Default HTG hotel image

Chesterfield Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Chesterfield holiday rentals

Exterior

1. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,256 reviews)
"Comfortable stay, well stocked kitchen and room."
United States
Charline
The price is NZ$193
includes taxes & fees
6 Dec - 7 Dec
Berkshire Mountain Lodge
A red barn with a black door and a heart-shaped cutout, surrounded by lush greenery and trees.

2. Charming, updated 3 bedroom farmhouse farm stay.

Charming, updated 3 bedroom farmhouse farm stay.
Williamsburg
10.0 out of 10, Exceptional, (44 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 NZ$706
includes taxes & fees
6 Dec - 7 Dec
Charming, updated 3 bedroom farmhouse farm stay.
A two-story house with a front porch, a sign reading "Victory Residence," and the address "1785."

3. Modern Studio Ideal for Traveling Professionals

Modern Studio Ideal for Traveling Professionals
Holyoke
10.0 out of 10, Exceptional, (4 reviews)
"The room was very clean and modern. The check-in process was easy and I had the best rest that I had in a long time. Being in the lower level with no windows provided a very quiet and dark ambiance at night. There is ample lighting throughout the unit if needed though, you can really unplug here. I would definitely stay here again"
United States
Kebreab H.
The price is NZ$385
includes taxes & fees
8 Nov - 9 Nov
Modern Studio Ideal for Traveling Professionals
A two-story house with a front porch, a staircase leading to the entrance, and a well-maintained garden.

4. 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 NZ$306
includes taxes & fees
8 Nov - 9 Nov
2 Twin beds on 1st floor with En-suite bathroom.
Exterior

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

Work, Play & Stay! Apt Near Holyoke Medical Center
Holyoke
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful apartment! Amazing finishes, well appointed, pristine apartment in Holyoke. Great communication from the host. A quick trip to Dam Coffee Shop for great coffee and breakfast options. Not too far from Stop & Shop for food and short ride to highway. Would book this spot again."
United States
Yvonne A.
The price is NZ$520
includes taxes & fees
15 Nov - 16 Nov
Work, Play & Stay! Apt Near Holyoke Medical Center
A blue house with a porch, a wooden bench, and a door.

6. 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
9.4 out of 10, Exceptional, (11 reviews)
"Very satisfied with the stay . Clean quiet and relaxing stay."
United States
JAMES S.
The price is NZ$403
includes taxes & fees
9 Nov - 10 Nov
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
A modern fireplace with a glass enclosure, decorative items, and a sign that reads 'blessed.'

7. A Scenic Townhouse Near Amherst (Next to a Horse Farm)

A Scenic Townhouse Near Amherst (Next to a Horse Farm)
Sunderland
The price is NZ$494
includes taxes & fees
9 Nov - 10 Nov
A Scenic Townhouse Near Amherst (Next to a Horse Farm)
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

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

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
9.6 out of 10, Exceptional, (4 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 NZ$501
includes taxes & fees
11 Nov - 12 Nov
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.

9. Private room with En-suite bathroom Marigold Room

Private room with En-suite bathroom Marigold Room
Shelburne Falls
The price is NZ$350
includes taxes & fees
10 Nov - 11 Nov
Private room with En-suite bathroom Marigold Room
A two-story house with a front porch, a sign reading "Victory Residence," and the address "1785."

10. Modern Studio Ideal for Traveling Professionals

Modern Studio Ideal for Traveling Professionals
3.0 star property
Holyoke
The price is NZ$414
includes taxes & fees
8 Nov - 9 Nov
Modern Studio Ideal for Traveling Professionals
A modern kitchen with dark cabinets, a granite countertop, a built-in oven, a microwave, and a large window providing natural light.

11. Penthouse overlooking downtown Amherst!

Penthouse overlooking downtown Amherst!
Amherst
10.0 out of 10, Exceptional, (1 review)
"Great space. Great location."
United States
Mike S.
The price is NZ$880
includes taxes & fees
6 Dec - 7 Dec
Penthouse overlooking downtown Amherst!
A cozy room with two beds, large windows, and a view of a snowy landscape.

12. 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 NZ$471
includes taxes & fees
9 Nov - 10 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.

13. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (73 reviews)
"Easy parking. Works for a short trip. Convenient to get to."
United States
heather
The price is NZ$419
includes taxes & fees
8 Nov - 9 Nov
Lovely 2nd Floor Apartment
A modern kitchen with a central island, bar stools, and a bicycle.

14. Button's Modern Luxury Walkup Downtown Northampton

Button's Modern Luxury Walkup Downtown Northampton
Northampton
10.0 out of 10, Exceptional, (8 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 NZ$853
includes taxes & fees
17 Nov - 18 Nov
Button's Modern Luxury Walkup Downtown Northampton
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.

15. 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, (10 reviews)
"My wife and I had a lovely time staying here. Great location, only a couple of miles away from Jacobs Pillow. The lakes are clean and great for paddle boarding. Check in and out was a breeze, Nicole was a pleasure to work with. Thanks for a nice get away."
United States
Brian C.
The price is NZ$631
includes taxes & fees
9 Nov - 10 Nov
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A lakeside picnic area with a bench and umbrella, surrounded by autumn-colored trees.

16. 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, (41 reviews)
"The house was very clean! The hot tub was great! From checking in and checking out the host made everything so easy. We will definitely stay again!"
United States
Kyle R.
The price is NZ$707
includes taxes & fees
10 Nov - 11 Nov
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
A modern kitchen with white cabinetry, a stainless steel dishwasher, and a window with a view.

17. 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, (35 reviews)
"Very smooth process for check in and directions. Well provisioned, super clean rooms. Really enjoyed learning about Dalton. And so many sights nearby we love!"
United States
Marcia O.
The price is NZ$531
includes taxes & fees
10 Nov - 11 Nov
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

18. Balcony Room in Victorian Home private bath

Balcony Room in Victorian Home private bath
Shelburne Falls
The price is NZ$338
includes taxes & fees
19 Nov - 20 Nov
Balcony Room in Victorian Home private bath
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

19. Rose room Victorian home queen bed private bath

Rose room Victorian home queen bed private bath
Shelburne Falls
8.0 out of 10, Very good, (1 review)
"Very cute and welcoming B&B guest house. It was not clear to me that our private bathroom was across the hall. Some are and some not so check for that."
United States
Mikaela M.
The price is NZ$327
includes taxes & fees
8 Nov - 9 Nov
Rose room Victorian home queen bed private bath
A hot tub with a string of lights above it, set against a dark night sky.

20. 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, (20 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is NZ$652
includes taxes & fees
9 Nov - 10 Nov
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chesterfield Hotel Reviews

The Ellery

The Ellery

10/10 Excellent
"The hotel was immaculate. The lobby was New England quaint. Our king sized mattress was extremely comfortable and the room was large. We will definitely return."
John 1-night trip
Posted 11 hours ago
The Ellery

Find out more about Chesterfield

Everything you need to know about Chesterfield holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chesterfield holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chesterfield holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chesterfield holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesterfield. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesterfield holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesterfield holiday rentals we have selected for you start as low as NZ$193 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chesterfield rentals

At Expedia, we put the best Chesterfield holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chesterfield rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chesterfield holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chesterfield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 Chesterfield Gorge Reservation 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.