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Our top choices for Chester hotels

Fullerton Inn

Fullerton Inn
2.5 star property
Chester Depot
8.2 out of 10, Very good, (433 reviews)
"The staff were incredible and the property have the perfect vibes for a ski trip. The food was great and everything was very clean and comfy."
United States
Rob
The price is CA $176
CA $192 total
includes taxes & fees
Apr 30 - May 1
Fullerton Inn

Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (118 reviews)
"Great stay! Very cozy and homey. Very yummy breakfast! "
United States
Olena
The price is CA $263
CA $286 total
includes taxes & fees
Apr 29 - Apr 30
Stone Hearth Inn and Eatery

Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very good, (967 reviews)
"Everyone was nice!"
United States
Jon
The price is CA $178
CA $195 total
includes taxes & fees
May 4 - May 5
Hampton Inn Brattleboro

Brittany Motel

Brittany Motel
2.0 star property
Manchester Center
9.4 out of 10, Exceptional, (348 reviews)
"Clean comfortable room for a great price, offering snacks and board games to boot. Phone staff accommodating and answer quickly. "
United States
Natalie
The price is CA $102
CA $112 total
includes taxes & fees
May 7 - May 8
Brittany Motel

Lincoln Inn & Gallery

Lincoln Inn & Gallery
3.0 star property
West Woodstock
8.8 out of 10, Excellent, (66 reviews)
"Super friendly and knowledgeable staff. The Inn is historic, in a lovely spot, and reasonably priced. Dining recommendations were spot on. "
United States
Christina
The price is CA $132
CA $145 total
includes taxes & fees
Apr 29 - Apr 30
Lincoln Inn & Gallery

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (802 reviews)
"The room was clean and the staff was wonderful"
United States
Julianne
The price is CA $201
CA $221 total
includes taxes & fees
May 2 - May 3
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
8.6 out of 10, Excellent, (1,002 reviews)
"Great stay "
United States
Rashida
The price is CA $184
CA $200 total
includes taxes & fees
Apr 29 - Apr 30
Keene Elm City Hotel, an Ascend Collection Hotel

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very good, (1,005 reviews)
"The stay was great"
United States
Devon
The price is CA $196
CA $213 total
includes taxes & fees
Apr 29 - Apr 30
Best Western Plus Keene Hotel

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very good, (1,006 reviews)
"Pleasant stay!"
United States
Steven
The price is CA $128
CA $141 total
includes taxes & fees
May 19 - May 20
The Putney Inn

Claremont Motor Lodge

Claremont Motor Lodge
2.5 star property
Claremont
8.8 out of 10, Excellent, (496 reviews)
"Great staff.. super clean rooms comfy beds definitely will be back"
United States
Maryann
The price is CA $138
CA $150 total
includes taxes & fees
May 1 - May 2
Claremont Motor Lodge

Best Western Springfield Hotel

Best Western Springfield Hotel
2.5 star property
Springfield
8.8 out of 10, Excellent, (854 reviews)
"Location and amenities were great and so was breakfast "
United States
Adina
The price is CA $220
CA $241 total
includes taxes & fees
May 5 - May 6
Best Western Springfield Hotel

Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (441 reviews)
"We had an enjoyable stay and would stay again. "
United States
Donna
The price is CA $115
CA $126 total
includes taxes & fees
May 10 - May 11
Bromley View Inn

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (352 reviews)
"The hotel was very clean, the staff were friendly and welcoming, and the breakfast was delicious."
United States
Sahand
The price is CA $202
CA $222 total
includes taxes & fees
May 12 - May 13
Colonel Williams Inn

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (33 reviews)
"My stay was wonderful. Great accommodations, friendly and helpful staff, the pub downstairs was perfect to grab a quick bite and a drink. I will be staying again next time I am in the area"
United States
Glenn
The price is CA $169
CA $184 total
includes taxes & fees
May 6 - May 7
Four Columns Inn

Chalet 239

Chalet 239
2.0 star property
West Dover
9.4 out of 10, Exceptional, (124 reviews)
"The room was clean and staff were kind and friendly. "
United States
Sung
The price is CA $159
CA $175 total
includes taxes & fees
Apr 29 - Apr 30
Chalet 239

Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (259 reviews)
"Staff were wonderful, food was excellent, environment was peaceful, everything was clean and in decent condition."
United States
Charles
The price is CA $200
CA $218 total
includes taxes & fees
Apr 29 - Apr 30
Harvest Barn Inn

Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow
2.0 star property
West Dover
8.8 out of 10, Excellent, (90 reviews)
"Was perfect for ski weekend. Will come back for sure!"
United States
Brett
The price is CA $133
CA $146 total
includes taxes & fees
Apr 30 - May 1
Hideaway Inn Mt. Snow

Aerie Inn of Vermont

Aerie Inn of Vermont
2.0 star property
East Dorset
9.4 out of 10, Exceptional, (180 reviews)
"Very comfortable room and nice staff. Will stay there again. "
United States
Laura
The price is CA $158
CA $172 total
includes taxes & fees
Apr 29 - Apr 30
Aerie Inn of Vermont

Black Mountain Inn

Black Mountain Inn
2.0 star property
Brattleboro
7.4 out of 10, Good, (490 reviews)
"Small place. Retro style. Nice for a stop over. Clean room. Felt safe. Super helpful staff. "
United States
Grace
The price is CA $147
CA $162 total
includes taxes & fees
Apr 30 - May 1
Black Mountain Inn

The Covered Bridge Inn

The Covered Bridge Inn
2.5 star property
Brattleboro
7.6 out of 10, Good, (1,000 reviews)
"Clean room, quiet, good price "
United States
Derek
The price is CA $135
CA $148 total
includes taxes & fees
Apr 30 - May 1
The Covered Bridge Inn
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Where to stay in Chester

Find the best Chester areas and neighborhoods for the activities you enjoy most.

Chester Depot

If you're spending some time in Chester Depot, DaVallia Art & Accents and Bonnie's Bundles Dolls are top sights worth seeing.

Stay near popular Chester attractions

Learn more about Chester

Nestled in a relaxing small-town setting, Chester invites visitors to explore DaVallia Art & Accents and browse handcrafted treasures at Bonnie's Bundles Dolls. Outdoor enthusiasts can enjoy nearby Stoughton Pond Recreation Area or take a scenic drive to Lowell Lake State Park and the charming Vermont Country Store.

aerial view of the Quechee Covered Bridge, over the Ottauquechee River, Quechee Vermont

Top Chester Hotel Reviews

Recent Reviews in Chester

More cheap stays in Chester

Hotels in Chester with star rating

Find out more about Chester

Top reasons to visit Chester

  • Outdoor Adventures: Chester is perfect for skiing, hiking, and exploring local parks, catering to all adventure enthusiasts.
  • Rich History: History buffs can explore the area’s heritage at the local history museum, offering insights into the past.
  • Charming Accommodations: Enjoy a variety of cozy bed & breakfasts and agritourism properties for a unique stay.
  • Scenic Beauty: The picturesque surroundings provide stunning views and a tranquil atmosphere away from crowds.
  • Family-Friendly Activities: Chester offers various activities for families, ensuring a well-rounded vacation experience.

Find great hotels near Chester

Discover a charming selection of accommodations in Chester, Vermont, where agritourism properties and cozy bed & breakfasts cater to every type of traveler. Whether you're seeking family-friendly options, adventurous getaways, or pet-friendly stays, Chester offers a variety of hotels and inns to ensure a memorable experience. Explore the best hotels in the area, including the inviting Chester Inn, to enjoy a delightful stay in this picturesque New England town.

  • Best Western Springfield Hotel: Embrace a pet-friendly getaway at the Best Western Springfield Hotel, located 12.9km from Chester. This welcoming property is perfect for travellers looking to bring their furry friends along for the adventure. With amenities tailored for pets, including designated areas for dogs and a relaxed atmosphere, guests can enjoy a comfortable stay while exploring the surrounding beauty of Vermont. Convenience meets hospitality in this family-friendly hotel, making it an excellent choice for those seeking a home away from home.
  • Pointe at Castle Hill Resort: Experience the perfect blend of business and leisure at Pointe at Castle Hill Resort, just 14.5km from Chester. This 3.5-star hotel caters to business travellers with accessible meeting rooms and a fully equipped business centre. For those craving adventure, the resort offers a variety of outdoor activities, including fishing, skiing, and ziplining. After an exhilarating day, unwind at the full-service spa featuring massages and body treatments. Whether you're here for business or pleasure, this resort ensures an enriching stay.
  • Jackson Gore Village: Ideal for families and golf enthusiasts, Jackson Gore Village is located 20.9km from Chester and offers a delightful blend of relaxation and recreation. With amenities designed for children, including a playground and arcade games, families can enjoy quality time together. Golfers will appreciate the on-site golfing experience, while the full-service spa provides rejuvenating treatments like hot stone and deep tissue massages. This 3-star hotel combines family fun with wellness, making it an excellent choice for a memorable vacation.

