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Compare 135 Vacation Homes in Chesterfield with updated reviews, rates, and availability.

Secluded Vermont Retreat w/ 25 Acres to Explore--Dog Heaven! Mountain Views!
Winter wonderland!

Secluded Vermont Retreat w/ 25 Acres to Explore--Dog Heaven! Mountain Views!

9.8 out of 10, Exceptional, (110)
"Every need accommodated including a back-up generator! Well appointed kitchen and bathrooms. Very cozy and spacious home inside. Very comfortable bed mattress in master bedroom. Lots of yard for dogs to run free. Nature all around. Lots of books and board games there. Laundry room was a big plus. Remote setting but lots to see and explore within reach. Very lovely stay and hosts were very responsive."
Secluded Vermont Retreat w/ 25 Acres to Explore--Dog Heaven! Mountain Views!
Charming Waterfront Log Cabin
Exterior

Charming Waterfront Log Cabin

9.4 out of 10, Exceptional, (36)
"We really appreciated the solitude and quiet retreat this cabin offered. "
Charming Waterfront Log Cabin
Hilltop Home with Great Views
Exterior

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

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

9.4 out of 10, Exceptional, (3)
"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
Old Ark Retreat | Secluded & spacious dog-friendly home in Wilmington

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
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
Plenty of private open space to explore with the whole family!

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

10.0 out of 10, Exceptional, (49)
"We loved this property with stunning foliage, hiking trails, and perfect views. The house had everything we needed to accommodate a large group and more with lots of thoughtful touches. Plenty of space, panoramic views, screened in porch, fireplace, pool table, and connected speakers throughout. We have stayed at many different rentals for our annual trip over the years and this one is our new favorite."
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
Inviting mountain view home with game room, balcony & W/D

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

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
Royalston Vacation Rental | 4BR | 2BA | Stairs to Access | 3,200 Sq Ft

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!
Aerial view

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 AED 657
AED 1,769 total
includes taxes & fees
10 Dec - 11 Dec
14mi to Mt. Snow! Arcade, Private Suite, King Bed!
Exquisite home with fireplace, balcony, fast WiFi, jetted tub & washer/dryer

Exquisite home with fireplace, balcony, fast WiFi, jetted tub & washer/dryer

2.0 out of 10, (1)
"This property was misrepresented and unacceptable as a rental property. The property manager is completely unresponsive and hinds behind Vcasa. Vcasa is completely inept and gives all power to the local manager who is allowed to be unresponsive and rent a unlivable propriety with no repercussions. My family and friends (3 families, 6 adults and 6 children) were at risk of grease fire from the stove/oven which was unusable due to this issue. Additionally, the oven barely worked and only 1 burner...
Exquisite home with fireplace, balcony, fast WiFi, jetted tub & washer/dryer
Lovely Contemporary Vermont Home
Snowbound & Cozy...

Lovely Contemporary Vermont Home

10.0 out of 10, Exceptional, (4)
"My extended family and I had a very nice getaway here. We relaxed, skied at Mt Snow and some even shopped one day. House is well equipped and clean and updated. Bed were comfortable, plenty of towels and everything else like hot water, laundry facilities etc was all up to what I would have in my own home. Great place for a VT getaway no matter what your activity or goal."
Lovely Contemporary Vermont Home
The Inn at Kampfires
Room

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
Dover Vacation Rental | 3BR | 3.5BA | 3 Steps to Access | 2,400 Sq Ft

Relaxing Home Mins from Mt Snow, Hiking, & Lakes

10.0 out of 10, Exceptional, (3)
"Excellent"
Relaxing Home Mins from Mt Snow, Hiking, & Lakes
Cozy & chill 5 bdrm, ski hill close,walk 2 village,fam/friends/pets, decks, wbfp
Exterior

Cozy & chill 5 bdrm, ski hill close,walk 2 village,fam/friends/pets, decks, wbfp

Cozy & chill 5 bdrm, ski hill close,walk 2 village,fam/friends/pets, decks, wbfp
Amazing Views, Skiing Nearby and Amenities Galore!
Sunset view

Amazing Views, Skiing Nearby and Amenities Galore!

10.0 out of 10, Exceptional, (1)
"We had a great stay. The house was very large and not cookie cutter to say the least. It took us a few days to start to remember the layout. It made it fun. But there was a lot of times where I had to search for the billiards room etc. We didn't use the sauna or hot tub but I imagine they would be great after a day of skiing. The view is just flat out spectacular from the great room. This is an older house. Maybe 1960. Most of the VRBOs we have stayed at in this area of VT and NH are...
Amazing Views, Skiing Nearby and Amenities Galore!
Charming 3-bedroom waterfront house in Harrisville
Exterior

Charming 3-bedroom waterfront house in Harrisville

Charming 3-bedroom waterfront house in Harrisville
Charming 4 bedroom house with Views, 200 acres, Private Schools, Ski, Hiking
Property grounds

Charming 4 bedroom house with Views, 200 acres, Private Schools, Ski, Hiking

The price is AED 1,833
AED 3,158 total
includes taxes & fees
27 Dec - 28 Dec
Charming 4 bedroom house with Views, 200 acres, Private Schools, Ski, Hiking
Family Friendly Hilltop House In Putney Vermont
Aerial view

Family Friendly Hilltop House In Putney Vermont

9.4 out of 10, Exceptional, (53)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
The price is AED 716
AED 1,263 total
includes taxes & fees
27 Nov - 28 Nov
Family Friendly Hilltop House In Putney Vermont
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
Rear Deck for barbecues looking across rear yard.

Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby

9.8 out of 10, Exceptional, (15)
"Very nice house and property! "
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
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

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

9.0 out of 10, Wonderful, (42)
"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
Exterior

Charming Waterfront Log Cabin

9.4 out of 10, Exceptional, (36)
"We really appreciated the solitude and quiet retreat this cabin offered. "
Charming Waterfront Log Cabin
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT
Living area

Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT

10.0 out of 10, Exceptional, (48)
"Peaceful, beautiful property. Was a relaxing stay, had everything we needed. "
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT
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.