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Chester hotels and places to stay

Waterfront Log Cabin on the Williams River in Chester, now with AC~VT~
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4.35 km from city centre
4.7/5Exceptional! (52 reviews)
Awesome cabin in a great location

"We had an amazing stay at the Wilkins cabin. The place is clean, and has everything you need for a great stay. We enjoyed sitting outside and listening to the river nearby. The cabin is in a great location, close to town but feels secluded and private. Thank you Wilkins family for sharing your great ..."…"

Reviewed on Oct. 25, 2019

Waterfront Log Cabin on the Williams River in Chester, now with AC~VT~
Come Stay @ the 1843 Stone House! 3bd/2bath
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0.45 km from city centre
5/5Exceptional! (52 reviews)
Loved it

"Best VRBO experience. Everything needed great communication and easy to find everything. Thank you."…"

Reviewed on Mar. 18, 2020

Come Stay @ the 1843 Stone House! 3bd/2bath
Vacation Rental - Choose From 5 Nearby Mountains or Relax in Peace & Comfort
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1.66 km from city centre
4.7/5Exceptional! (3 reviews)
Very pleasant stay for leaf peeping in Vermont

"We enjoyed staying in the very well appointed home. I would stay there again. My wife had some concerns with the ceiling mounted camera in the dining area pointed towards the front door, but the owner had no problem with us unplugging it while we were there."…"

Reviewed on Oct. 31, 2019

Vacation Rental - Choose From 5 Nearby Mountains or Relax in Peace & Comfort
Historic Vermont Village Home & Guest Suite - Hike, Bike, & Relax
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0.91 km from city centre
4.8/5Exceptional! (12 reviews)
Fabulous Chester, VT Home

"We have stayed here multiple times and always enjoy our stay. The home is beautiful and location is perfect. I was especially pleased with how well stocked the kitchen is. I had every pot, pan and utensil I needed to cook a delicious Thanksgiving dinner."…"

Reviewed on Nov. 30, 2019

Historic Vermont Village Home & Guest Suite - Hike, Bike, & Relax
Best Western Springfield Hotel
2.5 out of 5
818 Charlestown Rd, Springfield, VT
The price is CA $207 per night
12.97 km from city centre
4.3/5Excellent! (393 reviews)

"We stayed there for a funeral and they where very accommodating to all who stayed"…"

Reviewed on Mar. 7, 2020

Best Western Springfield Hotel
Motel in the Meadow
2.5 out of 5
936 VT Route 11 West, Chester, VT
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2.34 km from city centre
4.2/5Very Good! (71 reviews)

"Cute little motel. Basic but has what you need. Yummy muffins for breakfast too."…"

Reviewed on Mar. 2, 2020

Motel in the Meadow
Hugging Bear Inn and Shoppe
2.5 out of 5
244 Main Street, Chester, VT
The price is CA $164 per night
0.14 km from city centre
4.5/5Wonderful! (97 reviews)

"Inn is clean, conveniently located, breakfast is great, and Kristen is an amazing host, which is why we keep coming back."…"

Reviewed on Feb. 27, 2020

Hugging Bear Inn and Shoppe
Fullerton Inn
2.5 out of 5
40 The Common, Chester, VT
Free CancellationReserve now, pay when you stay
The price is CA $157 per night
0.13 km from city centre
3.9/5Good! (71 reviews)

"Quiet country atmosphere. Room was clean and very comfortable. Will definitely book here again."…"

Reviewed on Mar. 9, 2020

Fullerton Inn
Rose Arbour Bed & Breakfast
2.5 out of 5
55 School Street, Chester, VT
The price is CA $160 per night
0.08 km from city centre
4/5Very Good! (76 reviews)
Perfect spot for a get away...

"My wife and I went to the Grafton Food Festival and decided to stay in the area over night. Rose Arbour was close and fit the bill. Nice spot, close to the Chester down town. The owner is very friendly. We fond the place to be clean and the breakfast in the morning was delicious."…"

Reviewed on Jul. 20, 2019

Rose Arbour Bed & Breakfast
Palmer House Resort
3 out of 5
5383 Main St, Manchester Center, VT
The price is CA $155 per night
37.66 km from city centre
4.3/5Excellent! (412 reviews)
Nice spacious rooms

"Although not clear in the description, this is a motel. The rooms are nice, spacious, and recently renovated. It is very clean. We enjoyed our stay. We had some issues that required maintenance and they had no maintenance staff on hand on a busy weekend. They did refund part of our $$. Staff was ..."…"

Reviewed on Mar. 20, 2020

Palmer House Resort
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Chester Hotel Guide

Planning to spend some time in Central Vermont- Killington? Hoping to book somewhere to stay in the Chester area? Within a 0.1-kilometre (0.06-mile) radius of its central area, you can find 5 Expedia-listed accommodation options.