Things to do near Chester

Chester, Vermont, offers an exciting blend of skiing and outdoor adventures, making it an ideal destination for sports enthusiasts. Visitors can enjoy various activities at local ski resorts, explore scenic sightseeing opportunities, and unwind around cozy fire pits. Whether you're hitting the slopes or relaxing in the great outdoors, Chester promises a memorable vacation experience for all.

Shopping

In Chester, visit the Vermont Country Store, a charming spot located 9.7km away, offering unique gifts and Vermont-made products. My Minds Design, also 9.7km away, features eclectic home décor. If you're up for a drive, the West River Farmers Market, 17.7km away, showcases local produce and crafts.

Recreation

Experience the scenic Fox Run Golf Course, just 19.3km from Chester, where you can enjoy outdoor sports in a vibrant atmosphere. Alternatively, indulge in wellness and relaxation at The Ice House Ice Skating, located 20.9km away, perfect for unwinding with friends and family.

Adventure

At Okemo Mountain Resort, located 17.7km from Chester, experience thrilling skiing amidst stunning landscapes. Morningside Flight Park, 19.3km away, offers breathtaking scenic flights that will elevate your adventure. For more excitement, try the Solitude Express Ski Lift, also 19.3km from Chester, providing exhilarating access to the slopes.

Nightlife

In Chester, Vermont, the nightlife offers a mix of culture and entertainment. The Weston Playhouse and Bellows Falls Opera House provide captivating theatrical experiences, while Maple Lanes ArcadeAdventureZone adds an adventurous twist with fun arcade games, perfect for families and friends seeking a lively night out.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Chester

To save money on your trip to Chester, Vermont, consider visiting during the off-peak months of April to May and November for lower accommodation prices. Tuesdays are the most affordable days to stay, while Fridays tend to be pricier. Use Expedia’s search tool to find budget-friendly options, and consider eco-certified hotels for sustainable choices. Additionally, combining your hotel, flights, and activities into an Expedia package can lead to significant savings. Take advantage of free activities in the area, and explore on foot to save on transportation costs.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Chester are April to May and November, where the prices are slightly lower. This is in comparison to January to February and October, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Chester is Tuesday. The most expensive day to stay in Chester is Friday.
  • Find cheap hotels on Expedia: Utilize Expedia’s search tool to refine your preferences based on your budget, desired location, and preferred hotel type. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels that are currently available. To find the best prices and deals, simply sort the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your hotel stay in Chester with your flights and activities by choosing an Expedia package.

Best time to go to Chester

The best time to visit Chester can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Chester falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Chester falls in January, visitor numbers are slightly low and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January20.7°F (-6.3°C)Light RainMostly CloudySlightly LowSlightly High
February22.6°F (-5.2°C)Light RainMostly CloudySlightly LowSlightly High
March30.7°F (-0.7°C)Light RainMostly CloudySlightly LowAverage
April42.8°F (6.0°C)Light RainMostly CloudyAverageSlightly Low
May55.8°F (13.2°C)Light RainMostly SunnyAverageSlightly Low
June63.1°F (17.3°C)Light RainMostly SunnyAverageAverage
July69.3°F (20.7°C)Light RainMostly SunnySlightly HighAverage
August67.3°F (19.6°C)Light RainMostly SunnySlightly HighAverage
September60.3°F (15.7°C)Light RainMostly SunnySlightly HighAverage
October48.6°F (9.2°C)Light RainMostly SunnyAverageSlightly High
November36.1°F (2.3°C)Light RainMostly SunnyAverageSlightly Low
December27.3°F (-2.6°C)Light RainMostly CloudyAverageAverage

