Chesterfield Vacation Rentals

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Vacation Rentals in Chesterfield

Cozy apartment located in quiet Williamsburg
Fridge, microwave, oven, stovetop
Cozy apartment located in quiet Williamsburg
9.8 out of 10, Exceptional, 34 reviews
"Nice place!"
The price is ￥23,231
per night
Jun 6 - Jun 7
Cozy apartment located in quiet Williamsburg
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
Interior
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
9.8 out of 10, Exceptional, 32 reviews
"We loved our time, very cozy cabin"
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
Pristine Home In Becket Woods
Fridge, microwave, oven, stovetop
Pristine Home In Becket Woods
10.0 out of 10, Exceptional, 7 reviews
"My wife and young daughters live in central CT, and the drive to Becket was both scenic and relatively short at around an hour and a half. The property offers great privacy in a remote wooded setting in the heart of the always beautiful Berkshires. We brought our dog along, and we all were able to relax by the fire, read our favorite books, as well as peruse interesting titles on the impressive bookshelf built into the living room wall—a book lover’s delight. We admired the openness and light...
Pristine Home In Becket Woods
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Private Lake House in the Berkshires
Pool
Private Lake House in the Berkshires
9.8 out of 10, Exceptional, 15 reviews
"This was our first VRBO experience, and we are hooked. We had a wedding in Pittsfield with events over three days, so we decided to try this lakeside retreat, and it was a treat! The Berkshires in the fall are absolutely beautiful and Hinsdale is a pretty little town. Ozzie's is definitely worth the trip for breakfast. The lake is lovely and we were looking forward to kayaking and fishing. Unfortunately the weather was not on our side, but we still got one fish! Mary is a wonderful host who is...
Private Lake House in the Berkshires
Bear Creek Cabin
Exterior
Bear Creek Cabin
10.0 out of 10, Exceptional, 14 reviews
"Very well thought out rental home. Everything you could possibly need for cooking and all thought out to reduce your time cleaning and more time on the river. No issues and we had a great time. Thanks again,"
The price is ￥61,948
per night
Jun 6 - Jun 7
Bear Creek Cabin
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, 52 reviews
"Wonderful place to stay, had a great time lots of instruments to try, had lots of space to spread out and hangout, the hot tub was very nice and clean. Overall had a fantastic stay the lighted walkway is amazing! All the amenities available where also great, Jon was a great host and we had a great time speaking with him!"
The price is ￥24,779
per night
Jun 10 - Jun 11
The Creation Station is a cozy place so make yourself at home.
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, 195 reviews
"We’ve stayed at the cabin with our dog four times and always enjoy our peaceful stay. It’s cozy, clean and private. Also, the Sherwood Shoppe - just down the road - is a wonderful place for breakfast, homemade chili and much more."
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Peace and quiet on the lake
Interior
Peace and quiet on the lake
9.6 out of 10, Exceptional, 184 reviews
"My husband and I had a very peaceful and relaxing long weekend at this lake house! It was very clean and has everything you need. We spent the majority of our time on the wonderful screened-in porch. The location was great and there was a little store/restaurant only a couple minutes walk up the street that was convenient and the food was really good! Overall, a great place to stay!"
Peace and quiet on the lake
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
Terrace/patio
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
9.8 out of 10, Exceptional, 81 reviews
"Exactly what you see is what you get! Cute place on farm like setting. Beds are comfortable and most anything you need is there from fans, pack and plays, and a high chair. Lee provided some fresh eggs, cranberry bread, and fresh butter. Looking to stay again next year when my daughter graduates!"
The price is ￥22,456
per night
Jun 6 - Jun 7
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
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, 117 reviews
"Another great stay at Hawley. House never disappoints. Weather even cooperated. Thanks Again Lark! Lew"
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Hearts Desire is a furnished whole house in a small, colorful garden center.
Terrace/patio
Hearts Desire is a furnished whole house in a small, colorful garden center.
10.0 out of 10, Exceptional, 66 reviews
"Probably one of the cleanest places I have ever stayed. The house is perfect. Beautiful views!"
Hearts Desire is a furnished whole house in a small, colorful garden center.
Easthampton Vacation Rental - Walk to Breweries!
2 bedrooms, iron/ironing board, internet, bed sheets
Easthampton Vacation Rental - Walk to Breweries!
9.4 out of 10, Exceptional, 3 reviews
"This is one of the best properties in the Pioneer Valley for the price. Comfortable, clean, and central. The team at Evolve and the local property manager are incredibly kind and responsive. Check-in was flawless and our stay was an absolute 10/10 from top to bottom. Keep in mind this property does have stairs to get to the bathroom and bedrooms, but the double railings made it a breeze for my elderly parents. The location is unbeatable, so many things to do within a five minute walk from the...
Easthampton Vacation Rental - Walk to Breweries!
Serene Acreage - Pond - Hiking Trails Nearby
Property grounds
Serene Acreage - Pond - Hiking Trails Nearby
10.0 out of 10, Exceptional, 4 reviews
"Perfect place to relax and have dogs as part of a mini vacation. Very clean, organized, and provided helpful local information. Will definitely stay there again."
Serene Acreage - Pond - Hiking Trails Nearby
Berkshires Cabin 2 Mi to Appalachian Trail!
Interior
Berkshires Cabin 2 Mi to Appalachian Trail!
9.8 out of 10, Exceptional, 6 reviews
"My wife and I were looking for a nice little getaway within reasonable driving distance and came across this great property. As soon as we saw the big windows in the living room we were sold. Definitely getting added to our short list of places to go back to."
Berkshires Cabin 2 Mi to Appalachian Trail!
Private Island - Largest Fresh Water Reservoir in Mass....
Property grounds
Private Island - Largest Fresh Water Reservoir in Mass....
10.0 out of 10, Exceptional, 3 reviews
"So grateful to Bill for such a wonderful stay! The cottage was so lovely and had everything you could need for a weekend on the lake. Will definitely be returning in the future 😊"
Private Island - Largest Fresh Water Reservoir in Mass....
Etinde House is located ten minutes from Umass, Amherst College, Hampshire mall, Mount Holyoke College and a minute from Hampshire College
Exterior
Etinde House is located ten minutes from Umass, Amherst College, Hampshire mall, Mount Holyoke College and a minute from Hampshire College
6.6 out of 10, 11 reviews
"This house is one of the worst places I have ever stayed. I booked for 13 people and only 2 of the 3 showers worked which they never disclosed to us. The house was a total pigsty. Dirty dishes in the sink. Old food in the fridge. Frozen food in the freezer and the freezer was disgusting with frozen spills that looked like they were there for years. Holes in the walls & doors, burn marks on the counters, dirty table cloth. Bathrooms were filthy. No shades on 90 % of the windows & no curtains at...
The price is ￥170,357
per night
Jun 6 - Jun 7
Etinde House is located ten minutes from Umass, Amherst College, Hampshire mall, Mount Holyoke College and a minute from Hampshire College
Massachusetts Vacation Rental w/ Deck
Fridge, dishwasher, coffee/tea maker, cookware/dishes/utensils
Massachusetts Vacation Rental w/ Deck
9.4 out of 10, Exceptional, 10 reviews
"Great property. Easy check in and communication with the owner."
Massachusetts Vacation Rental w/ Deck
Tranquil 3-BR Waterfront Retreat
Exterior
Tranquil 3-BR Waterfront Retreat
10.0 out of 10, Exceptional, 7 reviews
"The house is immaculate! One of the cleanest properties we've stayed in. The house was the perfect size for my family of 4 (2 adults, 2 teens) with room for more. The beds are comfortable, and there were plenty of linens and towels. The linens and towels are high quality, very soft. The kids had fun fishing in the pond and made good use of the kayak (they caught some bass, pickerel and sun fish). The neighborhood is nice and quiet, dirt roads, no traffic...great for taking walks. We used the...
Tranquil 3-BR Waterfront Retreat
The Meadows House @ Otis Ridge w/ 7-person hot tub
Property grounds
The Meadows House @ Otis Ridge w/ 7-person hot tub
9.8 out of 10, Exceptional, 20 reviews
"Relaxing get away. Great hot tub, table shuffleboard. 3 floors of comfort."
The Meadows House @ Otis Ridge w/ 7-person hot tub
Quintessential 6-BR Berkshires Lodge
Exterior
Quintessential 6-BR Berkshires Lodge
10.0 out of 10, Exceptional, 4 reviews
"We had a great time. Place is amazing. Highly recommend. We had four different families and we never felt cramped. Lovely open main room allowed us to stay connected. Bedrooms were nice and spacious, good bed options. Nice decor."
Quintessential 6-BR Berkshires Lodge
Don't see what you're looking for?
See all available properties in Chesterfield
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.

