Chesterfield Holiday Rentals

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Check prices for these dates

Tonight
8 Aug - 9 Aug
Tomorrow
9 Aug - 10 Aug
This weekend
8 Aug - 10 Aug
Next weekend
15 Aug - 17 Aug

Holiday Rentals in Chesterfield

Easthampton Vacation Rental - Walk to Breweries!
Interior

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
Outdoor pool

The Clearing - Quiet - Close To Nature

10.0 out of 10, Exceptional, (195)
"Wonderful getaway, lovely hosts, great location, overall a fabulous place to relax and recharge. "
The Clearing - Quiet - Close To Nature
Peace and quiet on the lake
Interior

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
Interior

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
10 Aug - 11 Aug
Lovely 2nd Floor Apartment
comfort, luxury, privacy
Fridge, microwave, oven, stovetop

comfort, luxury, privacy

9.8 out of 10, Exceptional, (69)
"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
Exterior

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
Fridge, microwave, oven, stovetop

Charming Chicopee Getaway

The price is HK$887
HK$2,253 total
includes taxes & fees
8 Sept - 9 Sept
Charming Chicopee Getaway
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Property grounds

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
Property grounds

Deluxe Queen Room with 2 Queen Beds

2.0 star property
2.0 out of 10, (2)
"The chemical smell in the room was overwhelming. There was no personal contact We called the number provided and was told We would get a full refund."
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!
Fridge, microwave, oven, stovetop

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

9.0 out of 10, Wonderful, (6)
"Great property! Thank you for a wonderful stay."
The price is HK$1,476
HK$2,990 total
includes taxes & fees
14 Aug - 15 Aug
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!
Charming Apt in 18th c Berkshire Farmhouse
1 bedroom, WiFi, bed sheets

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
Big farmhouse in the foothills of the Berkshires
Property grounds

Big farmhouse in the foothills of the Berkshires

10.0 out of 10, Exceptional, (139)
"It is a quiet and beautiful home. The surrounding nature is peaceful and we saw many kinds of birds."
The price is HK$1,570
HK$2,854 total
includes taxes & fees
11 Aug - 12 Aug
Big farmhouse in the foothills of the Berkshires
Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath. Sleeps 7.
Terrace/patio

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$1,962
HK$4,007 total
includes taxes & fees
14 Aug - 15 Aug
Button's Modern Luxury Walkup Downtown Northampton
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
TV, fireplace, DVD player

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
Bear Creek Cabin
Exterior

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
14 Aug - 15 Aug
Bear Creek Cabin
Stylish new 2 bedroom property in enchanting Shelburne Falls Village.
Exterior

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....
Interior

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
Exterior

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!
Outdoor dining

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!
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

Fairfield Inn & Suites Springfield Holyoke

Fairfield Inn & Suites Springfield Holyoke

10/10 Excellent
"It was convenient for the one night we were there."
Thomas 1-night trip
Posted 1 day ago
Fairfield Inn & Suites Springfield Holyoke

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?

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets. : This holiday home rental outside of Chesterfield offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

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.