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Check prices for these dates

Next weekend
2 May - 4 May
In two weeks
9 May - 11 May
In one month
23 May - 25 May
In two months
20 Jun - 22 Jun

Compare 177 Vacation Homes in Chesterfield with updated reviews, rates, and availability.

Cozy Home Near Downtown, Shops, and Restaurants.
Exterior

Cozy Home Near Downtown, Shops, and Restaurants.

2.0 star property
10.0 out of 10, Exceptional, (3)
"Online info was accurate. Nice spot to rent with family."
The price is AED 1,300
AED 2,152 total
includes taxes & fees
5 May - 6 May
Cozy Home Near Downtown, Shops, and Restaurants.
The Jelly Mill-A River Retreat
Exterior

The Jelly Mill-A River Retreat

10.0 out of 10, Exceptional, (49)
"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
Potter's Place | House in Jamaica with mountain views
Fridge, microwave, oven, stovetop

Potter's Place | House in Jamaica with mountain views

9.6 out of 10, Exceptional, (4)
"Stayed at this lovely home for a short weekend trip in the winter. Very convenient location, clean and well kept. Be sure to have AWD and proper tires if you visit in the winter!"
Potter's Place | House in Jamaica with mountain views
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!
Family Friendly Hilltop House In Putney Vermont
Exterior

Family Friendly Hilltop House In Putney Vermont

9.6 out of 10, Exceptional, (54)
"We were caught in the winter storm, and the host was so kind in helping us navigate our car situation. Our kids had such a great time playing in the snow, exploring the books and games they had. "
The price is AED 716
AED 1,242 total
includes taxes & fees
28 Apr - 29 Apr
Family Friendly Hilltop House In Putney Vermont
Bright three-level home with water views, jetted tub, firepit, and pool table
Fridge, microwave, oven, stovetop

Bright three-level home with water views, jetted tub, firepit, and pool table

8.4 out of 10, Very Good, (27)
"Awesome Cabin, private and peaceful location."
Bright three-level home with water views, jetted tub, firepit, and pool table
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck
3 bedrooms, internet, bed sheets

Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck

7.0 out of 10, Good, (15)
"We enjoyed our stay. AWD is a must for the driveway. The number of security cameras around the property is uncomfortable."
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck
Lovely 2nd Floor Apartment
Exterior detail

Lovely 2nd Floor Apartment

10.0 out of 10, Exceptional, (21)
"Clean, comfortable and quiet. All necessities for kitchen provided. "
The price is AED 474
AED 808 total
includes taxes & fees
7 May - 8 May
Lovely 2nd Floor Apartment
2.5mi from the lake! Fire pit, arcade, yard games!
Fridge, microwave, oven, stovetop

2.5mi from the lake! Fire pit, arcade, yard games!

10.0 out of 10, Exceptional, (12)
"This place is immaculate and the host is responsive. We stayed here to ski in Mount snow which is about 25 minutes drive. We arrived later in the evening and the place was warm and cozy. "
The price is AED 657
AED 1,753 total
includes taxes & fees
28 Apr - 29 Apr
2.5mi from the lake! Fire pit, arcade, yard games!
Countryside, mountain-view house near eagle's nest with patios - dog-friendly
Fridge, microwave, oven, stovetop

Countryside, mountain-view house near eagle's nest with patios - dog-friendly

9.6 out of 10, Exceptional, (5)
"Perfect little spot for a ski trip to Stratton!"
Countryside, mountain-view house near eagle's nest with patios - dog-friendly
Hilltop Home with Great Views
Interior

Hilltop Home with Great Views

9.2 out of 10, Wonderful, (12)
"Michelle made our experience super easy and memorable! Drive up a private road and a pretty steep hill (4wd a must in winter) to a secluded, beautiful house with plenty of space. Just you and nature. The house itself has all the amenities - full kitchen, sitting areas, and even a wood stove that Michelle started up before we got there. Beds are comfortable, and the bathrooms have insane mountaintop views. Michele even left a few eggs for starter breakfast which was much appreciated. You can’t...
Hilltop Home with Great Views
Two-story, dog-friendly house with wood fireplace
Fridge, microwave, oven, stovetop

Two-story, dog-friendly house with wood fireplace

8.4 out of 10, Very Good, (29)
"House was awesome! Fit a large group well! Would recommend for sure!"
Two-story, dog-friendly house with wood fireplace
Rustic, dog-friendly escape with private pool, sweeping views, & W/D
TV

Rustic, dog-friendly escape with private pool, sweeping views, & W/D

9.4 out of 10, Exceptional, (15)
"The house was great and offered amazing views of the VT mountains! Definitely recommend it and will be back!"
Rustic, dog-friendly escape with private pool, sweeping views, & W/D
Mt Snow for families! Sprawling home, great views, skiing, snowmobiling, hiking
Smart TV, fireplace, foosball, books

Mt Snow for families! Sprawling home, great views, skiing, snowmobiling, hiking

10.0 out of 10, Exceptional, (30)
"Lovely home with everything you need. Enjoyed yard and the game room. Perfect place for our family ski gathering! Hope to stay here again next year"
Mt Snow for families! Sprawling home, great views, skiing, snowmobiling, hiking
Spacious Pet Friendly Waterfront w/ Hot Tub & Yogo Studio-Sleeps 10!
Fridge, microwave, oven, stovetop

Spacious Pet Friendly Waterfront w/ Hot Tub & Yogo Studio-Sleeps 10!

Spacious Pet Friendly Waterfront w/ Hot Tub & Yogo Studio-Sleeps 10!
Beautiful, private log cabin with huge, relaxing screened porch
4 bedrooms, free WiFi, bed sheets

Beautiful, private log cabin with huge, relaxing screened porch

10.0 out of 10, Exceptional, (35)
"The cabin was perfect for me and my extended family. It was clean comfortable and had everything we needed for a great stay."
Beautiful, private log cabin with huge, relaxing screened porch
Charming Private Cabin w/ Full Kitchen & High-Speed WiFi - Near Mountain
Exterior

Charming Private Cabin w/ Full Kitchen & High-Speed WiFi - Near Mountain

9.2 out of 10, Wonderful, (23)
"We had a great little getaway for our anniversary and this place was perfect for my husband and I. It’s cozy and private. Would definitely stay again."
Charming Private Cabin w/ Full Kitchen & High-Speed WiFi - Near Mountain
Mount Snow Post and Beam House
TV, fireplace, DVD player, video library

Mount Snow Post and Beam House

10.0 out of 10, Exceptional, (38)
"We had a great weekend, the place was as decribed."
Mount Snow Post and Beam House
Cozy farmhouse, sleeps 8,ski hill 5 min drive, walk 2 village,pets, decks, wbfp
Exterior

Cozy farmhouse, sleeps 8,ski hill 5 min drive, walk 2 village,pets, decks, wbfp

10.0 out of 10, Exceptional, (1)
"Our mostly young adult group enjoyed our stay at this fun cozy house! Enough space for everyone and easy to find everything you need for a long ski weekend with family and friends! We loved that dogs are welcome, as we often have one along. Easy communication with host. Overall great stay! "
Cozy farmhouse, sleeps 8,ski hill 5 min drive, walk 2 village,pets, decks, wbfp
Perfect - Cozy Townhouse in Mount Snow- Vt
Exterior

Perfect - Cozy Townhouse in Mount Snow- Vt

10.0 out of 10, Exceptional, (45)
"Great place, not too far from The mountain, 5 mins away."
Perfect - Cozy Townhouse in Mount Snow- Vt
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, (49)
"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
Exterior

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.