Chesterfield Holiday Rentals

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Check prices for these dates

Tonight
10 Aug - 11 Aug
Tomorrow
11 Aug - 12 Aug
Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug

Holiday Rentals in Chesterfield

Easthampton Vacation Rental - Walk to Breweries!
Enter a cozy space with a comfortable room featuring a dresser and TV.

Easthampton Vacation Rental - Walk to Breweries!

9.6 out of 10, Exceptional, (21)
"Our group had a wonderful time and we will not hesitate to book again in the future. The place was exceptionally clean, well appointed, and very comfortable. Overall it was a great experience! "
Easthampton Vacation Rental - Walk to Breweries!
The Clearing - Quiet - Close To Nature
Surrounded by a serene lawn and a tranquil pond, this peaceful setting offers a serene escape.

The Clearing - Quiet - Close To Nature

10.0 out of 10, Exceptional, (195)
"Amazing views, lovely cottage!"
The Clearing - Quiet - Close To Nature
Peace and quiet on the lake
Enjoy the airy feel of this room with a high ceiling and skylight, featuring a balcony with a railing.

Peace and quiet on the lake

9.6 out of 10, Exceptional, (217)
"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! "
Peace and quiet on the lake
Lovely 2nd Floor Apartment
Relax in a serene space with a comfortable armchair, console table, and lush greenery.

Lovely 2nd Floor Apartment

10.0 out of 10, Exceptional, (31)
"Easy stay, good location for us. Would stay again. "
The price is HK$911
HK$1,579 total
includes taxes & fees
13 Aug - 14 Aug
Lovely 2nd Floor Apartment
comfort, luxury, privacy
Effortlessly prepare meals in this well-equipped kitchen featuring a refrigerator, dishwasher, microwave, and oven.

comfort, luxury, privacy

9.8 out of 10, Exceptional, (70)
"Clean and comfortable property! Perfect for visiting the Amherst area. It was easy to get to the Dickinson House and the Eric Carle Museum. Would definitely stay again. "
comfort, luxury, privacy
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Surrounded by lush trees, this cabin features a spacious porch and a covered area with multiple windows.

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

9.6 out of 10, Exceptional, (217)
"Cabin was exactly what we were looking for in a weekend away. Great location, quiet, and had everything we needed. Hope to go back again soon! "
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Charming Chicopee Getaway
Kitchen features a white stove, cabinetry, and a coffee maker.

Charming Chicopee Getaway

The price is HK$879
HK$2,244 total
includes taxes & fees
8 Sept - 9 Sept
Charming Chicopee Getaway
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Escape to a serene lakeside retreat surrounded by lush greenery and vibrant flowers.

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

9.6 out of 10, Exceptional, (14)
"Very friendly hosts, great location. "
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Deluxe Queen Room with 2 Queen Beds
Guest rooms lead to a covered walkway with a tiled floor.

Deluxe Queen Room with 2 Queen Beds

2.0 star property
2.0 out of 10, (4)
"Pool is caving in with pool cover partly pulled away. Gate to access pool area was unlocked. Hazard for children. Staff is not onsite. Room was clean, but sheets had stains. Used bar of soap left on bathroom sink. "
The price is HK$777
HK$1,043 total
includes taxes & fees
1 Sept - 2 Sept
Deluxe Queen Room with 2 Queen Beds
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!
Enjoy cooking in this well-lit kitchen with a central island, stainless steel appliances, and a brick backsplash.

Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!

9.0 out of 10, Wonderful, (7)
"Great property! Thank you for a wonderful stay."
The price is HK$1,476
HK$2,990 total
includes taxes & fees
11 Aug - 12 Aug
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!
Charming Apt in 18th c Berkshire Farmhouse
Two single beds with bedside tables and lamps, set against a rustic wooden wall and a textured rug.

