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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, (31)
"The deer valley inn was a cozy small guesthouse . The staff were very kind and helpful. Highly recommend the place . The staff manager was originally from turkey. Really sorry I forgot the name at this moment but he was wonderful . "
The price is AED 307
AED 439 total
includes taxes & fees
6 Nov - 7 Nov
Deerfield Valley Inn
Colonel Williams Inn
Front of property
Colonel Williams Inn
3.0 star property
9.6 out of 10, Exceptional, (282)
"We absolutely loved our stay! The property is beautiful, and Brian & Victoria were so sweet and accommodating. Not to mention that the breakfast spread was fabtastic! We can't wait to visit again."
The price is AED 538
AED 586 total
includes taxes & fees
7 Nov - 8 Nov
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 671
AED 728 total
includes taxes & fees
2 Dec - 3 Dec
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 709
AED 780 total
includes taxes & fees
7 Nov - 8 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 584
AED 617 total
includes taxes & fees
2 Dec - 3 Dec
Centennial House
Harvest Barn Inn
Porch
Harvest Barn Inn
3.0 star property
9.8 out of 10, Exceptional, (192)
"The young couple who own the Harvest Barn Inn are wonderful. The breakfasts were well thought out and excellent. Coffee and cookies were available in the afternoon and the cookies were delicious. The inn is located on a quiet road close to the VT Country Store and downtown Bellows Falls is unique and inviting. Beautiful views. Can’t say enough good things about this inn. "
The price is AED 650
AED 709 total
includes taxes & fees
13 Nov - 14 Nov
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
18 Nov - 19 Nov
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
6 Nov - 7 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
6 Nov - 7 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 483
AED 527 total
includes taxes & fees
6 Nov - 7 Nov
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, (41)
"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
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
Plenty of private open space to explore with the whole family!
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
10.0 out of 10, Exceptional, (48)
"The House, Lands and View of this place are all amazing. Great for big family gathering to escape and rejoice and relax. We came to explore a bit of Vermont, which we did, but we also found ourselves reluctant to go out as the house and property were so captivating all on their own!"
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
Charming Waterfront Log Cabin
Exterior
Charming Waterfront Log Cabin
9.4 out of 10, Exceptional, (34)
"Awesome"
Charming Waterfront Log Cabin
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.