Search for Cheap Deals on
Hotels in Chester

Last Minute Hot Rate® Hotel Deals in Chester

We Hide Hotel Names So You Can Find 4-Star Hotels At 2-Star Prices. Choose the Location, Star Rating & Amenities. Let Hotwire Find You the Best Deal. Book Today!

Choose from 2942 Chester Hotel Deals

The Covered Bridge Inn
The Covered Bridge Inn
2.5 out of 5
1043 Putney Road, Brattleboro, VT
  • 1 hour drive from Bonnie's Bundles Dolls
The price is $81 per night from Apr 28 to Apr 29
$81
per night
Apr 28 - Apr 29
Stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
8.2/10 Very Good! (1,002 reviews)
"Beds were squeaky but rooms are big"

Reviewed on Apr 19, 2024

The Covered Bridge Inn
Stone Hearth Inn and Eatery
Stone Hearth Inn and Eatery
2 out of 5
698 VT-11, Chester, VT
  • 24 min walk from Bonnie's Bundles Dolls
The price is $212 per night from Apr 28 to Apr 29
$212
per night
Apr 28 - Apr 29
Stay at this B&B in Chester. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Bonnie's Bundles Dolls and DaVallia Art & Accents are located ...
9/10 Wonderful! (47 reviews)
After the eclipse
"Vicky and her family are wonderful hosts. We stayed on the last day of their season and received as welcoming a reception as you might expect at the height of the season. Stonehearth Inn is a labor of love and it shows."

Reviewed on Apr 10, 2024

Stone Hearth Inn and Eatery
Colonial Motel And Spa
Colonial Motel And Spa
3 out of 5
889 Putney Rd, Brattleboro, VT
  • 1 hour drive from Bonnie's Bundles Dolls
The price is $138 per night from Apr 27 to Apr 28
$138
per night
Apr 27 - Apr 28
Stay at this 3-star spa motel in Brattleboro. Enjoy free WiFi, free parking, and 2 indoor pools. Our guests praise the helpful staff and the clean rooms in our ...
6.8/10 (1,000 reviews)
"Very comfortable"

Reviewed on Apr 21, 2024

Colonial Motel And Spa
Woodstock Inn & Resort
Woodstock Inn & Resort
4.5 out of 5
Fourteen The Green, Woodstock, VT
  • 1 hour drive from Bonnie's Bundles Dolls
The price is $289 per night from Apr 30 to May 1
$289
per night
Apr 30 - May 1
Stay at this luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Popular attractions Woodstock Town Hall Theatre and Red Wagon ...
9.2/10 Wonderful! (437 reviews)
"The Inn is very cozy and comfortable. There are lots of areas to relax, read or have a cocktail. The restaurants are very good. Our room was spacious and clean. We will definitely be back."

Reviewed on Apr 15, 2024

Woodstock Inn & Resort
The Equinox Golf Resort & Spa
The Equinox Golf Resort & Spa
4.5 out of 5
3567 Main Street Route 7A, Manchester, VT
  • 1 hour drive from Bonnie's Bundles Dolls
The price is $151 per night from May 1 to May 2
$151
per night
May 1 - May 2
Stay at this 4.5-star luxury hotel in Manchester. Enjoy free parking, 4 restaurants, and a golf course. Our guests praise the helpful staff and the property ...
7.2/10 Good! (349 reviews)
"No thanks"

Reviewed on Apr 8, 2024

The Equinox Golf Resort & Spa
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 Apr 28 to Apr 29
$169
per night
Apr 28 - Apr 29
Stay at this 3.5-star spa hotel in Cavendish. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
8.6/10 Excellent! (726 reviews)
"My family enjoyed our stay very much! The outdoor pool and hot tub was a real treat before heading north to see the eclipse. My kids haven't stopped talking about our trip to Vermont! We will be sure to come back."

Reviewed on Apr 14, 2024

Pointe at Castle Hill Resort
Hampton Inn and Suites Manchester
Hampton Inn and Suites Manchester
2.5 out of 5
4519 Main St, Manchester Center, VT
  • 58 min drive from Bonnie's Bundles Dolls
The price is $144 per night from May 5 to May 6
$144
per night
May 5 - May 6
Stay at this business-friendly hotel in Manchester Center. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9.4/10 Exceptional! (1,002 reviews)
"Convenient,immaculate and reasonably priced."

Reviewed on Apr 21, 2024

Hampton Inn and Suites Manchester
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 $145 per night from May 19 to May 20
$145
per night
May 19 - May 20
Stay at this 3-star spa resort in Stratton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
7.4/10 Good! (827 reviews)
"It is an excellent ski hotel with friendly service and great beds."

