- Change your mindBook hotels with free cancellation
- Be pickySearch almost a million properties worldwide
Find vacation rentals that suit your style

Aparthotels

Apartments
Our top choices for Chester vacation homes

1. Real Estate: Therapy - Lake, Laundry, Love it
Real Estate: Therapy - Lake, Laundry, Love itSherwood Forest
9.6 out of 10, Exceptional, (4 reviews)
The price is CA $86
CA $406 total
includes taxes & fees
Nov 12 - Nov 13

2. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, CanoeingSherwood Forest
9.6 out of 10, Exceptional, (20 reviews)
The price is CA $226
CA $532 total
includes taxes & fees
Nov 9 - Nov 10

3. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!Sherwood Forest
10.0 out of 10, Exceptional, (10 reviews)
The price is CA $206
CA $508 total
includes taxes & fees
Nov 9 - Nov 10

4. Big farmhouse in the foothills of the Berkshires
Big farmhouse in the foothills of the BerkshiresRussell
10.0 out of 10, Exceptional, (155 reviews)
The price is CA $280
CA $469 total
includes taxes & fees
Nov 9 - Nov 10

5. 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, (79 reviews)
The price is CA $254
CA $377 total
includes taxes & fees
Nov 23 - Nov 24

6. Charming, updated 3 bedroom farmhouse farm stay.
Charming, updated 3 bedroom farmhouse farm stay.Williamsburg
10.0 out of 10, Exceptional, (44 reviews)
The price is CA $348
CA $562 total
includes taxes & fees
Dec 6 - Dec 7

7. Cozy Home in Holyoke with 3 bedrooms
Cozy Home in Holyoke with 3 bedroomsHolyoke
9.8 out of 10, Exceptional, (22 reviews)
The price is CA $218
CA $486 total
includes taxes & fees
Dec 7 - Dec 8

8. Townhouse with Pool Table - Renovated w/ King Bed
Townhouse with Pool Table - Renovated w/ King BedChicopee
10.0 out of 10, Exceptional, (18 reviews)
The price is CA $284
CA $594 total
includes taxes & fees
Nov 9 - Nov 10

9. Sun Filled Lenox Retreat - Minutes to Tanglewood!
Sun Filled Lenox Retreat - Minutes to Tanglewood!Lee
10.0 out of 10, Exceptional, (12 reviews)
The price is CA $449
CA $853 total
includes taxes & fees
Nov 9 - Nov 10

10. Red Door Retreat West Springfield 3 bedroom w/ Game Room! Near Big E & Six Flags
Red Door Retreat West Springfield 3 bedroom w/ Game Room! Near Big E & Six FlagsWest Springfield
10.0 out of 10, Exceptional, (1 review)
The price is CA $229
CA $446 total
includes taxes & fees
Nov 9 - Nov 10

11. Leaf-Peeper Paradise in the Berkshires
Leaf-Peeper Paradise in the BerkshiresGreat Barrington
9.6 out of 10, Exceptional, (29 reviews)
The price is CA $286
CA $425 total
includes taxes & fees
Nov 9 - Nov 10

12. Secluded Family Home in Serene Stockbridge Woods
Secluded Family Home in Serene Stockbridge WoodsStockbridge
10.0 out of 10, Exceptional, (30 reviews)
The price is CA $482
CA $868 total
includes taxes & fees
Nov 9 - Nov 10

13. 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, (42 reviews)
The price is CA $650
CA $1,165 total
includes taxes & fees
Dec 1 - Dec 2

14. 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
8.6 out of 10, Excellent, (11 reviews)
The price is CA $380
CA $668 total
includes taxes & fees
Nov 10 - Nov 11

15. Maya's Garden House: A Converted 3-Bedroom Barndominium on 32 Acres in Great Barrington
Maya's Garden House: A Converted 3-Bedroom Barndominium on 32 Acres in Great BarringtonGreat Barrington
The price is CA $1,372
CA $1,904 total
includes taxes & fees
Nov 30 - Dec 1
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.
Learn more about Chester
Experience the hiking, camping, and theater in Chester!

Top reviews in Chester

The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection HotelLee





































































































