Chesterfield Vacation Rentals

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Nov 15 - Nov 16
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Nov 21 - Nov 23
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Nov 28 - Nov 30

Vacation Rentals in Chesterfield

Interior
Peace and quiet on the lake

Peace and quiet on the lake

Sherwood Forest
9.6 out of 10, Exceptional, (228)
"Property was very clean and had all amenities that we needed. It was perfect for a cozy winter getaway weekend. Would definitely stay there again! "
United States
Anika J.
Peace and quiet on the lake
Outdoor pool
The Clearing - Quiet - Close To Nature

The Clearing - Quiet - Close To Nature

Cummington
10.0 out of 10, Exceptional, (207)
"It was a warm place. John was kind. "
United States
Seung Gyou B.
The Clearing - Quiet - Close To Nature
Dining
FaLL Western Mass Getaway-Airhockey-Firepit

FaLL Western Mass Getaway-Airhockey-Firepit

Colrain
9.8 out of 10, Exceptional, (38)
"Couldn’t have been happier with our stay. The space was absolutely perfect for our large family, and the owners couldn’t have been nicer or more helpful. Phenomenal kitchen space (love the island!). Can’t wait to stay here again!"
United States
Taylor C.
$564 nightly
The price is $630
Nov 17 - Nov 18
Total with taxes and fees
FaLL Western Mass Getaway-Airhockey-Firepit
Exterior
Bear Creek Cabin

Bear Creek Cabin

Charlemont
10.0 out of 10, Exceptional, (42)
"We enjoyed our stay!!"
United States
Hillary S.
$536 nightly
The price is $599
Nov 17 - Nov 18
Total with taxes and fees
Bear Creek Cabin
Fridge, microwave, oven, stovetop
comfort, luxury, privacy

comfort, luxury, privacy

Amherst
9.8 out of 10, Exceptional, (72)
"We really enjoyed our stay - it was charming that this property is on a farm, my baby daughter loved the chickens in the yard. Lee was very generous with us and we loved the farm-fresh eggs for breakfast."
United States
Marie M.
comfort, luxury, privacy
Terrace/patio
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!

Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!

Lanesborough
10.0 out of 10, Exceptional, (6)
"Everything was just as advertised and we really enjoyed the view and the hot tub. Perfect spot for a quick getaway! "
United States
Cindy B.
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!
Fridge, microwave, oven, stovetop
Amore Estate - beautiful room with many places to explore and relax in.

Amore Estate - beautiful room with many places to explore and relax in.

Lenox
9.2 out of 10, Wonderful, (32)
"Beautiful property with tons of space and fantastic for a group of friends or family"
United States
Greg S.
Amore Estate - beautiful room with many places to explore and relax in.
Property grounds
Experience Three Sisters Sanctuary in Goshen, MA

Experience Three Sisters Sanctuary in Goshen, MA

2.0 star property
Goshen
10.0 out of 10, Exceptional, (1)
"We had such a great time staying here as always. "
United States
David F.
Experience Three Sisters Sanctuary in Goshen, MA
Exterior
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, (33)
"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.
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Property grounds
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, (70)
"A very short but a really fun stay. Great location to just relax and get away from it all."
United States
Naseem P.
$249 nightly
The price is $278
Nov 17 - Nov 18
Total with taxes and fees
The Creation Station is a cozy place so make yourself at home.
Property grounds
Riverbend Berkshire East Basecamp - 3 bedrooms available

Riverbend Berkshire East Basecamp - 3 bedrooms available

Charlemont
$352 nightly
The price is $393
Nov 18 - Nov 19
Total with taxes and fees
Riverbend Berkshire East Basecamp - 3 bedrooms available
Fridge, microwave, oven, stovetop
Charming Chicopee Getaway

Charming Chicopee Getaway

Chicopee
6.0 out of 10, (2)
"The apartment didn't look anything like the pictures. It was dingy and had a smell to it that we couldn't tolerate and that lingered in our nostrils for hours after we left. The kitchen area was unusable -- what passed for a table was at the same level as the chair seats, which made it impossible to use. Finally, we had to move a big trash bag full of trash out of the way before even being able to get in the door. We left within minutes after arriving and went to a hotel. "
United States
Kenneth M.
$214 nightly
The price is $250
Nov 17 - Nov 18
Total with taxes and fees
Charming Chicopee Getaway
Terrace/patio
Old Deerfield Treasure!

Old Deerfield Treasure!

2.0 star property
Deerfield
$492 nightly
The price is $536
Nov 17 - Nov 18
Total with taxes and fees
Old Deerfield Treasure!
Exterior
Stylish new 2 bedroom property in enchanting Shelburne Falls Village.

Stylish new 2 bedroom property in enchanting Shelburne Falls Village.

2.0 star property
Shelburne Falls
10.0 out of 10, Exceptional, (18)
"Everything was lovely, thank you!"
United States
Chelsea D.
Stylish new 2 bedroom property in enchanting Shelburne Falls Village.
Exterior
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Sherwood Forest
9.6 out of 10, Exceptional, (229)
"Very clean and well stocked cabin. Everything you need is there. Very quiet neighborhood. Perfect place to get away and relax. I would highly recommend this place especially if you like being close to nature. "
United States
Sharon Z.
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Property grounds
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Hinsdale
9.8 out of 10, Exceptional, (19)
"Rich was an amazing host. Beautiful lake and sunsets. I would love to stay there again"
United States
maria f.
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Property grounds
Hadley Amherst Location.Explore the Valley Colleges!

Hadley Amherst Location.Explore the Valley Colleges!

Hadley
10.0 out of 10, Exceptional, (132)
"Such a wonderful property and amazing host! A convenient location to the area as well as shopping and beautiful bike/walking trail!Thank you Colleen!"
United States
John M.
Hadley Amherst Location.Explore the Valley Colleges!
Property grounds
Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires

Russell
10.0 out of 10, Exceptional, (143)
"We enjoyed our stay in this beautiful old farmhouse. Plenty of room for everyone and kitchen and linens were fully stocked."
United States
Nicole K.
$287 nightly
The price is $303
Nov 17 - Nov 18
Total with taxes and fees
Big farmhouse in the foothills of the Berkshires
Interior
Wildlife Lakeside Cottage beautiful views, amazing wildlife, great location

Wildlife Lakeside Cottage beautiful views, amazing wildlife, great location

Lanesborough
9.6 out of 10, Exceptional, (73)
"Beautiful house and location that was perfect for a family weekend. Would 100% recommend!"
United States
Shaun L.
Wildlife Lakeside Cottage beautiful views, amazing wildlife, great location
Fridge, microwave, oven, stovetop
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

2.0 star property
Dalton
10.0 out of 10, Exceptional, (14)
"The property was very clean, easy to access and amazing with all the extras that most places don’t include. The water was really hot and it never ran out. The bed was out of this world comfortable. Property owner was very responsive and more than willing to help. Dogs welcome. I would definitely recommend this property. I hope to return sometime in the near future "
United States
S Michele C.
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
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

Quality Inn West Springfield

Quality Inn West Springfield

10/10 Excellent
"Very courteous staff. Comfortable, clean room. Always interesting people travelling through."
Scot 2-night trip
Posted 1 day ago
Quality 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 $250 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 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.