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Our top choices for Chester vacation homes

Chester Farmhouse Ski Retreat near Slopes

Chester Farmhouse Ski Retreat near Slopes
Chester Depot
9.6 out of 10, Exceptional, (17 reviews)
"This was my second time staying at this property. Everything was great just like last year. I highly recommend it if you are staying in Chester, VT. "
United States
Lori N.
The price is ¥25,216
¥57,016 total
includes taxes & fees
Jan 19 - Jan 20
Chester Farmhouse Ski Retreat near Slopes

Cozy Vermont Cabin · Mountain Views · Near Okemo

Cozy Vermont Cabin · Mountain Views · Near Okemo
Chester
10.0 out of 10, Exceptional, (3 reviews)
"We really enjoyed our stay at this home. It had everything we needed and was very comfortable. The countryside around this part of Vermont is beautiful. We found lots of great museums and restaurants. "
United States
Donald M.
The price is ¥99,769
¥176,217 total
includes taxes & fees
Jan 25 - Jan 26
Cozy Vermont Cabin · Mountain Views · Near Okemo

Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River

Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River
Newport
9.8 out of 10, Exceptional, (19 reviews)
"The tree house was just as pictured, beautiful inside and we had great views of the River. It was a great trip and we look forward to coming back!"
United States
Kimberly R.
The price is ¥28,521
¥59,141 total
includes taxes & fees
Jan 18 - Jan 19
Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River

Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (59 reviews)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
United States
Louis T.
The price is ¥29,022
¥50,977 total
includes taxes & fees
Jan 26 - Jan 27
Family Friendly Hilltop House In Putney Vermont

Lake Front Family Friendly Escape

Lake Front Family Friendly Escape
Newport
10.0 out of 10, Exceptional, (4 reviews)
"Great visit! The house is perfectly outfitted for a relaxing vacation. Super clean and updated. Really enjoyed the warm waters of Crescent Lake!"
United States
Ann R.
The price is ¥17,128
¥54,547 total
includes taxes & fees
Jan 25 - Jan 26
Lake Front Family Friendly Escape

Enjoy this authentic and cozy VT Barn with Brand New Hot Tub

Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
2.0 star property
Londonderry
8.0 out of 10, Very Good, (1 review)
"I was "sold" & excited when I saw the pictures online bc the barn looked really neat. Although the barn was a neat concept, the pictures ARE NOT accurate, it is not as updated as pictured & it was VERY DISAPPOINTING. I now understand the non-refundable policy bc what you see online is definitely NOT what you walked into when you opened the door & they don't want to have to give people their back. Although we had fun, the accommodations were VERY misleading & disappointing. "
United States
Christine M.
The price is ¥40,250
¥79,173 total
includes taxes & fees
Jan 21 - Jan 22
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub

Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9

Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
Walpole
10.0 out of 10, Exceptional, (50 reviews)
"We had a very lovely stay. "
United States
mary c.
The price is ¥45,817
¥94,279 total
includes taxes & fees
Jan 21 - Jan 22
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9

Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!

Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Keene
10.0 out of 10, Exceptional, (2 reviews)
"Thanks to Bill and Angela. We had a wonderful few days staying in your clean, quiet, and very comfortable home. We often choose VRBOs for our travels, whether in the U.S. or abroad—Freiburg, Paris, Bangkok—and this has truly been one of the best experiences.The highlight: this home is the most well-equipped place we’ve ever stayed in—everything we could possibly need was provided, and more. Complete in every way!On top of that, the location is perfect—close to shopping, hiking, fishing, and even...
United States
Xilin J.
The price is ¥33,462
¥95,845 total
includes taxes & fees
Jan 19 - Jan 20
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!

Secluded Vermont Chalet w/ Sweeping Mountain Views

Secluded Vermont Chalet w/ Sweeping Mountain Views
2.0 star property
Dover
The price is ¥21,568
¥80,597 total
includes taxes & fees
Jan 26 - Jan 27
Secluded Vermont Chalet w/ Sweeping Mountain Views

Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!

Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
Dover
10.0 out of 10, Exceptional, (10 reviews)
"Nice in all respects,"
United States
Ken
The price is ¥113,371
¥230,169 total
includes taxes & fees
Jan 19 - Jan 20
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!

