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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

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, (41 reviews)
"Great hosts! Very nice and helpful. "
United States
Anonymous traveller
The price is AU$566
includes taxes & fees
31 Aug - 1 Sept
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, (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 AU$390
includes taxes & fees
1 Sept - 2 Sept
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, (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 AU$286
includes taxes & fees
1 Sept - 2 Sept
Lovely 2nd Floor Apartment
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
The price is AU$427
includes taxes & fees
13 Sept - 14 Sept
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 AU$300
includes taxes & fees
1 Sept - 2 Sept
Private bed with En-suite bathroom Marigold Room
A hot tub with a string of lights above it, set against a dark night sky.

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 AU$554
includes taxes & fees
25 Aug - 26 Aug
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
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.

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 AU$557
includes taxes & fees
25 Aug - 26 Aug
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A hallway with wooden flooring, white walls, and a bed in the background.

8. Cozy private 2 bed apartment in Shelburne Falls

Cozy private 2 bed apartment in Shelburne Falls
Shelburne Falls
The price is AU$506
includes taxes & fees
24 Aug - 25 Aug
Cozy private 2 bed apartment in Shelburne Falls
A modern kitchen with stainless steel appliances, a granite countertop, and a view into the dining area.

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 AU$529
includes taxes & fees
26 Aug - 27 Aug
Cozy Home in Holyoke with 3 bedrooms
A house with a porch, a garden with pink flowers, and a stone wall along the road.

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 AU$484
includes taxes & fees
13 Sept - 14 Sept
Big farmhouse in the foothills of the Berkshires
A bedroom with a bed, curtains, a bedside table, and a lamp.

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 AU$670
includes taxes & fees
24 Aug - 25 Aug
Townhouse with Pool Table - Renovated w/ King Bed
A wooden deck with two chairs and a table, overlooking a green landscape with a tree and hills.

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.
The price is AU$646
includes taxes & fees
28 Aug - 29 Aug
Riverbend Berkshire East Basecamp - 3 bedrooms available
A cozy living room with a fireplace, a large TV, a Christmas tree, and a leather sofa.

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.
The price is AU$948
includes taxes & fees
24 Aug - 25 Aug
5BR Berkshire Home Mins To The Mountain
A modern kitchen with white cabinets, a wooden staircase, and a dining area with a table and chairs.

14. Chef's Kitchen Family Basecamp Amherst

Chef's Kitchen Family Basecamp Amherst
3.0 star property
East Village Historic District
The price is AU$957
includes taxes & fees
31 Aug - 1 Sept
Chef's Kitchen Family Basecamp Amherst
A modern kitchen with wooden countertops, a central island with stools, hanging pendant lights, and a chalkboard menu.

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
A wooden deck with a table and chairs, surrounded by a white railing.

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 AU$776
includes taxes & fees
24 Aug - 25 Aug
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

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 AU$815
includes taxes & fees
16 Sept - 17 Sept
Treetop Hideaway in Tyringham
A modern kitchen with white cabinetry, stainless steel appliances, and a marble countertop.

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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

8/10 Good
"This hotel is a good option for Tanglewood concerts—only 15 minutes from the grounds, with nearby markets to grab food and wine along the way—but I would also consider going back with my family for another vacation. The room was large and had a separate bedroom and kitchenette/dining table, which aren’t easy to find and good for stays with kids. The indoor pool was large, and the game room looked cute. There is no food on site, which is the only main negative about this property. But there are plenty of options nearby."
Adrienne 1-night trip
Posted less than an hour ago
Berkshire Mountain Lodge

Find out more about Chesterfield

Chesterfield Holiday Homes information

Number of reviews
464
Accommodation
160 Holiday Homes
Lowest Price
AU$286
Highest Price
AU$957