The nearest major airports for your trip to Chester

To visit Chester, Vermont, you have several airport options. Lebanon Municipal Airport (LEB) is situated 46.7km away, with nearby accommodations like the 4-star Hanover Inn Dartmouth, 8.0km from the airport, and the 3-star Hotel Coolidge, 3.2km from LEB. Rutland Southern Vermont Regional Airport (RUT) is 28.0km away, with options such as the 3.5-star Killington Grand Hotel, 16.1km from RUT. Lastly, Hartness State Airport (VSF) is conveniently located just 11.3km from Chester, with nearby stays like the 4-star Inn at Weathersfield, 1.6km away. Each airport offers various transportation services to ensure a smooth arrival.

Frequently asked questions

What is the best area to stay in Chester?
The best area to stay in Chester, Vermont, is the historic downtown village.

This area is the heart of Chester, centred around Main Street (Route 11) and North Street (Route 103). It's characterised by its attractive historic buildings, including the iconic stone village library and the Chester Green. You'll find a selection of local shops, art galleries, and eateries, all within an easily walkable distance.

For couples seeking a relaxing getaway, the village offers a delightful setting. You can enjoy strolls past historic homes, browse unique shops, and dine at charming local restaurants. Many of the guesthouses and inns in this area provide a cosy, intimate experience great for a romantic break.

Families will also find the village a convenient and pleasant base. The Chester Green provides open space for children to play, and the proximity to local ice cream parlours and family-friendly dining options makes evenings easy.
What are the best hotels in Chester that travellers recommend?
Two of the best hotels in Chester that receive consistently high recommendations from travellers are the Stone Hearth Inn and Eatery and the King & Queen Suite in Historic Inn Circa 1780.

The 3-star Stone Hearth Inn and Eatery, with a 9.2 rating, is highly praised for its comfortable and clean rooms, as well as its excellent breakfast and food. Guests appreciate the beautiful location with mountain views and the convenience of a free buffet breakfast.

Another outstanding option is the King & Queen Suite in Historic Inn Circa 1780, which has an exceptional 9.8 rating. This accommodation features a kitchen, patio, and is situated in a mountainous setting. Guests frequently mention the good coffee provided.
What are the best family hotels in Chester?
The best family hotels in Chester include the Stone Hearth Inn and Eatery, the King & Queen Suite in Historic Inn Circa 1780, and Room in Historic Inn. 20 Minutes to Okemo.

The 3-star Stone Hearth Inn and Eatery, with an impressive 9.2 rating, is an excellent choice for families. It offers a variety of amenities tailored for children, such as games and books, along with highchairs and free cribs, making it very convenient for young families. Guests frequently praise the delicious breakfast and the comfortable, clean rooms. The hotel also boasts a beautiful mountain location, with mountain views and activities like mountain climbing and mountain biking nearby.

Another highly-rated option is the King & Queen Suite in Historic Inn Circa 1780, which has an outstanding 9.8 rating. This accommodation provides games for children and a kitchen, which can be very useful for families. It is also situated in a scenic mountain location.

Finally, Room in Historic Inn. 20 Minutes to Okemo. with a 9.2 rating, is another great choice. It features a sofa bed and a kitchen, offering flexibility and convenience for families. Guests often highlight the super comfortable pillows. This property also benefits from a mountain location and includes outdoor spaces like a deck or patio.
What hotels in Chester offer free breakfast?
For hotels in Chester that offer complimentary breakfast, consider the Stone Hearth Inn and Eatery, the Fullerton Inn, or the Motel in the Meadow.

The 3-star Stone Hearth Inn and Eatery, with an impressive 9.2 rating, provides a free buffet breakfast. Guests often praise the delicious breakfast and comfortable, clean rooms. The inn is set in a beautiful mountain location, offering mountain views and easy access to mountain climbing and mountain biking activities. Free WiFi and parking are also available.

Another good option is the Fullerton Inn, rated 8.2. This inn offers a free continental breakfast, and guests frequently praise the great food, cozy and clean rooms, and friendly staff. Free WiFi and parking are included.

The Motel in the Meadow, with an 8.4 rating, also provides a free continental breakfast. This motel is a convenient choice for those travelling with pets, as pets stay free. Free WiFi and parking are also provided. Find more hotels with free breakfast in Chester
What are the top pet-friendly hotels in Chester?
For a top pet-friendly hotel in Chester, consider the Motel in the Meadow.

