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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

Compare 27 B&B in Chesterfield with updated reviews, rates, and availability.

Colonel Williams Inn
Front of property

Colonel Williams Inn

3.0 star property
9.8 out of 10, Exceptional, (303)
"The inn keepers are always super friendly and the place is kept well. The breakfast is delicious. Great for families who prefer quiet and quaint."
The price is AED 492
AED 536 total
includes taxes & fees
6 May - 7 May
Colonel Williams Inn
Deerfield Valley Inn
Exterior

Deerfield Valley Inn

3.0 star property
9.4 out of 10, Exceptional, (50)
"Nice quiet bed and breakfast. Staff was great. Walking distance to three restaurants. "
Deerfield Valley Inn
Deerhill Inn
Exterior

Deerhill Inn

3.5 star property
9.6 out of 10, Exceptional, (219)
"Amazing property! Absolutely will return again"
The price is AED 685
AED 754 total
includes taxes & fees
15 May - 16 May
Deerhill Inn
Windham Hill Inn
Romantic Room, 1 King Bed | Mountain view

Windham Hill Inn

3.5 star property
8.4 out of 10, Very Good, (33)
"Amazing trip. Beautiful property. Hope to return someday. "
The price is AED 665
AED 725 total
includes taxes & fees
18 May - 19 May
Windham Hill Inn
The Carriage Barn Inn
Free daily continental breakfast

The Carriage Barn Inn

3.0 star property
9.6 out of 10, Exceptional, (146)
"This is a great place to stay. Host, Joe, was very friendly and helpful. The room was clean and cozy , and nicely furnished. Common areas were very comfortable and welcoming. We will definitely come back! "
The price is AED 644
AED 699 total
includes taxes & fees
5 May - 6 May
The Carriage Barn Inn
Harvest Barn Inn
Porch

Harvest Barn Inn

3.0 star property
9.8 out of 10, Exceptional, (210)
"Nice and comfortable great breakfast"
The price is AED 739
AED 806 total
includes taxes & fees
9 May - 10 May
Harvest Barn Inn
Centennial House
Exterior detail

Centennial House

3.5 star property
9.6 out of 10, Exceptional, (152)
"This historic property is very nice. Beds are comfortable. The hosts are very welcoming and communication was very good. Breakfast was outstanding! I highly recommend this property and hope to return for another visit someday. "
The price is AED 710
AED 751 total
includes taxes & fees
18 May - 19 May
Centennial House
Inn on Putney Road
Exterior

Inn on Putney Road

4.0 star property
9.8 out of 10, Exceptional, (45)
"Excellent"
The price is AED 1,043
AED 1,148 total
includes taxes & fees
4 May - 5 May
Inn on Putney Road
Four Columns Inn
Deluxe Room | Living area | 20-inch TV with cable channels

Four Columns Inn

3.0 star property
8.8 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, (12)
"The perfect Vermont Bed and Breakfast. "
The price is AED 661
AED 720 total
includes taxes & fees
6 May - 7 May
The Engel House
Chesterfield Inn
Lobby

Chesterfield Inn

4.0 star property
9.0 out of 10, Wonderful, (101)
"Charming place with friendly staff and owners."
The price is AED 1,106
AED 1,200 total
includes taxes & fees
4 May - 5 May
Chesterfield Inn
The One Cat B&B
Exterior detail

The One Cat B&B

2.5 star property
9.6 out of 10, Exceptional, (75)
"Such nice innkeepers! And a bespoke breakfast to boot. I hope I'm back in Brattleboro soon so I can spend another night at the One Cat B&B. Next time I hope to meet the cat."
The price is AED 826
AED 909 total
includes taxes & fees
6 May - 7 May
The One Cat B&B
The Brattleboro
Seasonal outdoor pool

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 - Suite Room
Interior

Deerfield Valley Inn - Suite Room

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

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

Deerfield Valley Inn, 5min. to M.Snow Room Entire Inn
Deerfield Valley Inn - Standard Room 6
1 bedroom, iron/ironing board, WiFi, bed sheets

Deerfield Valley Inn - Standard Room 6

Deerfield Valley Inn - Standard Room 6
Deerfield Valley Inn - Budget Club Room 3
1 bedroom, iron/ironing board, WiFi, bed sheets

Deerfield Valley Inn - Budget Club Room 3

Deerfield Valley Inn - Budget Club Room 3
Deerfield Valley Inn - Deluxe Room with Fireplace Room 4
1 bedroom, iron/ironing board, bed sheets

Deerfield Valley Inn - Deluxe Room with Fireplace Room 4

Deerfield Valley Inn - Deluxe Room with Fireplace Room 4
Deerfield Valley Inn - Deluxe Room with Fireplace Room 5
1 bedroom, WiFi, bed sheets

Deerfield Valley Inn - Deluxe Room with Fireplace Room 5

Deerfield Valley Inn - Deluxe Room with Fireplace Room 5
Deerfield Valley Inn - Deluxe Room with Fireplace Room 8
1 bedroom, iron/ironing board, WiFi, bed sheets

Deerfield Valley Inn - Deluxe Room with Fireplace Room 8

Deerfield Valley Inn - Deluxe Room with Fireplace Room 8
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

GAMERS HAVEN, River Wine Inn!
Game room

GAMERS HAVEN, River Wine Inn!

2.0 star property
10.0 out of 10, Exceptional, (11)
"Such a large house with so many areas for activities. Close to a lot of fun things to do like axe throwing, an escape room, distilleries, breweries, etc."
GAMERS HAVEN, River Wine Inn!
Lovely 2nd Floor Apartment
Interior

Lovely 2nd Floor Apartment

10.0 out of 10, Exceptional, (21)
"Easy stay, good location for us. Would stay again. "
The price is AED 474
AED 808 total
includes taxes & fees
7 May - 8 May
Lovely 2nd Floor Apartment
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Outdoor dining

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

8.8 out of 10, Excellent, (47)
"really enjoyed our stay. Place would be much better if there was a microwave."
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
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. When you want to explore some attractions in town, Asbury United Methodist Church and Pisgah State Park 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 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. 10.2 mi (16.4 km) from the downtown core. Centennial House: 5 rooms. 13.2 mi (21.2 km) from the heart of downtown. Enjoy the free full breakfast and unique décor. Inn on Putney Road: 6 rooms. Located 4.8 mi (7.7 km) from the core of Chesterfield. Enjoy the free full breakfast and onsite spa services.
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. You might check out 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) 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.