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Check prices for these dates

Next weekend
28 Mar - 30 Mar
In two weeks
4 Apr - 6 Apr
In one month
18 Apr - 20 Apr
In two months
16 May - 18 May

Compare 149 Vacation Homes in Chesterfield with updated reviews, rates, and availability.

Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck
Fridge, microwave, oven, stovetop

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

7.0 out of 10, Good, (15)
"Great place. Clean and comfortable. Nicely stocked kitchen with newer appliances. Sauna was amazing. Had 10 inches of snow one morning and it was fully plowed by 7am!"
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck
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)
"Had a fantastic weekend at this cabin. Beautifully maintained, sparking clean and beautiful cabin. Everything was exactly as pictured and is even better in person. Would stay here again x100"
Bright three-level home with water views, jetted tub, firepit, and pool table
Mount Snow Post and Beam House
Fridge, oven, stovetop, dishwasher

Mount Snow Post and Beam House

10.0 out of 10, Exceptional, (38)
"Doug’s house is gorgeous and he was very communicative and helpful the entirety of our stay! Special thanks to Ryan for making sure we got out following a massive snow storm"
Mount Snow Post and Beam House
Lovely 2nd Floor Apartment
Fridge, microwave, oven, stovetop

Lovely 2nd Floor Apartment

9.8 out of 10, Exceptional, (19)
"Clean, comfortable and quiet. All necessities for kitchen provided. "
The price is AED 474
AED 792 total
includes taxes & fees
19 Mar - 20 Mar
Lovely 2nd Floor Apartment
14mi to Mt. Snow! Arcade, Private Suite, King Bed!
Fridge, microwave, oven, stovetop

14mi to Mt. Snow! Arcade, Private Suite, King Bed!

9.8 out of 10, Exceptional, (10)
"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 1,748 total
includes taxes & fees
18 Mar - 19 Mar
14mi to Mt. Snow! Arcade, Private Suite, King Bed!
Countryside, mountain-view house near eagle's nest with patios - dog-friendly
Interior

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
The Jelly Mill-A River Retreat
Exterior

The Jelly Mill-A River Retreat

10.0 out of 10, Exceptional, (44)
"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
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
Fridge, microwave, oven, stovetop

Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

10.0 out of 10, Exceptional, (52)
"Overall, the property checked all of our boxes. Location, space for number of guests, amenities, etc. Kitchen was fully stocked.Plowing of the driveway was key with a snow/ice storm in the middle of our stay.Internet speed was also fast as well for a full house of connected teens.There are not quite enough full bathrooms/showers for the number of possible guests especially in the upstairs space.The main tv/apps were glitchy. That needs to be looked at and updated. The firestick in the main...
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
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 1,230 total
includes taxes & fees
18 Mar - 19 Mar
Family Friendly Hilltop House In Putney Vermont
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)
"This is a great house to stay in, but we did feel the house wasn’t overly clean. They also don’t have a simple vacuum or counter spray available so you can tidy up. The kitchen was large and great but there were barely any supplies. The pans are all scratched teflon, and it was a struggle to find proper cooking tools. The rooms were great, house stayed warm and it was a very easy commute to mount snow (only about 16 minutes). It is dog friendly and you.can tell- some dog hair left behind.The...
Two-story, dog-friendly house with wood fireplace
GAMERS HAVEN, River Wine Inn!
Game room

GAMERS HAVEN, River Wine Inn!

2.0 star property
10.0 out of 10, Exceptional, (7)
"We really enjoyed ourselves in Marcella's home, to the point where we did not want to leave the house to go skiing/snowboarding. Upon arrival you are greeted with a cute little bridge to cross over and you see a beautiful red house and barn. The home was very comfortable, with enough bedrooms and space for us our group to be in the kitchen or playing in the pool area, basketball court, ping pong table or 3 different sitting areas and hot tub. The kitchen has everything that you need from...
GAMERS HAVEN, River Wine Inn!
Beautiful, private log cabin with huge, relaxing screened porch
Outdoor dining

Beautiful, private log cabin with huge, relaxing screened porch

10.0 out of 10, Exceptional, (35)
"The property is exactly as stated in the listing. The host is extremely responsive and great at communicating. The beds were very comfortable and plenty of space for 6 adults. The kitchen was well stocked as well as the wood pile for the stove. Nothing but the best for the property and host. Thank you, Beth!"
Beautiful, private log cabin with huge, relaxing screened porch
Beautiful Custom Built Timber Frame Home, Sleeps 11
Smart TV, fireplace, DVD player, table tennis

Beautiful Custom Built Timber Frame Home, Sleeps 11

10.0 out of 10, Exceptional, (103)
"Home was big, clean, and close to mt snow. We had a great stay. Thanks!"
Beautiful Custom Built Timber Frame Home, Sleeps 11
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)
"We had a fun time enjoying the view and playing board games plus outdoor pursuits. Thanks for sharing your home."
Rustic, dog-friendly escape with private pool, sweeping views, & W/D
Perfect - Cozy Townhouse in Mount Snow- Vt
Fridge, microwave, oven, stovetop

Perfect - Cozy Townhouse in Mount Snow- Vt

10.0 out of 10, Exceptional, (45)
"A nice townhouse that has everything you need. The location was great for us. Thank you Ewa!"
Perfect - Cozy Townhouse in Mount Snow- Vt
New-Lakehouse w/Hot Tub. Min from town and Skiing
Terrace/patio

New-Lakehouse w/Hot Tub. Min from town and Skiing

8.0 out of 10, Very Good, (2)
"Place was perfect for our large family. Hot tub after skiing and great kitchen area for cooking and still feeling part of the crowd. "
New-Lakehouse w/Hot Tub. Min from town and Skiing
NEW! High Peak Lodge (5-Bedroom Home) with Pool
Smart TV, fireplace, foosball, table tennis

NEW! High Peak Lodge (5-Bedroom Home) with Pool

NEW! High Peak Lodge (5-Bedroom Home) with Pool
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
Tyler House, 4 Bedrooms, 2 Bathrooms, House to steps to Lake Spofford
Property grounds

Tyler House, 4 Bedrooms, 2 Bathrooms, House to steps to Lake Spofford

9.8 out of 10, Exceptional, (25)
"We had an amazing week at the Tyler House. The house and location are among the best on the lake. The host lives nearby and is happy to assist with any requests."
Tyler House, 4 Bedrooms, 2 Bathrooms, House to steps to Lake Spofford
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

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, (46)
"The cabin is cozy and sweet- we have a dog and small family and wanted to ski at Mt Snow. Cabin is short 20 minute drive to ski. Super cute town of Wilmington just a few minutes away. Go to Dots or Alpen Glow! Shaws grocery 2 minutes away. House has Pottery Barn vibes. Decent sized kitchen sitting and dining area. 2Bedroom 2 bath. This is not a house for a large crew but for a family getaway it was perfect. Street is quiet and residential. Neighbors seem really friendly. We would love to come...
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
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)
"Had a fantastic weekend at this cabin. Beautifully maintained, sparking clean and beautiful cabin. Everything was exactly as pictured and is even better in person. Would stay here again x100"
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
Fridge, microwave, oven, stovetop

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

7.0 out of 10, Good, (15)
"Great place. Clean and comfortable. Nicely stocked kitchen with newer appliances. Sauna was amazing. Had 10 inches of snow one morning and it was fully plowed by 7am!"
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck
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.