Chesterfield Vacation Rentals

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Vacation Rentals in Chesterfield

comfort, luxury, privacy

9.8 out of 10, Exceptional, (57)
"Great place "
comfort, luxury, privacy

Deluxe Queen Room with 2 Queen Beds

2.0 star property
The price is CA $164
CA $214 total
includes taxes & fees
May 14 - May 15
Deluxe Queen Room with 2 Queen Beds

Cheerful 1 bedroom

9.8 out of 10, Exceptional, (34)
"This is my third stay here and I am always very happy with the cleanliness. This place is perfect for me and my dog."
Cheerful 1 bedroom

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

10.0 out of 10, Exceptional, (2)
"We all enjoyed our stay! As described."
The price is CA $343
CA $628 total
includes taxes & fees
May 14 - May 15
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!

Cozy Home in Holyoke with 2 bedrooms

10.0 out of 10, Exceptional, (3)
"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 CA $179
CA $393 total
includes taxes & fees
May 14 - May 15
Cozy Home in Holyoke with 2 bedrooms

kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

9.8 out of 10, Exceptional, (98)
"We were attending a horse show locally. We stayed a few nights and everything about this day was easy from start to finish."
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

The Clearing - Quiet - Close To Nature

10.0 out of 10, Exceptional, (187)
"Wonderful getaway, lovely hosts, great location, overall a fabulous place to relax and recharge. "
The Clearing - Quiet - Close To Nature

Easthampton Vacation Rental - Walk to Breweries!

9.6 out of 10, Exceptional, (13)
"It was a perfect location close to our family. The place was clean and instructions clear. Definitely will be back"
Easthampton Vacation Rental - Walk to Breweries!

Chic Downtown Retreat Furnished 2-Bedroom with Trail Access & Outdoor Oasis

5.0 out of 10, (2)
"Perfect location and good place to stay!"
Chic Downtown Retreat Furnished 2-Bedroom with Trail Access & Outdoor Oasis

Charming 4Bds+1crib house with patio Amherst Center

2.0 star property
10.0 out of 10, Exceptional, (2)
"A great place for a family stay in downtown Amherst. "
The price is CA $328
CA $619 total
includes taxes & fees
May 8 - May 9
Charming 4Bds+1crib house with patio Amherst Center

Bring Your Pet & Visit Springfield: Westfield Home

2.0 star property
7.8 out of 10, Good, (6)
"The house looked like an abandoned property. It was dirty and gross. The sheets had hair on them. We actually couldn't stay. We were hopeful that after taking pictures and sending them, we have some sort of recoupment but we did not. Even though we booked through vrbo, it was apparently another company's listing and they were also no help. We won't use vrbo again. Also watch out for Evelve,"
Bring Your Pet & Visit Springfield: Westfield Home

Lovely 2nd Floor Apartment

10.0 out of 10, Exceptional, (21)
"Clean, comfortable and quiet. All necessities for kitchen provided. "
The price is CA $178
CA $297 total
includes taxes & fees
May 26 - May 27
Lovely 2nd Floor Apartment

The Meadows House @ Otis Ridge w/ 7-person hot tub

9.8 out of 10, Exceptional, (28)
"We had a great time staying at Lars place. The hot tub was very relaxing and the location was just what we were looking for to get away for a few days."
The Meadows House @ Otis Ridge w/ 7-person hot tub

Easthampton Apartment Near Breweries & Rail Trail!

9.8 out of 10, Exceptional, (12)
"Clean unit, comfy beds, plentiful soft towels. Good location for our visit with family, plenty of parking."
Easthampton Apartment Near Breweries & Rail Trail!

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

9.6 out of 10, Exceptional, (214)
"The cabin is quiet, tidy, and comfortable. It is within driving distance of several hiking trails and was a great place to spend a long weekend. The host was friendly and communicative, and made sure that we had everything we needed for a nice stay. "
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Berkshires Lakefront Retreat

10.0 out of 10, Exceptional, (6)
"Amazing view!!!They thought of everything even things we didn’t think we wanted, right down to little things like motion sensing lights in the bathrooms. I’m a chef and cooked for my friends and I was surprised they had everything I needed. We are looking forward to coming back for another stay."
Berkshires Lakefront Retreat

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

10.0 out of 10, Exceptional, (72)
"Very spacious and comfortable. Biggest selling point was its proximity to family in the area."
1810 Brook Side Mill/House / EV Level 2 Charging on Site

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

9.8 out of 10, Exceptional, (11)
"We had a great stay at Nick's place. place was very clean and spacious, good layout. Nick was easy to reach and communication was great. We would definitely book again! thank you! "
The price is CA $228
CA $386 total
includes taxes & fees
May 18 - May 19
Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails

Peace and quiet on the lake

9.6 out of 10, Exceptional, (214)
"We enjoyed the privacy and quiet of the location. The house itself is very well kept inside and cozy. "
Peace and quiet on the lake

Bear Creek Cabin

9.8 out of 10, Exceptional, (29)
"Loved it, will definitely book again!"
The price is CA $552
CA $812 total
includes taxes & fees
May 14 - May 15
Bear Creek Cabin
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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Other types of properties in Chesterfield you may be interested in

D. Hotel Suites & Spa

3.0 star property
9.4 out of 10, Exceptional, (2279)
"Very nice hotel with friendly staff. "
The price is CA $164
CA $191 total
includes taxes & fees
May 5 - May 6
D. Hotel Suites & Spa

Howard Johnson by Wyndham Amherst Hadley

2.0 star property
7.2 out of 10, Good, (1000)
"Location proximity to Amherst UMASS "
The price is CA $152
CA $169 total
includes taxes & fees
May 4 - May 5
Howard Johnson by Wyndham Amherst Hadley

Comfort Inn & Suites

2.5 star property
9.2 out of 10, Wonderful, (1001)
"Enjoyed the stay"
The price is CA $175
CA $196 total
includes taxes & fees
May 5 - May 6
Comfort Inn & Suites
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.

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?

Deluxe Queen Room with 2 Queen Beds: Visitors like this Chesterfield vacation home rental. It is equipped with an outdoor pool, air-conditioning, and WiFi to help you feel comfortable during your stay.

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 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.