Reviewed on Apr 8, 2024

The Black Bear Lodge at Stratton Mountain 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 $159 per night from Apr 26 to Apr 27
$159
per night
Apr 26 - Apr 27
Stay at this 3-star spa hotel in Ludlow. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the property condition in our reviews. Popular attractions ...
8.4/10 Very Good! (618 reviews)
"Really loved the whole experience!"

Reviewed on Apr 10, 2024

Jackson Gore Village
The Shire Woodstock
The Shire Woodstock
3 out of 5
46 Pleasant St., Woodstock, VT
  • 1 hour drive from Bonnie's Bundles Dolls
The price is $181 per night from May 5 to May 6
$181
per night
May 5 - May 6
Stay at this 3-star hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Popular attractions Billings Park and Trail and Red Wagon Toy ...
8.6/10 Excellent! (540 reviews)
"I enjoyed my stay at the Shire. It’s an odd mix of comfort, luxury, bargain and practicality. The room was clean and comfortable, if a bit worn. I sprang for a river front room, which was an excellent idea. The deck outside my door was right off of the lawn at the edge of the water, and it was a ..."

Reviewed on Apr 15, 2024

The Shire Woodstock
Courtyard by Marriott Keene Downtown
Courtyard by Marriott Keene Downtown
3 out of 5
75 Railroad St, Keene, NH
  • 1 hour drive from Bonnie's Bundles Dolls
The price is $118 per night from Apr 30 to May 1
$118
per night
Apr 30 - May 1
Stay at this 3-star business-friendly hotel in Keene. Enjoy free WiFi, free parking, and breakfast. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (892 reviews)
"The room is large, clean, and comfortable. It is also quiet and the staff is very helpful and welcoming."

Reviewed on Apr 19, 2024

Courtyard by Marriott Keene Downtown
Hampton Inn Brattleboro
Hampton Inn Brattleboro
2.5 out of 5
1378 Putney Road, Brattleboro, VT
  • 1 hour drive from Bonnie's Bundles Dolls
The price is $113 per night from Apr 29 to Apr 30
$113
per night
Apr 29 - Apr 30
Stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free parking, and internet. Our guests praise the breakfast and the helpful staff ...
8.2/10 Very Good! (893 reviews)
"Good stay"

Reviewed on Apr 13, 2024

Hampton Inn Brattleboro
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.

Find cheap hotels in Chester

You’re not an average traveler—and Hotwire knows it. Your wanderlust takes you off the beaten path to discover unique adventures and every travel destination’s lesser-known tourist scenes. Hotwire has the hookup! Book your Chester hotel with Hotwire to complete your one-of-a-kind travel checklist.

For you, intrepid voyager, Hotwire has a large selection of the best hotels in Chester.

Choosing the right hotel in Vermont has everything to do with the way you want your trip to go. If you’ve scribbled a few obscure destinations on your itinerary, you probably already have a good sense of how your getaway is taking shape. Lean into that by booking one of Chester’s 2,942 hotels. Choose the one that best catches your trip’s tourist drift.

If you’re traveling during the week for business, Hotwire can score you a luxury hotel for as low as $81. In town for pleasure? Hotwire still has you covered. If you’re in the mood for a quick last-minute weekend getaway or spa retreat, you can get up to 60% Chester hotel deals at the last minute.

While traveling, where you stay plays a major role in your overall vacation enjoyment. Choosing the right hotel is just as important as making sure you book the right flight and car rental. If you’re traveling with family or friends, you may need to book a hotel with connecting rooms. If you enjoy an elegant and relaxing hotel ambiance, opt for one of Hotwire’s luxury hotels in Chester. No matter your reason for visiting Chester, with Hotwire’s large selection of hotels in the area, you’re sure to book a hotel that meets all your accommodation needs.

Frequently Asked Questions About Chester hotels

Where can I find the best last-minute travel deals?

If you’re traveling in the spirit of spontaneity, you’ll love the idea of leaving your exact hotel choice up to chance. With Hotwire Hot Rates, you can save up to 60% off your next flight, hotel, or car rental. Just plug in your general preferences and let Hotwire choose last-minute hotel deals in Chester for as low as $81.

How many hotels are there in Chester?

With over 2,942 hotels in Chester, you’re sure to find one that best matches your travel mood. When you book with Hotwire, you can score a stellar home away from home for as low as $81.

How to find cheap car rentals in Chester?

Finding a cheap car rental deal in Chester is as easy as scoring cheap hotels in Chester. Hotwire partners with top-of-the-line car rental companies to bring you a large selection of affordable options. Whether you’re in need of a large SUV for the entire family or a more compact but stylish vehicle, Hotwire has you covered. You can even save up to 60% off a car rental deal if you book a Hotwire Hot Rate at the last minute.

Is it safe to travel to Chester now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to Chester right now?” When it’s time to book your getaway, be sure to check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.