Chesterfield Vacation Rentals

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Dec 5 - Dec 6
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Dec 6 - Dec 7
This weekend
Dec 5 - Dec 7
Next weekend
Dec 12 - Dec 14

Vacation Rentals in Chesterfield

Terrace/patio
Cozy Home in Holyoke with 3 bedrooms

Vacation Home in Holyoke

9.8 out of 10, Exceptional, (12)
"What a great house and such gracious hosts!The location is just minutes from Mount Holyoke College which was perfect for our trip Super clean and well maintained house. I highly recommend staying here."
United States
Eric W.
$288 nightly
The price is $322
Dec 7 - Dec 8
Total with taxes and fees
Cozy Home in Holyoke with 3 bedrooms
Exterior detail
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

Apartment in Greenfield

8.8 out of 10, Excellent, (3)
"We had an amazing stay! The property was spotless and comfortable. We felt right at home and can’t wait to stay here again! "
United States
Garth P.
$186 nightly
The price is $208
Dec 7 - Dec 8
Total with taxes and fees
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Property grounds
The Creation Station is a cozy place so make yourself at home.

Vacation Home in Easthampton Ma.

10.0 out of 10, Exceptional, (72)
"The place is wonderful. Our 2nd visit and will be back. Has everything you need and then some. For us its centrally located so more family came for day trips. "
United States
Connie P.
$248 nightly
The price is $277
Dec 8 - Dec 9
Total with taxes and fees
The Creation Station is a cozy place so make yourself at home.
Private kitchen
Home in the Woods

Vacation Home in Russell

10.0 out of 10, Exceptional, (3)
"We really enjoyed our stay at the Home in the Woods. We stayed for 1 night on the way to Amherst for a graduation. The home is very cozy and clean. Jessica was easy to communicate with and the check-in/check out process was simple. Highly recommend!"
United States
Travis H.
$303 nightly
The price is $320
Dec 6 - Dec 7
Total with taxes and fees
Home in the Woods
Fridge, microwave, oven, stovetop
Cozy Rustic Apt in 18th c Berkshire Farmhouse

Apartment in Lanesborough

9.6 out of 10, Exceptional, (67)
"Great value, so much better than all the touristy motels in the area!"
United States
Chris G.
$185 nightly
The price is $203
Dec 8 - Dec 9
Total with taxes and fees
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Interior
Lovely 2nd Floor Apartment

Vacation Home in Greenfield

10.0 out of 10, Exceptional, (45)
"Our stay was so amazing. The hosts were wonderul and really adapatable to our family needs."
United States
Wendy M.
$181 nightly
The price is $202
Dec 7 - Dec 8
Total with taxes and fees
Lovely 2nd Floor Apartment
Outdoor dining
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Vacation Home in Sherwood Forest

10.0 out of 10, Exceptional, (5)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
$337 nightly
The price is $376
Dec 8 - Dec 9
Total with taxes and fees
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
Fridge, microwave, oven, stovetop
Charming Chicopee Getaway

Apartment in Chicopee

7.4 out of 10, Good, (3)
"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.
$243 nightly
The price is $284
Jan 5 - Jan 6, 2026
Total with taxes and fees
Charming Chicopee Getaway
Exterior
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Cabin in Hinsdale

9.8 out of 10, Exceptional, (34)
"Great cottage - well appointed and very clean. No air conditioning so a bit warm when it’s hot out, but all in all a great stay"
United States
Lindsey E.
$375 nightly
The price is $419
Dec 8 - Dec 9
Total with taxes and fees
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Fridge, microwave, oven, stovetop
Townhouse with Pool Table - Renovated w/ King Bed

Vacation Home in Chicopee

10.0 out of 10, Exceptional, (11)
"The townhouse was perfect for our short trip. It was located close to everything we needed. The house was as described and we would stay here again."
United States
Matt G.
$339 nightly
The price is $385
Dec 7 - Dec 8
Total with taxes and fees
Townhouse with Pool Table - Renovated w/ King Bed
Smart TV, fireplace, printers
Cozy Valley View Post & Beam Villa!

