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Chesterfield Holiday Rentals

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Chesterfield holiday rentals

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)
"It was a charming farmhouse on a beautiful farm property with goats and ducks. The hosts made sure that all of our needs were met from electronic outlet extensions to kitchen utensils to bathroom supplies. There were even fresh-cut flowers in the kitchen for us to enjoy. We had a lovely two night stay."
United States
Jamie M.
The price is HK$1,905
HK$3,249 total
includes taxes & fees
31 Aug - 1 Sept
Charming, updated 3 bedroom farmhouse farm stay.
Exterior

2. Nurse-Ready Studio Retreat! 2 Mi to Dtwn Holyoke

Nurse-Ready Studio Retreat! 2 Mi to Dtwn Holyoke
Holyoke
10.0 out of 10, Exceptional, (3 reviews)
"The studio was clean, new and modern. There are no windows so it was dark and quiet to sleep. "
United States
Michelle
The price is HK$557
HK$2,014 total
includes taxes & fees
16 Sept - 17 Sept
Nurse-Ready Studio Retreat! 2 Mi to Dtwn Holyoke
Lobby

3. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,102 reviews)
"A nice place to stay in the Berkshires."
United States
Robert
The price is HK$742
HK$1,004 total
includes taxes & fees
31 Aug - 1 Sept
Berkshire Mountain Lodge
Room

4. 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 HK$1,411
HK$2,207 total
includes taxes & fees
31 Aug - 1 Sept
The Creation Station is a cozy place so make yourself at home.
Interior

5. Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke

Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke
3.0 star property
Holyoke
The price is HK$941
HK$2,122 total
includes taxes & fees
31 Aug - 1 Sept
Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke
Interior

6. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (63 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 HK$910
HK$1,604 total
includes taxes & fees
1 Sept - 2 Sept
Lovely 2nd Floor Apartment
Interior

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

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
8.0 out of 10, Very good, (1 review)
"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 HK$368
HK$2,216 total
includes taxes & fees
13 Sept - 14 Sept
Real Estate: Therapy - Lake, Laundry, Love it
Private kitchen

8. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Dalton
9.8 out of 10, Exceptional, (31 reviews)
"This was a wonderful place to stay. We especially loved the easy access to the toys so the kids could start playing while we unloaded the car. It was perfect and just what we needed."
United States
Megan A.
The price is HK$1,023
HK$2,562 total
includes taxes & fees
31 Aug - 1 Sept
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Exterior

9. Work, Play & Stay! Apt Near Holyoke Medical Center

Work, Play & Stay! Apt Near Holyoke Medical Center
Holyoke
10.0 out of 10, Exceptional, (3 reviews)
"Closer to downtown able to"
United States
Jeremy R.
The price is HK$572
HK$2,636 total
includes taxes & fees
29 Sept - 30 Sept
Work, Play & Stay! Apt Near Holyoke Medical Center
Exterior

10. 2 Twin beds on 1st floor with En-suite bathroom.

2 Twin beds on 1st floor with En-suite bathroom.
Shelburne Falls
The price is HK$721
HK$1,419 total
includes taxes & fees
31 Aug - 1 Sept
2 Twin beds on 1st floor with En-suite bathroom.
Interior

11. 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 HK$1,150
HK$2,975 total
includes taxes & fees
9 Sept - 10 Sept
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Interior

12. Button's Modern Luxury Walkup Downtown Northampton

Button's Modern Luxury Walkup Downtown Northampton
Northampton
10.0 out of 10, Exceptional, (6 reviews)
"The apartment was very comfortable and had everything we needed for the weekend including nice coffee, cava and a treat. Well equipped kitchen and good bed, towels, storage. Will stay here again"
United States
AMY
The price is HK$1,914
HK$3,942 total
includes taxes & fees
7 Sept - 8 Sept
Button's Modern Luxury Walkup Downtown Northampton
Outdoor spa tub

13. 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 HK$1,256
HK$3,111 total
includes taxes & fees
7 Sept - 8 Sept
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Exterior

14. Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
The price is HK$941
HK$1,690 total
includes taxes & fees
8 Sept - 9 Sept
Private bed with En-suite bathroom Marigold Room
Property grounds

15. 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 HK$1,341
HK$2,619 total
includes taxes & fees
13 Sept - 14 Sept
Big farmhouse in the foothills of the Berkshires
Room

16. Cozy private 2 bed apartment in Shelburne Falls

Cozy private 2 bed apartment in Shelburne Falls
Shelburne Falls
The price is HK$1,262
HK$2,864 total
includes taxes & fees
2 Sept - 3 Sept
Cozy private 2 bed apartment in Shelburne Falls
Living area

17. Spacious & Cozy Ground Floor 2/3 Bed private suite

Spacious & Cozy Ground Floor 2/3 Bed private suite
Shelburne Falls
9.6 out of 10, Exceptional, (5 reviews)
"Wonderful property with an exceptional host!"
United States
Russ D.
The price is HK$1,427
HK$3,074 total
includes taxes & fees
31 Aug - 1 Sept
Spacious & Cozy Ground Floor 2/3 Bed private suite
Property grounds

18. Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.8 out of 10, Exceptional, (39 reviews)
"Gorgeous place.Great stay.Will diff be backG"
United States
Gerard C.
The price is HK$2,101
HK$4,370 total
includes taxes & fees
24 Sept - 25 Sept
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Private kitchen

19. 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 HK$1,411
HK$3,109 total
includes taxes & fees
7 Sept - 8 Sept
Cozy Home in Holyoke with 3 bedrooms
Exterior detail

20. Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Greenfield
9.6 out of 10, Exceptional, (9 reviews)
"We had a great"
United States
Meredith B.
The price is HK$1,129
HK$2,443 total
includes taxes & fees
29 Sept - 30 Sept
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
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 UMass

Hotel UMass

10/10 Excellent
"Parking was super easy with a connected garage - great being right in the center of campus (with an EV charger that lets you charge overnight!)."
Ryan 1-night trip
Posted 5 hours ago
Hotel UMass

Find out more about Chesterfield

Search for holiday rentals in Chesterfield on Expedia! You can easily find your home rentals, villas, holiday apartments in Chesterfield using one of the methods below:

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Look no further and take a look at our great range of rental properties in Chesterfield!

Frequently asked questions

Can I find holiday rentals in Chesterfield?

Yes, there are holiday rentals close to the most popular sights in Chesterfield, or you can select a more secluded option if you're looking for a relaxing stay. Chesterfield is known for its restaurants and shopping. Make sure you have time to check out the parks while you're in the area.

What are some of the best holiday rentals that Chesterfield has to offer?

Experience Three Sisters Sanctuary in Goshen, MA: This holiday home rental outside of Chesterfield is equipped with a garden, air conditioning and a Smart TV to help you feel comfortable during your stay.

What’s there to see and do in Chesterfield?

Chesterfield Gorge and Westfield River are a couple of lovely local spots to get outside and enjoy nature. Chesterfield Public Library and Chesterfield Town Hall are other places to visit while you're in town.

What’s a holiday rental in Chesterfield like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chesterfield. Holiday rentals feature amenities like kitchens and laundry facilities so you'll have everything you want. If you're concerned about a sanitised environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for a family getaway.