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Chesterfield
Chesterfield Inn
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75 photos
Chesterfield Inn Nature photoChesterfield Inn Exterior photoChesterfield Inn Exterior photo

Welcome to Chesterfield Inn - Your Luxury Hotel in Chesterfield

Book on our site
up to 10% cheaper
than Booking.com
Check rooms and rates
From$301 /night
Check-in
30May
Check-out
31May
Rooms and Guests2 Guests, 1 Room
Key details

About the Hotel

20 Cross Road, Chesterfield, 3466
-
Near Madame Sherri's "Castle"
Perfect
9.8
9.7
/10
4.8
4.9
/5

Loved by Chesterfield Inn guests

Spacious rooms
Attentive staff
Delicious breakfast
On-site restaurant
"Our room was beautiful and the view amazing."
KATHLEEN R from United States
read full review
"We enjoyed dinner so much on our first night that we cancelled all our reservations in town and ate there four nights in a row!"
Lisa P. from United States
read full review
"We were in one of the four rooms that allow pets, and it was spacious, beautiful, and inviting."
SuziJaye from United States
read full review
"The Cat in the Lobby reception area is the greeter and has been a fixture for years."
Ernest K from United States
read full review

Dining & Breakfast

The on-site restaurant serves locally-sourced seasonal cuisine and has earned recognition for culinary excellence. A complimentary homemade breakfast is served each morning, featuring house-made ingredients and dishes like cinnamon French toast with warm local maple syrup. Afternoon tea and freshly baked cookies are offered daily, and room service is available for both breakfast and dinner.

Rooms & Accommodations

Guest rooms include options with gas fireplaces, jetted tubs, private patios, and decks overlooking the meadow. Certain rooms are two-room suites with a separate living area and gas fireplace, while others have a private balcony. Pet-friendly accommodations feature private entries and outdoor spaces, with amenities such as a refrigerator and CD player in each room.

Property & Grounds

The inn sits on 10 acres of scenic beauty with a garden, terrace, pond, and views of the Vermont mountains. Guests have access to outdoor furniture and a firepit for evening relaxation. The property is a member of Select Registry, a nonprofit association of distinguished inns, and was named to Yelp's Top 100 Places to Stay in New England.

Pet-Friendly & Outdoor Activities

The inn offers pet-friendly rooms with private entries and outdoor spaces, and dogs are welcome on the patio during dinner. Nearby outdoor activities include diverse hiking trails in Madame Sherri Forest, winter sports at nearby ski resorts, and kayaking on the Connecticut River. The property provides ski storage for winter guests and concierge service to arrange equipment rentals.

Location & Awards

Chesterfield Inn is located just off I-91 near the Vermont border, 14 km from Fort Dummer State Park and 22 km from Santa's Land USA. Keene, NH and Brattleboro, VT are within a short drive, offering local dining, shopping, and cultural attractions. The inn has received recognition from Yelp's Top 100 Places to Stay in New England and is a member of the Select Registry of distinguished inns.

Highlights

Awards: Yelp's Top 100 Places to Stay in New England

Dining: On-site gourmet restaurant with locally-sourced seasonal cuisine

Breakfast: Complimentary homemade breakfast with house-made ingredients

Rooms: Fireplaces, jetted tubs, private patios, and pet-friendly options

Property: 10 acres with pond, garden, and mountain views

Pets: Pet-friendly rooms with private entries and outdoor spaces

“This inn provides a truly restorative escape, evident from the thoughtful accommodations, including pet-friendly rooms and fireplaces, to the consistently exceptional meals served. The proprietors and staff clearly prioritize guest comfort, demonstrating a genuine attentiveness that enhances the tranquil, country setting. Its proximity to Brattleboro also adds a convenient layer for those seeking to explore the surrounding area.”
Hotel logo
James DavidEditor-in-Chief at Excelsiorhotels

