A rural landscape with a grassy field, a dirt path, and a hill covered with autumn-colored trees.

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Check prices for these dates

Next weekend
11 Sept - 13 Sept
In two weeks
18 Sept - 20 Sept
In one month
2 Oct - 4 Oct
In two months
30 Oct - 1 Nov

Our top choices for Chesterfield bed & breakfast

Land view from property

1. Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (54 reviews)
"Lovely grounds, great location, wonderful restaurant. Staff was very pleasant and helpful. Just booke another stay."
United States
Raymond
The price is AU$218
includes taxes & fees
13 Sept - 14 Sept
Four Columns Inn
Front of property

2. Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (358 reviews)
"A very historic and well maintained bed and breakfast. The owners are wonderful and the rooms were cozy. The hand made breakfast was a highlight"
United States
Robert
The price is AU$231
includes taxes & fees
8 Sept - 9 Sept
Colonel Williams Inn
Exterior

3. Inn on Putney Road

Inn on Putney Road
4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (61 reviews)
"Helpful staff, wonderful breakfast and homey ambiance."
United States
Karla
The price is AU$450
includes taxes & fees
8 Sept - 9 Sept
Inn on Putney Road
Breakfast area

4. The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (176 reviews)
"Perfectly clean and quaint. Friendly owner, great location"
United States
Jonathan
The price is AU$225
includes taxes & fees
8 Sept - 9 Sept
The Carriage Barn Inn
Property entrance

5. The One Cat B&B

The One Cat B&B
2.5 star property
Brattleboro
9.8 out of 10, Exceptional, (81 reviews)
"Breakfast was fantastic Did not need any shops Hosts were super friendly We enjoyed our short stay"
United States
marjie
The price is AU$444
includes taxes & fees
8 Sept - 9 Sept
The One Cat B&B
Front of property

6. Centennial House

Centennial House
3.5 star property
Northfield
9.6 out of 10, Exceptional, (177 reviews)
"David was incredibly hospitable. I thoroughly enjoyed my stay. "
United States
Amy
The price is AU$253
includes taxes & fees
13 Sept - 14 Sept
Centennial House
Front of property – evening/night

7. Chesterfield Inn

Chesterfield Inn
4.0 star property
West Chesterfield
9.0 out of 10, Wonderful, (106 reviews)
"Great stay"
United States
Wayne
Chesterfield Inn
Porch

8. Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (278 reviews)
"Beautiful views of the river excellent breakfast"
United States
Michael
The price is AU$245
includes taxes & fees
11 Sept - 12 Sept
Harvest Barn Inn
Exterior

9. Deerfield Valley Inn

Deerfield Valley Inn
2.0 star property
West Dover
9.4 out of 10, Exceptional, (132 reviews)
"Good price, really quite, clean, person on site very friendly helpful with places we can go & things to do I recommend the place"
United States
Patrick
The price is AU$167
includes taxes & fees
20 Sept - 21 Sept
Deerfield Valley Inn
Outdoor dining

10. 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 AU$472
includes taxes & fees
13 Sept - 14 Sept
Private bedroom in the Green River Bridge Inn. A full breakfast is included.
Room, 1 Queen Bed, Garden View | Mountain view

11. Windham Hill Inn

Windham Hill Inn
4.0 star property
West Townshend
8.6 out of 10, Excellent, (44 reviews)
"The view of mountains id stunning, as is the aroma of fresh air and the enchanting songbirds. We had a great time in the small but adequate swimming pool. It is easy to miss the turn onto Laurence Lane, so it would be good if a sign were to be installed there."
United States
Nadine
The price is AU$352
includes taxes & fees
22 Sept - 23 Sept
Windham Hill Inn
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

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent
"All around great stay. Thank you."
Christina 3-night trip
Posted 15 hours ago
Keene Elm City Hotel, an Ascend Collection Hotel

Find out more about Chesterfield

Chesterfield B&B information

Number of reviews
1,362
Accommodation
14 B&B
Lowest Price
AU$167
Highest Price
AU$472

Frequently asked questions

Searching for B&Bs in Chesterfield?
Whether you're on a family holiday and want a small, cosy place to stay, or you're travelling solo and hoping to get some tips from locals, a B&B might be the right choice for your trip. When you want to explore some attractions in town, Pisgah State Park and Asbury United Methodist Church are worth a stop.
How do you know if a B&B is a good option for your stay?
With attentive service, an atmosphere suited to mingling with other guests and delectable breakfasts, B&Bs offer a one-of-a-kind setting.
What are the top B&Bs in Chesterfield?
Here are some B&Bs in the area: Harvest Barn Inn: 7 rooms. 18.1 mi (29.1 km) from the heart of Chesterfield. Enjoy the free full breakfast and patio area. Centennial House: 5 rooms. Situated 13.2 mi (21.2 km) from the heart of Chesterfield. Enjoy the free full breakfast and unique decor. The Carriage Barn Inn: 4 rooms. 10.2 mi (16.4 km) from the city centre. Four Columns Inn: 15 rooms. Located 11.6 mi (18.7 km) from the core of Chesterfield. Enjoy the unique decor and on-site dining.
When should I stay at a B&B in Chesterfield?
When you're dreaming of a escape to Chesterfield, make sure that you take the year-round temperatures into account. The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Chesterfield are January, March, November and February, with each month seeing an average of 23 cm of snowfall.
What is there to do in Chesterfield?
When you want to explore some things to do in town, Pisgah State Park and Asbury United Methodist Church are some notable sights to visit. You could visit Chesterfield Town Hall 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) away from the city centre. Otherwise, you can search for flights to Manchester, NH (MHT-Manchester-Boston Regional), which is 52.3 mi (84.2 km) away. If you'd like to venture out around the area, you may want a rental car for your journey.

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