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Hotels in Chester

Last Minute Hot Rate® Hotel Deals in Chester

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Choose from 1459 Chester Hotel Deals

Windsor Mansion Inn
Windsor Mansion Inn
3.5 out of 5
153 Pembroke Road, Windsor, VT
  • 46 min drive from Bonnie's Bundles Dolls
The price is $125 per night from Dec 5 to Dec 5
Situated in a regional park, this bed & breakfast is within 3 mi (5 km) of American Precision Museum, Cornish-Windsor Covered Bridge, and Harpoon Brewery. Saint-Gaudens ...
Windsor Mansion Inn
Fullerton Inn
Fullerton Inn
2.5 out of 5
40 The Common, Chester, VT
  • 11 min walk from Bonnie's Bundles Dolls
The price is $129 per night from Dec 1 to Dec 1
Located in Chester Depot, this inn is within 9 mi (15 km) of Grafton Historical Society, Vermont Museum of Mining and Minerals, and Hunter Gallery of Fine Art. ...
Fullerton Inn
Rose Arbour Bed & Breakfast
Rose Arbour Bed & Breakfast
2.5 out of 5
55 School Street, Chester, VT
  • 12 min walk from Bonnie's Bundles Dolls
The price is $146 per night from Dec 1 to Dec 1
Located in Chester Depot, this bed & breakfast is within 9 mi (15 km) of Grafton Historical Society, Vermont Museum of Mining and Minerals, and Hunter Gallery ...
Rose Arbour Bed & Breakfast
Inn Victoria
Inn Victoria
4 out of 5
321 Main St, Chester, VT
  • 10 min walk from Bonnie's Bundles Dolls
Located in Chester Depot, this bed & breakfast is within 9 mi (15 km) of Grafton Historical Society, Vermont Museum of Mining and Minerals, and Hunter Gallery ...
Inn Victoria
Chester House Inn
Chester House Inn
3 out of 5
266 Main Street, Chester, VT
  • 11 min walk from Bonnie's Bundles Dolls
Located in Chester Depot, this bed & breakfast is within 9 mi (15 km) of Grafton Historical Society, Vermont Museum of Mining and Minerals, and Hunter Gallery ...
Chester House Inn
Motel in the Meadow
Motel in the Meadow
2.5 out of 5
936 VT Route 11 West, Chester, VT
  • 27 min walk from Bonnie's Bundles Dolls
Situated in Chester, this motel is within 9 mi (15 km) of Grafton Historical Society, Vermont Museum of Mining and Minerals, and Hunter Gallery of Fine Art. ...
Motel in the Meadow
The Karass Inn
The Karass Inn
3 out of 5
225 Pleasant Street, Chester, VT
  • 22 min walk from Bonnie's Bundles Dolls
Located in Chester Depot, this bed & breakfast is within 9 mi (15 km) of Grafton Historical Society, Vermont Museum of Mining and Minerals, and Gallery North ...
The Karass Inn
The Black Bear Lodge at Stratton Mountain Resort
The Black Bear Lodge at Stratton Mountain Resort
3 out of 5
5 Village Lodge Road, Stratton, VT
  • 45 min drive from Bonnie's Bundles Dolls
The price is $150 per night from Dec 1 to Dec 1
This family-friendly Stratton resort is located in the mountains, within 1 mi (2 km) of Stratton Mountain Summit Gondola Ski Lift and Stratton Mountain Resort. ...
The Black Bear Lodge at Stratton Mountain Resort
506 On the River Inn
506 On the River Inn
4 out of 5
1653 West Woodstock Road, Woodstock, VT
  • 57 min drive from Bonnie's Bundles Dolls
The price is $259 per night from Dec 7 to Dec 7
Conveniently near skiing facilities, this West Woodstock hotel is located on a river within 3 mi (5 km) of Union Arena Community Center, Billings Park and Trail, ...
506 On the River Inn
Pointe at Castle Hill Resort
Pointe at Castle Hill Resort
3.5 out of 5
2940 State Route 103, Cavendish, VT
  • 20 min drive from Bonnie's Bundles Dolls
The price is $169 per night from Dec 1 to Dec 1
Situated in a rural location, this spa hotel is within 6 mi (10 km) of Dorsey Park, Okemo Mountain Resort, and Jackson Gore Ski Resort at Okemo. Fox Run Golf ...
Pointe at Castle Hill Resort
Jackson Gore Village
Jackson Gore Village
3 out of 5
111 Jackson Gore Road, Ludlow, VT
  • 30 min drive from Bonnie's Bundles Dolls
The price is $208 per night from Dec 1 to Dec 1
Offering ski-in/ski-out access, this hotel in Ludlow is in the mountains, within a 15-minute walk of Jackson Gore Ski Resort at Okemo and Okemo Mountain Resort, ...
Jackson Gore Village
Castle Hill Resort And Spa
Castle Hill Resort And Spa
3.5 out of 5
2940 Route 103, Cavendish, VT
  • 20 min drive from Bonnie's Bundles Dolls
The price is $279 per night from Dec 1 to Dec 1
Situated in Cavendish, this luxury resort is within 6 mi (10 km) of Dorsey Park, Okemo Mountain Resort, and Jackson Gore Ski Resort at Okemo. Fox Run Golf Course ...
Castle Hill Resort And Spa
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.

