Chesterfield Vacation Rentals

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Check prices for these dates

In two weeks
Sep 5 - Sep 7
In two months
Oct 17 - Oct 19
In three months
Nov 14 - Nov 16
In four months
Dec 12 - Dec 14

Browse Select Chesterfield Vacation Homes

Our top choices for Chesterfield vacation homes

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Fridge, microwave, oven, stovetop

Sun Filled Lenox Retreat - Minutes to Tanglewood!

10.0 out of 10, Exceptional, (1)
"Very charming, comfortable, and clean. It was in a great location and only minutes away from a lot of sightseeing locations. House management was very accommodating and friendly. I would stay here again."
The price is CA $315
CA $715 total
includes taxes & fees
Sep 4 - Sep 5
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (255)
"Host was very friendly and helpful. House was absolutely adorable and decorated well. Plenty of parking. Beautiful, well-maintained property. Great for hikes. Lovely fire pit area and lots of wood. Very convenient location to recreation in The Berkshires. I would stay here again. "
The price is CA $208
CA $310 total
includes taxes & fees
Sep 16 - Sep 17
Berkshire Village Carriage House - Super Private!!
Cozy Home in Holyoke with 3 bedrooms
Exterior detail

Cozy Home in Holyoke with 3 bedrooms

9.8 out of 10, Exceptional, (7)
"We stayed in Holyoke as my daughter was performing at UMASS Amherst and this was a great location only 25 minutes of so away from campus. The home is spacious with two bedrooms and bathrooms. A very clean and well maintained the home. Would definitely recommend and will visit again!! "
The price is CA $248
CA $535 total
includes taxes & fees
Aug 21 - Aug 22
Cozy Home in Holyoke with 3 bedrooms
Lovely 2nd Floor Apartment
Interior

Lovely 2nd Floor Apartment

10.0 out of 10, Exceptional, (32)
"Easy stay, good location for us. Would stay again. "
The price is CA $134
CA $249 total
includes taxes & fees
Aug 21 - Aug 22
Lovely 2nd Floor Apartment
The Creation Station is a cozy place so make yourself at home.
Property grounds

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 CA $248
CA $385 total
includes taxes & fees
Aug 21 - Aug 22
The Creation Station is a cozy place so make yourself at home.
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
Outdoor dining

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."
The price is CA $225
CA $553 total
includes taxes & fees
Sep 1 - Sep 2
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
Button's Modern Luxury Walkup Downtown Northampton
Oven, stovetop, dishwasher

Button's Modern Luxury Walkup Downtown Northampton

The price is CA $345
CA $695 total
includes taxes & fees
Sep 9 - Sep 10
Button's Modern Luxury Walkup Downtown Northampton
Townhouse with Pool Table - Renovated w/ King Bed
Fridge, microwave, oven, stovetop

Townhouse with Pool Table - Renovated w/ King Bed

10.0 out of 10, Exceptional, (8)
"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 CA $291
CA $585 total
includes taxes & fees
Sep 8 - Sep 9
Townhouse with Pool Table - Renovated w/ King Bed
Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails
Fridge, microwave, oven, stovetop

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

9.6 out of 10, Exceptional, (15)
"Great overnight stay! "
The price is CA $206
CA $369 total
includes taxes & fees
Sep 3 - Sep 4
Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails
Charming 4Bds+1crib house with patio Amherst Center
Property grounds

Charming 4Bds+1crib house with patio Amherst Center

2.0 star property
9.0 out of 10, Wonderful, (7)
"A great place for a family stay in downtown Amherst. "
The price is CA $447
CA $782 total
includes taxes & fees
Aug 24 - Aug 25
Charming 4Bds+1crib house with patio Amherst Center
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Fridge, microwave, oven, stovetop

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 CA $413
CA $726 total
includes taxes & fees
Sep 11 - Sep 12
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Couples 2 Bedroom Retreat - Hot Tub- Air Hockey -Close to ShelburneFalls
Dining

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

10.0 out of 10, Exceptional, (3)
"Friends and I were in the area for a concert at Tree House Brewing. This house wasn’t far and it is a gorgeous home. Super clean and had all amenities. Would stay here again!"
The price is CA $235
CA $513 total
includes taxes & fees
Aug 21 - Aug 22
Couples 2 Bedroom Retreat - Hot Tub- Air Hockey -Close to ShelburneFalls
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Smart TV, books

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 CA $222
CA $545 total
includes taxes & fees
Sep 1 - Sep 2
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Bungalow in the Berkshires
Exterior

Bungalow in the Berkshires

10.0 out of 10, Exceptional, (1)
"Renting this house was very last minute because the place we initially booked fell through - and we're so glad it did! The house was charming, cozy, up-to-date, and beautifully decorated. The neighborhood was nice and quiet, and the drive to downtown was short. I highly recommend this house!"
The price is CA $520
CA $717 total
includes taxes & fees
Aug 24 - Aug 25
Bungalow in the Berkshires
Spacious 5-Bedroom Home with Game Room in Amherst - Mins to UMass
Fridge, microwave, oven, stovetop

Spacious 5-Bedroom Home with Game Room in Amherst - Mins to UMass

10.0 out of 10, Exceptional, (5)
The price is CA $1,385
CA $2,226 total
includes taxes & fees
Aug 30 - Aug 31
Spacious 5-Bedroom Home with Game Room in Amherst - Mins to UMass
Luxury Retreat inAmherst
Dining

Luxury Retreat inAmherst

The price is CA $749
CA $1,177 total
includes taxes & fees
Sep 2 - Sep 3
Luxury Retreat inAmherst
3-bedroom house in beautiful Berkshires, close to amenities!
Property grounds

3-bedroom house in beautiful Berkshires, close to amenities!

The price is CA $264
CA $441 total
includes taxes & fees
Sep 9 - Sep 10
3-bedroom house in beautiful Berkshires, close to amenities!
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)
"Lovely old farmhouse with authentic yet comfortable furnishings. Would recommend!"
The price is CA $276
CA $502 total
includes taxes & fees
Aug 21 - Aug 22
Big farmhouse in the foothills of the Berkshires
FaLL Western Mass Getaway-Airhockey-Hot tub-Firepit
Dining

FaLL 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 CA $399
CA $882 total
includes taxes & fees
Aug 21 - Aug 22
FaLL Western Mass Getaway-Airhockey-Hot tub-Firepit
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, (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 CA $137
CA $184 total
includes taxes & fees
Sep 1 - Sep 2
Deluxe Queen Room with 2 Queen Beds
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

Hotel Northampton

Hotel Northampton

10/10 Excellent
"Nice overall"
Ron 1-night trip
Posted 20 hours ago
Hotel Northampton