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Our top choices for Chester vacation homes

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
16 Feb - 17 Feb
Cozy Home in Holyoke with 3 bedrooms

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.

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
16 Feb - 17 Feb
Townhouse with Pool Table - Renovated w/ King Bed

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

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

3-bedroom house in beautiful Berkshires, close to amenities!
Pittsfield
The price is AED 664
AED 1,132 total
includes taxes & fees
23 Feb - 24 Feb
3-bedroom house in beautiful Berkshires, close to amenities!

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
16 Feb - 17 Feb
Big farmhouse in the foothills of the Berkshires

Family Ski Getaway in the Berkshires

Family Ski Getaway in the Berkshires
Great Barrington
9.2 out of 10, Wonderful, (9 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is AED 744
AED 1,093 total
includes taxes & fees
19 Feb - 20 Feb
Family Ski Getaway in the Berkshires

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (33 reviews)
"A college friends' retreat was fantastic, in part due to the location, cleanliness and amenities in this 3 bedroom house. Furniture was comfortable and kitchen was stocked with everything we needed. "
United States
cathy c.
The price is AED 1,098
AED 2,388 total
includes taxes & fees
17 Feb - 18 Feb
Walk into town, soak up sun on enclosed porch & steps away from nature trails!

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 1,752 total
includes taxes & fees
16 Feb - 17 Feb
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

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

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!

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

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 2,261 total
includes taxes & fees
23 Feb - 24 Feb
Secluded Sophistication in the Berkshires - 49 Acres of Quiet Luxury in Becket.

Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi
Lee
8.8 out of 10, Excellent, (3 reviews)
"House was clean and made our Thanksgiving great with it's size and amenities. "
United States
Khalil S.
The price is AED 1,745
AED 3,163 total
includes taxes & fees
9 Mar - 10 Mar
Spacious 5-bedroom house in charming Lee with WiFi
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