Find a Bed and Breakfast in Chesterfield from CA $107

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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Chesterfield B&B

Colonel Williams Inn
Front of property

Colonel Williams Inn

3.0 star property
9.8 out of 10, Exceptional, (310)
"Excellent. Wonderful breakfast. "
The price is CA $184
CA $203 total
includes taxes & fees
Aug 7 - Aug 8
Colonel Williams Inn
Centennial House
Free daily full breakfast

Centennial House

3.5 star property
9.6 out of 10, Exceptional, (159)
"Lovely property and innkeepers, I was in the area for an event and hope to come back. "
The price is CA $250
CA $264 total
includes taxes & fees
Aug 10 - Aug 11
Centennial House
The Carriage Barn Inn
Free daily continental breakfast

The Carriage Barn Inn

3.0 star property
9.6 out of 10, Exceptional, (153)
"Loved our stay. Beautifully decorated and I was able to play the house guitar in common room which was a unique touch I really enjoyed. Would gladly stay here again."
The price is CA $244
CA $265 total
includes taxes & fees
Sep 2 - Sep 3
The Carriage Barn Inn
Harvest Barn Inn
Porch

Harvest Barn Inn

3.0 star property
9.8 out of 10, Exceptional, (223)
"A refurbished old Vermont home with a beautiful view of the Connecticut river. The young couple who own the home were delightful and very attentive. It was comfortable and very unique. I would certainly stay here again."
The price is CA $194
CA $212 total
includes taxes & fees
Aug 18 - Aug 19
Harvest Barn Inn
Green River Bridge Inn
Exterior

Green River Bridge Inn

3.0 star property
8.4 out of 10, Very good, (7)
"The area is beautiful and the inn is lovely. I would highly recommend to anyone visiting the area. "
The price is CA $279
CA $304 total
includes taxes & fees
Aug 7 - Aug 8
Green River Bridge Inn
Inn on Putney Road
Exterior

Inn on Putney Road

4.0 star property
9.8 out of 10, Exceptional, (49)
"The folks were nice and accommodating. The breakfast was absolutely fantastically delicious. We would recommend this B&B to all our family and friends."
The price is CA $406
CA $447 total
includes taxes & fees
Aug 10 - Aug 11
Inn on Putney Road
Deerfield Valley Inn
Exterior

Deerfield Valley Inn

3.0 star property
9.6 out of 10, Exceptional, (54)
"I liked that it was right on the scenic route"
The price is CA $107
CA $156 total
includes taxes & fees
Aug 24 - Aug 25
Deerfield Valley Inn
Windham Hill Inn
Mountain view

Windham Hill Inn

4.0 star property
8.4 out of 10, Very good, (36)
"This place was amazing, beautiful and the staff was great. We will be coming back here again. Visit the waterfalls in the area, beautiful. Great romantic getaway. "
The price is CA $250
CA $273 total
includes taxes & fees
Aug 7 - Aug 8
Windham Hill Inn
Chesterfield Inn
Lobby

Chesterfield Inn

4.0 star property
9.0 out of 10, Wonderful, (104)
"Great stay"
The price is CA $415
CA $450 total
includes taxes & fees
Aug 7 - Aug 8
Chesterfield Inn
The One Cat B&B
Exterior

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 CA $265
CA $292 total
includes taxes & fees
Aug 27 - Aug 28
The One Cat B&B
The Engel House
Exterior

The Engel House

3.0 star property
9.4 out of 10, Exceptional, (13)
"The perfect Vermont Bed and Breakfast. "
The price is CA $239
CA $261 total
includes taxes & fees
Aug 10 - Aug 11
The Engel House
Four Columns Inn
Deluxe Room | Living area

Four Columns Inn

3.0 star property
8.8 out of 10, Excellent, (3)
"Friendliest Staff Ever!"
Four Columns Inn
Deerhill Inn
Exterior

Deerhill Inn

3.5 star property
9.6 out of 10, Exceptional, (219)
"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 CA $260
CA $287 total
includes taxes & fees
Aug 10 - Aug 11
Deerhill Inn
The Brattleboro
Hiking

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
Deluxe Room with Fireplace Room 2
1 bedroom, iron/ironing board, WiFi, bed sheets

Deluxe Room with Fireplace Room 2

Deluxe Room with Fireplace Room 2
Deluxe Room with Fireplace Room 1
1 bedroom, iron/ironing board, WiFi, bed sheets

Deluxe Room with Fireplace Room 1

Deluxe Room with Fireplace Room 1
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 - 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 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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Top Chesterfield Hotel Reviews

Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG

10/10 Excellent
"Good room, great breakfast options "
Nathan 1-night trip
Posted 21 hours ago
Holiday Inn Express Hotel & Suites Brattleboro by IHG

Frequently asked questions

What is the nightly rate for a B&B in Chesterfield?
Prices for B&Bs in Chesterfield often vary, but you can find a great deal from CA $107 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Chesterfield B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
What is the difference between a Chesterfield Bed and Breakfast and a hotel?
Every Chesterfield B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Chesterfield B&Bs.