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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, (33)
"What a great place to stay! To spend a few nights away! From the hustle and bustle."
The price is AED 246
AED 371 total
includes taxes & fees
24 Nov - 25 Nov
Deerfield Valley Inn
Colonel Williams Inn
Front of property

Colonel Williams Inn

3.0 star property
9.6 out of 10, Exceptional, (283)
"My boyfriend and I had a fabulous stay here this past weekend! Stayed here for the night so we could try a restaurant in Brattleboro and it was the perfect 15 min drive. The room was very clean and had a beautiful view of the pond. The staff was incredibly friendly and ready upon our arrival. The lounge/ living room was cozy for watching a movie at night and the breakfast was absolutely to die for! "
The price is AED 509
AED 555 total
includes taxes & fees
24 Dec - 25 Dec
Colonel Williams 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 AED 664
AED 721 total
includes taxes & fees
24 Nov - 25 Nov
The Carriage 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 AED 716
AED 788 total
includes taxes & fees
27 Nov - 28 Nov
Deerhill Inn
Centennial House
Breakfast area

Centennial House

3.5 star property
9.6 out of 10, Exceptional, (145)
"Lovely bed & breakfast!!! We appreciate the hospitality and delicious breakfast. "
The price is AED 657
AED 695 total
includes taxes & fees
25 Nov - 26 Nov
Centennial House
Harvest Barn Inn
Porch

Harvest Barn Inn

3.0 star property
9.8 out of 10, Exceptional, (194)
"Such an excellent stay. Beautiful view, felt safe and quiet. Blessing was kind enough to make us breakfast in the morning, highly recommended "
The price is AED 579
AED 631 total
includes taxes & fees
1 Dec - 2 Dec
Harvest Barn 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 AED 760
AED 829 total
includes taxes & fees
8 Dec - 9 Dec
Windham Hill Inn
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 One Cat B&B
Inn on Putney Road
Exterior

Inn on Putney Road

4.0 star property
9.8 out of 10, Exceptional, (42)
"A lovely four day stay in Vermont. Inn was perfect, with gardens to enjoy and lots of lounges and nooks to spend time and read. We had a suite with a separate sitting room, which allowed us to have our daughter accompany us on a last minute visit. Paul and his staff are super accommodating and are genuinely friendly hosts. Paul also cooks all the breakfasts which are superb! Different breakfasts each day, beautifully presented and absolutely delicious!"
The price is AED 980
AED 1,078 total
includes taxes & fees
24 Nov - 25 Nov
Inn on Putney Road
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 AED 1,106
AED 1,200 total
includes taxes & fees
24 Nov - 25 Nov
Chesterfield Inn
Four Columns Inn
Garden

Four Columns Inn

3.0 star property
8.6 out of 10, Excellent, (3)
"Friendliest Staff Ever!"
Four Columns Inn
The Engel House
Exterior

The Engel House

3.0 star property
9.2 out of 10, Wonderful, (11)
"The "
The price is AED 528
AED 575 total
includes taxes & fees
4 Dec - 5 Dec
The Engel House
The Brattleboro
Room

The Brattleboro

4.0 star property
10.0 out of 10, Exceptional, (4)
"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

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

9.0 out of 10, Wonderful, (42)
"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
Charming Waterfront Log Cabin
Exterior

Charming Waterfront Log Cabin

9.4 out of 10, Exceptional, (36)
"We really appreciated the solitude and quiet retreat this cabin offered. "
Charming Waterfront Log Cabin
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT
Living area

Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT

10.0 out of 10, Exceptional, (48)
"Amazing place. Offered everything we needed and more. Very warm and comfortable. Well appointed too. We will be back for a longer stay in 2025. "
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT
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 B&Bs in the area: Colonel Williams Inn: 9 rooms. 12.4 mi (20 km) from the heart of Chesterfield. 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. 18.1 mi (29.1 km) from the heart of downtown. 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, April, and November, 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, Pisgah State Park and Asbury United Methodist Church are some notable sights to visit. Spofford Lake and Madame Sherri Forest 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.