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Check prices for these dates

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

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 ￥42,665
￥69,650 total
includes taxes & fees
Oct 18 - Oct 19
Charming, updated 3 bedroom farmhouse farm stay.
A round wooden table with a woven placemat, a wicker basket, and a small potted plant.

2. 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 ￥19,778
￥33,748 total
includes taxes & fees
Oct 18 - Oct 19
Lovely 2nd Floor Apartment
A bathroom with a bathtub, a sink, a toilet, and a shower.

3. 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 ￥28,444
￥44,127 total
includes taxes & fees
Nov 9 - Nov 10
The Creation Station is a cozy place so make yourself at home.
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

4. 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 ￥11,699
￥50,329 total
includes taxes & fees
Nov 3 - Nov 4
Real Estate: Therapy - Lake, Laundry, Love it
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

5. Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
The price is ￥18,962
￥33,712 total
includes taxes & fees
Nov 16 - Nov 17
Private bed with En-suite bathroom Marigold Room
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 ￥23,051
￥59,302 total
includes taxes & fees
Oct 27 - Oct 28
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A bedroom with a four-poster bed, a dresser, a chair, and a large window.

7. Steps from Amherst town common, 3 BR charmer

Steps from Amherst town common, 3 BR charmer
East Village Historic District
The price is ￥39,051
￥49,977 total
includes taxes & fees
Nov 4 - Nov 5
Steps from Amherst town common, 3 BR charmer
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 ￥24,664
￥57,041 total
includes taxes & fees
Oct 27 - Oct 28
Cozy Home in Holyoke with 3 bedrooms
A hot tub with a string of lights above it, set against a dark night sky.

9. 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 ￥25,328
￥62,197 total
includes taxes & fees
Oct 28 - Oct 29
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
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 ￥33,184
￥67,604 total
includes taxes & fees
Oct 20 - Oct 21
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 ￥30,988
￥56,818 total
includes taxes & fees
Oct 22 - Oct 23
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 ￥33,279
￥70,921 total
includes taxes & fees
Oct 27 - Oct 28
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 ￥157,862
￥256,820 total
includes taxes & fees
Nov 4 - Nov 5
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 ￥94,702
￥119,380 total
includes taxes & fees
Nov 5 - Nov 6
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 ￥51,351
￥114,754 total
includes taxes & fees
Oct 18 - Oct 19
5BR Berkshire Home Mins To The Mountain
A modern kitchen with wooden countertops, a central island with stools, hanging pendant lights, and a chalkboard menu.

16. Spacious 5BR w/ Hot Tub & Games

Spacious 5BR w/ Hot Tub & Games
Colrain
10.0 out of 10, Exceptional, (56 reviews)
"This is the second time we have stayed at this property. It is very spacious, cozy, and clean. The beds are very comfortable. It had everything we needed "
United States
Staci M.
Spacious 5BR w/ Hot Tub & Games
A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

17. 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 ￥42,349
￥88,524 total
includes taxes & fees
Nov 16 - Nov 17
Treetop Hideaway in Tyringham
A living room with a sofa, armchairs, a coffee table, and a television.

18. 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 ￥50,203
￥100,381 total
includes taxes & fees
Oct 30 - Oct 31
Sun Filled Lenox Retreat - Minutes to Tanglewood!
A wooden deck with a table and chairs, surrounded by a white railing.

19. 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 ￥42,523
￥77,858 total
includes taxes & fees
Oct 25 - Oct 26
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

River Valley Inn

River Valley Inn

10/10 Excellent
"This is a remodeled and updated classic motel. Knowing that there was no breakfast provided we made use of the microwave and fridge by bring items for our own breakfast. We had the deluxe room and it was super clean and comfy and the owners were very helpful at the check-in with suggestions and the offer of morning coffee in the office. For the area this is a great bargain and we would stay again if we are back in the vicinity."
Lynn 1-night trip
Posted 5 hours ago
River Valley Inn

Find out more about Chesterfield

Chesterfield Vacation Homes information

Number of reviews
486
Accommodation
155 Vacation Homes
Lowest Price
￥33,712
Highest Price
￥256,820