Chesterfield Vacation Rentals

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Our top choices for Chesterfield vacation rentals

Vacation Home in Holyoke

Cozy Home in Holyoke with 3 bedrooms
9.8 out of 10, Exceptional, (13 reviews)
"Very neat and clean. Decorated for Fall, which was nice. All amenities made for a really nice time."
United States
Stacy G.
$288 nightly
The price is $322
Jan 13 - Jan 14
Total with taxes and fees
Cozy Home in Holyoke with 3 bedrooms
10.0 out of 10, Exceptional, (72 reviews)
"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.
$203 nightly
The price is $227
Jan 12 - Jan 13
Total with taxes and fees
The Creation Station is a cozy place so make yourself at home.
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"Overall had a great stay, the space is cozy and welcoming."
United States
Gracie B.
$298 nightly
The price is $338
Jan 13 - Jan 14
Total with taxes and fees
Welcoming 3-bedroom house- Gardner home

Vacation Home in Greenfield

Lovely 2nd Floor Apartment
10.0 out of 10, Exceptional, (46 reviews)
"Close to downtown, clean & comfortable!"
United States
Robbi C.
$180 nightly
The price is $201
Jan 12 - Jan 13
Total with taxes and fees
Lovely 2nd Floor Apartment
2.0 star property
$236 nightly
The price is $264
Jan 16 - Jan 17
Total with taxes and fees
Beautiful 2-bedroom cottage on Robert Frost Trail
10.0 out of 10, Exceptional, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
$337 nightly
The price is $376
Jan 12 - Jan 13
Total with taxes and fees
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
9.6 out of 10, Exceptional, (10 reviews)
"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.
$353 nightly
The price is $395
Jan 12 - Jan 13
Total with taxes and fees
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
10.0 out of 10, Exceptional, (11 reviews)
"Perfect stay for a family. Enjoyed the pool table. Beds were comfortable. Showers were perfect. Beautifully decorated. We felt right at home. Would definitely stay again. "
United States
Tonya Z.
$339 nightly
The price is $385
Jan 12 - Jan 13
Total with taxes and fees
Townhouse with Pool Table - Renovated w/ King Bed
9.8 out of 10, Exceptional, (21 reviews)
"Absolutely perfect quiet get away to relax and recharge will be back! "
United States
Dana V.
$457 nightly
The price is $510
Jan 16 - Jan 17
Total with taxes and fees
Little Longbow Lakefront Chalet
10.0 out of 10, Exceptional, (8 reviews)
"Thanks for a great stay"
United States
Andrea M.
$677 nightly
The price is $756
Jan 12 - Jan 13
Total with taxes and fees
Cozy Valley View Post & Beam Villa!
9.8 out of 10, Exceptional, (35 reviews)
"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.
$380 nightly
The price is $424
Jan 12 - Jan 13
Total with taxes and fees
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
10.0 out of 10, Exceptional, (2 reviews)
"nice cozy home in a quiet neighborhood. easy access to highways. would stay here again. "
United States
Christopher P.
$179 nightly
The price is $203
Jan 14 - Jan 15
Total with taxes and fees
Cozy 2-bedroom apartment in Chicopee
10.0 out of 10, Exceptional, (1 review)
"The apartment is lovely, so comfortable and quiet!! Caitlin was a wonderful host, very responsive. Would absolutely stay again! "
United States
Anna B.
$423 nightly
The price is $473
Jan 13 - Jan 14
Total with taxes and fees
Terrific 3-bedroom unit in charming Leverett with AC

Vacation Home in Amherst

Luxury Retreat inAmherst
10.0 out of 10, Exceptional, (1 review)
"Very helpful and easy communication. Very clean and nice place. We were very busy and only really were at the place to sleep but it is quiet and perfect for a restful stay."
United States
Robert
$750 nightly
The price is $838
Jan 12 - Jan 13
Total with taxes and fees
Luxury Retreat inAmherst
$157 nightly
The price is $175
Jan 12 - Jan 13
Total with taxes and fees
2 Twin beds on 1st floor with En-suite bathroom.
9.0 out of 10, Wonderful, (22 reviews)
"It was a great location for our stay. Near family and wedding venue. House had everything we needed for a weekend stay. "
United States
Kristine P.
$253 nightly
The price is $267
Jan 12 - Jan 13
Total with taxes and fees
Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails
2.0 star property
9.6 out of 10, Exceptional, (14 reviews)
"Adams is a beautiful town and looks and feels like the appalachian trail! "
United States
judy r.
$218 nightly
The price is $244
Jan 12 - Jan 13
Total with taxes and fees
Penthouse Apartment on Park Street
10.0 out of 10, Exceptional, (1 review)
"Very nice house and the stay was unproblematic!"
United States
Noah K.
$378 nightly
The price is $422
Jan 12 - Jan 13
Total with taxes and fees
Riverbend Berkshire East Basecamp - 3 bedrooms available
10.0 out of 10, Exceptional, (143 reviews)
"Perfect spot for a family celebration!"
United States
Kerry P.
$322 nightly
The price is $340
Jan 14 - Jan 15
Total with taxes and fees
Big farmhouse in the foothills of the Berkshires
9.4 out of 10, Exceptional, (3 reviews)
"The house is in a great location and is very user friendly and well equipped. The only suggestion I would make is to put an air conditioner in the third bedroom. Overall, a lovely stay."
United States
Sarah D.
$412 nightly
The price is $460
Jan 12 - Jan 13
Total with taxes and fees
Sun Filled Lenox Retreat - Minutes to Tanglewood!
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

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 $201 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?

Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!: Visitors like this Chesterfield vacation home rental. It offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub.

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 Krug Sugarbush 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.