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Check prices for these dates

Next weekend
28 Saf. - 2 Rab. I
In two weeks
7 Rab. I - 9 Rab. I
In one month
21 Rab. I - 23 Rab. I
In two months
18 Rab. II - 20 Rab. II

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
9.6 out of 10, Exceptional, (45)
"Amazing stay. We really recommend this place for anyone with Pet. Thanks"
The price is SAR 784
SAR 965 total
includes taxes & fees
24 Feb - 25 Feb
Deerfield Valley Inn
Colonel Williams Inn
Front of property

Colonel Williams Inn

3.0 star property
9.8 out of 10, Exceptional, (295)
"The owners were so kind. My boyfriend and I woke up a little late for breakfast the second day of our ski trip, and one of the hosts still made us a beautiful spread. Truly it was some of the best French toast I’ve had in years! The Christmas decorations were charming and sweet, not to mention the property itself is beautiful. They also had this amazing studio Ghibli gingerbread house that they made themselves! It’s located about 25 minutes from Mount snow. The rooms themselves are spacious and...
The price is SAR 520
SAR 567 total
includes taxes & fees
26 Mar - 27 Mar
Colonel Williams Inn
Deerhill Inn
Exterior

Deerhill Inn

3.5 star property
9.6 out of 10, Exceptional, (214)
"Never disappoints!"
The price is SAR 731
SAR 804 total
includes taxes & fees
24 Feb - 25 Feb
Deerhill Inn
Harvest Barn Inn
Porch

Harvest Barn Inn

3.0 star property
9.8 out of 10, Exceptional, (205)
"We had a wonderful weekend stay at the Inn! The 3 course breakfast was fantastic, the bed was comfortable, the shower was amazing, and the space was homey and cute. We would absolutely stay again!"
The price is SAR 634
SAR 691 total
includes taxes & fees
7 Mar - 8 Mar
Harvest Barn Inn
The Carriage Barn Inn
Exterior

The Carriage Barn Inn

3.0 star property
9.6 out of 10, Exceptional, (144)
"I was in town for the Harris Hill Ski Jump Challenge in Brattleboro, VT and decided to stay in Keene, NH a town I always wanted to visit. I couldn't have picked a better location. What a lovely place and a brisk 5-minute walk got me into town with a great bakery, running store and restaurants. I'll be back, so much more to do and see. Even got an afternoon of skiing in at Granite Gorge."
The price is SAR 637
SAR 691 total
includes taxes & fees
24 Feb - 25 Feb
The Carriage Barn Inn
Centennial House
Breakfast area

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 SAR 761
SAR 804 total
includes taxes & fees
28 Feb - 1 Mar
Centennial House
Windham Hill Inn
Exterior

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 SAR 679
SAR 740 total
includes taxes & fees
27 Feb - 28 Feb
Windham Hill Inn
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 SAR 880
SAR 968 total
includes taxes & fees
4 Mar - 5 Mar
Inn on Putney Road
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 SAR 584
SAR 637 total
includes taxes & fees
24 Feb - 25 Feb
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 SAR 1,153
SAR 1,251 total
includes taxes & fees
24 Feb - 25 Feb
Chesterfield 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
Four Columns Inn
Garden

Four Columns Inn

3.0 star property
8.8 out of 10, Excellent, (3)
"Friendliest Staff Ever!"
Four Columns Inn
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
Deluxe Room with Fireplace Room 2
Room

Deluxe Room with Fireplace Room 2

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

Deerfield Valley Inn - Suite Room

Deerfield Valley Inn - Suite Room
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
Deerfield Valley Inn - Standard Room 7
Room

Deerfield Valley Inn - Standard Room 7

Deerfield Valley Inn - Standard Room 7
Deerfield Valley Inn - Standard Room 6
Room

Deerfield Valley Inn - Standard Room 6

Deerfield Valley Inn - Standard Room 6
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
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

8.8 out of 10, Excellent, (45)
"A great little cabin close to Mt. Snow. Accurate description. Fire place didn’t work. Would stay here again. "
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck

Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck

7.0 out of 10, Good, (14)
"Great place. Clean and comfortable. Nicely stocked kitchen with newer appliances. Sauna was amazing. Had 10 inches of snow one morning and it was fully plowed by 7am!"
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck
This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!
Winter wonderland!

This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!

9.8 out of 10, Exceptional, (113)
"Beautiful and peaceful, great house for a winter getaway with the family. We loved the yard and location. Grab your groceries on the way up, and enjoy the amazing house with your crew, (And dog too) "
This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular 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 heart of Chesterfield. Enjoy the local cuisine breakfast and library. 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.