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Check prices for these dates

Next weekend
May 9 - May 11
In two weeks
May 16 - May 18
In one month
May 30 - Jun 1
In two months
Jun 27 - Jun 29

Compare 9 Condo Rentals in Chesterfield with updated reviews, rates, and availability.

Ski-in/Ski-out Condo with central air -Seasons on Mt. Snow
Terrace/patio

Ski-in/Ski-out Condo with central air -Seasons on Mt. Snow

9.8 out of 10, Exceptional, (96)
"We had a wonderful family time away in a lovely condo. Thank you for sharing your home with us!"
Ski-in/Ski-out Condo with central air -Seasons on Mt. Snow
3-story mountain condo with deck, balcony, shuttle to slopes, fireplace, & W/D
Fridge, microwave, oven, stovetop

3-story mountain condo with deck, balcony, shuttle to slopes, fireplace, & W/D

10.0 out of 10, Exceptional, (3)
"Great stay while visiting mount snow. Plenty of room for the whole family. Everything worked as expected, would love to stay again!"
3-story mountain condo with deck, balcony, shuttle to slopes, fireplace, & W/D
Dover Condo w/ Grill & Balcony: 3 Mi to Mt Snow!
Dining

Dover Condo w/ Grill & Balcony: 3 Mi to Mt Snow!

8.8 out of 10, Excellent, (3)
"We had a great time at this home for our 3-day ski getaway with our 4 children. The home was clean and well stocked and the property manager super responsive with anything we needed! Mt. Snow is right up the road so the location was very convenient as well. We hope to be back next year!"
Dover Condo w/ Grill & Balcony: 3 Mi to Mt Snow!
Minutes from Mount Snow Quaint 2 bedroom condo with Loft at Dover Green
Fridge, microwave, oven, stovetop

Minutes from Mount Snow Quaint 2 bedroom condo with Loft at Dover Green

9.0 out of 10, Wonderful, (2)
"very clean place. very timely responses from the host for any questions"
Minutes from Mount Snow Quaint 2 bedroom condo with Loft at Dover Green
Cozy condo w/ wood-burning fireplace, deck, wifi, w/d, bus route, TVs, cable
TV, fireplace

Cozy condo w/ wood-burning fireplace, deck, wifi, w/d, bus route, TVs, cable

2.0 star property
Cozy condo w/ wood-burning fireplace, deck, wifi, w/d, bus route, TVs, cable
Trailside Ski Condo at Mt. Snow VT.; Avail; for skiing and boarding.

Trailside Ski Condo at Mt. Snow VT.; Avail; for skiing and boarding.

9.8 out of 10, Exceptional, (39)
"Great Spot, Next to Carinthia parking area. Stephen was responsive and all the little touches (panini press, fireplace, ski locker) were great."
Trailside Ski Condo at Mt. Snow VT.; Avail; for skiing and boarding.
Woodsy Wilmington Condo 7 Mi to Mount Snow!
Fridge, microwave, stovetop, dishwasher

Woodsy Wilmington Condo 7 Mi to Mount Snow!

8.0 out of 10, Very Good, (1)
"n"
Woodsy Wilmington Condo 7 Mi to Mount Snow!
Luxury Condo on Mount Snow access Road Sleeps 12
Exterior

Luxury Condo on Mount Snow access Road Sleeps 12

Luxury Condo on Mount Snow access Road Sleeps 12
Cozy Vermont Getaway Near Slopes, Hikes & Bites!
Fridge, microwave, stovetop, coffee/tea maker

Cozy Vermont Getaway Near Slopes, Hikes & Bites!

10.0 out of 10, Exceptional, (2)
"Small and cozy getaway! We absolutely loved it!"
Cozy Vermont Getaway Near Slopes, Hikes & Bites!
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 property types in Chesterfield

GAMERS HAVEN, River Wine Inn!
Game room

GAMERS HAVEN, River Wine Inn!

2.0 star property
10.0 out of 10, Exceptional, (11)
"Such a large house with so many areas for activities. Close to a lot of fun things to do like axe throwing, an escape room, distilleries, breweries, etc."
GAMERS HAVEN, River Wine Inn!
The Jelly Mill-A River Retreat
Exterior

The Jelly Mill-A River Retreat

10.0 out of 10, Exceptional, (50)
"Great location, communicative and welcoming hosts, and great amenities. We loved grilling and using the firepit. The surrounding area is great to walk around in. Easy drive from here to Mt Snow."
The Jelly Mill-A River Retreat
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Outdoor dining

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

8.8 out of 10, Excellent, (47)
"really enjoyed our stay. Place would be much better if there was a microwave."
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
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

Why book your condo in Chesterfield with Expedia?
Booking a condo in Chesterfield is as easy as working out your travel dates and choosing an option that suits your style. Looking for something budget friendly or upmarket, or a stay that also features a kitchen and laundry? Use Expedia’s search filters to further narrow your search results and find the ideal fit.
How can I find cheap condos in Chesterfield?
With Expedia’s user-friendly filter tool, booking cheap condos in Chesterfield is a cinch. To find properties that’ll make your wallet happy, narrow down your search by amenities, budget and star rating.
What is there to do in Chesterfield near my condo?
If you’re ready to explore the sights of Chesterfield, make tracks to Asbury United Methodist Church. It’s a winner with visitors and locals alike.