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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 878
AED 1,571 total
includes taxes & fees
27 Apr - 28 Apr

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, (150)

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, (71)

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 1,033 total
includes taxes & fees
7 May - 8 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, (57)

Deluxe Queen Room with 2 Queen Beds
Deluxe Queen Room with 2 Queen Beds
The price is AED 400
AED 529 total
includes taxes & fees
30 Apr - 1 May

Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!
10.0 out of 10, Exceptional, (2)
The price is AED 687
AED 1,395 total
includes taxes & fees
28 Apr - 29 Apr
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

Fairfield Inn & Suites Springfield Holyoke
5/5 Excellent
"This property provided to our expectations. Breakfast was good. There’s all day coffee and tea available. Clean property outside and out. Would stay again."
A verified traveler from Rahway stayed at Fairfield Inn & Suites Springfield Holyoke
Posted 2 days ago
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