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Compare 164 Vacation Homes in Chesterfield with updated reviews, rates, and availability.

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (243)
"What a great spot to stay for the few days we were there Can’t wait to come back! "
The price is SAR 563
SAR 855 total
includes taxes & fees
5 May - 6 May
Berkshire Village Carriage House - Super Private!!

Author Stephen Oates Once Owned

8.0 out of 10, Very Good, (1)
"The house is very close to Amherst on a quiet street. Plenty of room, comfortable beds, and well supplied. We’d stay again! "
The price is SAR 1,496
SAR 2,300 total
includes taxes & fees
4 May - 5 May
Author Stephen Oates Once Owned

4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi

10.0 out of 10, Exceptional, (151)
"Hi,The views are spectacular, house is spacious and close to skiing. We had a great time staying in this house. We even talked about coming back in warmer weather. "
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi

kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

9.8 out of 10, Exceptional, (98)
"We were attending a horse show locally. We stayed a few nights and everything about this day was easy from start to finish."
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

1810 Brook Side Mill/House / EV Level 2 Charging on Site

10.0 out of 10, Exceptional, (72)
"Very spacious and comfortable. Biggest selling point was its proximity to family in the area."
1810 Brook Side Mill/House / EV Level 2 Charging on Site

Peace and quiet on the lake

9.6 out of 10, Exceptional, (214)
"We enjoyed the privacy and quiet of the location. The house itself is very well kept inside and cozy. "
Peace and quiet on the lake

Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails

9.8 out of 10, Exceptional, (11)
"We had a great stay at Nick's place. place was very clean and spacious, good layout. Nick was easy to reach and communication was great. We would definitely book again! thank you! "
The price is SAR 619
SAR 1,050 total
includes taxes & fees
11 May - 12 May
Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails

Owl's Nest - Cozy Westfield Home w/ Fire Pit

9.0 out of 10, Wonderful, (4)
"Property worked well for us "
Owl's Nest - Cozy Westfield Home w/ Fire Pit

Hilltown Nest is a wonderful place for family and friends to gather.

9.8 out of 10, Exceptional, (15)
"Sadly we were only here for a couple of nights, but this place was very nice. I manage vacation rentals myself and i was very impressed by the cleanliness of this place, especially considering the size of it. The house is great for a family with lots of room to spread out. Our grandkids enjoyed tinkling on the piano and playing in the backyard. Would definitely choose to stay here again!"
Hilltown Nest is a wonderful place for family and friends to gather.

Mountain Blossom Retreat by Evergreen Home

10.0 out of 10, Exceptional, (5)
"We spent a wonderful weekend at this truly stunning property! The house is incredible, so well equipped, every detail has been thought of and the interior is beautiful. The outdoor spaces are amazing, the pool, hot tub, fire pit, outdoor seating, beautiful gardens are stunning! The location of the house is perfect, so close to lots of farms and orchards. We so look forward to making a return visit I!"
Mountain Blossom Retreat by Evergreen Home

Quintessential 6-BR Berkshires Lodge

10.0 out of 10, Exceptional, (11)
"The house was perfect for our group of couples and young kids. Large bedrooms and beautiful property "
Quintessential 6-BR Berkshires Lodge

Amherst, Perfect Location, UMass, Smith, MHC!

10.0 out of 10, Exceptional, (14)
"House was great, very comfortable, location was perfect for our needs. All of us had an excellent stay."
Amherst, Perfect Location, UMass, Smith, MHC!

Historic Farmhouse Near Mountains & Colleges!

10.0 out of 10, Exceptional, (7)
"Loved our stay at this adorable ranch home. Cute and comfy and clean. "
Historic Farmhouse Near Mountains & Colleges!

Granby Home w/ Deck < 1/2 Mi to Aldrich Lake!

9.6 out of 10, Exceptional, (30)
"Great place to stay. House was spacious, very clean, and well maintained "
Granby Home w/ Deck < 1/2 Mi to Aldrich Lake!

6 Mi to Skiing: Pet-Friendly Home in Pittsfield!

9.6 out of 10, Exceptional, (5)
"We usually don’t book places that don’t have several reviews, but since we knew the area, we decided to “take a chance”. We are very glad we did! We stayed 5 nights and were very happy. The heat pumps were great since the temperature dipped below 0. The accommodations were very comfortable and we had everything we needed to make our stay enjoyable. "
6 Mi to Skiing: Pet-Friendly Home in Pittsfield!

Lakeside 5-BR Home in Idyllic Berkshires

10.0 out of 10, Exceptional, (2)
"Celebrated a birthday with a group of old friends. Great location near Lee. Enjoyed the lake views. Fires inside and outside. Home is well decorated and clean."
Lakeside 5-BR Home in Idyllic Berkshires

Lovely 2nd Floor Apartment

10.0 out of 10, Exceptional, (21)
"Clean, comfortable and quiet. All necessities for kitchen provided. "
The price is SAR 484
SAR 825 total
includes taxes & fees
18 May - 19 May
Lovely 2nd Floor Apartment

Pristine Home In Becket Woods

10.0 out of 10, Exceptional, (14)
"Near Jacob's Pillow!"
Pristine Home In Becket Woods

The Meadows House @ Otis Ridge w/ 7-person hot tub

9.8 out of 10, Exceptional, (28)
"We had a great time staying at Lars place. The hot tub was very relaxing and the location was just what we were looking for to get away for a few days."
The Meadows House @ Otis Ridge w/ 7-person hot tub

Charming 4Bds+1crib house with patio Amherst Center

2.0 star property
10.0 out of 10, Exceptional, (2)
"A great place for a family stay in downtown Amherst. "
The price is SAR 893
SAR 1,684 total
includes taxes & fees
5 May - 6 May
Charming 4Bds+1crib house with patio Amherst Center
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

9.8 out of 10, Exceptional, (57)
"Great place "
comfort, luxury, privacy

Deluxe Queen Room with 2 Queen Beds

2.0 star property
The price is SAR 446
SAR 582 total
includes taxes & fees
4 May - 5 May
Deluxe Queen Room with 2 Queen Beds

Cheerful 1 bedroom

9.8 out of 10, Exceptional, (34)
"This is my third stay here and I am always very happy with the cleanliness. This place is perfect for me and my dog."
Cheerful 1 bedroom
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.