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Compare 140 Vacation Homes in Chesterfield with updated reviews, rates, and availability.

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

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

Beautiful Custom Built Timber Frame Home, Sleeps 11

10.0 out of 10, Exceptional, (101)
"Great house and property. Best great room around! Location is perfect. The owner is very friendly and knowledgeable about the house and location."
Beautiful Custom Built Timber Frame Home, Sleeps 11

The dreamiest place in Southern Vermont!

10.0 out of 10, Exceptional, (2)
"This was a great property! Only wish there was a larger fridge/ freezer and ice maker! Otherwise great! We did not get to use the fire pit as we were hardly there but it was great for what we needed."
The price is AED 1,267
AED 2,984 total
includes taxes & fees
12 Jan - 13 Jan
The dreamiest place in Southern Vermont!

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

9.6 out of 10, Exceptional, (4)
"Everything about the listing was accurate. It was very clean and had cute decor that reqlly felt like youre in vermont. The little neighborhood is very cute, quiet and safe feeling. Ita right by my friends house and will most likely be booking again!"
Countryside, mountain-view house near eagle's nest with patios - dog-friendly

The Jelly Mill-A River Retreat

10.0 out of 10, Exceptional, (43)
"It is a beautiful home with a ton of space (we only had 3 people, but it easily sleeps 6), very clean and well-kept. Our hosts provided everything we needed to make our stay perfect. I also like that the hosts were not overboard with all the rules, as with some other rentals. The hosts were beyond friendly and had excellent communication throughout the whole process. If you are looking for a lovely home with a ton of space to stay while exploring Vermont and Massachusetts, I highly recommend...
The Jelly Mill-A River Retreat

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

6.6 out of 10, (12)
"My boyfriend and I (and our dog) really enjoyed this place. It’s on a quiet road, tucked up into a woodsy hill which gives the feeling of being secluded, while in actuality not being far from a main road. The listing is pretty accurate; the house is absolutely covered in windows, which allows for plenty of fresh air and natural light. The master bed is super comfortable, and the master bathroom is really nice too. I was a little apprehensive about the lack of air conditioning, but there is a...
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck

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

Serene SoVT Retreat l 12 Min to Mt Snow l Pet-Friendly l Hot Tub & Fire Pit

10.0 out of 10, Exceptional, (13)
"Very nice and cosy house for a weekend gateway. House is spacious with everything you need for a weekend. The outside hot-tub brings something magical to the stay. 100% recommand!"
Serene SoVT Retreat l 12 Min to Mt Snow l Pet-Friendly l Hot Tub & Fire Pit

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

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

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 2nd Floor Apartment

9.8 out of 10, Exceptional, (17)
"Nice place on a quiet street. Stay went perfect "
The price is AED 437
AED 751 total
includes taxes & fees
14 Jan - 15 Jan
Lovely 2nd Floor Apartment

Mount Snow Post and Beam House

10.0 out of 10, Exceptional, (36)
"Beautiful home in a stunning location"
Mount Snow Post and Beam House

Lovely Contemporary Vermont Home

10.0 out of 10, Exceptional, (5)
"Enjoyed our stay."
Lovely Contemporary Vermont Home

The Inn at Kampfires

3.5 star property
9.4 out of 10, Exceptional, (43)
"We very much enjoyed our stay. The people were super friendly and welcoming!"
The Inn at Kampfires

Relaxing Home Mins from Mt Snow, Hiking, & Lakes

10.0 out of 10, Exceptional, (4)
"Mark and David are very easy and helpful The property is excellent We will come back!"
Relaxing Home Mins from Mt Snow, Hiking, & Lakes

Relaxing Mountain Refuge: 4 Miles to Mt Snow!

10.0 out of 10, Exceptional, (6)
"This unit was so clean and well cared for. We felt right at home! And so close to both Mt Snow and all of the restaurants in Wilmington. We really enjoyed our stay and plan to return again."
Relaxing Mountain Refuge: 4 Miles to Mt Snow!

New Construction Ski/Lake home

New Construction Ski/Lake home

3 story cozy townhouse minutes from mount snow

3 story cozy townhouse minutes from mount snow
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

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

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

8.8 out of 10, Excellent, (43)
"Cabin was perfect for our long weekend. Master bed mattress needs an update, but otherwise everything was fantastic."
Cottage in the woods with a firepit, grill, washer/dryer, & AC - 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
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.