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Compare 167 Vacation Homes in Chesterfield with updated reviews, rates, and availability.

Berkshire Village Carriage House - Super Private!!
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (243)
The price is AED 551
AED 841 total
includes taxes & fees
3 May - 4 May

Author Stephen Oates Once Owned
Author Stephen Oates Once Owned
8.0 out of 10, Very Good, (1)
The price is AED 1,466
AED 2,252 total
includes taxes & fees
4 May - 5 May

4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
10.0 out of 10, Exceptional, (151)

kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
9.8 out of 10, Exceptional, (98)

1810 Brook Side Mill/House / EV Level 2 Charging on Site
1810 Brook Side Mill/House / EV Level 2 Charging on Site
10.0 out of 10, Exceptional, (72)

Peace and quiet on the lake
Peace and quiet on the lake
9.6 out of 10, Exceptional, (214)

Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails
Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails
9.8 out of 10, Exceptional, (11)
The price is AED 606
AED 1,029 total
includes taxes & fees
11 May - 12 May

Owl's Nest - Cozy Westfield Home w/ Fire Pit
Owl's Nest - Cozy Westfield Home w/ Fire Pit
9.0 out of 10, Wonderful, (4)
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

comfort, luxury, privacy
comfort, luxury, privacy
9.8 out of 10, Exceptional, (58)

Deluxe Queen Room with 2 Queen Beds
Deluxe Queen Room with 2 Queen Beds
The price is AED 437
AED 570 total
includes taxes & fees
4 May - 5 May

Cheerful 1 bedroom
Cheerful 1 bedroom
9.8 out of 10, Exceptional, (34)
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.
Recent reviews of Chesterfield hotels
Recent reviews of Chesterfield hotels

Tru by Hilton Chicopee Springfield
5/5 Excellent
Love this place !
"This place never disappoints, very clean , comfortable , hot real breakfast, very very nice Day time staff , I’ve stayed twice already and plan on again , also everything you need is either at the hotel or around you . Btw housekeepers may wanna wait before coming in ur room before checkout , would be my only thing , don’t assume people left, could be a simple mistake def going back thanks Tru. "
A verified traveler stayed at Tru by Hilton Chicopee Springfield
Posted 1 day ago
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