The best deals on hotels when visiting Chester in Vermont.

From game day to getaway, save even more on every hotel stay.

Save up to 70% when booking as a group. Select 9+ rooms to get started.

Top 24 Hotels In Chester, Vermont 05143

Pointe at Castle Hill Resort

2940 State Route 103 Cavendish, VT

With a perfect blend of comfort and sophistication, Pointe at Castle Hill Resort near Chester offers relaxed rooms, with inviting rates starting at $155.99 per night. Relax in sophisticated surroundings, where every detail has been considered to offer you a superior stay.

From Pointe at Castle Hill Resort, the drive into downtown Chester is simple and convenient, making it easy for guests to explore the city while enjoying a more relaxed stay. Find out how exceptional Chester can be with a hotel that knows how to impress—reserve now!

  Call (855) 239-5277 to book with an agent.
  6.7 miles from Chester, VT 05143

Starting at

$155.99

per night

Read Reviews View Amenities View All Rooms

Best Western Springfield Hotel

818 Charlestown Rd Springfield, VT

At Best Western Springfield Hotel, guests bound for Chester can enjoy inviting accommodations with rates starting at $124.99, creating a warm and welcoming environment. Experience the community feel at Best Western, where guests are encouraged to interact and share travel stories.

From Best Western Springfield Hotel, the drive to downtown Chester is quick and convenient, allowing guests to explore the city’s attractions while returning to a peaceful stay afterward. Choose accommodations in Chester that offer a great blend of value and comfort—book now!

  Call (855) 234-2997 to book with an agent.
  9.2 miles from Chester, VT 05143

Starting at

$124.99

per night

Read Reviews View Amenities View All Rooms

The Upper Pass Lodge at Magic Mountain

420 Magic Mountain Access Road Londonderry, VT

For budget-savvy travelers, The Upper Pass Lodge at Magic Mountain offers safe comfort with rates beginning at $81.99, creating a warm and inviting atmosphere perfect for relaxation. Enjoy a straightforward lodging experience, where rooms provide basic amenities, clean surroundings, and friendly service.

With a simple drive into downtown Chester, guests at The Upper Pass Lodge at Magic Mountain can balance the excitement of city exploration with the quiet of their stay. Take your Chester experience to the next level with cost-effective, well-equipped lodging—reserve now!

  Call (855) 235-6136 to book with an agent.
  9.8 miles from Chester, VT 05143

Starting at

$81.99

per night

Read Reviews View Amenities View All Rooms

Jackson Gore Village

111 Jackson Gore Road Ludlow, VT

Stay at Jackson Gore Village as you explore Chester, where comfortable rooms create a relaxing ambiance, with welcoming rates beginning at $158.99 per night. Relax in accommodations that provide a warm and welcoming atmosphere, complete with all the modern amenities you need.

Rest easy at Jackson Gore Village, where peaceful surroundings create a calming retreat, while downtown Chester remains within driving distance. Enjoy exceptional amenities and affordability for your Chester visit—secure your room now!

  Call (855) 234-5074 to book with an agent.
  10.5 miles from Chester, VT 05143

Starting at

$158.99

per night

Read Reviews View Amenities View All Rooms

Rodeway Inn

593 Rockingham Rd Bellows Falls, VT

Guests bound for Chester will appreciate the mellifluous accommodations at Rodeway Inn, with rooms starting at $99.99, providing a warm, welcoming space for rest. Enjoy standard amenities in well-maintained rooms that provide a comfortable environment at a budget-friendly price.

Travelers staying at Rodeway Inn can appreciate the calm environment, with downtown Chester still close enough for city adventures. Stay comfortably and save more on your Chester trip—book your hotel room today!

  Call (855) 239-5277 to book with an agent.
  11.6 miles from Chester, VT 05143

Starting at

$99.99

per night

Read Reviews View Amenities View All Rooms

Holiday Inn Club Vacations Mount Ascutney Resort an IHG Hotel

485 Hotel Road Brownsville, VT

Relax in the mellifluous surroundings of Holiday Inn Club Vacations Mount Ascutney Resort an IHG Hotel when traveling to Chester, where inviting rooms create a comfortable stay, with nightly rates from $164.00. Experience the unique charm of each Holiday Inn location, reflecting the local culture and community in its design and offerings.

Unwind in the serene surroundings of Holiday Inn Club Vacations Mount Ascutney Resort an IHG Hotel, where quiet surroundings provide a restful stay and downtown Chester remains close by. Get the most out of your Chester visit with a hotel that takes care of all your needs—lock in today!

