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Compare 7 B&B in Chesterfield with updated reviews, rates, and availability.

The Ellery
Exterior

The Ellery

3.5 star property
9.0 out of 10, Wonderful, (575)
"Great location, comfy bed, and so very many thoughtful touches—from cookies in the lobby to pictures of famous Smith alums in the breakfast nook to scented hand soap in the room. I loved the breakfast (oatmeal with lots of toppings!) in the common space with a roaring fire. We look forward to returning!"
The price is AED 511
AED 570 total
includes taxes & fees
13 Jan - 14 Jan
The Ellery
Black Walnut Inn
Front of property

Black Walnut Inn

2.0 star property
9.8 out of 10, Exceptional, (41)
"Best place to stay near UMASS! This was our 3rd stay. Rooms are Huge with a lodgey feel. And the homemade breakfast is an awesome perk! Hidden gem. "
The price is AED 558
AED 623 total
includes taxes & fees
15 Jan - 16 Jan
Black Walnut Inn
Old Mill Inn
Living area

Old Mill Inn

3.0 star property
9.4 out of 10, Exceptional, (467)
"A short overnight trip to see family after the holiday. We didn’t want to leave. Justin and Deb were so friendly and helpful. A lovely immaculate and comfortable room. The breakfast buffet was delicious with many choices to please. We will definitely stay there again when visiting. Thank you "
The price is AED 623
AED 695 total
includes taxes & fees
13 Jan - 14 Jan
Old Mill Inn
The Trail in Adams - Berkshires’ Art Hotel
Terrace/patio

The Trail in Adams - Berkshires’ Art Hotel

2.5 star property
8.8 out of 10, Excellent, (126)
"Best place I have been. Beautiful place. Excellent host. "
The price is AED 592
AED 662 total
includes taxes & fees
15 Jan - 16 Jan
The Trail in Adams - Berkshires’ Art Hotel
Harbour House Inn
Room

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (49)
"Lovely space and welcoming host."
The price is AED 925
AED 978 total
includes taxes & fees
14 Jan - 15 Jan
Harbour House Inn
The Red Door B&B
Exterior

The Red Door B&B

3.0 star property
10.0 out of 10, Exceptional, (5)
"We loved staying at this b&b. The owners were very accommodating, kind and helpful. Because of the pandemic, they only took us for the weekend. The breakfasts were above and beyond our expectations, simply fantastic. We highly recommend this beautiful place and we will be back for sure. "
The Red Door B&B
Daniel Stebbins House
Exterior

Daniel Stebbins House

3.0 star property
10.0 out of 10, Exceptional, (45)
"What is not to love about being welcomed into Richard and Ruth’s home. They are wonderful hosts and spent hours talking to us both during our stay. The house is an amazing building and learning about its history was wonderful. We walked into the tiny town and got some dinner, lovely options available. We can not wait to visit again and will be recommending anyone travelling around this area should certainly book a stay."
Daniel Stebbins House
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

Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (234)
"A beautiful lodge nestled in the woods surrounded by an abundance of trails to hike. "
The price is AED 551
AED 833 total
includes taxes & fees
12 Jan - 13 Jan
Berkshire Village Carriage House - Super Private!!
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Sandisfield Vacation Rental | 4BR | 3BA | 1,978 Sq Ft | Stairs Required

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

9.6 out of 10, Exceptional, (39)
"We had a wonderful stay. The cabin was clean and comfortable! "
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Peace and quiet on the lake
Exterior

Peace and quiet on the lake

9.6 out of 10, Exceptional, (201)
"My family and I really enjoyed our stay at the lake. My kids enjoyed playing outside in the snow. We had such a quality family time playing board games, watching movies and drinking hot cocoa. Justin was such a great host and really helpful when needed. We’re definitely coming back!"
Peace and quiet on the lake
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?
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: The Ellery: 11 mi (17.7 km) from the heart of Chesterfield.Old Mill Inn: 12 rooms. 11.9 mi (19.1 km) from the downtown core. Enjoy the deli and unique décor. Black Walnut Inn: 10 rooms. Situated 15.8 mi (25.4 km) from the heart of Chesterfield. Enjoy the free full breakfast and unique décor.
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 Chesterfield Public Library and Chesterfield Town Hall 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.