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Compare 23 B&B in Chesterfield with updated reviews, rates, and availability.

Deerfield Valley Inn
Front of property

Deerfield Valley Inn

3.0 star property
9.8 out of 10, Exceptional, (38)
"no frills, but convenient, clean, attentive staff, "
The price is SAR 635
SAR 802 total
includes taxes & fees
6 Jan - 7 January 2025
Deerfield Valley Inn
Colonel Williams Inn
Front of property

Colonel Williams Inn

3.0 star property
9.6 out of 10, Exceptional, (284)
"Great New England hospitality!....delicious breakfast and comfortable bedding. The location was great - between the small town of Wilmington, Mt. Snow and Brattleboro. Victoria and Brian could not have been more accommodating and friendly! Would definitely stay again when in the area. "
The price is SAR 503
SAR 548 total
includes taxes & fees
30 Dec - 31 Dec
Colonel Williams Inn
Harvest Barn Inn
Porch

Harvest Barn Inn

3.0 star property
9.8 out of 10, Exceptional, (197)
"No Complaints, Excellent breakfast "
The price is SAR 592
SAR 645 total
includes taxes & fees
6 Jan - 7 January 2025
Harvest Barn Inn
Deerhill Inn
Exterior

Deerhill Inn

3.5 star property
9.6 out of 10, Exceptional, (211)
"The innkeepers were such nice, friendly, helpful people, going out of their way to see that we had a delicious breakfast before our early departure. We loved everything about this inn! "
The price is SAR 733
SAR 806 total
includes taxes & fees
1 Jan - 2 January 2025
Deerhill Inn
The Carriage Barn Inn
Exterior

The Carriage Barn Inn

3.0 star property
9.6 out of 10, Exceptional, (142)
"Lovely old BnB, easy to find, very convenient Very clean room Great continental breakfast Loved ease of walking to downtown, many stores and restaurants Informative and very friendly and helpful owner"
The price is SAR 574
SAR 623 total
includes taxes & fees
31 Dec - 1 January 2025
The Carriage Barn Inn
Inn on Putney Road
Exterior

Inn on Putney Road

4.0 star property
9.8 out of 10, Exceptional, (43)
"Great stop on our way out of N Vermont. Nice warm room on a cold night."
The price is SAR 881
SAR 969 total
includes taxes & fees
1 Jan - 2 January 2025
Inn on Putney Road
Centennial House
Breakfast area

Centennial House

3.5 star property
9.6 out of 10, Exceptional, (147)
"Lovely bed & breakfast!!! We appreciate the hospitality and delicious breakfast. "
The price is SAR 748
SAR 790 total
includes taxes & fees
17 Jan - 18 January 2025
Centennial House
Chesterfield Inn
Lobby

Chesterfield Inn

4.0 star property
9.0 out of 10, Wonderful, (101)
"Lots of things were lovely; fantastic room service food (unbelievably fresh and delicious, better than anywhere I’ve ever eaten in a hotel while traveling), beautiful serene natural setting, and wonderful design of the buildings plus COOKIES and tea in the afternoon. The service was also fantastic. The paint could use freshening and the bathroom grout needs redoing (or consider retiling). A piece of one window pane, a wood bit, fell off… so I stuck it back, obviously needs a proper repair. With...
The price is SAR 1,155
SAR 1,253 total
includes taxes & fees
24 Jan - 25 January 2025
Chesterfield Inn
Four Columns Inn
Garden

Four Columns Inn

3.0 star property
8.8 out of 10, Excellent, (3)
"Friendliest Staff Ever!"
Four Columns Inn
Windham Hill Inn
Exterior

Windham Hill Inn

3.0 star property
8.2 out of 10, Very Good, (32)
"The rustic charm of a beautifully renovated New England barn, with spacious rooms that provide quiet solitude and comfortable furnishings, wall to wall! The king size bed, the oversized bathroom with a giant jetted tub beneath a skylight…SO INCREDIBLY PEACEFUL!! And outdoors there are numerous trails and Adirondack chairs placed at scenic spots to take in the beauty of the land in front of you and to enjoy the star filled wide-open sky above at night, which we did and thoroughly enjoyed! We...
The price is SAR 778
SAR 848 total
includes taxes & fees
7 Jan - 8 January 2025
Windham Hill Inn
The Engel House
Exterior