  Call (855) 234-2997 to book with an agent.
  14.3 miles from Chester, VT 05143

Starting at

$164.00

per night

Read Reviews View Amenities View All Rooms

Claremont Motor Lodge

16 Beauregard St Claremont, NH

At Claremont Motor Lodge, guests bound for Chester can enjoy inviting rooms with rates starting at $120.99, creating a clean and comfortable space ideal for relaxation. Stay in accommodations that provide enhanced comfort with additional amenities, making your visit both pleasant and affordable.

Relax in the serene environment of Claremont Motor Lodge, where peaceful surroundings provide a restful stay and downtown Chester is within reach. Enjoy the best of Chester with a hotel that puts your comfort first—lock in your room now!

  Call (855) 234-5074 to book with an agent.
  14.8 miles from Chester, VT 05143

Starting at

$120.99

per night

Read Reviews View Amenities View All Rooms

Royal Inn Claremont

24 Sullivan St Claremont, NH

Guests visiting Chester will find budget-friendly comfort at Royal Inn Claremont, where inviting rooms begin at $110.99, creating a clean, enchanting environment perfect for rest. Experience a welcoming stay in rooms that provide essential amenities and a comfortable setting, all at an economical price.

Guests staying at Royal Inn Claremont will enjoy the balance of easy city access and the peaceful retreat offered by the hotel. Stay affordably and enjoy extra perks on your Chester trip—reserve your room today!

  Call (855) 233-7850 to book with an agent.
  15.1 miles from Chester, VT 05143

Starting at

$110.99

per night

Read Reviews View Amenities View All Rooms

The Common Man Inn & Restaurant

21 Water Street Claremont, NH

Relax in the refined surroundings of The Common Man Inn & Restaurant near Chester, where secure accommodations create a warm stay, with budget-friendly rates from $166.00. Enjoy a harmonious blend of comfort and luxury, with rooms that feature thoughtful amenities and refined elegance.

Unwind in the peaceful environment at The Common Man Inn & Restaurant, where the calm atmosphere is complemented by easy access to downtown Chester. Relax in Chester with accommodations that blend elegance with modern conveniences—lock in today!

  Call (855) 235-6136 to book with an agent.
  15.2 miles from Chester, VT 05143

Starting at

$166.00

per night

Read Reviews View Amenities View All Rooms

Fat Sheep Farm & Cabins

122 Best Rd Windsor, VT

Fat Sheep Farm & Cabins provides a welcoming stay for travelers to Chester, where inviting rooms create a easygoing environment, with affordable rates starting at $159.99. Enjoy a stay that features thoughtful amenities and a focus on guest comfort, ensuring a pleasant and relaxing visit.

With downtown Chester just a drive away, Fat Sheep Farm & Cabins offers the perfect place to relax after a day of exploration. Embrace your Chester adventure with accommodations that add a touch of luxury—lock in today!

  Call (855) 234-7135 to book with an agent.
  18.5 miles from Chester, VT 05143

Starting at

$159.99

per night

Read Reviews View Amenities View All Rooms

Long Trail House at Stratton Mountain Resort

761 Stratton Access Rd Stratton, VT

Long Trail House at Stratton Mountain Resort offers a enchanting stay for travelers heading to Chester, with restful accommodations that create a welcoming ambiance, all starting from $317.99. Find a comfortable escape in rooms that provide extra amenities and services, designed for a more enjoyable stay.

For those seeking both relaxation and city access, Long Trail House at Stratton Mountain Resort provides tranquility while downtown Chester remains easily accessible. Stay in Chester with a hotel that takes your experience to new heights—lock in your room today!

  Call (855) 239-5277 to book with an agent.
  18.8 miles from Chester, VT 05143

Starting at

$317.99

per night

Read Reviews View Amenities View All Rooms

The Black Bear Lodge at Stratton Mountain Resort

5 Village Lodge Road Stratton, VT

Uncover cushy accommodations at The Black Bear Lodge at Stratton Mountain Resort on your journey to Chester, where restful rooms create a welcoming environment, with rates beginning at $145.99. Experience a stay that offers a little extra, with rooms equipped to provide a higher level of comfort and convenience.

Rest in the calm environment at The Black Bear Lodge at Stratton Mountain Resort, knowing downtown Chester is a simple drive away for easy access to city attractions. Stay comfortably in Chester with a hotel that takes care of every detail—book today!

