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Holiday Homes in Chesterfield

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Chesterfield holiday homes

Property grounds

1. Charming, updated 3 bedroom farmhouse farm stay.

Charming, updated 3 bedroom farmhouse farm stay.
Williamsburg
10.0 out of 10, Exceptional, (41 reviews)
"Great hosts! Very nice and helpful. "
United States
Anonymous traveller
The price is €342
includes taxes & fees
31 Aug - 1 Sept
Charming, updated 3 bedroom farmhouse farm stay.
Room

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, (77 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 €236
includes taxes & fees
1 Sept - 2 Sept
The Creation Station is a cozy place so make yourself at home.
Interior

3. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (62 reviews)
"Beautiful decor, cozy furnishings, comfy comfy beds, all the amenities we needed and more, such a perfect apartment. Great communication with the host. Lots of yummy restaurant options in the area. We loved staying here!"
United States
Christa B.
The price is €180
includes taxes & fees
20 Aug - 21 Aug
Lovely 2nd Floor Apartment
Interior

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

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is €259
includes taxes & fees
13 Sept - 14 Sept
Real Estate: Therapy - Lake, Laundry, Love it
Exterior

5. Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
The price is €190
includes taxes & fees
20 Aug - 21 Aug
Private bed with En-suite bathroom Marigold Room
Outdoor spa tub

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

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (16 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is €340
includes taxes & fees
25 Aug - 26 Aug
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Interior

7. 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, (7 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is €344
includes taxes & fees
9 Sept - 10 Sept
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Room

8. Cozy private 2 bed apartment in Shelburne Falls

Cozy private 2 bed apartment in Shelburne Falls
Shelburne Falls
The price is €319
includes taxes & fees
24 Aug - 25 Aug
Cozy private 2 bed apartment in Shelburne Falls
Private kitchen

9. 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 €332
includes taxes & fees
26 Aug - 27 Aug
Cozy Home in Holyoke with 3 bedrooms
Property grounds

10. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (149 reviews)
"Great location"
United States
Will G.
The price is €300
includes taxes & fees
23 Aug - 24 Aug
Big farmhouse in the foothills of the Berkshires
Room

11. 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 €440
includes taxes & fees
17 Sept - 18 Sept
Townhouse with Pool Table - Renovated w/ King Bed
Property grounds

12. Riverbend Berkshire East Basecamp - 3 bedrooms available

Riverbend Berkshire East Basecamp - 3 bedrooms available
Charlemont
10.0 out of 10, Exceptional, (5 reviews)
"Very nice house and the stay was unproblematic!"
United States
Noah K.
Riverbend Berkshire East Basecamp - 3 bedrooms available
Living area

13. 5BR Berkshire Home Mins To The Mountain

5BR Berkshire Home Mins To The Mountain
Charlemont
10.0 out of 10, Exceptional, (6 reviews)
"What an amazing house to stay at! Tons of room, well equipped kitchen and a great location! "
United States
Jason F.
5BR Berkshire Home Mins To The Mountain
House, 4 Bedrooms | Interior

14. Chef's Kitchen Family Basecamp Amherst

Chef's Kitchen Family Basecamp Amherst
3.0 star property
East Village Historic District
The price is €586
includes taxes & fees
31 Aug - 1 Sept
Chef's Kitchen Family Basecamp Amherst
Private kitchen

15. Spacious 5BR w/ Hot Tub & Games

Spacious 5BR w/ Hot Tub & Games
Colrain
10.0 out of 10, Exceptional, (53 reviews)
"Our 4th week here and our crew could not be happier with the accommodations"
United States
Maureen A.
Spacious 5BR w/ Hot Tub & Games
Outdoor dining

16. 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 clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
The price is €486
includes taxes & fees
2 Sept - 3 Sept
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Living area

17. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 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 €504
includes taxes & fees
16 Sept - 17 Sept
Treetop Hideaway in Tyringham
Private kitchen

18. Spacious Holyoke Home: Work, Play & Unwind!

Spacious Holyoke Home: Work, Play & Unwind!
Holyoke
10.0 out of 10, Exceptional, (4 reviews)
"This was a beautiful place to stay and was perfect for our needs. It was very clean and we enjoyed our stay. We didn't realize the house had three separate areas but it worked out well for our dance competition in Springfield."
United States
Celeste D.
Spacious Holyoke Home: Work, Play & Unwind!
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

Hotel Northampton

Hotel Northampton

10/10 Excellent
"Our room was clean. Parking was easy and the staff was very friendly."
Meg 1-night trip
Posted 1 hour ago
Hotel Northampton

Find out more about Chesterfield

Chesterfield Holiday Homes information

Number of reviews
464
Accommodation
152 Holiday Homes
Lowest Price
€180
Highest Price
€586