Chesterfield Vacation Rentals

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Vacation Rentals in Chesterfield

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

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

9.6 out of 10, Exceptional, (219)
"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

The Clearing - Quiet - Close To Nature

10.0 out of 10, Exceptional, (197)
"Amazing views, lovely cottage!"
The Clearing - Quiet - Close To Nature

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. "
The price is CA $168
CA $416 total
includes taxes & fees
Sep 9 - Sep 10
Charming Chicopee Getaway

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 CA $187
CA $288 total
includes taxes & fees
Aug 24 - Aug 25
Charming Apt in 18th c Berkshire Farmhouse

Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft

9.6 out of 10, Exceptional, (37)
"My wife and I had a wonderful and relaxing time celebrating our anniversary. We really enjoyed sitting by the river."
Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft

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 CA $345
CA $635 total
includes taxes & fees
Sep 2 - Sep 3
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!

Lovely 2nd Floor Apartment

10.0 out of 10, Exceptional, (32)
"Easy stay, good location for us. Would stay again. "
The price is CA $161
CA $279 total
includes taxes & fees
Aug 27 - Aug 28
Lovely 2nd Floor Apartment

Lakefront Bungalow

9.6 out of 10, Exceptional, (10)
"Nice location on water, clean, kitchen had all our needs--would stay there again."
Lakefront Bungalow

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

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....

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.

Bear Creek Cabin

10.0 out of 10, Exceptional, (35)
"Enjoyed our stay"
The price is CA $555
CA $830 total
includes taxes & fees
Aug 31 - Sep 1
Bear Creek Cabin

Little Longbow Lakefront Chalet

9.6 out of 10, Exceptional, (15)
"Our stay was great. The property was extremely clean and the host was absolutely amazing. The property is located on a pond which we could kayak and do some fishing. Just sitting on the beautiful deck overlooking the pond was relaxing. The property offered exactly what we were looking for for this trip. "
Little Longbow Lakefront Chalet

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!

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

10.0 out of 10, Exceptional, (67)
"This was our second time staying here and we had a great time!"
The price is CA $250
CA $384 total
includes taxes & fees
Aug 26 - Aug 27
The Creation Station is a cozy place so make yourself at home.

Quintessential 6-BR Berkshires Lodge

10.0 out of 10, Exceptional, (15)
"House was very nice, spacious and updated. Property was secluded with a nice jacuzzi and fire pit area. "
Quintessential 6-BR Berkshires Lodge

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

9.8 out of 10, Exceptional, (30)
"We had a great time in the cottage. It was perfectly cozy for our family of 6. The cottage has everything you need to have fun on a cold winter night. We especially enjoyed the hot tub and board games! Thanks for a lovely stay - we will come back in the summer!"
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

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 3 - Sep 4
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

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 8 - Sep 9
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

Frequently asked questions

Can I find vacation rentals in Chesterfield?

Yes, we have vacation rentals near popular attractions in Chesterfield, or you can go with a secluded option if you want a relaxing place to 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 vacation rentals in Chesterfield?

Peace and quiet on the lake: Visitors like this Chesterfield vacation home rental. It is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection 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 vacation rental in Chesterfield like?

Vacation rentals are private properties you can stay in for a few weeks or just a few days in Chesterfield. Vacation rentals offer amenities like kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of privacy away from shared hotel elevators and busy concierge desks while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great option for a family trip or a small group gathering.