  Call (855) 239-4019 to book with an agent.
  18.8 miles from Chester, VT 05143

Starting at

$145.99

per night

Read Reviews View Amenities View All Rooms

The Lodge at West River

1086 VT Route 30 Newfane, VT

Guests traveling to Chester will find hospitable accommodations at The Lodge at West River, where rooms begin at $146.99, creating a warm, inviting environment ideal for relaxation. Experience a more satisfying visit in accommodations that offer additional amenities and enhanced comfort.

At The Lodge at West River, travelers will appreciate the calm surroundings, while downtown Chester is still nearby for a day of adventure. Unwind in Chester at a hotel that provides comfort and value in every way—reserve today!

  Call (855) 234-7135 to book with an agent.
  18.8 miles from Chester, VT 05143

Starting at

$146.99

per night

Read Reviews View Amenities View All Rooms

Four Winds Country Motel

7379 Main Street Manchester Center, VT

For a intimate-feeling stay, Four Winds Country Motel offers budget-friendly rooms with rates beginning at $101.99, creating a warm and welcoming environment ideal for guests visiting Chester. Find comfort in rooms that are designed for affordability and practicality, offering the basics for a pleasant stay.

At Four Winds Country Motel, guests are treated to restful accommodations with the advantage of being close to Chester's top destinations. Plan your Chester adventure with comfort and affordability—reserve your hotel today!

  Call (855) 235-0725 to book with an agent.
  21.5 miles from Chester, VT 05143

Starting at

$101.99

per night

Read Reviews View Amenities View All Rooms

The Manchester View

77 High Meadow Way & VT 7A Manchester Center, VT

At The Manchester View, travelers to Chester will find cushy rooms with rates starting at $157.99, creating a clean, welcoming space perfect for a relaxing stay. Relax in a setting that emphasizes cleanliness and basic comforts, with rooms offering everything needed for a pleasant stay.

Unwind at The Manchester View, where guests can relax in spacious comfort while keeping Chester's excitement within easy reach. Maximize your Chester adventure with well-rounded, cost-effective accommodations—secure now!

  Call (855) 234-2997 to book with an agent.
  21.8 miles from Chester, VT 05143

Starting at

$157.99

per night

Read Reviews View Amenities View All Rooms

506 on the River Inn

1653 West Woodstock Road Woodstock, VT

With exquisite details, 506 on the River Inn near Chester promises an elevated stay, where inviting accommodations come at budget-friendly rates starting from $197.10. Experience luxury redefined in accommodations that provide exquisite decor and meticulous attention to every detail.

Escape to the serenity of 506 on the River Inn, a restful hideaway with Chester's lively attractions only a short drive away. Relax in Chester at a hotel that offers a unique blend of comfort and sophistication—secure now!

  Call (855) 235-0725 to book with an agent.
  22.4 miles from Chester, VT 05143

Starting at

$197.10

per night

Read Reviews View Amenities View All Rooms

Aspen at Manchester

5669 Main Street Manchester Center, VT

Guests bound for Chester can enjoy mellifluous comfort at Aspen at Manchester, where rooms start at $116.99, creating a welcoming environment ideal for relaxation. Relax in a setting that offers a bit more comfort and convenience, designed to make your stay both pleasant and economical.

Explore the sights of Chester from the peaceful base of Aspen at Manchester, where a quiet retreat awaits you after your adventures. Get the most out of your Chester visit with well-appointed, budget-friendly lodging—lock in today!

  Call (855) 233-0132 to book with an agent.
  22.8 miles from Chester, VT 05143

Starting at

$116.99

per night

Read Reviews View Amenities View All Rooms

The Palmer House Resort Ascend Hotel Collection

5383 Main St Manchester Center, VT

Uncover a relaxing retreat at The Palmer House Resort Ascend Hotel Collection near Chester, where inviting rooms create a welcoming ambiance, with affordable nightly rates from $134.11. Relax in rooms that offer a higher level of comfort and amenities, designed to make your stay as enjoyable as possible.

Experience a serene stay at The Palmer House Resort Ascend Hotel Collection, where calm surroundings create a restful retreat while keeping Chester within reach. Stay refreshed and recharged in Chester with a hotel that delivers exceptional service—lock in today!

