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Check prices for these dates

Next weekend
May 8 - May 10
In two weeks
May 15 - May 17
In one month
May 29 - May 31
In two months
Jun 26 - Jun 28

Our top choices for Chesterfield bed & breakfast

Deluxe Room, 1 King Bed | Hypo-allergenic bedding, individually decorated, individually furnished

Black Walnut Inn

Black Walnut Inn
2.0 star property
North Amherst
9.8 out of 10, Exceptional, (114 reviews)
"Beautiful property, lovely staff, very nice room, yummy breakfast!"
United States
Lisa
$184 nightly
The price is $205
May 11 - May 12
Total with taxes and fees
Black Walnut Inn
Exterior

UU Rowe Camp and Conference Center

UU Rowe Camp and Conference Center
2.0 star property
Rowe
10.0 out of 10, Exceptional, (1 review)
"Yes"
United States
Stuart
$191 nightly
The price is $202
May 4 - May 5
Total with taxes and fees
UU Rowe Camp and Conference Center
Exterior

Daniel Stebbins House

Daniel Stebbins House
3.0 star property
South Hadley
10.0 out of 10, Exceptional, (52 reviews)
"Quaint B&B in the heart of South Hadley. Within walking distance of town and Mount Holyoke College. (Stairs to second floor are a bit steep for anyone with accessibility issues.) Great overall local place to stay. "
United States
Jason
$270 nightly
The price is $302
May 3 - May 4
Total with taxes and fees
Daniel Stebbins House
Exterior

Old Mill Inn

Old Mill Inn
3.0 star property
Hatfield
9.4 out of 10, Exceptional, (506 reviews)
"Lovely breakfast, clean and charming accommodations. Highly recommend!"
United States
Michaela
$197 nightly
The price is $220
May 11 - May 12
Total with taxes and fees
Old Mill Inn
Terrace/patio

The Trail in Adams - Berkshires’ Art Hotel

The Trail in Adams - Berkshires’ Art Hotel
2.5 star property
Adams
8.8 out of 10, Excellent, (146 reviews)
"Great little Inn with a well equipped kitchen, clean rooms, and art books. It made for a lovely base for our two day Berkshires adventure."
United States
selmin
$174 nightly
The price is $194
May 3 - May 4
Total with taxes and fees
The Trail in Adams - Berkshires’ Art Hotel
Exterior

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53 reviews)
"Nice place for a weekend away."
United States
Gregory
$233 nightly
The price is $246
May 4 - May 5
Total with taxes and fees
Harbour House Inn
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

Red Roof Inn PLUS+ West Springfield

Red Roof Inn PLUS+ West Springfield

10/10 Excellent
"Clean"
Denise 1-night trip
Posted 10 hours ago
Red Roof Inn PLUS+ West Springfield

Find out more about Chesterfield

Chesterfield B&B information

Number of reviews
872
Accommodation
17 B&B
Lowest Price
$194
Highest Price
$302

Frequently asked questions

Searching for B&Bs in Chesterfield?
If you want to find an accommodation with a small number of rooms and a cozy environment, a B&B might be a great fit for your trip to Chesterfield. While you're here, you can get to know Chesterfield by exploring its natural beauty. Consider a stop by Chesterfield Gorge and Knightville Dam & Reservation.
How do you know if a B&B is the best choice for your stay?
With attentive service, an atmosphere suited to mingling with other guests, and of course a scrumptious breakfast, B&Bs provide a one-of-a-kind setting.
What are the top B&Bs in Chesterfield?
Here are some B&Bs in the surrounding area: Old Mill Inn: 12 rooms. 11.9 mi (19.1 km) from the heart of Chesterfield. Enjoy the deli and unique décor. Black Walnut Inn: 10 rooms. 15.8 mi (25.4 km) from the downtown core. Enjoy the free full breakfast and unique décor. Daniel Stebbins House: 5 rooms. Located 16.3 mi (26.3 km) from the core of Chesterfield. Enjoy the designer toiletries and arcade game room.
What's the best time of year to stay at a B&B in Chesterfield?
When you're dreaming of a trip to Chesterfield, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 68°F, while the coldest months are January and February with an average of 30°F. The snowiest months in Chesterfield are January, February, November, and March, with each month seeing an average of 6 inches of snowfall.
What is there to do in Chesterfield?
Spend some time exploring Chesterfield Gorge and Westfield River if you're hoping to see some of the area's natural features. You might put Silvio O. Conte National Fish and Wildlife Refuge and Chesterfield Public Library on your list if you want to see more of the area.
How can I get to and around Chesterfield?
Planning your excursions in and around Chesterfield is easier with these transportation options. Fly into Westfield, MA (BAF-Barnes Municipal), which is located 16.6 mi (26.8 km) away from the heart of the city. You can also search for flights into Pittsfield, MA (PSF-Pittsfield Municipal), which is 23.2 mi (37.3 km) away. If you'd like to venture out around the area, consider renting a car to take in more sights.

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