Book Cheap Hotels in Chester

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Check prices in Chester for tonight, Oct 22 - Oct 23
Oct 22 - Oct 23
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Check prices in Chester for tomorrow night, Oct 23 - Oct 24
Oct 23 - Oct 24
This weekend
Check prices in Chester for this weekend, Oct 24 - Oct 26
Oct 24 - Oct 26
Next weekend
Check prices in Chester for next weekend, Oct 31 - Nov 2
Oct 31 - Nov 2

Most frequently booked Chester hotels

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
40.53 km from city centre
The price is CA $489 per night
CA $489
CA $600 total
Nov 16 - Nov 17
includes taxes & fees
Stay at this 4.5-star luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Middle Covered Bridge and Woodstock Town Hall Theatre are located nearby.
Pool
Hot tub
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St., Woodstock, VT
41.03 km from city centre
Get rates
Stay at this 3-star hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Billings Park and Trail and Red Wagon Toy Company are located nearby.
Pet-friendly
Parking included
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
3567 Main Street Route 7A, Manchester, VT
Free cancellation
Reserve now, pay when you stay
40.25 km from city centre
The price is CA $195 per night
CA $195
CA $291 total
Oct 26 - Oct 27
includes taxes & fees
Stay at this 4.5-star luxury hotel in Manchester. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the property condition in our reviews. Popular attractions Golf Club at Equinox and American Museum of Fly Fishing are located nearby.
Pool
Hot tub
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
3835 Main St., Manchester, VT
40.02 km from city centre
The price is CA $234 per night
CA $234
CA $312 total
Nov 3 - Nov 4
includes taxes & fees
Stay at this 4-star golf hotel in Manchester. Enjoy an outdoor pool, breakfast (surcharge), and room service. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Golf Club at Equinox and American Museum of Fly Fishing are located nearby.
Pool
Pet-friendly
Jackson Gore Village

Jackson Gore Village

3 out of 5
111 Jackson Gore Road, Ludlow, VT
20.29 km from city centre
The price is CA $261 per night
CA $261
CA $317 total
Oct 23 - Oct 24
includes taxes & fees
Stay at this 3-star spa hotel in Ludlow. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Okemo Mountain Resort and Jackson Gore Parking are located nearby.
Pool
Hot tub
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
2940 State Route 103, Cavendish, VT
14.11 km from city centre
The price is CA $176 per night
CA $176
CA $201 total
Oct 26 - Oct 27
includes taxes & fees
Stay at this 3.5-star spa hotel in Cavendish. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Okemo Mountain Resort and Phineas Gage Memorial are located nearby.
Pool
Hot tub
Mountaineer Inn

Mountaineer Inn

2 out of 5
270 Handle Rd, West Dover, VT
Free cancellation
Reserve now, pay when you stay
41.12 km from city centre
The price is CA $201 per night
CA $201
CA $232 total
Oct 31 - Nov 1
includes taxes & fees
Stay at this motel in West Dover. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Mount Snow and Heavy Metal Ski Lift are located nearby.
Pool
Pet-friendly
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

2.5 out of 5
175 Key Rd, Keene, NH
Free cancellation
Reserve now, pay when you stay
44.68 km from city centre
The price is CA $175 per night
CA $175
CA $190 total
Oct 29 - Oct 30
includes taxes & fees
Book a stay at this business-friendly hotel in Keene. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Ashuelot River and Cheshire Children's Museum are located nearby.
Pool
Breakfast included
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
485 Hotel Road, Brownsville, VT
24.72 km from city centre
The price is CA $195 per night
CA $195
CA $232 total
Nov 17 - Nov 18
includes taxes & fees
Stay at this 3-star resort in Brownsville. Enjoy an outdoor pool, a business center, and a fireplace in the lobby. Our guests praise the helpful staff in our reviews. Popular attractions Mount Ascutney and Mt Ascutney State Park are located nearby.
Pool
Restaurant
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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.

Top cheap Chester hotel deals

Motel in the Meadow

Motel in the Meadow

936 VT Route 11 West, Chester, VT
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Top hotels in Chester for Extended Stay

Ski-In Resort Room | 2 Queen Beds

Ski-In Resort Room | 2 Queen Beds

West Dover
The price is CA $243 per night from Oct 29 to Oct 30
CA $243
CA $307 total
Oct 29 - Oct 30
includes taxes & fees
10/10 Exceptional! (1 review)
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 hotels essential information

Accommodation
2,993 hotels
Lowest Price
CA $190
Highest Price
CA $601
Popular hotels
Woodstock Inn & Resort, The Shire Woodstock, The Equinox Golf Resort & Spa, Kimpton Taconic Hotel by IHG, Jackson Gore Village, Pointe at Castle Hill Resort, Mountaineer Inn, Keene Elm City Hotel, an Ascend Collection Hotel, Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Frequently asked questions

What are the top kid-friendly hotels in Chester?
Family vacations are where lifelong memories are made, but traveling with children can be tricky. These kid-friendly Chester hotels offer perks designed to keep old and young alike relaxed and happy: You'll be well taken care of at Charming Farmhouse in Chester. It comes with a fireplace, pet-friendly facilities and a flair for making families feel welcome. Otherwise, spend your nights enjoying the comforts of Rose Arbour Bed & Breakfast. Take advantage of complimentary breakfast, a cafe and more here.
Where can I find cheap hotels in Chester?
At Travelocity you'll find really nice hotels in Chester at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Chester rather than in Chester. We may find you even better rates, too.
How do I find the best Chester hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Chester then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Chester?
The cheapest hotel in Chester is CA $190 This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Chester?
There are 2,993 hotels in Chester on Travelocity.
What are the best hotels in Chester?
Chester has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Chester for you!
When is the best time to visit Chester?
If you want the joy of a fun-filled trip in peak season, visit Chester during December, January and February. If you'd prefer the peace of off-season, book a stay during quieter months, such as March, April and August.
When is the cheapest time to stay in Chester?
Based on historic data is usually the cheapest month to visit Chester. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Chester?
There are multiple hotels in Chester that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Chester. We have plenty of kid-friendly hotels in Chester to choose from on Travelocity!
Why book a hotel in Chester through Travelocity?
Because we have the top hotels in Chester! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Chester on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Chester hotel reviews by fellow wanderers

Claremont Motor Lodge

Claremont Motor Lodge

5 out of 5
Posted 4 days ago
Travelocity Verified Review
"It was clean safe and staff was is friendly and helpful "
A verified traveller stayed at Claremont Motor Lodge
Claremont Motor Lodge

Hotels near…

Areas of Chester