Chesterfield Holiday Rentals

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Holiday Rentals in Chesterfield

Charming Chicopee Getaway
10.0 out of 10, Exceptional, (1)
"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. "
Tamara S.
The price is AU$434
includes taxes & fees
11 Nov - 12 Nov
Charming Chicopee Getaway
Cozy Home in Holyoke with 3 bedrooms
9.6 out of 10, Exceptional, (9)
"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."
Eric W.
The price is AU$503
includes taxes & fees
23 Oct - 24 Oct
Cozy Home in Holyoke with 3 bedrooms
The Creation Station is a cozy place so make yourself at home.
10.0 out of 10, Exceptional, (69)
"This was our second time staying here and we had a great time!"
Andy L.
The price is AU$435
includes taxes & fees
20 Oct - 21 Oct
The Creation Station is a cozy place so make yourself at home.
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!
9.2 out of 10, Wonderful, (15)
"Great property! Thank you for a wonderful stay."
David
The price is AU$480
includes taxes & fees
22 Oct - 23 Oct
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!
Townhouse with Pool Table - Renovated w/ King Bed
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."
Matt G.
The price is AU$585
includes taxes & fees
20 Oct - 21 Oct
Townhouse with Pool Table - Renovated w/ King Bed
Lovely 2nd Floor Apartment
10.0 out of 10, Exceptional, (40)
"Quiet location and comfortable stay. The space was clean and perfect for a quick overnight. Owner was on site and very responsive. "
Shanyn
The price is AU$312
includes taxes & fees
30 Oct - 31 Oct
Lovely 2nd Floor Apartment
Humble home with free breakfast
7.0 out of 10, Good, (2)
The price is AU$507
includes taxes & fees
3 Nov - 4 Nov
Humble home with free breakfast
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
10.0 out of 10, Exceptional, (3)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
Sharon K.
The price is AU$622
includes taxes & fees
28 Oct - 29 Oct
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
9.6 out of 10, Exceptional, (8)
"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."
James D.
The price is AU$610
includes taxes & fees
28 Oct - 29 Oct
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails
9.4 out of 10, Exceptional, (17)
"Great overnight stay! "
Carrie M.
The price is AU$418
includes taxes & fees
19 Oct - 20 Oct
Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails
Park Street Penthouse Apartment
9.6 out of 10, Exceptional, (11)
"Adams is a beautiful town and looks and feels like the appalachian trail! "
judy r.
The price is AU$303
includes taxes & fees
27 Oct - 28 Oct
Park Street Penthouse Apartment
Couples 2 Bedroom Retreat - Hot Tub- Air Hockey -Close to ShelburneFalls
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. "
KayKay S.
The price is AU$579
includes taxes & fees
19 Oct - 20 Oct
Couples 2 Bedroom Retreat - Hot Tub- Air Hockey -Close to ShelburneFalls
Charming 2-bedroom house in beautiful countryside of Cummington, Ma
2.0 star property
The price is AU$444
includes taxes & fees
20 Oct - 21 Oct
Charming 2-bedroom house in beautiful countryside of Cummington, Ma
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
9.8 out of 10, Exceptional, (32)
"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"
Lindsey E.
The price is AU$743
includes taxes & fees
28 Oct - 29 Oct
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Button's Modern Luxury Walkup Downtown Northampton
10.0 out of 10, Exceptional, (1)
"This was the best rental apartment I've stayed at and definitely the cleanest. Check-in is easy, the pictures are accurate, the kitchen and bathroom are great, and the location in downtown Northampton is super walkable to cafes, shops, Smith, etc. If I'm ever back anywhere near the area, I will definitely try to stay there again. 10/10"
Meghan C.
The price is AU$785
includes taxes & fees
3 Nov - 4 Nov
Button's Modern Luxury Walkup Downtown Northampton
Historic downtown house. Unscented products and sustainability practices.
10.0 out of 10, Exceptional, (5)
"It’s a beautiful home that worked for our stay as a family "
Camilo W.
The price is AU$937
includes taxes & fees
3 Nov - 4 Nov
Historic downtown house. Unscented products and sustainability practices.
Big farmhouse in the foothills of the Berkshires
10.0 out of 10, Exceptional, (140)
"Lovely old farmhouse with authentic yet comfortable furnishings. Would recommend!"
Jon O.
The price is AU$572
includes taxes & fees
19 Oct - 20 Oct
Big farmhouse in the foothills of the Berkshires
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
2.0 star property
7.8 out of 10, Good, (6)
"Very clean and spacious! We enjoyed our stay with our small pup!"
Ann C.
The price is AU$764
includes taxes & fees
27 Oct - 28 Oct
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Sun Filled Lenox Retreat - Minutes to Tanglewood!
9.4 out of 10, Exceptional, (3)
"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."
Sarah D.
The price is AU$728
includes taxes & fees
30 Oct - 31 Oct
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 holiday rentals

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

Chesterfield holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesterfield holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesterfield holiday rentals we have selected for you start as low as AU$312 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chesterfield rentals

At Expedia, we put the best Chesterfield holiday 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 holiday.

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 holiday rentals in Chesterfield?

Yes, there are holiday rentals close to the most popular sights in Chesterfield, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that Chesterfield has to offer?

Amore Estate - beautiful room with many places to explore and relax in.: This holiday home rental outside of Chesterfield offers an outdoor pool, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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 holiday rental in Chesterfield like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chesterfield. Holiday rentals feature amenities like kitchens and laundry facilities so you'll have everything you want. If you're concerned about a sanitised environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for a family getaway.