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Chesterfield Vacation Rentals

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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Chesterfield vacation rentals

Interior

1. Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature

Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature
Otis
$309 nightly
The price is $345
Aug 17 - Aug 18
Total with taxes and fees
Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature
Property grounds

2. 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 traveler
$392 nightly
The price is $414
Aug 31 - Sep 1
Total with taxes and fees
Charming, updated 3 bedroom farmhouse farm stay.
Lobby

3. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,050 reviews)
"Clean room, friendly staff, nice property"
United States
Joseph
$141 nightly
The price is $155
Aug 31 - Sep 1
Total with taxes and fees
Berkshire Mountain Lodge
Exterior

4. 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
$233 nightly
The price is $260
Aug 11 - Aug 12
Total with taxes and fees
Nurse-Ready Studio Retreat! 2 Mi to Dtwn Holyoke
Desk, iron/ironing board, travel crib, WiFi

5. 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
$248 nightly
The price is $277
Aug 10 - Aug 11
Total with taxes and fees
The Creation Station is a cozy place so make yourself at home.
Interior

6. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (60 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.
$180 nightly
The price is $201
Aug 9 - Aug 10
Total with taxes and fees
Lovely 2nd Floor Apartment
Apartment (0 Bedroom) | Interior

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

Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke
3.0 star property
Holyoke
$227 nightly
The price is $254
Aug 11 - Aug 12
Total with taxes and fees
Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke
Coffee/tea maker, fridge, microwave, oven

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, (30 reviews)
"Had a fantastic time at Cathy’s place. So clean and everything you need for a great stay. Hope to visit again ! "
United States
Susan M.
$291 nightly
The price is $324
Aug 10 - Aug 11
Total with taxes and fees
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
1 bedroom, desk, iron/ironing board, WiFi

9. Balcony Room in Victorian Home private bath

Balcony Room in Victorian Home private bath
Shelburne Falls
$189 nightly
The price is $211
Aug 30 - Aug 31
Total with taxes and fees
Balcony Room in Victorian Home private bath
Outdoor dining

10. Historic downtown apartment. Unscented products and sustainability practices.

Historic downtown apartment. Unscented products and sustainability practices.
Northampton
10.0 out of 10, Exceptional, (11 reviews)
"Location was great, space had everything we needed ! Cozy, cute, clean and beds were very comfortable. "
United States
Kaitlin N.
$376 nightly
The price is $419
Aug 9 - Aug 10
Total with taxes and fees
Historic downtown apartment. Unscented products and sustainability practices.
Interior

11. 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
$448 nightly
The price is $501
Aug 17 - Aug 18
Total with taxes and fees
Button's Modern Luxury Walkup Downtown Northampton
Interior

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

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
$322 nightly
The price is $360
Aug 26 - Aug 27
Total with taxes and fees
Real Estate: Therapy - Lake, Laundry, Love it
Exterior detail

13. 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.
$256 nightly
The price is $286
Sep 8 - Sep 9
Total with taxes and fees
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Exterior

14. Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
$191 nightly
The price is $213
Aug 24 - Aug 25
Total with taxes and fees
Private bed with En-suite bathroom Marigold Room
Coffee/tea maker, fridge, microwave, oven

15. Cozy Home in Holyoke with 3 bedrooms

Cozy Home in Holyoke with 3 bedrooms
Holyoke
9.8 out of 10, Exceptional, (21 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.
$348 nightly
The price is $389
Aug 18 - Aug 19
Total with taxes and fees
Cozy Home in Holyoke with 3 bedrooms
Property grounds

16. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (148 reviews)
"Great location"
United States
Will G.
$311 nightly
The price is $329
Aug 23 - Aug 24
Total with taxes and fees
Big farmhouse in the foothills of the Berkshires
Property grounds

17. 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.
$474 nightly
The price is $529
Sep 1 - Sep 2
Total with taxes and fees
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
TV

18. Charming Chicopee Getaway

Charming Chicopee Getaway
Chicopee
7.6 out of 10, Good, (4 reviews)
"We really appreciated the stay to get together with family. There was plenty of space to play with the toddler and set up the pack-n-play for the infant. And then plenty of room to play board games after the babies were put to bed. "
United States
Tamara S.
$215 nightly
The price is $251
Aug 26 - Aug 27
Total with taxes and fees
Charming Chicopee Getaway
Iron/ironing board, WiFi, bed sheets

19. Cozy private 2 bed apartment in Shelburne Falls

Cozy private 2 bed apartment in Shelburne Falls
Shelburne Falls
$327 nightly
The price is $365
Aug 9 - Aug 10
Total with taxes and fees
Cozy private 2 bed apartment in Shelburne Falls
Interior

20. 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, (6 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
$378 nightly
The price is $422
Sep 8 - Sep 9
Total with taxes and fees
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the 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

Comfort Inn & Suites Hadley - Amherst

Comfort Inn & Suites Hadley - Amherst

10/10 Excellent
"Always safe, clean, friendly, reliable & convenient. Never any issues. We will continue to stay there when we need a room in the area."
Claire 1-night trip
Posted 9 hours ago
Comfort Inn & Suites Hadley - Amherst

Find out more about Chesterfield

Everything you need to know about Chesterfield vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chesterfield vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chesterfield vacation 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 low season months. For more hustle and bustle, you may prefer to visit Chesterfield in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $155 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chesterfield rentals

At Expedia, we put the best Chesterfield vacation 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 vacation.

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 vacation rentals in Chesterfield?

Yes, we have vacation rentals near popular attractions in Chesterfield, or you can go with a secluded option if you want a relaxing place to 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 vacation rentals in Chesterfield?

Experience Three Sisters Sanctuary in Goshen, MA: Visitors like this Chesterfield vacation home rental. It 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?

Westfield River and Chesterfield Gorge 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 vacation rental in Chesterfield like?

Vacation rentals are private properties you can stay in for a few weeks or just a few days in Chesterfield. Vacation rentals offer amenities like kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of privacy away from shared hotel elevators and busy concierge desks while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great option for a family trip or a small group gathering.