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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Chesterfield vacation homes

A red barn with a black door and a heart-shaped cutout, surrounded by lush greenery and trees.

1. Charming, updated 3 bedroom farmhouse farm stay.

Charming, updated 3 bedroom farmhouse farm stay.
Williamsburg
10.0 out of 10, Exceptional, (43 reviews)
"Wonderful place to stay with our two teens. We visited family in Amherst, looked at colleges and had a great time touring historic sites. Definitely recommend!"
United States
Nancy M.
The price is AED 992
AED 1,619 total
includes taxes & fees
18 Oct - 19 Oct
Charming, updated 3 bedroom farmhouse farm stay.
A cozy room with two beds, large windows, and a view of a snowy landscape.

2. 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)
"We had such a great stay at the Creation Station! The host John, showed us around the property and explained how to use everything. He also recommended a great restaurant in town. It was a great experience and would definitely recommend it!"
United States
Paula
The price is AED 661
AED 1,017 total
includes taxes & fees
3 Nov - 4 Nov
The Creation Station is a cozy place so make yourself at home.
A round wooden table with a woven placemat, a wicker basket, and a small potted plant.

3. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (70 reviews)
"It was absolutely amazing Beautiful apartment Clean cozy Beautiful back yard I will definitely stay here again if I am back in this area It’s a 10 out of 10 Thank you David"
United States
Jane P.
The price is AED 459
AED 784 total
includes taxes & fees
18 Oct - 19 Oct
Lovely 2nd Floor Apartment
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

4. Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
The price is AED 441
AED 784 total
includes taxes & fees
16 Nov - 17 Nov
Private bed with En-suite bathroom Marigold Room
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

5. Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
9.4 out of 10, Exceptional, (3 reviews)
"Very good trip overall. Great location. Just a few things needed to make it over the top!"
United States
William C B.
The price is AED 272
AED 1,169 total
includes taxes & fees
3 Nov - 4 Nov
Real Estate: Therapy - Lake, Laundry, Love it
A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

6. 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, (9 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AED 536
AED 1,378 total
includes taxes & fees
27 Oct - 28 Oct
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A hot tub with a string of lights above it, set against a dark night sky.

7. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.6 out of 10, Exceptional, (19 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is AED 588
AED 1,445 total
includes taxes & fees
28 Oct - 29 Oct
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
A modern kitchen with stainless steel appliances, a granite countertop, and a view into the dining area.

8. Cozy Home in Holyoke with 3 bedrooms

Cozy Home in Holyoke with 3 bedrooms
Holyoke
9.8 out of 10, Exceptional, (22 reviews)
"Fantastic stay in Holyoke. House is close to town, well outfitted, and super clean. Easy check in process and great experience all around. "
United States
Grant J.
The price is AED 566
AED 1,317 total
includes taxes & fees
27 Oct - 28 Oct
Cozy Home in Holyoke with 3 bedrooms
A bedroom with a four-poster bed, a dresser, a chair, and a large window.

9. Steps from Amherst town common, 3 BR charmer

Steps from Amherst town common, 3 BR charmer
East Village Historic District
The price is AED 907
AED 1,161 total
includes taxes & fees
4 Nov - 5 Nov
Steps from Amherst town common, 3 BR charmer
A hallway with wooden flooring, white walls, and a bed in the background.

10. Cozy private 2 bed apartment in Shelburne Falls

Cozy private 2 bed apartment in Shelburne Falls
Shelburne Falls
"I really enjoyed the kitchen setup and how everything I needed was there. The beds were very comfortable and having a light nearby for reading was a plus. The walk to downtown was nice. We explored Shelburne Falls out days and it did have something for everyone. I would stay here again."
United States
maureen
The price is AED 771
AED 1,571 total
includes taxes & fees
19 Oct - 20 Oct
Cozy private 2 bed apartment in Shelburne Falls
A house with a porch, a garden with pink flowers, and a stone wall along the road.

11. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (153 reviews)
"Great place and stunning location. Absolutely loved the quiet and perfect mix of old times with modern convenience. Had a short stay this trip but intend on returning in the future."
United States
Dale B.
The price is AED 720
AED 1,320 total
includes taxes & fees
22 Oct - 23 Oct
Big farmhouse in the foothills of the Berkshires
A bedroom with a bed, curtains, a bedside table, and a lamp.

12. Townhouse with Pool Table - Renovated w/ King Bed

Townhouse with Pool Table - Renovated w/ King Bed
Chicopee
10.0 out of 10, Exceptional, (17 reviews)
"Comfortable stay"
United States
Nicholas B.
The price is AED 774
AED 1,648 total
includes taxes & fees
27 Oct - 28 Oct
Townhouse with Pool Table - Renovated w/ King Bed
A dining area with a long wooden table set for six, surrounded by chairs. There are hanging pendant lights above the table.

13. Spacious 5-Bedroom Home with Game Room in Amherst - Mins to UMass

Spacious 5-Bedroom Home with Game Room in Amherst - Mins to UMass
Amherst
10.0 out of 10, Exceptional, (13 reviews)
"Perfect location, clean house, great for families with kids!"
United States
Emily Robustelli K.
The price is AED 3,669
AED 5,970 total
includes taxes & fees
4 Nov - 5 Nov
Spacious 5-Bedroom Home with Game Room in Amherst - Mins to UMass
A modern kitchen with a central island, stainless steel appliances, and pendant lighting.

14. Amherst -NEW - Campus Convenience & Social Privacy

Amherst -NEW - Campus Convenience & Social Privacy
Amherst
10.0 out of 10, Exceptional, (4 reviews)
"Enjoyed our stay!"
United States
Susan N.
The price is AED 2,200
AED 2,773 total
includes taxes & fees
5 Nov - 6 Nov
Amherst -NEW - Campus Convenience & Social Privacy
A cozy living room with a fireplace, a large TV, a Christmas tree, and a leather sofa.

15. 5BR Berkshire Home Mins To The Mountain

5BR Berkshire Home Mins To The Mountain
Charlemont
10.0 out of 10, Exceptional, (8 reviews)
"What an amazing house to stay at! Tons of room, well equipped kitchen and a great location! "
United States
Jason F.
The price is AED 1,193
AED 2,666 total
includes taxes & fees
18 Oct - 19 Oct
5BR Berkshire Home Mins To The Mountain
A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

16. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.0 out of 10, Wonderful, (12 reviews)
"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "
United States
Samantha G.
The price is AED 984
AED 2,058 total
includes taxes & fees
16 Nov - 17 Nov
Treetop Hideaway in Tyringham
A living room with a sofa, armchairs, a coffee table, and a television.

17. Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
10.0 out of 10, Exceptional, (11 reviews)
"We had a lovely stay! The home was so well equipped and comfortable. Beautiful area, great restaurant choices and staying here made our Miraval experience perfect."
United States
Patricia O.
The price is AED 1,167
AED 2,333 total
includes taxes & fees
19 Oct - 20 Oct
Sun Filled Lenox Retreat - Minutes to Tanglewood!
A wooden deck with a table and chairs, surrounded by a white railing.

18. 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
8.4 out of 10, Very good, (10 reviews)
"Very comfortable and clean accommodations in a nice neighborhood, and a great deck to appreciate the view."
United States
Stephen L.
The price is AED 988
AED 1,810 total
includes taxes & fees
18 Oct - 19 Oct
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
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 Chesterfield Hotel Reviews

The Ellery

The Ellery

10/10 Excellent
"This was the perfect place to stay and visit Smith College and our daughter. It was well appointed, cozy, and comfortable. The breakfasts were delicious, the staff was hospitable and friendly and the common spaces were uplifted and quiet."
Janelle 3-night trip
Posted 1 hour ago
The Ellery