HOTW-Hotel-Deals-726-959@2x.jpg (1918×258)*Savings based on Hot Rate® hotel bookings as compared with the lowest published rates found on leading retail travel sites. Hot Rates are different from retail rates. With Hot Rates you enter the date, location and star rating. Hotel revealed only after booking. All bookings final.

Chester is calling — find the perfect hotel

Everyone wants to score a deal on travel, but price is just one factor to consider when booking an unforgettable hotel. Whether you’re visiting family, attending a conference or taking a well-earned vacation in Chester, having an awesome experience should be a no-brainer.

Hotwire will hook you up! From restful nights near your flight to that prime spot in the city’s heart, we’ve done our research to bring the best options to your fingertips. Book your Chester hotel with us now and start your next adventure.

You’re not the average traveler — and we know it

You’ve done your homework and know exactly where you want to go. We’re here to help with some Hotwire travel geek-approved tips on how to save on your booking.

Get away for the weekend

Hotels in bigger cities usually charge higher rates during the week, when people are traveling for business. Weekends can be a bargain! It’s the other way around for vacation spots, so if you’re looking for a beach escape, consider a mid-week trip.

Give yourself some wiggle room

If your plans are flexible, play around with some different travel dates – a shift of a few days either way can help you save big. Prices usually jump the weekends before and after popular holidays, so we recommend steering clear of them. Or consider visiting during the off-season, when prices are generally lower.

Plan around big events

Are prices surprisingly high? There might be a huge conference or festival in town. Consider shifting your dates if you can. Of course, if that’s why you’re going, you’ll have to bite the bullet. We’ll still work to get you the best rates out there.

Noodle over new adventures

Set aside time to plan what you want to see, taste and discover. Nothing completes a trip, big or small, like a few new experiences! Check city apps or area websites to find out what’s new and what events are happening during your stay. Even during a family reunion, you can detour to that locals-only fish taco stand or under-the-radar music club. Your cousins will be impressed.

Frequently Asked Questions About Chester

When is the best time of the year to find Chester hotel deals?

April is the best time to find cheap Chester hotel deals.

When should I vacation to Chester?

February, July, October are very popular times to take vacations to Chester.

Where can I find the best last minute travel deals for Chester?

Only on Hotwire can you find last minute hotel deals for over 1459 Chester hotels. Save big with Hot Rate - score exclusive, unbeatable deals from our hotel suppliers.

What if I have to cancel my trip to Chester?

The fastest path to canceling your booking is through one of our self-serve tools found at https://vacation.hotwire.com/lp/coronavirus-travel

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