Select your room type

Chesterfield Inn offers a variety of rooms including double rooms, family rooms, and suites with breakfast, free cancelations, and special deals
    Deluxe Queen Room
    2 persons
    28 sq. feet
    1 King-size bed
    Air conditioning
    Balcony
    room details
    Double Room Spa Bath
    2 persons
    37 sq. feet
    1 King-size bed
    Air conditioning
    Balcony
    room details
    King Room
    2 persons
    28 sq. feet
    1 King-size bed
    Air conditioning
    Heating
    room details
Show all rooms

Price and Room Availability Calendar

Check availability and prices for your dates now!
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Check-in/ Check-out

Facilities

Chesterfield Inn offers amenities for your comfortable stay and unforgettable experiences
Facilities: Perfect
10.0/10Review score

General

  • No smoking on site
  • Wi-Fi
  • Parking
  • VIP check-in/ -out
  • Express check-in/ -out
  • Concierge desk
  • Pets allowed
  • Luggage storage
  • Ski storage
  • Smoke detectors
  • Electric vehicle charging station
  • Fire extinguishers
  • Key access

Sports & Fitness

  • Skiing
  • Hiking

Services

  • Room service
  • Housekeeping
  • Welcome drink

Dining

  • In-room breakfast
  • Restaurant
  • Bar/ Lounge area
  • Outdoor dining area
  • Special diet menus

Business

  • Meeting/ Banquet facilities
  • Fax/Photocopying

Children

  • Cots
  • Board games
  • Children's menu

Spa & Leisure

  • Garden area
  • Full body massage

Room features

  • Air conditioning
  • Heating
  • Mini-bar
  • Sitting area
  • Patio
  • Terrace
  • Garden furniture
  • Tea and coffee facilities
  • Ironing facilities

Bathroom

  • Free toiletries

Media

  • Flat-screen TV
  • CD player
  • AM/FM alarm clock

Room decor

  • Carpeted floor
Show more

Dining Onsite

At Chesterfield Inn, the onsite dining experience embraces the essence of American cuisine, each dish inspired by the splendor of the Connecticut River Valley. With a romantic ambiance that complements its stunning natural surroundings, this intimate dining venue highlights seasonal ingredients crafted into gourmet creations.
Chesterfield Inn Restaurant photo
Chesterfield Inn Restaurant photo
Chesterfield Inn Restaurant photo

Restaurant #1

Gourmet American
Ambiance
Romantic setting amidst the serene beauty of the Connecticut River Valley
Key Offerings
Indulge in signature dishes such as French toast topped with baked apple and locally sourced Mitchell Farm maple syrup, alongside a dessert menu featuring Maple Crème Brulee and Flourless Chocolate Cake for a sweet finish.
Reservation
Recommended
Dinner only; hours vary.

