Holiday Homes in Chester

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Check prices for these dates

In two weeks
13 Mar - 15 Mar
In two months
24 Apr - 26 Apr
In three months
22 May - 24 May
In four months
19 June - 21 June

Our top choices for Chester holiday homes

Dining

Holiday Home in Chester Depot

Chester Farmhouse Ski Retreat near Slopes
9.6 out of 10, Exceptional, (18 reviews)
"House was in a perfect location. The town was adorable. "
United States
Michelle A.
The price is AU$601
includes taxes & fees
2 Mar - 3 Mar
Chester Farmhouse Ski Retreat near Slopes
Exterior

Holiday Home in Chester

Cozy Vermont Cabin · Mountain Views · Near Okemo
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 AU$1,546
includes taxes & fees
2 Mar - 3 Mar
Cozy Vermont Cabin · Mountain Views · Near Okemo
Exterior

Holiday Home in Newport

Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River
9.8 out of 10, Exceptional, (21 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 AU$522
includes taxes & fees
8 Mar - 9 Mar
Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River
Terrace/patio

Holiday Home in Walpole

Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
10.0 out of 10, Exceptional, (50 reviews)
"We had a very lovely stay. "
United States
mary c.
The price is AU$822
includes taxes & fees
2 Mar - 3 Mar
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
Interior

Holiday Home in Dover

Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.
10.0 out of 10, Exceptional, (11 reviews)
"We enjoyed our stay."
United States
Anonymous traveller
The price is AU$806
includes taxes & fees
4 Mar - 5 Mar
Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.
Property grounds

Holiday Home in Putney

Family Friendly Hilltop House In Putney Vermont
9.4 out of 10, Exceptional, (59 reviews)
"The host and her daughter were lovely and kind and very quick with all communication."
United States
Susan O.
The price is AU$415
includes taxes & fees
1 Apr - 2 Apr
Family Friendly Hilltop House In Putney Vermont
Interior

Holiday Home in Stratton

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
7.6 out of 10, Good, (54 reviews)
"Location was great, pool, hot tubs and sauna were great"
United States
Lin M.
The price is AU$424
includes taxes & fees
1 Apr - 2 Apr
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Property grounds

Holiday Home in Newport

Lake Front Family Friendly Escape
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 AU$495
includes taxes & fees
8 Mar - 9 Mar
Lake Front Family Friendly Escape
Fridge, oven, stovetop, dishwasher

Holiday Home in Londonderry

Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
7.0 out of 10, Good, (2 reviews)
"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 AU$685
includes taxes & fees
16 Mar - 17 Mar
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
Fridge, microwave, oven, stovetop

Holiday Home in Keene

Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
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 AU$710
includes taxes & fees
2 Mar - 3 Mar
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
TV, books, stereo

Holiday Home in Dover

Secluded Vermont Chalet w/ Sweeping Mountain Views
The price is AU$742
includes taxes & fees
31 Mar - 1 Apr
Secluded Vermont Chalet w/ Sweeping Mountain Views
Interior

Holiday Home in Wardsboro

Stratton Woods · Secluded Vermont Cabin Retreat
10.0 out of 10, Exceptional, (2 reviews)
"Cabin was wonderful!Thank you,The Katz Family "
United States
kim k.
The price is AU$562
includes taxes & fees
24 Mar - 25 Mar
Stratton Woods · Secluded Vermont Cabin Retreat
Interior

Holiday Home in Ludlow

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
9.8 out of 10, Exceptional, (84 reviews)
"We had a great stay at this home for a long weekend skiing at Okemo. "
United States
Lisa W.
The price is AU$614
includes taxes & fees
2 Mar - 3 Mar
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Fridge, microwave, oven, stovetop

Holiday Home in Ludlow

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
9.8 out of 10, Exceptional, (106 reviews)
"Had a wonderful stay. Clean,well kept and cozy."
United States
Edwin G.
The price is AU$636
includes taxes & fees
2 Mar - 3 Mar
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Fridge, microwave, oven, stovetop

Holiday Home in Dover

Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful neighborhood to take walks. Home was very clean, as you see in the photo. Very spacious and relaxing. Pretty home overall."
United States
Stephen G.
The price is AU$1,638
includes taxes & fees
1 Apr - 2 Apr
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
Property grounds

Holiday Home in Bridgewater

Large Killington Area Home | Sleeps 7 | Game Room
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 AU$904
includes taxes & fees
4 Mar - 5 Mar
Large Killington Area Home | Sleeps 7 | Game Room
Dining

Holiday Home in Ludlow

New Ludlow Village Home with Stunning Okemo Mountain View
10.0 out of 10, Exceptional, (13 reviews)
"Vacationing with friends. The home was great; good location, lots of space, very clean and well kept. Would definitely stay there again. "
United States
Linda H.
The price is AU$1,219
includes taxes & fees
3 Mar - 4 Mar
New Ludlow Village Home with Stunning Okemo Mountain View
Exterior

Holiday Home in Jamaica

Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft
9.6 out of 10, Exceptional, (24 reviews)
"I stayed here for a few days in October with friends. We had some initial confusion with the door locks, but the hosts were able to resolve it quickly.Great location, tons of sleeping and living space, and the hot tub was a welcome addition. We had a great time and would recommend this spot."
United States
Jonathan E.
The price is AU$1,380
includes taxes & fees
24 Mar - 25 Mar
Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft
TV, fireplace

Holiday Home in Bridgewater

Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.
8.0 out of 10, Very good, (2 reviews)
"Great place for a ski weekend"
United States
Kathryn F.
The price is AU$943
includes taxes & fees
2 Mar - 3 Mar
Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.
Smart TV, fireplace, video games, books

Holiday Home in Mt Holly

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
9.8 out of 10, Exceptional, (38 reviews)
"Wonderful cabin, well stocked, host was attentive and quick to address any questions."
United States
Eyal O.
The price is AU$829
includes taxes & fees
22 Mar - 23 Mar
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
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

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

10/10 Excellent
"Clean room"
marie 1-night trip
Posted 22 hours ago
Comfort Inn & Suites Brattleboro I-91

Find out more about Chester

Chester Holiday Homes information

Number of reviews
401
Accommodation
944 Holiday Homes
Lowest Price
AU$415
Highest Price
AU$1,638