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The Karass Inn
3 out of 5
225 Pleasant Street, Chester, VT
Free cancellationReserve now, pay when you stay
The price is CA $150 per night from Oct 19 to Oct 20
1.13 km from city centre
4.5/5Wonderful! (57 reviews)

"The Karass Inn is a very nice place for a relaxing weekend. Great location and the staff are very helpful. Bedding and room were super clean. I should mention we loved our breakfast each morning."…"

Reviewed on Jul. 19, 2020

The Karass Inn
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! (56 reviews)
Wonderful!!!!!

"Loved it was a little disappointing that we couldn't swim due to the river being so low but the weather was on our side and keep it cool. Loved the farm down the road and the train was such a highlight for my husband. If it was available for future use we would of made it our cabin to go to all the ..."…"

Reviewed on Aug. 26, 2020

Waterfront Log Cabin on the Williams River in Chester, now With Ac~vt~
Beautifully Renovated Circa 1900 Farmhouse on 31 Magnificient Acres
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5.34 km from city centre
5/5Exceptional! (2 reviews)
A rare opportunity to experience an idyllic Vermont farm.

"As someone who knows Vermont very well, I am pleased to recommend this stay. Glenn and his family have, top to bottom, carefully restored a beautifully sited farmhouse and barn. The surrounding fields and forest... the apple trees, pond, and bullfrogs offer a wonderful hilltop place to reconnect ..."…"

Reviewed on Sep. 8, 2020

Beautifully Renovated Circa 1900 Farmhouse on 31 Magnificient Acres

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Secluded log Cabin on 25 Acres Bordering State Forest With Trails Nearby
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7 km from city centre
5/5Exceptional! (4 reviews)
The perfect place for a peaceful stay

"Everything was great, will definitely come back as soon as possible, very peaceful, very clean, beautiful house, host was very helpful."…"

Reviewed on Sep. 9, 2020

Secluded log Cabin on 25 Acres Bordering State Forest With Trails Nearby
Come Stay @ the 1843 Stone House! 3bd/2bath
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0.45 km from city centre
5/5Exceptional! (44 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
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
Free cancellationReserve now, pay when you stay
The price is CA $183 per night from Sep 20 to Sep 21
12.97 km from city centre
4.3/5Excellent! (399 reviews)

"Was a quick stay. But very convenient location. Big pool kids love."…"

Reviewed on Mar. 8, 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
Windsor Mansion Inn
3.5 out of 5
153 Pembroke Road, Windsor, VT
The price is CA $164 per night from Oct 19 to Oct 20
30.06 km from city centre
4.6/5Wonderful! (132 reviews)

"Lovely room and excellent location. Andy was a great host. Good value!"…"

Reviewed on Sep. 8, 2020

Windsor Mansion Inn
Fullerton Inn
2.5 out of 5
40 The Common, Chester, VT
Free cancellationReserve now, pay when you stay
The price is CA $170 per night from Sep 19 to Sep 20
0.13 km from city centre
3.9/5Good! (74 reviews)
Good value

"Nice and good price."…"

Reviewed on Apr. 10, 2020

Fullerton Inn
The Manchester View - Near Manchester Designer Outlets
2.5 out of 5
77 High Meadow Way & VT-7A, Manchester Center, VT
Free cancellationReserve now, pay when you stay
The price is CA $184 per night from Sep 20 to Sep 21
35.98 km from city centre
4.5/5Wonderful! (212 reviews)

"Loved the view of the mountains! Room was nice and big"…"

Reviewed on Sep. 16, 2020

The Manchester View - Near Manchester Designer Outlets
Rose Arbour Bed & Breakfast
2.5 out of 5
55 School Street, Chester, VT
The price is CA $192 per night from Sep 20 to Sep 21
0.08 km from city centre
4/5Very Good! (76 reviews)

"Had to leave before breakfast and Suzanne was kind enough to get me a scone and a few strawberries the night before. That’s about the best I can say about my stay. I woke up in the middle of the night frozen to the bone. Next morning I realized the there was about an inch of air between the window ..."…"

Reviewed on Oct. 22, 2019

Rose Arbour Bed & Breakfast
Holiday Inn Club Vacations Mount Ascutney Resort
3 out of 5
485 Hotel Road, Brownsville, VT
Free cancellation
The price is CA $199 per night from Sep 21 to Sep 22
24.69 km from city centre
4.3/5Excellent! (466 reviews)

"Super clean, super big apartment style rooms. The resort has a lot to do. Including indoor and outdoor pool (super big and warm), Tennis courts, walking trails, fire pit and a nice restaurant. The rooms have a full kitchen with everything you need to make a nice meal. Highly recommend!"…"

Reviewed on Sep. 4, 2020

Holiday Inn Club Vacations Mount Ascutney Resort
Palmer House Resort
3 out of 5
5383 Main St, Manchester Center, VT
Free cancellationReserve now, pay when you stay
The price is CA $176 per night from Sep 20 to Sep 21
37.66 km from city centre
4.3/5Excellent! (425 reviews)

"Clean quiet close to everything will defiantly go back"…"

Reviewed on Sep. 10, 2020

Palmer House Resort
Hugging Bear Inn and Shoppe
2.5 out of 5
244 Main Street, Chester, VT
The price is CA $183 per night from Sep 19 to Sep 20
0.14 km from city centre
4.5/5Wonderful! (98 reviews)

"Very friendly and attentive! Quiet and cozy bed and breakfast- walkable you restaurants in Chester. Enjoyed our stay."…"

Reviewed on Mar. 1, 2020

Hugging Bear Inn and Shoppe
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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?
Hugging Bear Inn and Shoppe is ranked highly by Expedia customers. This B&B offers free breakfast and free WiFi. Another top choice for your visit based on reviews is 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 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?
Rose Arbour Bed & Breakfast is a top B&B for hitting the ski slopes, and features free breakfast and free WiFi. This B&B is located 20 minutes by car from Magic Mountain Ski Resort. Other good options to stay near skiing include The Karass Inn and Chester House Inn.
What are some accommodations with pools in Chester?
Come Stay @ the 1843 Stone House! 3bd/2bath: Offers an outdoor tennis court, a communal pool, and an in-room kitchen.

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