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Check prices for these dates

Next weekend
21 Saf. - 23 Saf.
In two weeks
28 Saf. - 2 Rab. I
In one month
14 Rab. I - 16 Rab. I
In two months
11 Rab. II - 13 Rab. II

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

MGM Springfield
Exterior

MGM Springfield

4.0 star property
8.8 out of 10, Excellent, (1282)
"Great stay. "
The price is SAR 559
SAR 719 total
includes taxes & fees
19 Feb - 20 Feb
MGM Springfield
Days Inn by Wyndham Windsor Locks / Bradley Intl Airport
Exterior

Days Inn by Wyndham Windsor Locks / Bradley Intl Airport

2.0 star property
6.6 out of 10, (1461)
"Dated rooms but clean. Toilet seat hinge was broken. Simple repair that housekeeping should report and get fixed immediately. Big plus was the comfortable bedding. Nice pillows and mattress. They also had an airport shuttle. Stay was in February and we arrived in room at 7:30 pm. Heat was turned off so the room was cold!! Thank you!! They knew we were coming as we had a reservation. I imagine it’s hard to get dedicated employees for these motels that are in the cashing out fix only what’s...
The price is SAR 261
SAR 300 total
includes taxes & fees
8 Mar - 9 Mar
Days Inn by Wyndham Windsor Locks / Bradley Intl Airport
D. Hotel Suites & Spa
Front of property

D. Hotel Suites & Spa

3.0 star property
9.4 out of 10, Exceptional, (2360)
"Comfortable. Homey. Desk clerk was friendly and helpful "
The price is SAR 499
SAR 580 total
includes taxes & fees
18 Feb - 19 Feb
D. Hotel Suites & Spa
La Quinta Inn & Suites by Wyndham Hartford - Bradley Airport
Exterior

La Quinta Inn & Suites by Wyndham Hartford - Bradley Airport

2.5 star property
8.2 out of 10, Very Good, (1503)
"Great pre-flight place to stay. Convenient and economical"
The price is SAR 367
SAR 422 total
includes taxes & fees
16 Feb - 17 Feb
La Quinta Inn & Suites by Wyndham Hartford - Bradley Airport
Candlewood Suites Windsor Locks Bradley Arpt by IHG
Exterior

Candlewood Suites Windsor Locks Bradley Arpt by IHG

2.5 star property
8.2 out of 10, Very Good, (807)
"Fair price except for the security deposit they don't tell you about. No one likes surprises when it comes to spending more money. Never understood this logic. I did like the shower set up. Spacious bathroom, curved shower rod adding lots of space to shower, but the showerhead made a terrible, piercing whistling sound. They hold their own with the kitchenette area. The separate seating area/living room and bedroom was great. I felt very comfortable in the room. Plenty of closest space, and a lot...
The price is SAR 349
SAR 401 total
includes taxes & fees
22 Feb - 23 Feb
Candlewood Suites Windsor Locks Bradley Arpt by IHG
Life House Berkshires
Lobby

Life House Berkshires

3.5 star property
9.0 out of 10, Wonderful, (496)
"Amazing property we will be back"
The price is SAR 363
SAR 405 total
includes taxes & fees
25 Feb - 26 Feb
Life House Berkshires
Fairfield Inn & Suites by Marriott Springfield Enfield
Exterior

Fairfield Inn & Suites by Marriott Springfield Enfield

2.5 star property
8.8 out of 10, Excellent, (1004)
"Great stay, just didn’t like that we had to pay for parking as a guest "
The price is SAR 350
SAR 402 total
includes taxes & fees
2 Mar - 3 Mar
Fairfield Inn & Suites by Marriott Springfield Enfield
The Williams Inn
Front of property - evening/night

The Williams Inn

4.0 star property
9.6 out of 10, Exceptional, (411)
"Rooms were new and very clean. However, they were not even a little bit soundproof. My room was by the elevator ans the beverage station and a group of people were being loud late at night (past midnight). I could hear them clearly "
The price is SAR 807
SAR 901 total
includes taxes & fees
26 Feb - 27 Feb
The Williams Inn
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires
Property amenity

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires

3.5 star property
9.0 out of 10, Wonderful, (595)
"Room was clean and facility was nice"
The price is SAR 446
SAR 551 total
includes taxes & fees
24 Feb - 25 Feb
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires
Hotel Downstreet, Ascend Hotel Collection
Exterior

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.6 out of 10, Excellent, (1000)
"Staff were extremely nice and accommodating."
The price is SAR 443
SAR 495 total
includes taxes & fees
26 Feb - 27 Feb
Hotel Downstreet, Ascend Hotel Collection
The Black Swan Lee - Lenox, Ascend Hotel Collection
Exterior

