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Our top choices for Chester vacation homes
Cozy Home in Holyoke with 3 bedrooms
Cozy Home in Holyoke with 3 bedroomsHolyoke
9.8 out of 10, Exceptional, (12)
"What a great house and such gracious hosts!The location is just minutes from Mount Holyoke College which was perfect for our trip Super clean and well maintained house. I highly recommend staying here."
Eric W.
The price is SAR 488
SAR 1,207 total
includes taxes & fees
5 Jan - 6 January 2026
10.0 out of 10, Exceptional, (1)
"Overall had a great stay, the space is cozy and welcoming."
Gracie B.
The price is SAR 450
SAR 1,268 total
includes taxes & fees
23 Dec - 24 Dec
Townhouse with Pool Table - Renovated w/ King Bed
Townhouse with Pool Table - Renovated w/ King BedChicopee
10.0 out of 10, Exceptional, (11)
"The townhouse was perfect for our short trip. It was located close to everything we needed. The house was as described and we would stay here again."
Matt G.
The price is SAR 675
SAR 1,443 total
includes taxes & fees
4 Jan - 5 January 2026
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, (72)
"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. "
Connie P.
The price is SAR 675
SAR 1,039 total
includes taxes & fees
5 Jan - 6 January 2026
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!Sherwood Forest
10.0 out of 10, Exceptional, (5)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
Sharon K.
The price is SAR 554
SAR 1,410 total
includes taxes & fees
4 Jan - 5 January 2026
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, DineSherwood Forest
9.6 out of 10, Exceptional, (10)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
James D.
The price is SAR 668
SAR 1,559 total
includes taxes & fees
5 Jan - 6 January 2026
Big farmhouse in the foothills of the Berkshires
Big farmhouse in the foothills of the BerkshiresRussell
10.0 out of 10, Exceptional, (143)
"Perfect spot for a family celebration!"
Kerry P.
The price is SAR 750
SAR 1,364 total
includes taxes & fees
29 Dec - 30 Dec
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, (6)
"Very clean and spacious! We enjoyed our stay with our small pup!"
Ann C.
The price is SAR 1,009
SAR 1,852 total
includes taxes & fees
3 Jan - 4 January 2026
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 Chester Hotel Reviews
Hotel Northampton
10/10 Excellent
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