Other types of properties in Chesterfield you may be interested in

Quality Inn West Springfield
Lobby
Quality Inn West Springfield
2.5 star property
7.2 out of 10, Good, 1,014 reviews
"Affordable and convenient "
The price is ￥12,795
per night
Jul 2 - Jul 3
Quality Inn West Springfield
Howard Johnson by Wyndham Amherst Hadley
Property amenity
Howard Johnson by Wyndham Amherst Hadley
2.0 star property
7.4 out of 10, Good, 1,005 reviews
"Good hotel with basic amenities. Staff not overly friendly. Our room had a view of a vent and the roof, not too nice. Breakfast was a good set up with alot of choices. Nice central location to different stores and restaurants. The only bad thing I can say is that the room we stayed in smelled very musty like a dirty wet carpet/ dog. "
The price is ￥16,981
per night
Jun 12 - Jun 13
Howard Johnson by Wyndham Amherst Hadley
D. Hotel Suites & Spa
Indoor pool
D. Hotel Suites & Spa
3.0 star property
9.4 out of 10, Exceptional, 2,279 reviews
"Nice staff, very accommodating 😊"
The price is ￥23,385
per night
Jun 6 - Jun 7
D. Hotel Suites & Spa
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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Look no further and take a look at our great range of rental properties in Chesterfield!

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?

Chesterfield Gorge and Westfield River are a couple of lovely local spots to get outside and enjoy nature. In the larger area, you’ll find Look Memorial Park and Smith College Botanic Garden.

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.

Recent reviews of Chesterfield properties
Expedia verified reviews

Comfort Inn & Suites

Comfort Inn & Suites

5/5 Excellent
"Good for a quick night stay "
A verified traveler stayed at Comfort Inn & Suites
Posted 2 days ago
Comfort Inn & Suites