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Check prices for these dates

Next weekend
13 Mar - 15 Mar
In two weeks
20 Mar - 22 Mar
In one month
3 Apr - 5 Apr
In two months
1 May - 3 May

Our top choices for Chesterfield bed & breakfast

Porch

Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (253 reviews)
"Everything was great. Awesome hosts, room, common areas and a fabulous breakfast. Can’t recommend too highly."
United States
Mark
Harvest Barn Inn
Room 4 | Hypo-allergenic bedding, free WiFi, bed sheets

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (349 reviews)
"The hotel was very clean, the staff were friendly and welcoming, and the breakfast was delicious."
United States
Sahand
The price is SAR 550
SAR 605 total
includes taxes & fees
18 Mar - 19 Mar
Colonel Williams Inn
Free daily continental breakfast

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (169 reviews)
"Very helpful and welcoming host. "
United States
Bruce
The price is SAR 521
SAR 566 total
includes taxes & fees
31 Mar - 1 Apr
The Carriage Barn Inn
Land view from property

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (23 reviews)
"Everything was great 👍 I will stay there again and highly recommend to others "
United States
Linda
Four Columns Inn
Front of property

The One Cat B&B

The One Cat B&B
2.5 star property
Brattleboro
9.6 out of 10, Exceptional, (79 reviews)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
United States
Cara
The price is SAR 919
SAR 1,011 total
includes taxes & fees
10 Mar - 11 Mar
The One Cat B&B
Exterior

Inn on Putney Road

Inn on Putney Road
4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (57 reviews)
"Room was super clean and the hosts are excellent. "
United States
Joe
The price is SAR 880
SAR 969 total
includes taxes & fees
5 Mar - 6 Mar
Inn on Putney Road
Room, 1 Queen Bed, Garden View | Mountain view

Windham Hill Inn

Windham Hill Inn
4.0 star property
West Townshend
8.4 out of 10, Very Good, (40 reviews)
"We had a fantastic room! Staff was very friendly and accommodating. Though we visited during peak foliage season, we’ll be trying to book again in the near future to try out the pool."
United States
J
The price is SAR 660
SAR 719 total
includes taxes & fees
18 Mar - 19 Mar
Windham Hill Inn
Front of property - evening/night

Chesterfield Inn

Chesterfield Inn
4.0 star property
West Chesterfield
9.0 out of 10, Wonderful, (104 reviews)
"Great stay"
United States
Wayne
The price is SAR 1,154
SAR 1,252 total
includes taxes & fees
5 Mar - 6 Mar
Chesterfield Inn
Exterior

Deerfield Valley Inn

Deerfield Valley Inn
3.0 star property
West Dover
9.4 out of 10, Exceptional, (113 reviews)
"Great location Host Oz cooked up a great breakfast Room was fine for one person "
United States
michael
Deerfield Valley Inn
Free full breakfast

Deerhill Inn

Deerhill Inn
3.5 star property
West Dover
9.6 out of 10, Exceptional, (227 reviews)
"Super clean and well appointed room. Lovely greeting "
United States
Kathleen
The price is SAR 716
SAR 787 total
includes taxes & fees
10 Mar - 11 Mar
Deerhill Inn
Outdoor dining

Private bedroom in the Green River Bridge Inn. A full breakfast is included.

Private bedroom in the Green River Bridge Inn. A full breakfast is included.
Guilford
The price is SAR 1,032
SAR 1,316 total
includes taxes & fees
10 Mar - 11 Mar
Private bedroom in the Green River Bridge Inn. A full breakfast is included.
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.
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Top Chesterfield Hotel Reviews

The White House Inn

The White House Inn

10/10 Excellent
"Beautiful and quaint. Restaurant had great food. The basement was very cool. Fireplace, pool table, and pictures of prohibition . Bring your drink down and relax. Definitely book a night or 2 you won’t be disappointed."
Amy 1-night trip
Posted 6 hours ago
The White House Inn

Frequently asked questions

Searching for B&Bs in Chesterfield?
Whether you're on a family vacation and want a small, cozy place to stay, or you're a solo traveler hoping to meet fellow tourists, a B&B can be a good choice for many different types of travelers. When you want to explore some attractions in town, Asbury United Methodist Church and Chesterfield Town Hall are worth a stop.
How do you know if a B&B is the best choice for your stay?
With attentive service, opportunities to mingle with other guests, and tasty breakfasts, B&Bs all have a truly one-of-a-kind setting.
What are the top B&Bs in Chesterfield?
Here are some well-liked B&Bs in the surrounding area: Four Columns Inn: 15 rooms. 11.6 mi (18.7 km) from the downtown core. Enjoy the unique décor and onsite dining. Colonel Williams Inn: 9 rooms. Situated 12.4 mi (20 km) from the heart of Chesterfield. Enjoy the local cuisine breakfast and library. Harvest Barn Inn: 7 rooms. Located 18.1 mi (29.1 km) from the core of Chesterfield. Enjoy the free full breakfast and patio area.
What's the best time of year to book my B&B in Chesterfield?
When you're dreaming of a trip to Chesterfield, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Chesterfield are January, March, November, and February, with each month seeing an average of 9 inches of snowfall.
What is there to do in Chesterfield?
When you want to explore some things to do in town, Asbury United Methodist Church and Chesterfield Town Hall are some notable sights to visit. You might check out Pisgah State Park if you have time to see more of the area.
How can I get to and around Chesterfield?
You can plan your excursions in and around Chesterfield ahead of time with these transportation options. Fly into Springfield, VT (VSF-Hartness State), which is located 31.6 mi (50.9 km) from the city center. Otherwise, look for flights into Manchester-Boston Regional Airport (MHT), which is 52.3 mi (84.2 km) away. If you'd like to venture out around the area, you may want to rent a car for your trip.