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Chesterfield Vacation Rentals

Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Chesterfield vacation rentals

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 traveler
$402 nightly
The price is $425
Sep 23 - Sep 24
Total with taxes and fees
Charming, updated 3 bedroom farmhouse farm stay.
A modern kitchen with a central island, bar stools, and a bicycle.

2. 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
$448 nightly
The price is $501
Sep 23 - Sep 24
Total with taxes and fees
Button's Modern Luxury Walkup Downtown Northampton
A modern two-story house with large windows and a balcony.

3. Cozy Valley View Post & Beam Villa!

Cozy Valley View Post & Beam Villa!
Whately
10.0 out of 10, Exceptional, (12 reviews)
"Thanks for a great stay"
United States
Andrea M.
$570 nightly
The price is $637
Sep 28 - Sep 29
Total with taxes and fees
Cozy Valley View Post & Beam Villa!
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

4. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,150 reviews)
"Clean & comfortable stay"
United States
Robert
$108 nightly
The price is $120
Oct 22 - Oct 23
Total with taxes and fees
Berkshire Mountain Lodge
A lakeside picnic area with a bench and umbrella, surrounded by autumn-colored trees.

5. 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)
"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.
$425 nightly
The price is $475
Sep 23 - Sep 24
Total with taxes and fees
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
A cozy room with two beds, large windows, and a view of a snowy landscape.

6. 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
$239 nightly
The price is $267
Sep 29 - Sep 30
Total with taxes and fees
The Creation Station is a cozy place so make yourself at home.
A hot tub with a string of lights above it, set against a dark night sky.

7. 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.
$344 nightly
The price is $384
Sep 27 - Sep 28
Total with taxes and fees
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.

8. 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.
$335 nightly
The price is $374
Sep 28 - Sep 29
Total with taxes and fees
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A cozy living room with a fireplace, a large TV, a Christmas tree, and a leather sofa.

9. 5BR Berkshire Home Mins To The Mountain

5BR Berkshire Home Mins To The Mountain
Charlemont
10.0 out of 10, Exceptional, (7 reviews)
"What an amazing house to stay at! Tons of room, well equipped kitchen and a great location! "
United States
Jason F.
$594 nightly
The price is $664
Sep 23 - Sep 24
Total with taxes and fees
5BR Berkshire Home Mins To The Mountain
A round wooden table with a woven placemat, a wicker basket, and a small potted plant.

10. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (66 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.
$197 nightly
The price is $220
Oct 12 - Oct 13
Total with taxes and fees
Lovely 2nd Floor Apartment
A house with a staircase leading to a porch, surrounded by snow and string lights.

11. Light-filled treetop apartment close to downtown Greenfield and Highland Park

Light-filled treetop apartment close to downtown Greenfield and Highland Park
Greenfield
10.0 out of 10, Exceptional, (12 reviews)
"Nice place"
United States
Tom
$254 nightly
The price is $284
Sep 28 - Sep 29
Total with taxes and fees
Light-filled treetop apartment close to downtown Greenfield and Highland Park
A two-story house with a front porch, a sign reading "Victory Residence," and the address "1785."

12. Modern Studio Ideal for Traveling Professionals

Modern Studio Ideal for Traveling Professionals
Holyoke
10.0 out of 10, Exceptional, (3 reviews)
"Overall a great experience. Need clear instructions/signage for the studio room."
United States
Todd J.
$217 nightly
The price is $242
Sep 23 - Sep 24
Total with taxes and fees
Modern Studio Ideal for Traveling Professionals

13. 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.
$298 nightly
The price is $333
Sep 23 - Sep 24
Total with taxes and fees
Work, Play & Stay! Apt Near Holyoke Medical Center
A modern kitchen with wooden countertops, a central island with stools, hanging pendant lights, and a chalkboard menu.

14. Spacious 5BR w/ Hot Tub & Games

Spacious 5BR w/ Hot Tub & Games
Colrain
10.0 out of 10, Exceptional, (55 reviews)
"This is the second time we have stayed at this property. It is very spacious, cozy, and clean. The beds are very comfortable. It had everything we needed "
United States
Staci M.
$581 nightly
The price is $649
Sep 23 - Sep 24
Total with taxes and fees
Spacious 5BR w/ Hot Tub & Games
A bedroom with a bed, dresser, mirror, and a television.

15. Penthouse overlooking downtown Amherst!

Penthouse overlooking downtown Amherst!
Amherst
$546 nightly
The price is $610
Sep 23 - Sep 24
Total with taxes and fees
Penthouse overlooking downtown Amherst!
A living room with a sofa set, a coffee table, and two lamps.

16. Cozy First Floor Apartment. Located in a quiet neighborhood.

Cozy First Floor Apartment. Located in a quiet neighborhood.
Chicopee
9.6 out of 10, Exceptional, (12 reviews)
"Check in was very easy. The apartment had all the necessities in the kitchen and bathroom. Location was convenient and the neighborhood very safe/quiet."
United States
Morrris
$272 nightly
The price is $309
Sep 23 - Sep 24
Total with taxes and fees
Cozy First Floor Apartment. Located in a quiet neighborhood.
A bedroom with a bed, curtains, a bedside table, and a lamp.

17. 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.
$393 nightly
The price is $446
Oct 6 - Oct 7
Total with taxes and fees
Townhouse with Pool Table - Renovated w/ King Bed
A garden area with potted plants, a wooden fence, and outdoor furniture.

18. Cozy Camper tucked into the woods

Cozy Camper tucked into the woods
Sandisfield
10.0 out of 10, Exceptional, (1 review)
"This was a completely hidden gem. I stayed here for one night because I was visiting a friend but I wished I had booked it longer. My friend and I ended up staying here the whole time. I woke up to the sounds of crickets and chickens, and had fresh eggs for breakfast. Then I went for a hike in the pristine woods. Matt and Grace offered to let me use the paddle boards to enjoy the lake! It was a total vacation… no need to go anywhere else. The camper itself was extremely clean and adorably...
United States
hannah w.
$175 nightly
The price is $195
Sep 23 - Sep 24
Total with taxes and fees
Cozy Camper tucked into the woods
A living room with a beige sofa, a patterned rug, and a wooden floor.

19. 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.
$371 nightly
The price is $415
Sep 28 - Sep 29
Total with taxes and fees
Spacious & Cozy Ground Floor 2/3 Bed private suite
A house with a porch, a garden with pink flowers, and a stone wall along the road.

20. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (151 reviews)
"Great location"
United States
Will G.
$335 nightly
The price is $354
Oct 6 - Oct 7
Total with taxes and fees
Big farmhouse in the foothills of 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

Hampton Inn West Springfield

Hampton Inn West Springfield

8/10 Good
"It’s an older model inside. The interior could use some updating. The doors to the rooms are not tight fitting it shows alot of light coming in from the hallway. Kids running up and down the hallway in the evening. Not quite"
Jennifer 1-night trip
Posted less than an hour ago
Hampton Inn West Springfield

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 $120 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?

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 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.