Search Resort Hotels in Chesterfield

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Check prices for these dates

Next weekend
Feb 21 - Feb 23
In two weeks
Feb 28 - Mar 2
In one month
Mar 14 - Mar 16
In two months
Apr 11 - Apr 13

Browse Select Chesterfield Resorts

MGM Springfield
8 restaurants, breakfast, lunch, dinner served; American cuisine

MGM Springfield

4.0 star property
8.8 out of 10, Excellent, (1282)
"The place was understaffed and it showed.."
The price is CA $213
CA $274 total
includes taxes & fees
Feb 20 - Feb 21
MGM Springfield
Days Inn by Wyndham Windsor Locks / Bradley Intl Airport
Lobby

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 CA $100
CA $115 total
includes taxes & fees
Mar 8 - Mar 9
Days Inn by Wyndham Windsor Locks / Bradley Intl Airport
D. Hotel Suites & Spa
Indoor pool

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 CA $180
CA $209 total
includes taxes & fees
Feb 13 - Feb 14
D. Hotel Suites & Spa
La Quinta Inn & Suites by Wyndham Hartford - Bradley Airport
Free daily buffet breakfast

La Quinta Inn & Suites by Wyndham Hartford - Bradley Airport

2.5 star property
8.2 out of 10, Very good, (1503)
"The location was great"
The price is CA $140
CA $161 total
includes taxes & fees
Feb 16 - Feb 17
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)
"Thank you "
The price is CA $133
CA $153 total
includes taxes & fees
Feb 16 - Feb 17
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 CA $154
CA $172 total
includes taxes & fees
Feb 13 - Feb 14
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 CA $157
CA $181 total
includes taxes & fees
Feb 18 - Feb 19
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)
"Beautiful Inn right in the center of Williamstown! The Barn restaurant was quite good! Very nice! "
The price is CA $312
CA $349 total
includes taxes & fees
Feb 17 - Feb 18
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)
"It was a great little getaway from the city, service was great and helpful nothing to complain about this spot"
The price is CA $170
CA $210 total
includes taxes & fees
Feb 24 - Feb 25
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires
Hotel Downstreet, Ascend Hotel Collection
Indoor pool, open 6:00 AM to 10 PM, sun loungers

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 CA $169
CA $189 total
includes taxes & fees
Feb 26 - Feb 27
Hotel Downstreet, Ascend Hotel Collection
The Black Swan Lee - Lenox, Ascend Hotel Collection
Lobby

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 CA $157
CA $175 total
includes taxes & fees
Feb 18 - Feb 19
The Black Swan Lee - Lenox, Ascend Hotel Collection
Homewood Suites by Hilton Windsor Locks Hartford
Lobby

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 CA $160
CA $184 total
includes taxes & fees
Feb 16 - Feb 17
Homewood Suites by Hilton Windsor Locks Hartford
Comfort Inn East Windsor - Springfield
Lobby

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 CA $123
CA $141 total
includes taxes & fees
Feb 23 - Feb 24
Comfort Inn East Windsor - Springfield
The Red Lion Inn
Outdoor pool, sun loungers

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 CA $206
CA $295 total
includes taxes & fees
Feb 17 - Feb 18
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 CA $115
CA $128 total
includes taxes & fees
Feb 24 - Feb 25
The Yankee, Trademark Collection by Wyndham
La Quinta Inn & Suites by Wyndham Springfield MA
Indoor pool

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 CA $154
CA $174 total
includes taxes & fees
Feb 24 - Feb 25
La Quinta Inn & Suites by Wyndham Springfield MA
Tru by Hilton Chicopee Springfield
Premium bedding, down comforters, blackout drapes, iron/ironing board

Tru by Hilton Chicopee Springfield

2.5 star property
8.8 out of 10, Excellent, (999)
"N /a"
The price is CA $138
CA $157 total
includes taxes & fees
Feb 23 - Feb 24
Tru by Hilton Chicopee Springfield
Comfort Inn & Suites
Lobby

Comfort Inn & Suites

2.5 star property
9.2 out of 10, Wonderful, (1002)
"Good for what we needed. "
The price is CA $181
CA $202 total
includes taxes & fees
Feb 16 - Feb 17
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 CA $175
CA $201 total
includes taxes & fees
Feb 15 - Feb 16
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)
"Very nice stuff, clean, convenient and easy property. Thank you "
The price is CA $140
CA $156 total
includes taxes & fees
Feb 28 - Mar 1
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!!
Fridge, microwave, oven, stovetop

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 CA $214
CA $327 total
includes taxes & fees
Feb 13 - Feb 14
Berkshire Village Carriage House - Super Private!!
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
TV, fireplace, DVD player

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
Fridge, microwave, oven, stovetop

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

What can I expect from a resort vacation in Chesterfield?
You deserve a getaway, and a resort is just the place to pamper yourself with the amenities and services you need for a relaxing time in Chesterfield. One of the comfortable resorts in the surrounding area might be just what you’re looking for, whether you want an amazing pool, a state-of-the-art fitness center, or nightly entertainment options.
What's the best resort in Chesterfield?
Here are our top-rated resorts around Chesterfield: Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot’s more! - 21.7 mi (34.9 km) from Chesterfield. Features a fitness center. Mountain Lodge Apt! - 21.7 mi (34.9 km) from Chesterfield. Has a fitness center.
What can I do in Chesterfield?
Chesterfield Gorge, Westfield River, and Chesterfield Public Library are a few of the interesting sights to visit. Chesterfield Gorge Reservation and Chesterfield Town Hall are a few additional attractions in the area that you might like.
What's the weather like in Chesterfield?
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's the best way to get to and around Chesterfield?
Fly into Westfield, MA (BAF-Barnes Municipal), which is located 16.6 mi (26.8 km) from the heart of the city. Otherwise, you can search for flights to Pittsfield, MA (PSF-Pittsfield Municipal), which is 23.2 mi (37.3 km) away. If you’d like to venture out around the area, you may want a rental car for your journey.