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

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 SAR 1,328
SAR 2,198 total
includes taxes & fees
3 Apr - 4 Apr
Cozy Home Near Downtown, Shops, and Restaurants.

The Jelly Mill-A River Retreat

10.0 out of 10, Exceptional, (46)
"Stayed for sugar season. Spring thaw makes river road a bit sketch but place and hosts were great! Will b back. "
The Jelly Mill-A River Retreat

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!

2.0 star property
10.0 out of 10, Exceptional, (8)
"We had such a great time staying here with endless games and activities! We would gladly stay here again and recommend to anyone!"
GAMERS HAVEN, River Wine Inn!

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 SAR 731
SAR 1,269 total
includes taxes & fees
1 Apr - 2 Apr
Family Friendly Hilltop House In Putney Vermont

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

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

Lovely 2nd Floor Apartment

9.8 out of 10, Exceptional, (19)
"Clean, comfortable and quiet. All necessities for kitchen provided. "
The price is SAR 484
SAR 809 total
includes taxes & fees
1 Apr - 2 Apr
Lovely 2nd Floor Apartment

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 SAR 671
SAR 1,794 total
includes taxes & fees
8 Apr - 9 Apr
14mi to Mt. Snow! Arcade, Private Suite, King Bed!

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

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

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

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

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

9.8 out of 10, Exceptional, (30)
"The house was so well stocked and very child friendly. So many personal touches that made us feel at home and comfortable. Would definitely stay again!"
Mt Snow for families! Sprawling home, great views, skiing, snowmobiling, hiking

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

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

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

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

9.2 out of 10, Wonderful, (23)
"Clean, well located cabin. Perfect for a family. "
Charming Private Cabin w/ Full Kitchen & High-Speed WiFi - Near Mountain

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

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
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

The Jelly Mill-A River Retreat

10.0 out of 10, Exceptional, (46)
"Stayed for sugar season. Spring thaw makes river road a bit sketch but place and hosts were great! Will b back. "
The Jelly Mill-A River Retreat

GAMERS HAVEN, River Wine Inn!

2.0 star property
10.0 out of 10, Exceptional, (8)
"We had such a great time staying here with endless games and activities! We would gladly stay here again and recommend to anyone!"
GAMERS HAVEN, River Wine Inn!

Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!

10.0 out of 10, Exceptional, (35)
"We were more than impressed by this property, and surpised by the total freedom from other people on the lands. We loved staying at this charming property that is rustic and thoughtfully decorated. The views are amazing and the place is completely quiet. There is a long driveway up from the 'main road', which is really a very lightly traveled road anyway. We enjoyed the silence, and the bucolic views and lifestyle. It was late winter and there was snow on the ground when we arrived, but the...
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
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.