Chesterfield Holiday Rentals

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Holiday Rentals in Chesterfield

Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails

9.6 out of 10, Exceptional, (14)
"Great overnight stay! "
The price is AU$414
includes taxes & fees
29 July - 30 July
Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails

Lovely 2nd Floor Apartment

10.0 out of 10, Exceptional, (31)
"Easy stay, good location for us. Would stay again. "
The price is AU$296
includes taxes & fees
28 July - 29 July
Lovely 2nd Floor Apartment

Home in the Woods

10.0 out of 10, Exceptional, (3)
"Jessica's spot is adorable and tidy, at the end of a quiet, shady lane, with lots of peace and privacy. It was a hot, muggy weekend but there were 2 window units and extra fans to keep us comfortable. The house is well-appointed—we had a busy schedule and were sad we didn't have a chance to use the lovely outdoor fire pit area. Good communication after a minor mixup. Would definitely stay again!"
The price is AU$487
includes taxes & fees
4 Aug - 5 Aug
Home in the Woods

Cozy Home in Holyoke with 3 bedrooms

9.8 out of 10, Exceptional, (7)
"Wonderful stay. Veronica was so kind and super responsive. The house was a great size and have everything we needed. We stayed there with 2 adults and 2 toddlers under 3. It was plenty of space. And a great location to all the area had to offer, museums, fun restaurants in North Hampton, etc. Would definitely stay again. "
The price is AU$595
includes taxes & fees
28 July - 29 July
Cozy Home in Holyoke with 3 bedrooms

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (253)
"One of the best properties i've ever stayed at "
The price is AU$455
includes taxes & fees
31 July - 1 Aug
Berkshire Village Carriage House - Super Private!!

Couples 2 Bedroom Retreat - Hot Tub- Air Hockey -Close to ShelburneFalls

10.0 out of 10, Exceptional, (2)
"This was such a nice stay. Not only was the house really clean, there were so many little touches. It gave cozy spa vibes. "
The price is AU$542
includes taxes & fees
28 July - 29 July
Couples 2 Bedroom Retreat - Hot Tub- Air Hockey -Close to ShelburneFalls

Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

10.0 out of 10, Exceptional, (1)
"We really enjoyed our stay here. Location was excellent. Very peaceful and quiet. The house was clean and had everything you needed. Would come again!"
The price is AU$637
includes taxes & fees
28 July - 29 July
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

The Creation Station is a cozy place so make yourself at home.

10.0 out of 10, Exceptional, (66)
"This was our second time staying here and we had a great time!"
The price is AU$423
includes taxes & fees
4 Aug - 5 Aug
The Creation Station is a cozy place so make yourself at home.

Townhouse with Pool Table - Renovated w/ King Bed

10.0 out of 10, Exceptional, (7)
"The home was perfect for our crew while working out of town. Everything was as listed and Mabel was a great host and even called to make sure we were settled in and didn't need anything. "
The price is AU$454
includes taxes & fees
23 July - 24 July
Townhouse with Pool Table - Renovated w/ King Bed

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

2.0 star property
9.0 out of 10, Wonderful, (4)
"Very clean and spacious! We enjoyed our stay with our small pup!"
The price is AU$942
includes taxes & fees
4 Aug - 5 Aug
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

9.8 out of 10, Exceptional, (7)
"My wife, two kids, and chocolate lab spent a few days at the cottage to enjoy the snow and hot tub. Everything was set up exactly as described and Nicole was very friendly and proactive. We had a great time and would do it again "
The price is AU$794
includes taxes & fees
6 Aug - 7 Aug
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Hummingbird Haven is a Berkshires Retreat surrounded by Nature and Local Charm.

10.0 out of 10, Exceptional, (3)
"This property was amazing! Very clean and spacious, perfect location for a nice peaceful getaway. Kendra was very communicative and made sure our stay was comfortable. 10/10 highly recommend you to stay here. "
The price is AU$954
includes taxes & fees
13 Aug - 14 Aug
Hummingbird Haven is a Berkshires Retreat surrounded by Nature and Local Charm.

Button's Modern Luxury Walkup Downtown Northampton

The price is AU$776
includes taxes & fees
5 Aug - 6 Aug
Button's Modern Luxury Walkup Downtown Northampton

Low-scent, historic, well-located, downtown house

10.0 out of 10, Exceptional, (4)
"It’s a beautiful home that worked for our stay as a family "
The price is AU$1,142
includes taxes & fees
26 July - 27 July
Low-scent, historic, well-located, downtown house

Big farmhouse in the foothills of the Berkshires

10.0 out of 10, Exceptional, (138)
"It is a quiet and beautiful home. The surrounding nature is peaceful and we saw many kinds of birds."
The price is AU$563
includes taxes & fees
27 July - 28 July
Big farmhouse in the foothills of the Berkshires

Western Mass Getaway-Airhockey-Hot tub-Firepit

9.8 out of 10, Exceptional, (36)
"Great place and convenient to get to and from Berkshire East."
The price is AU$975
includes taxes & fees
23 July - 24 July
Western Mass Getaway-Airhockey-Hot tub-Firepit

Luxury Retreat inAmherst

The price is AU$1,282
includes taxes & fees
2 Aug - 3 Aug
Luxury Retreat inAmherst

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 AU$224
includes taxes & fees
17 Aug - 18 Aug
Deluxe Queen Room with 2 Queen Beds

Sun Filled Lenox Retreat - Minutes to Tanglewood!

2.0 out of 10, (1)
"The management company told me there was an issue with the house the morning of my stay."
The price is AU$943
includes taxes & fees
20 Aug - 21 Aug
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

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.