Charming Apt in 18th c Berkshire Farmhouse

9.6 out of 10, Exceptional, (34)
"The property was perfect for us !! Lots of room and the beds are very comfortable. "
The price is HK$1,060
HK$1,630 total
includes taxes & fees
13 Aug - 14 Aug
Charming Apt in 18th c Berkshire Farmhouse
Bear Creek Cabin
Situated in a forested area, this cabin features a spacious porch, large windows, and a steeply pitched roof.

Bear Creek Cabin

10.0 out of 10, Exceptional, (34)
"Enjoyed our stay"
The price is HK$3,140
HK$4,726 total
includes taxes & fees
11 Aug - 12 Aug
Bear Creek Cabin
Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath. Sleeps 7.
Escape to a secluded cabin surrounded by trees, with a picnic table and comfortable seating.

Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath. Sleeps 7.

9.6 out of 10, Exceptional, (60)
"Great"
Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath. Sleeps 7.
Button's Modern Luxury Walkup Downtown Northampton
Oven, stovetop, dishwasher

Button's Modern Luxury Walkup Downtown Northampton

The price is HK$1,963
HK$4,007 total
includes taxes & fees
12 Aug - 13 Aug
Button's Modern Luxury Walkup Downtown Northampton
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Relax in this serene room with a large bed, stone fireplace, and forest views.

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

9.6 out of 10, Exceptional, (44)
"We had a wonderful stay. The cabin was clean and comfortable! "
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Stylish new 2 bedroom property in enchanting Shelburne Falls Village.
Stunning two-story home with a gabled roof and inviting front porch.

Stylish new 2 bedroom property in enchanting Shelburne Falls Village.

2.0 star property
10.0 out of 10, Exceptional, (12)
"The place was very comfortable and in a great location. "
Stylish new 2 bedroom property in enchanting Shelburne Falls Village.
Private Island - Largest Fresh Water Reservoir in Mass....
Relax in this cabin's open-plan living area with a fireplace, scenic lake views, and comfortable seating.

Private Island - Largest Fresh Water Reservoir in Mass....

9.0 out of 10, Wonderful, (7)
"We had a great time. The owner Bill was a great host."
Private Island - Largest Fresh Water Reservoir in Mass....
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Situated in a wooded area, this cabin features a welcoming front porch and a serene, secluded environment.

Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort

9.6 out of 10, Exceptional, (129)
"A cozy spot to watch the snow come down!"
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Amherst, Perfect Location, UMass, Smith, MHC!
Enjoy a quiet moment on the deck with a small table and two chairs, shaded by an umbrella.

Amherst, Perfect Location, UMass, Smith, MHC!

10.0 out of 10, Exceptional, (17)
"House was great, very comfortable, location was perfect for our needs. All of us had an excellent stay."
Amherst, Perfect Location, UMass, Smith, MHC!
1810 Brook Side Mill/House / EV Level 2 Charging on Site
Enjoy a functional kitchen with a central island, perfect for meal prep and dining.

1810 Brook Side Mill/House / EV Level 2 Charging on Site

10.0 out of 10, Exceptional, (81)
"Highly recommend this charming, historic place.  Well appointed. Has everything you need for your stay.  Cozy…yet plenty of space for everyone.  Looks like it was just renovated.  Took my daughter and two granddaughters for a ski weekend.  Wouldn’t hesitate to come back here.  "
1810 Brook Side Mill/House / EV Level 2 Charging on Site
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

Courtyard by Marriott West Springfield

Courtyard by Marriott West Springfield

10/10 Excellent
"We always stay once a year for summer. We love the hotel and specially the beds, they are the most confortable ever! The staff is always amazing and the hotel is very nice and peaceful. "
ARIEL 1-night trip
Posted 15 hours ago
Courtyard by Marriott West Springfield

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?

Peace and quiet on the lake: This holiday home rental outside of Chesterfield is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind.

What’s there to see and do in Chesterfield?

Westfield River and Chesterfield Gorge 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.