The Motel in the Meadow, rated 8.4, is an excellent choice for travellers with canine companions, as it welcomes dogs and offers a Pets Stay Free policy. Guests can also enjoy a complimentary continental breakfast during their stay. See more pet-friendly hotels in Chester
What are the best budget hotels in Chester?
For budget-friendly accommodation in Chester, consider the Stone Hearth Inn and Eatery, Motel in the Meadow, and Fullerton Inn.

The 3-star Stone Hearth Inn and Eatery, with an impressive 9.2 rating, offers complimentary WiFi, free toiletries, and a delicious free buffet breakfast. Guests consistently praise the great and delicious breakfast, comfortable and clean rooms, and excellent hospitality.

Another good option is the Motel in the Meadow, rated 8.4. This motel provides free WiFi, complimentary breakfast, and free self-parking. Pets are also welcome to stay free of charge.

The Fullerton Inn, with a rating of 8.2, also offers free WiFi, complimentary toiletries, and a free continental breakfast. Travellers have highlighted the great and delicious food, cozy and clean rooms, and friendly and helpful staff. The hotel also features a great on-site restaurant. View all budget hotels in Chester
What are the most romantic hotels in Chester for couples?
For a romantic stay in Chester, the Stone Hearth Inn and Eatery is a delightful option.

This 3-star inn, with an impressive 9.2 rating, is often praised by guests for its beautiful location and excellent hospitality. Couples particularly enjoy the comfortable and clean rooms, as well as the delicious food served. The inn offers complimentary breakfast, including a buffet option, and free WiFi. Its mountain views and proximity to mountain climbing and mountain biking activities make it a wonderful choice for an active yet romantic getaway. See all romantic hotels in Chester
What are the best hotels in Chester near Bonnie's Bundles Dolls?
For hotels in Chester conveniently located near Bonnie's Bundles Dolls, consider the Fullerton Inn, King & Queen Suite in Historic Inn Circa 1780, Room in Historic Inn. 20 Minutes to Okemo., and the Stone Hearth Inn and Eatery.

The Fullerton Inn, with an 8.2 rating, is particularly close to Bonnie's Bundles Dolls, just 0.9 km away. Guests appreciate the complimentary continental breakfast, free toiletries, and free WiFi, along with self-parking, making for a comfortable stay. Reviewers often mention the great food and friendly staff.

Even closer, at only 0.8 km from Bonnie's Bundles Dolls, are the King & Queen Suite in Historic Inn Circa 1780 and the Room in Historic Inn. 20 Minutes to Okemo.. The King & Queen Suite, boasting an exceptional 9.8 rating, offers amenities such as a kitchen and games for children, set within a historic inn with mountain views. The Room in Historic Inn., rated 9.2, also features a kitchen, a sofa bed, and a private deck or patio, superb for relaxing after a day of exploring.

A little further out, at 1.9 km from Bonnie's Bundles Dolls, is the 3-star Stone Hearth Inn and Eatery, which has a strong 9.2 rating. This family-friendly option provides amenities like highchairs, cribs, and books for children, along with free rollaway beds. Guests consistently praise the delicious breakfast, comfortable rooms, and the beautiful mountain location.
When is the best time to go to Chester?
The best time to go to Chester, Vermont, is during the autumn months of September and October for spectacular foliage, or in late spring and summer for pleasant weather and outdoor activities.

For those seeking the iconic New England autumn experience, September and October are ideal. The hills around Chester explode with vibrant reds, oranges, and yellows, making it a great time for scenic drives along routes like the Okemo Mountain Road or hiking on local trails. This period also often features local harvest festivals and craft fairs, offering a taste of local culture.

Late spring and summer, from May to August, offer warm, sunny days great for exploring the outdoors. You can enjoy activities such as cycling the Chester Green, fishing in the West River, or visiting nearby state parks. The weather is generally comfortable for walking around the village, browsing the antique shops, and dining al fresco.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Chester.
How can I save on a Chester hotel booking with Expedia?
Members always get our best prices. Find our best Chester hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.
How much is the nightly rate at a Chester hotel?
Prices for hotels in Chester often vary, but you can find a great deal from CA $141 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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