  Call (855) 234-5074 to book with an agent.
  22.9 miles from Chester, VT 05143

Starting at

$134.11

per night

Read Reviews View Amenities View All Rooms

The Putney Inn

57 Putney Landing Rd Putney, VT

With budget-friendly rooms beginning at $93.99, The Putney Inn is an ideal choice for guests traveling to Chester, creating a warm, inviting space. Enjoy a stay that prioritizes the basics, with rooms equipped with essential amenities and a focus on clean, comfortable lodging.

Enjoy a restful escape at The Putney Inn, where guests can relax and still have Chester's vibrant energy close at hand. Step into Chester comfort without the hefty price tag—lock in your hotel room today!

  Call (855) 236-8982 to book with an agent.
  23.0 miles from Chester, VT 05143

Starting at

$93.99

per night

Read Reviews View Amenities View All Rooms

Woodstock Inn & Resort

Fourteen The Green Woodstock, VT

Those visiting Chester will marvel at the splendor of Woodstock Inn & Resort, where premier surroundings guarantee a serene escape, with rates beginning at $409.99. Relax in accommodations that epitomize opulence, offering bespoke services and lavish interiors for a truly exceptional stay.

Find your tranquil escape at Woodstock Inn & Resort, perfectly found for guests seeking both relaxation and proximity to Chester. Indulge in a Chester getaway that embodies the essence of relaxation and style—secure now!

  Call (855) 239-4019 to book with an agent.
  23.6 miles from Chester, VT 05143

Starting at

$409.99

per night

Read Reviews View Amenities View All Rooms

Hampton Inn&Suites Manchester

4519 Main St Manchester Center, VT

At Hampton Inn&Suites Manchester, guests bound for Chester can enjoy budget-friendly accommodations with rooms starting at $157.99, creating a welcoming and comfortable space. Savor the convenience of Hampton's 24/7 Suite Shop®, offering snacks, drinks, and travel essentials anytime you need them.

Escape to Hampton Inn&Suites Manchester, where the peaceful atmosphere provides a break from the hustle, yet Chester remains easily reachable. Choose a hotel that brings comfort and affordability together in Chester—book now!

  Call (855) 236-8982 to book with an agent.
  23.7 miles from Chester, VT 05143

Starting at

$157.99

per night

Read Reviews View Amenities View All Rooms

The Shire Woodstock

46 Pleasant St. Woodstock, VT

Choose The Shire Woodstock for a welcoming stay when traveling to Chester, where quality rooms create a peaceful escape, with budget-friendly rates from $147.99. Relax in accommodations that offer a blend of style and comfort, with amenities that cater to your every need.

Enjoy a quiet retreat at The Shire Woodstock, perfectly positioned for those seeking both relaxation and proximity to Chester. Enjoy a Chester stay that delivers quality and affordability seamlessly—reserve your room now!

  Call (855) 239-5277 to book with an agent.
  23.9 miles from Chester, VT 05143

Starting at

$147.99

per night

Read Reviews View Amenities View All Rooms

Kimpton Taconic Hotel an IHG Hotel

3835 Main St. Manchester, VT

Those exploring Chester will be enchanted by Kimpton Taconic Hotel an IHG Hotel, where luxurious rooms offer the ultimate comfort, with rates starting from just $209.99. Bring along your furry friends to Kimpton, where pet-friendly services and amenities ensure they enjoy the getaway as much as you do.

Take a break from the city noise at Kimpton Taconic Hotel an IHG Hotel, offering restful accommodations and quick access to Chester's best spots. Discover a hotel in Chester that goes above and beyond to create an unforgettable experience—book today!

  Call (855) 236-8982 to book with an agent.
  24.3 miles from Chester, VT 05143

Starting at

$209.99

per night

Read Reviews View Amenities View All Rooms

The Equinox Golf Resort & Spa

3567 Main St. Route 7A Manchester, VT

Embrace a lavish lifestyle at The Equinox Golf Resort & Spa near Chester, where elegant accommodations ensure an exceptional experience, with inviting nightly rates starting from $249.99. Experience a stay that combines modern luxury with timeless sophistication, providing rooms that cater to your every need.

Unwind in the comfort of The Equinox Golf Resort & Spa, where the restful ambiance ensures a peaceful stay with Chester always close by. Embrace the serenity of Chester with accommodations that make tranquility effortless—lock in today!

  Call (855) 235-0725 to book with an agent.
  24.5 miles from Chester, VT 05143

Starting at

$249.99

per night

Read Reviews View Amenities View All Rooms