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Check prices for these dates

Next weekend
4 Apr - 6 Apr
In two weeks
11 Apr - 13 Apr
In one month
25 Apr - 27 Apr
In two months
23 May - 25 May

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, (302)
"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 526
AED 574 total
includes taxes & fees
13 Apr - 14 Apr
Colonel Williams Inn
Deerfield Valley Inn
Exterior

Deerfield Valley Inn

3.0 star property
9.6 out of 10, Exceptional, (48)
"Accommodating staff. Nice old Inn convenient to Mt. Snow and restaurants. Had a great stay. Would stay here again."
The price is AED 312
AED 444 total
includes taxes & fees
2 Apr - 3 Apr
Deerfield Valley Inn
Deerhill Inn
Exterior

Deerhill Inn

3.5 star property
9.6 out of 10, Exceptional, (217)
"Charming Inn! My daughter and I loved it here. We stayed in the Magnolia and the room was very clean, beautiful and comfortable. Everyone at the Inn was just lovely to talk to and the breakfast was delish! "
The price is AED 753
AED 828 total
includes taxes & fees
30 Mar - 31 Mar
Deerhill Inn
Windham Hill Inn
Romantic Room, 1 King Bed | Mountain view

Windham Hill Inn

3.0 star property
8.4 out of 10, Very Good, (33)
"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 665
AED 725 total
includes taxes & fees
13 Apr - 14 Apr
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 567
AED 615 total
includes taxes & fees
1 Apr - 2 Apr
The Carriage Barn Inn
Harvest Barn Inn
Porch

Harvest Barn Inn

3.0 star property
9.8 out of 10, Exceptional, (208)
"Nice and comfortable great breakfast"
The price is AED 528
AED 576 total
includes taxes & fees
29 Mar - 30 Mar
Harvest Barn Inn
Centennial House
Exterior detail

Centennial House

3.5 star property
9.6 out of 10, Exceptional, (150)
"We had a great stay at Centennial House! Myself and my 14 year old son stayed for one night -- the bed was very comfortable and breakfast was fabulous!!"
The price is AED 789
AED 834 total
includes taxes & fees
31 Mar - 1 Apr
Centennial House
Inn on Putney Road
Exterior

Inn on Putney Road

4.0 star property
9.8 out of 10, Exceptional, (44)
"Great stop on our way out of N Vermont. Nice warm room on a cold night."
The price is AED 862
AED 948 total
includes taxes & fees
31 Mar - 1 Apr
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 528
AED 575 total
includes taxes & fees
6 Apr - 7 Apr
The Engel 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 AED 1,129
AED 1,225 total
includes taxes & fees
30 Mar - 31 Mar
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)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
The price is AED 826
AED 909 total
includes taxes & fees
2 Apr - 3 Apr
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 - 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 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
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 - Standard Room 7
1 bedroom, iron/ironing board, WiFi, bed sheets

Deerfield Valley Inn - Standard Room 7

Deerfield Valley Inn - Standard Room 7
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

The Jelly Mill-A River Retreat
Exterior

The Jelly Mill-A River Retreat

10.0 out of 10, Exceptional, (46)
"Stayed for sugar season. Spring thaw makes river road a bit sketch but place and hosts were great! Will b back. "
The Jelly Mill-A River Retreat
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
Fridge, microwave, stovetop, coffee/tea maker

Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!

10.0 out of 10, Exceptional, (35)
"We were more than impressed by this property, and surpised by the total freedom from other people on the lands. We loved staying at this charming property that is rustic and thoughtfully decorated. The views are amazing and the place is completely quiet. There is a long driveway up from the 'main road', which is really a very lightly traveled road anyway. We enjoyed the silence, and the bucolic views and lifestyle. It was late winter and there was snow on the ground when we arrived, but the...
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
Cozy Home Near Downtown, Shops, and Restaurants.
Exterior

Cozy Home Near Downtown, Shops, and Restaurants.

2.0 star property
10.0 out of 10, Exceptional, (3)
"Online info was accurate. Nice spot to rent with family."
The price is AED 1,102
AED 1,909 total
includes taxes & fees
3 Apr - 4 Apr
Cozy Home Near Downtown, Shops, and Restaurants.
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 well-liked B&Bs in the surrounding 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 heart of downtown.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. 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.