Visitors hoping to find a great place to stay close to the center of Chester, should check out the latest offers at the Hugging Bear Inn and Shoppe and Rose Arbour Bed & Breakfast.

14 kilometres (8 miles) away from the heart of Chester, is the Castle Hill Resort And Spa. Alternatively, the Mountain Lodge at Okemo Mountain Resort is located 18 kilometres (11 miles) away. Some other places to stay are the Jackson Gore Inn and the The Andrie Rose Inn.

For those keen to see more of the forests and mountains that are a big feature in this part of the world, you might also plan some extra nights in other places in Central Vermont. Spend your time snowboarding, skiing and cross-country skiing or see the region's attractions. Comfortable hotels are available.

45 kilometres (29 miles) from Chester you'll find Killington, where visitors can enjoy Killington Ski Resort and Green Mountain National Golf Course. Should you wish to visit Killington, check out the Killington Grand Resort Hotel and Mountain Green Ski & Golf Resort. Or, you could stay in Rutland, 50 kilometres (30 miles) to the northwest of Chester, where you'll find the Hampton Inn Rutland and Best Western Inn & Suites Rutland-Killington. If you stay in Rutland, a couple of places to add to your itinerary are the Pine Hill Park and Vermont State Fairgrounds.

Get your sports fix with a journey to Verizon Wireless Arena, which is 95 kilometres (60 miles) to the east of Chester. Book accommodation near the action at the Hilton Garden Inn Manchester Downtown or the Radisson Hotel Manchester Downtown.

Now that you have learnt a little about accommodation options in Chester, take the time to check out Expedia's Chester travel guide for more great information on the many great attractions here.

Frequently asked questions

Where is the best place to stay in Chester?
Based on our traveler data, Hugging Bear Inn and Shoppe is one of the top choices for your stay. This B&B offers free breakfast and free WiFi. Other good options for your trip include Fullerton Inn and The Karass Inn.
If I need to cancel my hotel reservation in Chester, will I receive a refund?
Yes, the majority of hotel reservations are fully refundable provided that you cancel before the accommodation’s cancellation deadline, which is often 24 or 48 hours before the scheduled arrival. If you have a non-refundable reservation, it might still be possible to cancel it and be given a refund within 24 hours of booking. Enter dates in and click on “Search”, then you can filter by “free cancellation” to get the top deals on offer in Chester.
What's the best place to stay on a budget in Chester?
Based on reviews, Motel in the Meadow is a popular 2.5-star property for our travelers looking for an economical choice, and features free breakfast and free WiFi.
What's the best accommodation for a romantic vacation in Chester?
Fullerton Inn is a favorite B&B for couples.
What's the best pet-friendly accommodation in Chester?
Motel in the Meadow is a top dog-friendly property, and offers free WiFi for its human guests.
What's the best place to stay for a winter vacation in Chester?
Based on our travel data, The Karass Inn is a top 3-star B&B for a winter getaway, and features ski storage and free breakfast. Other good choices for your ski trip include Motel in the Meadow and Hugging Bear Inn and Shoppe. Spend your days on the slopes by visiting Okemo Mountain Resort, Magic Mountain Ski Resort, or Jackson Gore Ski Resort at Okemo.
What are some accommodations with pools in Chester?
Come Stay @ the 1843 Stone House! 3bd/2bath: Features an outdoor tennis court, a communal pool, and an in-room kitchen.
What is staying in Chester like?
Visitors to Chester are sure to enjoy the ski areas, coffeehouses, and shopping. Quaint and relaxing, this city also attracts tourists with its restaurants. Top sights around the area include Okemo Mountain Resort, Stratton Mountain Resort, and Magic Mountain Ski Resort. In Chester, there are 15 hotels and other accommodations to choose from.

Recent Reviews in Chester

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