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Check prices for these dates

Next weekend
25 Rab. II - 27 Rab. II
In two weeks
2 Jum. I - 4 Jum. I
In one month
16 Jum. I - 18 Jum. I
In two months
13 Jum. II - 15 Jum. II

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 SAR 502
SAR 548 total
includes taxes & fees
17 Apr - 18 Apr
Colonel Williams Inn
Deerfield Valley Inn
Exterior

Deerfield Valley Inn

3.0 star property
9.6 out of 10, Exceptional, (49)
"Nice quiet bed and breakfast. Staff was great. Walking distance to three restaurants. "
The price is SAR 319
SAR 454 total
includes taxes & fees
20 Apr - 21 Apr
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 SAR 769
SAR 846 total
includes taxes & fees
1 May - 2 May
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 SAR 680
SAR 741 total
includes taxes & fees
30 Apr - 1 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 SAR 638
SAR 692 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, (209)
"Great accomodations. Kaelan & Blessing were wonderful hosts and very accommodating to my requests. The breakfasts were excellent - well-balanced, nutritious, and filling. A quaint, inn in a quiet location with a nice view. A very nice weekend stay at a very reasonable price. Would highly recommend, and would certainly stay there again."
The price is SAR 591
SAR 644 total
includes taxes & fees
28 Apr - 29 Apr
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 SAR 726
SAR 767 total
includes taxes & fees
29 Apr - 30 Apr
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 SAR 937
SAR 1,030 total
includes taxes & fees
17 Apr - 18 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 SAR 539
SAR 588 total
includes taxes & fees
28 Apr - 29 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 SAR 1,130
SAR 1,226 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, (74)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
The price is SAR 844
SAR 929 total
includes taxes & fees
20 Apr - 21 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 - 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)
"Great place with an elite game room. "
GAMERS HAVEN, River Wine Inn!
The Jelly Mill-A River Retreat
Exterior

The Jelly Mill-A River Retreat

10.0 out of 10, Exceptional, (47)
"Was exactly as described. Had everything we needed and more. Only thing we had hoped for that wasn’t there was some olive oil, so bring your own if you want to cook. Not quite as remote as we were anticipating, but in a good way . Was still very rural, and we were grateful for the 4wheel drive vehicle we rented. Perfect, majestic, natural location for our family retreat."
The Jelly Mill-A River Retreat
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)
"Stayed twice would stay again"
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 Chesterfield Town Hall 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. Situated 10.2 mi (16.4 km) from the heart of Chesterfield. Inn on Putney Road: 6 rooms. 4.8 mi (7.7 km) from the heart of downtown. Enjoy the free full breakfast and onsite spa services. 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 Chesterfield Town Hall are some notable sights to visit. You might check out Pisgah State Park 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.