Villa in Whately

10.0 out of 10, Exceptional, (8)
"Thanks for a great stay"
United States
Andrea M.
$779 nightly
The price is $870
Dec 15 - Dec 16
Total with taxes and fees
Cozy Valley View Post & Beam Villa!
1 bedroom, iron/ironing board, bed sheets
Penthouse Apartment on Park Street

Apartment in Adams

2.0 star property
9.6 out of 10, Exceptional, (13)
"Adams is a beautiful town and looks and feels like the appalachian trail! "
United States
judy r.
$219 nightly
The price is $245
Dec 6 - Dec 7
Total with taxes and fees
Penthouse Apartment on Park Street
Exterior
2 Twin beds on 1st floor with En-suite bathroom.

Apartment in Shelburne Falls

$135 nightly
The price is $151
Dec 7 - Dec 8
Total with taxes and fees
2 Twin beds on 1st floor with En-suite bathroom.
Exterior
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Vacation Home in Sherwood Forest

9.6 out of 10, Exceptional, (10)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
$351 nightly
The price is $392
Dec 15 - Dec 16
Total with taxes and fees
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Fridge, microwave, oven, stovetop
Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails

Vacation Home in Granby

9.4 out of 10, Exceptional, (20)
"Great overnight stay! "
United States
Carrie M.
$255 nightly
The price is $269
Dec 6 - Dec 7
Total with taxes and fees
Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails
3 bedrooms, iron/ironing board, WiFi, bed sheets
Welcoming 3-bedroom house- Gardner home

Vacation Home in Chicopee

2.0 star property
$298 nightly
The price is $338
Dec 8 - Dec 9
Total with taxes and fees
Welcoming 3-bedroom house- Gardner home
Dining
Couples 2 Bedroom Retreat-Close to Shelburne Falls

Vacation Home in Colrain

10.0 out of 10, Exceptional, (4)
"This place was great! Even though it was raining we enjoyed the hot tub! It was super clean and comfortable. "
United States
KayKay S.
$316 nightly
The price is $352
Dec 7 - Dec 8
Total with taxes and fees
Couples 2 Bedroom Retreat-Close to Shelburne Falls
Exterior
Terrific 3-bedroom unit in charming Leverett with AC

Apartment in Leverett

10.0 out of 10, Exceptional, (1)
"The apartment is lovely, so comfortable and quiet!! Caitlin was a wonderful host, very responsive. Would absolutely stay again! "
United States
Anna B.
$395 nightly
The price is $441
Dec 16 - Dec 17
Total with taxes and fees
Terrific 3-bedroom unit in charming Leverett with AC
Property grounds
Big farmhouse in the foothills of the Berkshires

Vacation Home in Russell

10.0 out of 10, Exceptional, (143)
"Perfect spot for a family celebration!"
United States
Kerry P.
$344 nightly
The price is $364
Dec 7 - Dec 8
Total with taxes and fees
Big farmhouse in the foothills of the Berkshires
Living area
Joia Verde Chalet—Sleeps 8, Berkshire east ski haven on 127 secluded acres

Chalet in Charlemont

2.0 star property
$691 nightly
The price is $772
Dec 6 - Dec 7
Total with taxes and fees
Joia Verde Chalet—Sleeps 8, Berkshire east ski haven on 127 secluded acres
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

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"I enjoyed the holiday inn. I enjoyed the staff made me fell at home. I enjoyed the comfortable atmosphere and the room was nice and clean. I enjoyed the breakfast very much. The staff was very friendly. "
Brendan 1-night trip
Posted 1 day ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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 $202 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.

Explore a world of travel with Expedia

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?

Peace and quiet on the lake: Visitors like this Chesterfield vacation home rental. It is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection of games in this rental home to help you unwind.

What’s there to see and do in Chesterfield?

Chesterfield Gorge and Knightville Dam & Reservation are a couple of lovely local spots to get outside and enjoy nature. Chesterfield Public Library and Westfield River 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.