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Compare 145 Vacation Homes in Chesterfield with updated reviews, rates, and availability.

Lovely 2nd Floor Apartment

9.8 out of 10, Exceptional, (17)
"It was just as shown in the listing. Overall was very clean and comfortable. Futon took a little figuring out to get set up and securing the shower curtain to prevent spilling water on the bathroom floor took a do-over and some clean-up, but in general was very happy with our stay and the host was very courteous and responsive."
The price is SAR 484
SAR 813 total
includes taxes & fees
25 Jan - 26 Jan
Lovely 2nd Floor Apartment

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

Cozy cottage tucked away in the woods

10.0 out of 10, Exceptional, (39)
"We loved this place. It was very homey and warm. The fireplace in the living room and the Christmas tree were all we could wish for. Thank you very much. We will definitely come again if we will have a chance. "
Cozy cottage tucked away in the woods

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

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

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 728
SAR 1,878 total
includes taxes & fees
4 Feb - 5 Feb
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, (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

Large Home in Greenfield Sleeps 8, w/4 bedrooms & 3 baths

Large Home in Greenfield Sleeps 8, w/4 bedrooms & 3 baths

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

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!

The dreamiest place in Southern Vermont!

10.0 out of 10, Exceptional, (3)
"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 1,294
SAR 3,048 total
includes taxes & fees
26 Jan - 27 Jan
The dreamiest place in Southern Vermont!

The Harrisville Ranch - Monadnock Region Getaway!

10.0 out of 10, Exceptional, (2)
"We booked a longer stay over the holidays and we were very pleased with the accommodations. The property was clean and very spacious, on a wooded lot that was pleasant and quiet. It was like a home away from home during our stay. We would definitely recommend!"
The Harrisville Ranch - Monadnock Region Getaway!

Mount Snow Post and Beam House

10.0 out of 10, Exceptional, (37)
"Beautiful.home, open living space, great location for skiing at mt..snow. wet, rainy weather made driveway ride to the home very muddy. Communication with the owner, Doug, was easy and he was very accommodating. Furniture is dated and some mattresses need replacing. "
Mount Snow Post and Beam House

Perfect - Cozy Townhouse in Mount Snow- Vt

10.0 out of 10, Exceptional, (42)
"Perfect place for a short weekend stay in southern VT. This place is very near Mount Snow and a short drive to Stratton. Ewa is a great host, easy instructions for your stay, house was immaculately clean and tidy. 2 Bedrooms (1 with en-suite) are on 1st Floor with a dining area, lounge and kitchen on 2nd floor. There’s also 3 beds ( for Children) in a loft space above the lounge. We enjoyed our stay and I’d definitely go back. Thanks Ewa! Mark"
Perfect - Cozy Townhouse in Mount Snow- Vt

Lovely Contemporary Vermont Home

10.0 out of 10, Exceptional, (6)
"We had a wonderful extended family holiday visit. The property is spacious, well-appointed, and a blast for kids— inside playing games and outside playing in the snow. The fireplace was great, especially after dark as temps fell. The communications and instructions were helpful and clear. We would visit again!"
Lovely Contemporary Vermont Home

Idyllic lodge on 16-acres with fire pit & amazing views of Mt Snow- near skiing

7.4 out of 10, Good, (3)
"The house was beautiful and the view was stunning. We found mouse poop in one of the drawers in the kitchen. The trash was full when we arrived so there was no place to put our trash bags. There were cigarette butts on the ground despite it being a non- smoking property. We are outdoors people and would have loved to use the fire pit but the it was very far from the house and wood was not supplied. I cannot imagine having to pack wood and then lugging it that far. However, it was overall a...
Idyllic lodge on 16-acres with fire pit & amazing views of Mt Snow- near skiing

Cozy Vermont Escape w/ Deck, Near Skiing!

Cozy Vermont Escape w/ Deck, Near Skiing!

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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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

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

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

9.8 out of 10, Exceptional, (111)
"This house was a delight to stay in - warm and comfy with a gorgeous mountain-top view. All the amenities and great customer service from the hosts.Highly recommended."
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.