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Check prices for these dates

In two weeks
6 Mar - 8 Mar
In two months
17 Apr - 19 Apr
In three months
15 May - 17 May
In four months
12 Jun - 14 Jun

Our top choices for Chesterfield vacation homes

Fridge, microwave, oven, stovetop

Cozy Home in Holyoke with 3 bedrooms

Cozy Home in Holyoke with 3 bedrooms
Holyoke
9.8 out of 10, Exceptional, (14 reviews)
"Very neat and clean. Decorated for Fall, which was nice. All amenities made for a really nice time."
United States
Stacy G.
The price is AED 477
AED 1,206 total
includes taxes & fees
18 Feb - 19 Feb
Cozy Home in Holyoke with 3 bedrooms
3 bedrooms, desk, iron/ironing board, travel crib

Townhouse with Pool Table - Renovated w/ King Bed

Townhouse with Pool Table - Renovated w/ King Bed
Chicopee
10.0 out of 10, Exceptional, (12 reviews)
"Perfect stay for a family. Enjoyed the pool table. Beds were comfortable. Showers were perfect. Beautifully decorated. We felt right at home. Would definitely stay again. "
United States
Tonya Z.
The price is AED 661
AED 1,413 total
includes taxes & fees
18 Feb - 19 Feb
Townhouse with Pool Table - Renovated w/ King Bed
Desk, iron/ironing board, travel crib, WiFi

The Creation Station is a cozy place so make yourself at home.

The Creation Station is a cozy place so make yourself at home.
Easthampton Ma.
10.0 out of 10, Exceptional, (73 reviews)
"The place is wonderful. Our 2nd visit and will be back. Has everything you need and then some. For us its centrally located so more family came for day trips. "
United States
Connie P.
The price is AED 661
AED 1,017 total
includes taxes & fees
23 Feb - 24 Feb
The Creation Station is a cozy place so make yourself at home.
Interior

Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (48 reviews)
"Close to downtown, clean & comfortable!"
United States
Robbi C.
The price is AED 426
AED 739 total
includes taxes & fees
18 Feb - 19 Feb
Lovely 2nd Floor Apartment
Smart TV, books

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Sherwood Forest
9.8 out of 10, Exceptional, (11 reviews)
"Nicole was very attentive and very quick to respond to any question we had. Her cottage was perfect for a quiet getaway, just what everybody needs!"
United States
Matthew F.
The price is AED 588
AED 1,449 total
includes taxes & fees
23 Feb - 24 Feb
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Property grounds

Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (143 reviews)
"Perfect spot for a family celebration!"
United States
Kerry P.
The price is AED 735
AED 1,336 total
includes taxes & fees
18 Feb - 19 Feb
Big farmhouse in the foothills of the Berkshires
Exterior detail

3-bedroom house in beautiful Berkshires, close to amenities!

3-bedroom house in beautiful Berkshires, close to amenities!
Pittsfield
The price is AED 668
AED 1,115 total
includes taxes & fees
2 Mar - 3 Mar
3-bedroom house in beautiful Berkshires, close to amenities!
Dining

Charlemont Chalet - A 15 Acre Private Retreat

Charlemont Chalet - A 15 Acre Private Retreat
Charlemont
The price is AED 1,253
AED 2,397 total
includes taxes & fees
23 Feb - 24 Feb
Charlemont Chalet - A 15 Acre Private Retreat
Private kitchen

Welcoming 3-bedroom house- Gardner home

Welcoming 3-bedroom house- Gardner home
Chicopee
10.0 out of 10, Exceptional, (1 review)
"Overall had a great stay, the space is cozy and welcoming."
United States
Gracie B.
The price is AED 551
AED 1,421 total
includes taxes & fees
22 Feb - 23 Feb
Welcoming 3-bedroom house- Gardner home
Outdoor dining

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
7.8 out of 10, Good, (7 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
United States
Liz V.
The price is AED 988
AED 1,818 total
includes taxes & fees
21 Feb - 22 Feb
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Interior

Luxury Retreat inAmherst

Luxury Retreat inAmherst
Amherst
10.0 out of 10, Exceptional, (1 review)
"Very helpful and easy communication. Very clean and nice place. We were very busy and only really were at the place to sleep but it is quiet and perfect for a restful stay."
United States
Robert
The price is AED 1,983
AED 3,077 total
includes taxes & fees
18 Feb - 19 Feb
Luxury Retreat inAmherst
Property grounds

Riverbend Berkshire East Basecamp - 3 bedrooms available

Riverbend Berkshire East Basecamp - 3 bedrooms available
Charlemont
10.0 out of 10, Exceptional, (2 reviews)
"Very nice house and the stay was unproblematic!"
United States
Noah K.
The price is AED 588
AED 1,547 total
includes taxes & fees
24 Feb - 25 Feb
Riverbend Berkshire East Basecamp - 3 bedrooms available
Smart TV, fireplace, books

Five Bedroom Berkshire East Basecamp - Winter Vintage Vibe Retreat

Five Bedroom Berkshire East Basecamp - Winter Vintage Vibe Retreat
Charlemont
10.0 out of 10, Exceptional, (2 reviews)
"What an amazing house to stay at! Tons of room, well equipped kitchen and a great location! "
United States
Jason F.
The price is AED 1,056
AED 2,500 total
includes taxes & fees
22 Feb - 23 Feb
Five Bedroom Berkshire East Basecamp - Winter Vintage Vibe Retreat
Dining

Spacious 5-Bedroom Home with Game Room in Amherst - Mins to UMass

Spacious 5-Bedroom Home with Game Room in Amherst - Mins to UMass
Amherst
10.0 out of 10, Exceptional, (9 reviews)
"Perfect location, clean house, great for families with kids!"
United States
Emily Robustelli K.
The price is AED 1,466
AED 3,118 total
includes taxes & fees
18 Feb - 19 Feb
Spacious 5-Bedroom Home with Game Room in Amherst - Mins to UMass
Smart TV, books

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
9.6 out of 10, Exceptional, (4 reviews)
"Very charming, comfortable, and clean. It was in a great location and only minutes away from a lot of sightseeing locations. House management was very accommodating and friendly. I would stay here again."
United States
Paulo I.
The price is AED 661
AED 1,690 total
includes taxes & fees
22 Feb - 23 Feb
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Dining

King Bed w/ Game Room near Massmutual w/ Riverview

King Bed w/ Game Room near Massmutual w/ Riverview
Chicopee
The price is AED 1,146
AED 2,234 total
includes taxes & fees
22 Feb - 23 Feb
King Bed w/ Game Room near Massmutual w/ Riverview
Interior

Secluded Sophistication in the Berkshires - 49 Acres of Quiet Luxury in Becket.

Secluded Sophistication in the Berkshires - 49 Acres of Quiet Luxury in Becket.
Becket
The price is AED 1,230
AED 2,265 total
includes taxes & fees
23 Feb - 24 Feb
Secluded Sophistication in the Berkshires - 49 Acres of Quiet Luxury in Becket.
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

The Ellery

The Ellery

10/10 Excellent
"The Ellery is nice and quaint and the staff is very engaging and helpful. They treat people as their valued guests. The breakfast is outstanding and so is the attendant, Mare. "
Steven 1-night trip
Posted 1 day ago
The Ellery