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

Lovely 2nd Floor Apartment

9.8 out of 10, Exceptional, (18)
"Easy stay, good location for us. Would stay again. "
The price is SAR 484
SAR 808 total
includes taxes & fees
24 Feb - 25 Feb
Lovely 2nd Floor Apartment

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

10.0 out of 10, Exceptional, (51)
"This place was just about perfect with excellent hosts that were easy to communicate to. My only ask would be to get shades to block the sun in the morning in the bedroom to the left of the upstairs bathroom. We did not use that bedroom because of this reason. That being said, we loved this place so much that we already booked again for next year. "
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

Cozy cottage tucked away in the woods

10.0 out of 10, Exceptional, (42)
"We loved our stay at this cozy cottage. It was exactly the private getaway we needed and a bonus that we could bring our 2 dogs! The house was very clean, well stocked, and comfortable. River Bend Farm Market is only 12 minutes away and had everything we needed to cook dinner each night. We spent most of our days at Mount Snow, and took the extra drive to Okemo for one day. Everything about this trip was wonderful. We hope to be back again!"
Cozy cottage tucked away in the woods

Charming Waterfront Log Cabin

9.6 out of 10, Exceptional, (37)
"We really appreciated the solitude and quiet retreat this cabin offered. "
Charming Waterfront Log Cabin

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 1,815 total
includes taxes & fees
3 Mar - 4 Mar
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

8.6 out of 10, Excellent, (28)
"House was awesome! Fit a large group well! Would recommend for sure!"
Two-story, dog-friendly house with wood fireplace

The dreamiest place in Southern Vermont!

10.0 out of 10, Exceptional, (5)
"We enjoyed the quiet and convenience of this location to Mt. Snow. It was clean and well stocked. Host was kind and responsive."
The price is SAR 1,575
SAR 3,394 total
includes taxes & fees
24 Feb - 25 Feb
The dreamiest place in Southern Vermont!

3 story cozy townhouse minutes from mount snow

7.0 out of 10, Good, (2)
"The condo was exactly what we were looking for - cozy, clean and close to the mountain with some great restaurants within 5 minutes. We all slept great and the kitchen had all the supplies so we could make a big family meal after skiing. Would definitely stay again!"
3 story cozy townhouse minutes from mount snow

River House

2.0 star property
10.0 out of 10, Exceptional, (7)
"Everyone felt at home and loved the house, it was plenty big enough to spread out and have a good visit"
River House

Stay and Wander VT in this Charming 3-bedroom house in enchanting Dover

Stay and Wander VT in this Charming 3-bedroom house in enchanting Dover

The Dover Hideaway | Hot Tub & Close to Mt. Snow

The Dover Hideaway | Hot Tub & Close to Mt. Snow

Inviting mountain view home with game room, balcony & W/D

8.8 out of 10, Excellent, (8)
"We stayed at the Mountain View for a work field trip. We were celebrating the delivery of several pianos we rebuilt for the Yellow Barn I'm Putney. We spent most of our time outside, but when we came back, it was delightful. This is a beautiful property, very clean, and very cozy"
Inviting mountain view home with game room, balcony & W/D

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

Cozy Vermont Escape w/ Deck, Near Skiing!

10.0 out of 10, Exceptional, (1)
"Everyone had a great time and were talking about going back next year!"
Cozy Vermont Escape w/ Deck, Near Skiing!

Historic Home w/ Modern Updates on < 4 Acres

10.0 out of 10, Exceptional, (6)
"Stayed here with my brothers and cousins.. had a great time. Close proximity to Royalston Falls and a great hike through the forest "
Historic Home w/ Modern Updates on < 4 Acres

Peaceful 3-BR Cabin 40-Min to Stratton

2.0 star property
10.0 out of 10, Exceptional, (4)
"A beautiful cabin with all the amenities to relaxThank you "
Peaceful 3-BR Cabin 40-Min to Stratton

Tasteful Country Home on 5 Acres ~ 3 Mi to Lake!

10.0 out of 10, Exceptional, (4)
"Easily walkable to the very lovely village of Westmoreland, but secluded and with a beautiful view, really quiet and user-friendly. Attentive property owners checked in with us to make sure everything was okay, which was kind and made us feel at home. A terrific porch that's warm in the sunshine even in winter, with great views of birds, sky and stars. "
Tasteful Country Home on 5 Acres ~ 3 Mi to Lake!

Lovely Contemporary Vermont Home

10.0 out of 10, Exceptional, (7)
"This properly was fantastic! The home is immaculate and well appointed. It is comfortable and has a great layout. We appreciated the layout as we were all able to hang out in the space without feeling crowded. The host was fantastic. We enjoyed everything about this home. "
Lovely Contemporary Vermont Home
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

8.8 out of 10, Excellent, (45)
"A great little cabin close to Mt. Snow. Accurate description. Fire place didn’t work. Would stay here again. "
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

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

7.0 out of 10, Good, (14)
"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

This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!

9.8 out of 10, Exceptional, (113)
"Beautiful and peaceful, great house for a winter getaway with the family. We loved the yard and location. Grab your groceries on the way up, and enjoy the amazing house with your crew, (And dog too) "
This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!
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.