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Compare 137 Vacation Homes in Chesterfield with updated reviews, rates, and availability.

Fabulous Mountain Top Retreat - 10 minutes from mount snow!

Fabulous Mountain Top Retreat - 10 minutes from mount snow!

River House

2.0 star property
10.0 out of 10, Exceptional, (5)
"This property is newly renovated, exceptionally clean, well located next to the river, and uniquely decorated with owner created and produced items from dish sets to pillows and various artworks throughout the home. The hosts, Noelle and Eric, were extremely helpful with explaining the house and surroundings to us, and were always available for any questions or needs that we might have. A really exceptional house with gracious hosts nearby. Highly recommended and we hope to visit again."
River House

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

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

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 dreamiest place in Southern Vermont!

10.0 out of 10, Exceptional, (1)
"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 SAR 1,296
SAR 3,052 total
includes taxes & fees
5 Jan - 6 January 2025
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

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

Old Ark Retreat | Secluded & spacious dog-friendly home in Wilmington

8.0 out of 10, Very Good, (7)
"Great place, game room provided many laughs. It was clean, nice quite private property. We will stay again"
Old Ark Retreat | Secluded & spacious dog-friendly home in Wilmington

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

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

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

Potter's Place | House in Jamaica with mountain views

9.4 out of 10, Exceptional, (3)
"The house was clean, beds were comfortable and the area is very quiet. The deck was a very nice. Unfortunately the gas fireplace didn’t work. It actually looked like there were pieces missing which was disappointing because it was the final reason I chose this house. Also, there’s a dishwasher but no dish soap provided. The water pressure in the shower is a little more than a trickle. "
Potter's Place | House in Jamaica with mountain views

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

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

9.8 out of 10, Exceptional, (8)
" The home has everything that you could possibly need. The host was great in checking in to make sure our stay was going well and if we needed anything. The beds were comfortable, the living room spacious and a great place to hang out. The house was spotless. The outdoor area is beautiful and a fantastic place to enjoy the beautiful setting. Best VRBO that I have stayed at, we are hoping to make a return trip. Would highly recommend!"
The price is SAR 841
SAR 2,024 total
includes taxes & fees
7 Jan - 8 January 2025
14mi to Mt. Snow! Arcade, Private Suite, King Bed!

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

10.0 out of 10, Exceptional, (3)
"A spacious, comfortable, and quiet home perfect for our weekend getaway. The owners were kind and thoughtful--even left us a welcome gift!--and responsive to our needs. The house is well-appointed and well-maintained, including a piano, and handicapped-accessible shower. Great location nearby the lake, wineries, and scenic hiking trails. We would definitely stay here again, hopefully next time for a longer stay!"
Tasteful Country Home on 5 Acres ~ 3 Mi to Lake!

Lovely Contemporary Vermont Home

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

1770 House - An end of a dirt road hideaway where you can relax and unwind.

10.0 out of 10, Exceptional, (1)
"Views are outstanding. Kitchen is incredibly well stocked. Beds are comfortable. Swimming pool is a super good time. Lots of space in this house to enjoy with family and friends. Very convenient to center of Greenfield. Looking forward to staying there again."
1770 House - An end of a dirt road hideaway where you can relax and unwind.

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
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.