Chesterfield Inn Location

20 Cross Road, Chesterfield, 3466
Explore Chesterfield
Local Highlights
  • Top Attractions
  • Activities
  • Dining
  • Entertainment
Antique Carriage and Sleigh Museum
15 minutes' walk
A showcase of historical carriages and sleighs, offering insight into 19th-century transportation. Great for history enthusiasts.
Copper Cannon Distillery
5 minutes' drive
A local distillery known for handcrafted spirits. Guided tours and tastings highlight the distilling process and unique flavors.
Madame Sherri's 'Castle'
10 minutes' drive
A picturesque stone ruin nestled in nature, ideal for photography and scenic hikes. Popular spot for leisurely walks.
Discover the local attractions near Chesterfield Inn
Check out attractive sites near Chesterfield Inn that offer unique experiences and insights into the local culture
Great for enjoying fresh produce and scenic views: Scott Farm Orchard
Ideal for history enthusiasts and scenic explorations: Naulakha
Perfect for hiking and enjoying nature: Wantastiquet Mountain Natural Area
Well suited for family outings and educational experiences: Retreat Farm
Best for art lovers looking for regional exhibitions: Brattleboro Museum and Art Center
Ideal for appreciating locally crafted glass art: Solinglass
Well suited for casual gatherings and outdoor relaxation: Brattleboro Common
Perfect for architectural photography and exploration: Madame Sherri's Castle
Great for seasonal activities and family visits: Elysian Hills Tree Farm
Suited for tasting locally crafted spirits: Copper Cannon Distillery
Hiking at Wantastiquet Mountain Natural Area
8 minutes' drive
Ideal for thrill-seekers, this area offers scenic trails with varying difficulties, alongside breathtaking views of the landscape.
Yoga at Vermont Soul
10 minutes' drive
A serene studio offering regular classes and workshops aimed at relaxation and mindfulness. Perfect for unwinding after a busy day.
Chesterfield Inn
1 minute' walk
A cozy inn offering local specialties, with a warm atmosphere. Reservations recommended for their popular weekend brunch.
Canal Street Tavern
10 minutes' drive
Casual eatery featuring classic American dishes. Known for craft beers and lively ambiance. Vegetarian options are available.
Actors Theatre
15 minutes' walk
A local venue showcasing live performances, from plays to musicals. Offers family-friendly events on weekends.
Brattleboro Bowl
10 minutes' drive
A bowling alley featuring league games and family activities, along with a snacks bar. Great for casual fun with friends or family.
Getting around
  • City Centre
    Chesterfield 12 min  ·  3300 ft
  • Airports
    Lebanon Municipal (LEB) 151 min  ·  62.4 mi
    Rutland State (RUT) 162 min  ·  67.1 mi
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Property information and rules
Check-in
from 14:00-23:59
Check-out
until 11 am
Guest Parking
Private parking is possible on site for free.
Internet
Wireless internet is available in the entire hotel for free.
Breakfast
A full breakfast is served at the price of US$12 per person per day.
Children & extra beds
Maximum capacity of extra beds in a room is 2. 
Pets
Pets are allowed on request.
Number of rooms:
15

Reviews and Ratings

Feedback about Chesterfield Inn from previous guests about their experience.
Review score
Based on 179 verified reviews
10.0 /10
Perfect
100 %
Recommend
Cleanliness
10.0/10
Comfort
10.0/10
Facilities
10.0/10
Free WiFi
10.0/10
Location
10.0/10
Staff
10.0/10
Value for money
9.5/10
Guest reviews
based on 6 reviews
9.8/10
No reviews yet on our siteUnfortunately, our guests have not yet left any reviews for this hotel, but you can read reviews from Booking.com.
Open reviews
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FAQs
About Chesterfield Inn
What time can I check in and check out at Chesterfield Inn?
Check-in is at 14:00 and check-out is at 11:00.
How far is Chesterfield Inn from Lebanon Municipal Airport?
Chesterfield Inn is located 100 km from Lebanon Municipal Airport.
What dining options are available at Chesterfield Inn?
Chesterfield Inn features an on-site restaurant serving American cuisine and offers room service.
Is Wi-Fi available at Chesterfield Inn?
Yes, free Wi-Fi is available throughout Chesterfield Inn.
What amenities are included in the rooms at Chesterfield Inn?
Rooms are equipped with air conditioning, a flat-screen TV, free toiletries, and a CD player.
Are there any attractions near Chesterfield Inn?
Nearby attractions include Madame Sherri's Castle Forest (4 km) and Fort Dummer State Park (14 km).
What recreational activities can guests enjoy at Chesterfield Inn?
Guests can engage in activities such as hiking and skiing in the surrounding area.
Does Chesterfield Inn offer breakfast?
Chesterfield Inn provides an American breakfast for an additional charge of 12 USD.
What languages are spoken by the staff at Chesterfield Inn?
The staff at Chesterfield Inn speaks English.
Are there facilities for business services at Chesterfield Inn?
Chesterfield Inn offers a conference space and a range of business amenities.

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Check-in
30May
Check-out
31May
Rooms and Guests2 Guests, 1 Room
  • Overview
  • Rooms
  • Price calendar
  • Facilities
  • Location
  • Reviews