The Engel House

3.0 star property
9.2 out of 10, Wonderful, (11)
"The "
The price is SAR 494
SAR 539 total
includes taxes & fees
1 Jan - 2 January 2025
The Engel House
The One Cat B&B
Property entrance

The One Cat B&B

2.5 star property
9.6 out of 10, Exceptional, (74)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
The price is SAR 751
SAR 826 total
includes taxes & fees
26 Dec - 27 Dec
The One Cat B&B
The Brattleboro
Room

The Brattleboro

4.0 star property
10.0 out of 10, Exceptional, (5)
"Peaceful, comfortable, great views. We were made welcome and had wonderful beverage and snack options and the Breakfast were Superior. We will definitely return. "
The Brattleboro
Deerfield Valley Inn, 5min. to M.Snow Room Entire Inn
Exterior

Deerfield Valley Inn, 5min. to M.Snow Room Entire Inn

Deerfield Valley Inn, 5min. to M.Snow Room Entire Inn
Deerfield Valley Inn - Suite Room
Room

Deerfield Valley Inn - Suite Room

Deerfield Valley Inn - Suite Room
Deerfield Valley Inn - Deluxe Room with Fireplace Room 5
Room

Deerfield Valley Inn - Deluxe Room with Fireplace Room 5

Deerfield Valley Inn - Deluxe Room with Fireplace Room 5
Deluxe Room with Fireplace Room 2
Room

Deluxe Room with Fireplace Room 2

Deluxe Room with Fireplace Room 2
Deerfield Valley Inn - Standard Room 7
Room

Deerfield Valley Inn - Standard Room 7

Deerfield Valley Inn - Standard Room 7
Deerfield Valley Inn - Budget Club Room 3
Bathroom

Deerfield Valley Inn - Budget Club Room 3

Deerfield Valley Inn - Budget Club Room 3
Deerfield Valley Inn - Deluxe Room with Fireplace Room 4
Room

Deerfield Valley Inn - Deluxe Room with Fireplace Room 4

Deerfield Valley Inn - Deluxe Room with Fireplace Room 4
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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Other property types in Chesterfield

Charming Waterfront Log Cabin
Exterior

Charming Waterfront Log Cabin

9.6 out of 10, Exceptional, (37)
"We really appreciated the solitude and quiet retreat this cabin offered. "
Charming Waterfront Log Cabin
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

8.8 out of 10, Excellent, (43)
"Cabin was perfect for our long weekend. Master bed mattress needs an update, but otherwise everything was fantastic."
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Hilltop Home with Great Views
Exterior

Hilltop Home with Great Views

9.2 out of 10, Wonderful, (12)
"Michelle made our experience super easy and memorable! Drive up a private road and a pretty steep hill (4wd a must in winter) to a secluded, beautiful house with plenty of space. Just you and nature. The house itself has all the amenities - full kitchen, sitting areas, and even a wood stove that Michelle started up before we got there. Beds are comfortable, and the bathrooms have insane mountaintop views. Michele even left a few eggs for starter breakfast which was much appreciated. You can’t...
Hilltop Home with Great Views
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.

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. If your ideal vacation to Chesterfield includes spending lots of time outside, Pisgah State Park is a good spot to enjoy the scenery.
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: Colonel Williams Inn: 9 rooms. 12.4 mi (20 km) from the downtown core. Enjoy the local cuisine breakfast and library. The Carriage Barn Inn: 4 rooms. Situated 10.2 mi (16.4 km) from the heart of Chesterfield. 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 Pisgah State Park are some notable sights to visit. Spofford Lake and Madame Sherris Castle Ruins are also some sites to visit if you want 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.