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Check prices for these dates

Next weekend
16 Jan - 18 Jan
In two weeks
23 Jan - 25 Jan
In one month
6 Feb - 8 Feb
In two months
6 Mar - 8 Mar

Our top choices for Chester vacation homes

Dining
Chester Farmhouse Ski Retreat near Slopes

Chester Farmhouse Ski Retreat near Slopes

Chester Farmhouse Ski Retreat near Slopes
Chester Depot
9.6 out of 10, Exceptional, (17)
"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 AED 511
AED 1,238 total
includes taxes & fees
21 Jan - 22 Jan
Chester Farmhouse Ski Retreat near Slopes
Exterior
Cozy Vermont Cabin · Mountain Views · Near Okemo

Cozy Vermont Cabin · Mountain Views · Near Okemo

Cozy Vermont Cabin · Mountain Views · Near Okemo
Chester
10.0 out of 10, Exceptional, (3)
"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 AED 2,311
AED 4,077 total
includes taxes & fees
7 Jan - 8 Jan
Cozy Vermont Cabin · Mountain Views · Near Okemo
Exterior
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

Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River
Newport
9.8 out of 10, Exceptional, (18)
"Most comfortable king bed EVER!!"
United States
Trina H.
The price is AED 661
AED 1,371 total
includes taxes & fees
11 Jan - 12 Jan
Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River
Property grounds
Lake Front Family Friendly Escape

Lake Front Family Friendly Escape

Lake Front Family Friendly Escape
Newport
10.0 out of 10, Exceptional, (4)
"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 AED 397
AED 1,283 total
includes taxes & fees
11 Jan - 12 Jan
Lake Front Family Friendly Escape
Property grounds
Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (59)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
United States
Louis T.
The price is AED 624
AED 1,148 total
includes taxes & fees
7 Jan - 8 Jan
Family Friendly Hilltop House In Putney Vermont
TV, fireplace, books, stereo
Secluded Vermont Chalet w/ Sweeping Mountain Views

Secluded Vermont Chalet w/ Sweeping Mountain Views

Secluded Vermont Chalet w/ Sweeping Mountain Views
2.0 star property
Dover
The price is AED 742
AED 2,190 total
includes taxes & fees
4 Feb - 5 Feb
Secluded Vermont Chalet w/ Sweeping Mountain Views
Fridge, oven, stovetop, dishwasher
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub

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)
"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 AED 932
AED 1,838 total
includes taxes & fees
12 Jan - 13 Jan
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
Terrace/patio
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9

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)
"We had a very lovely stay. "
United States
mary c.
The price is AED 1,031
AED 2,159 total
includes taxes & fees
7 Jan - 8 Jan
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
Interior
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 Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Stratton
7.8 out of 10, Good, (52)
"Location was great, pool, hot tubs and sauna were great"
United States
Lin M.
The price is AED 433
AED 1,303 total
includes taxes & fees
7 Jan - 8 Jan
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Exterior detail
Charming Dorset Cottage Retreat.

Charming Dorset Cottage Retreat.

Charming Dorset Cottage Retreat.
2.0 star property
Dorset
10.0 out of 10, Exceptional, (7)
"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 AED 907
AED 2,452 total
includes taxes & fees
11 Jan - 12 Jan
Charming Dorset Cottage Retreat.
3 bedrooms, desk, iron/ironing board, travel crib
Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit
Bridgewater
9.6 out of 10, Exceptional, (17)
"Very nice home! Plenty of room for everyone and a short drive to the mountain! Perfect "
United States
Gerri B.
The price is AED 738
AED 2,119 total
includes taxes & fees
12 Jan - 13 Jan
Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit
Fridge, microwave, oven, stovetop
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!

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)
"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 AED 775
AED 2,220 total
includes taxes & fees
7 Jan - 8 Jan
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Interior
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.

Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.
Dover
9.8 out of 10, Exceptional, (6)
"We enjoyed our stay."
United States
Anonymous traveler
The price is AED 856
AED 2,159 total
includes taxes & fees
16 Jan - 17 Jan
Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.
Exterior
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

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)
"Had a great time."
United States
Neetesh B.
The price is AED 3,587
AED 7,684 total
includes taxes & fees
13 Jan - 14 Jan
6 bed 7 Bath close to ski & shop w/ hot tub at Greybourne House in Manchester VT
Smart TV, fireplace, video games, books
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

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Mt Holly
9.8 out of 10, Exceptional, (36)
"Wonderful cabin, well stocked, host was attentive and quick to address any questions."
United States
Eyal O.
The price is AED 826
AED 2,205 total
includes taxes & fees
11 Jan - 12 Jan
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Fridge, microwave, oven, stovetop
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

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Ludlow
9.8 out of 10, Exceptional, (104)
"Had a wonderful stay. Clean,well kept and cozy."
United States
Edwin G.
The price is AED 900
AED 1,751 total
includes taxes & fees
13 Jan - 14 Jan
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Smart TV, fireplace, table tennis
8mins Mount Snow - NEW Cabin 3600SF - Game Room - 20%OFF

8mins Mount Snow - NEW Cabin 3600SF - Game Room - 20%OFF

8mins Mount Snow - NEW Cabin 3600SF - Game Room - 20%OFF
2.0 star property
Wardsboro
8mins Mount Snow - NEW Cabin 3600SF - Game Room - 20%OFF
Property grounds
Killington Area Home | Sleeps 8 | Game Room

Killington Area Home | Sleeps 8 | Game Room

Killington Area Home | Sleeps 8 | Game Room
Bridgewater
9.6 out of 10, Exceptional, (7)
"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 AED 3,144
AED 5,126 total
includes taxes & fees
18 Jan - 19 Jan
Killington Area Home | Sleeps 8 | Game Room
Interior
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Ludlow
9.8 out of 10, Exceptional, (84)
"We had a great stay at this home for a long weekend skiing at Okemo. "
United States
Lisa W.
The price is AED 900
AED 1,751 total
includes taxes & fees
13 Jan - 14 Jan
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Fridge, microwave, oven, stovetop
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!!!

Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
Dover
10.0 out of 10, Exceptional, (9)
"Nice in all respects,"
United States
Ken
The price is AED 2,297
AED 4,916 total
includes taxes & fees
9 Jan - 10 Jan
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
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

Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

10/10 Excellent
"Staff, cleanliness, ambience, restaurant, all perfect! We can’t wait to return! "
Heather 1-night trip
Posted 2 days ago
Kimpton Taconic Hotel by IHG