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1001)
"Clean. Very nice location. Would be beautiful in the summer. Would go there again "
The price is SAR 411
SAR 459 total
includes taxes & fees
24 Feb - 25 Feb
The Black Swan Lee - Lenox, Ascend Hotel Collection
Homewood Suites by Hilton Windsor Locks Hartford
Outdoor pool

Homewood Suites by Hilton Windsor Locks Hartford

3.0 star property
8.6 out of 10, Excellent, (703)
"The room was amazing, absolutely recommended. Will be going back!"
The price is SAR 420
SAR 482 total
includes taxes & fees
14 Feb - 15 Feb
Homewood Suites by Hilton Windsor Locks Hartford
Comfort Inn East Windsor - Springfield
Exterior

Comfort Inn East Windsor - Springfield

2.5 star property
8.2 out of 10, Very Good, (939)
"Check in staff was friendly. The room was spacious and clean and breakfast was ok. The hotel is older. My first room had an issue with the water but they gave me a new room within minutes. The heating unit wasn’t working in the second room but they had 2 space heaters. Was too tired to request another change but the heaters did the job. I slept well-the bed was comfortable. Good for a one night stop over."
The price is SAR 321
SAR 369 total
includes taxes & fees
26 Feb - 27 Feb
Comfort Inn East Windsor - Springfield
The Red Lion Inn
Front of property

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1002)
"Property very historical. Check in and dinning very good food and excellent wait staff. Will recommend to others."
The price is SAR 497
SAR 723 total
includes taxes & fees
17 Feb - 18 Feb
The Red Lion Inn
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1004)
"Modern clean room that was very comfortable. Close to exit and parking. Great hut tub and pool, very clean with plenty of towels. Great value free breakfast included juice, cereal, eggs, sausage, waffle maker, fruit and pastries. Definitely will stay here again!"
The price is SAR 353
SAR 394 total
includes taxes & fees
3 Mar - 4 Mar
The Yankee, Trademark Collection by Wyndham
La Quinta Inn & Suites by Wyndham Springfield MA
Exterior

La Quinta Inn & Suites by Wyndham Springfield MA

3.0 star property
8.2 out of 10, Very Good, (1280)
"The staffs were very friendly and helpful. The hotel shares a parking lot with Dunkin and military building was right across the street which made you feel safe."
The price is SAR 402
SAR 456 total
includes taxes & fees
24 Feb - 25 Feb
La Quinta Inn & Suites by Wyndham Springfield MA
Tru by Hilton Chicopee Springfield
Exterior

Tru by Hilton Chicopee Springfield

2.5 star property
8.8 out of 10, Excellent, (999)
"💕"
The price is SAR 363
SAR 412 total
includes taxes & fees
23 Feb - 24 Feb
Tru by Hilton Chicopee Springfield
Comfort Inn & Suites
Exterior

Comfort Inn & Suites

2.5 star property
9.2 out of 10, Wonderful, (1002)
"Good for what we needed. "
The price is SAR 475
SAR 531 total
includes taxes & fees
17 Feb - 18 Feb
Comfort Inn & Suites
Holiday Inn Express & Suites Bradley Airport by IHG
Exterior

Holiday Inn Express & Suites Bradley Airport by IHG

2.5 star property
8.8 out of 10, Excellent, (1004)
"Very clean; close to the airport."
The price is SAR 460
SAR 529 total
includes taxes & fees
15 Feb - 16 Feb
Holiday Inn Express & Suites Bradley Airport by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (732)
"We stay here often because it is close to our daughter’s school in New York. We love staying here and choose this hotel every time. "
The price is SAR 368
SAR 411 total
includes taxes & fees
28 Feb - 1 Mar
Holiday Inn & Suites Pittsfield-Berkshires by IHG
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, (239)
"Property was very nice Kirchen could use some additons -starting with a ladle "
The price is SAR 563
SAR 855 total
includes taxes & fees
17 Feb - 18 Feb
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)
"A nice cabin in the woods. Only issue was rodents at the property. We had four sighting in three days. Would stay again if they resolved the mouse problem."
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Pristine Home In Becket Woods

Pristine Home In Becket Woods

10.0 out of 10, Exceptional, (13)
"Pristine can mean several different things. My interpretation was to be “like new”. This dwelling did not quite live up to that standard, but was clean, sans the “mud room” and what appeared to be mold on the peak of the ceiling above the living room. The original listing stated firewood was provided by the host. Then, the checkin instructions stated guests provided their own. Not huge, just misstated in the listing (since changed). There was a power outage while we were there, thus no...
Pristine Home In Becket Woods
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.Black Walnut Inn: 10 rooms. 15.8 mi (25.4 km) from the downtown core. Enjoy the free full breakfast and unique décor. Old Mill Inn: 12 rooms. Situated 11.9 mi (19.1 km) from the heart of Chesterfield. Enjoy the deli 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 Gorge Reservation 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.