Stratton Woods · Secluded Vermont Cabin Retreat

Stratton Woods · Secluded Vermont Cabin Retreat
2.0 star property
Wardsboro
The price is ¥26,802
¥38,674 total
includes taxes & fees
Jan 27 - Jan 28
Stratton Woods · Secluded Vermont Cabin Retreat

Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.

Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.
Dover
9.8 out of 10, Exceptional, (6 reviews)
"We enjoyed our stay."
United States
Anonymous traveler
The price is ¥35,540
¥91,413 total
includes taxes & fees
Jan 27 - Jan 28
Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.

Blueberry Hill Escape | Pet Friendly | HotTub | AC

Blueberry Hill Escape | Pet Friendly | HotTub | AC
Bridgewater
9.6 out of 10, Exceptional, (17 reviews)
"Very nice home! Plenty of room for everyone and a short drive to the mountain! Perfect "
United States
Gerri B.
The price is ¥31,559
¥91,119 total
includes taxes & fees
Jan 21 - Jan 22
Blueberry Hill Escape | Pet Friendly | HotTub | AC

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Ludlow
9.8 out of 10, Exceptional, (104 reviews)
"Had a wonderful stay. Clean,well kept and cozy."
United States
Edwin G.
The price is ¥34,255
¥69,513 total
includes taxes & fees
Jan 20 - Jan 21
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Stratton
7.8 out of 10, Good, (53 reviews)
"Location was great, pool, hot tubs and sauna were great"
United States
Lin M.
The price is ¥23,789
¥63,425 total
includes taxes & fees
Jan 22 - Jan 23
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

Charming Dorset Cottage Retreat.

Charming Dorset Cottage Retreat.
2.0 star property
Dorset
10.0 out of 10, Exceptional, (7 reviews)
"We had a wonderful stay at this beautiful, cozy cottage in Dorset. It’s close to multiple ski mountains and the charming town of Manchester, and the hosts were super friendly and helpful. Check-in and check-out were easy, and the place was just as advertised."
United States
Sarah S.
The price is ¥47,101
¥116,164 total
includes taxes & fees
Jan 23 - Jan 24
Charming Dorset Cottage Retreat.

Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft

Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft
Jamaica
9.6 out of 10, Exceptional, (23 reviews)
"Absolutely a wonderful place to vacation. The house is comfortable and warming. The hosts went above and beyond to make our stay great and responded to our questions promptly. We will definitely rent again. "
United States
Lee Anna C.
The price is ¥59,005
¥158,967 total
includes taxes & fees
Jan 19 - Jan 20
Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft

Large Killington Area Home | Sleeps 7 | Game Room

Large Killington Area Home | Sleeps 7 | Game Room
Bridgewater
9.6 out of 10, Exceptional, (7 reviews)
"My family enjoyed this house and there was plenty of space for sleeping and for the kids to play. Conveniently located for skiing at Killington."
United States
Owen C.
The price is ¥40,916
¥99,467 total
includes taxes & fees
Jan 20 - Jan 21
Large Killington Area Home | Sleeps 7 | Game Room

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Mt Holly
9.8 out of 10, Exceptional, (36 reviews)
"Wonderful cabin, well stocked, host was attentive and quick to address any questions."
United States
Eyal O.
The price is ¥40,678
¥100,268 total
includes taxes & fees
Jan 20 - Jan 21
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

6 bed 7 Bath close to ski & shop w/ hot tub at Greybourne House in Manchester VT

6 bed 7 Bath close to ski & shop w/ hot tub at Greybourne House in Manchester VT
Manchester Center
10.0 out of 10, Exceptional, (51 reviews)
"Had a great time."
United States
Neetesh B.
The price is ¥153,008
¥325,045 total
includes taxes & fees
Jan 26 - Jan 27
6 bed 7 Bath close to ski & shop w/ hot tub at Greybourne House in Manchester 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.
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Top Chester Hotel Reviews

Find out more about Chester

Chester Vacation Homes information

Number of reviews
396
Accommodation
944 Vacation Homes
Lowest Price
¥50,977
Highest Price
¥325,045