester? Look no further than our House, Renovated ski house near Okemo and Stratton. Enjoy top-rated amenities including Dryer, WiFi/Internet and Kitchen, and more.

vrbo logo
View deal
You can save with One Key
10.0 / 10.0
Outstanding(3 Ratings)
Maple Leaf Manor - 1864 Brick Federal Style Farmhouse with a modern touches.
House
 in Chester
8 guests · 4 bedrooms · 3 baths

Discover the beauty of Chester with a stay at Maple Leaf Manor - 1864 Brick Federal Style Farmhouse with a modern touches., a top rated House with amenities such as Family friendly, and more.

vrbo logo
View deal
Chester Farmhouse on 100 Acres, 15 Min to Okemo!
Cottage
 in Chester
2 guests · 5 bedrooms · 2 baths
Free WiFi/internet · Air conditioning · TV

Looking for a Cottage in Chester, this Cottage for $282 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

expedia logo
View deal
Historic ski getaway near Okemo with sledding hill- where memories are made
House
 in Chester
16 guests · 8 bedrooms · 4 baths

This inviting House in Chester can fit your needs for many types of vacations, at $811 per night.

vrbo logo
View deal
9.4 / 10.0
Outstanding(6 Ratings)
Modern Chalet w/ Serene Views and Jacuzzi Hot Tub- 15 Minutes to Okemo Mountain
Chalet
 in Chester
6 guests · 2 bedrooms · 2 baths
Free WiFi/internet · Air conditioning · TV

Looking to create some memories in Chester? Look no further than our Chalet, Modern Chalet w/ Serene Views and Jacuzzi Hot Tub- 15 Minutes to Okemo Mountain. Enjoy top-rated amenities including Air conditioning, Balcony/Terrace and Dryer, and more.

vrbo logo
View deal