Holiday Homes in Chester

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Check prices for these dates

In two weeks
12 Sept - 14 Sept
In one month
26 Sept - 28 Sept
In two months
24 Oct - 26 Oct
In three months
21 Nov - 23 Nov

Featured Holiday Homes in Chester

Whimsical Room & Private Bathroom in Historic Inn
Interior

Whimsical Room & Private Bathroom in Historic Inn

8.8 out of 10, Excellent, (9)
"After a long month of work I needed a weekend in VT to calm the nerves. This was a beautiful spot to be in, glad I was here!"
The price is AU$241
includes taxes & fees
1 Sept - 2 Sept
Whimsical Room & Private Bathroom in Historic Inn
WhiSki Cabin - 12 Acres With a Mountain View!
Fridge, microwave, oven, stovetop

WhiSki Cabin - 12 Acres With a Mountain View!

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. "
The price is AU$1,517
includes taxes & fees
13 Sept - 14 Sept
WhiSki Cabin - 12 Acres With a Mountain View!
Tranquil farmhouse in Manchester - perfect for ski or summer fun!
Exterior

Tranquil farmhouse in Manchester - perfect for ski or summer fun!

The price is AU$1,062
includes taxes & fees
6 Sept - 7 Sept
Tranquil farmhouse in Manchester - perfect for ski or summer fun!
Charming Chester Farmhouse – peaceful and close to everything!
Terrace/patio

Charming Chester Farmhouse – peaceful and close to everything!

9.6 out of 10, Exceptional, (13)
"Great location. Beautiful house. All the amenties. We came up for a ski trip and it was perfect. "
The price is AU$656
includes taxes & fees
1 Sept - 2 Sept
Charming Chester Farmhouse – peaceful and close to everything!
Charming 1-bedroom condo in delightful Dover
Fridge, microwave, oven, stovetop

Charming 1-bedroom condo in delightful Dover

10.0 out of 10, Exceptional, (1)
"The place was nice. It was clean, lots of supplies were provided, and it was in a great location. The host contacted me the day before, letting me know that the wifi was out, and the technician was unavailable until the next week. I was appreciative of the heads up. Unfortunately, the TV was unusable without wifi, no option to watch local channels. Cellular (Verizon) data was non-existent throughout the majority of daytime hours. Despite this smallish issue, I would stay here again! "
The price is AU$313
includes taxes & fees
4 Sept - 5 Sept
Charming 1-bedroom condo in delightful Dover
Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.
Smart TV, fireplace, ping pong

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

10.0 out of 10, Exceptional, (4)
"Great location to Mt Snow and its surroundings. Easy, pleasant and accommodating communications with the host. Comfortable accommodations. "
The price is AU$672
includes taxes & fees
1 Sept - 2 Sept
Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Interior

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

7.8 out of 10, Good, (50)
"The place was deserted "
The price is AU$373
includes taxes & fees
1 Sept - 2 Sept
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Lake Front Family Friendly Escape
Fridge, microwave, oven, stovetop

Lake Front Family Friendly Escape

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!"
The price is AU$607
includes taxes & fees
8 Sept - 9 Sept
Lake Front Family Friendly Escape
The White Birch near Mount Snow
Smart TV, fireplace

The White Birch near Mount Snow

The price is AU$714
includes taxes & fees
7 Sept - 8 Sept
The White Birch near Mount Snow
The Mountain Escape!
Outdoor spa tub

The Mountain Escape!

9.8 out of 10, Exceptional, (18)
"Easy booking, clean home, great location and the owner very easy to get in touch with."
The price is AU$867
includes taxes & fees
1 Sept - 2 Sept
The Mountain Escape!
Charming Cavendish Guesthouse
Interior

Charming Cavendish Guesthouse

9.8 out of 10, Exceptional, (7)
"Very cozy and had all the essentials we needed for our trip! Check in and check out were easy, and it was perfect for our winter trip. It's a short drive to Okemo, which is super convenient - would definitely stay here again!"
The price is AU$428
includes taxes & fees
1 Sept - 2 Sept
Charming Cavendish Guesthouse
Family Friendly Hilltop House In Putney Vermont
Property grounds

Family Friendly Hilltop House In Putney Vermont

9.4 out of 10, Exceptional, (56)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
The price is AU$528
includes taxes & fees
14 Sept - 15 Sept
Family Friendly Hilltop House In Putney Vermont
The Carol - 10 minutes to Okemo & Newly Renovated
Fridge, microwave, oven, stovetop

The Carol - 10 minutes to Okemo & Newly Renovated

10.0 out of 10, Exceptional, (6)
"Check in and check out were incredibly easy, house decor was eclectic upscale, beds were super comfortable. Thank you Chris! Would definitely stay here again"
The price is AU$458
includes taxes & fees
2 Sept - 3 Sept
The Carol - 10 minutes to Okemo & Newly Renovated
Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit
Fridge, microwave, oven, stovetop

Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

9.4 out of 10, Exceptional, (16)
"We celebrated my sister's 80th birthday at Blueberry Hill. It was very quiet, pleasant and perfect for our family."
The price is AU$765
includes taxes & fees
2 Sept - 3 Sept
Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit
Mtn View & Hot Tub-Peaceful Property w/ stream-mins to Hiking, Biking, Swimming
Fridge, microwave, oven, stovetop

Mtn View & Hot Tub-Peaceful Property w/ stream-mins to Hiking, Biking, Swimming

9.0 out of 10, Wonderful, (2)
"Our family had the best time staying here. The home was spacious and gave our two young children plenty of room to roam and explore. It was also close enough to the main road where everything was accessible but also isolated enough where you feel like you're getting away. Erin was great about answering any questions and making sure our stay was comfortable. We'd definitely return here!"
The price is AU$639
includes taxes & fees
3 Sept - 4 Sept
Mtn View & Hot Tub-Peaceful Property w/ stream-mins to Hiking, Biking, Swimming
Ski in Ski out Condo! Pool access
Terrace/patio

Ski in Ski out Condo! Pool access

9.0 out of 10, Wonderful, (2)
"Great location with plenty of space for the whole family. Highly recommend!"
The price is AU$799
includes taxes & fees
3 Sept - 4 Sept
Ski in Ski out Condo! Pool access
Killington Vistas 92: 4-Bedroom Luxury Ski On Ski Off Home w/ Hot Tub, Mountain Views.
Exterior

Killington Vistas 92: 4-Bedroom Luxury Ski On Ski Off Home w/ Hot Tub, Mountain Views.

2.0 star property
The price is AU$2,287
includes taxes & fees
1 Sept - 2 Sept
Killington Vistas 92: 4-Bedroom Luxury Ski On Ski Off Home w/ Hot Tub, Mountain Views.
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
2 bedrooms, WiFi, bed sheets

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

2.0 star property
The price is AU$766
includes taxes & fees
1 Sept - 2 Sept
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
Cozy Home Near Downtown, Shops, and Restaurants.
Exterior

Cozy Home Near Downtown, Shops, and Restaurants.

2.0 star property
10.0 out of 10, Exceptional, (7)
"This was just a few minutes drive from the city of Keene and was a perfect family rental. It had everything we needed. "
The price is AU$850
includes taxes & fees
2 Sept - 3 Sept
Cozy Home Near Downtown, Shops, and Restaurants.
Mountain Oasis - Hot Tub, Sauna, Fire Pit, & MORE!
Outdoor spa tub

Mountain Oasis - Hot Tub, Sauna, Fire Pit, & MORE!

9.8 out of 10, Exceptional, (26)
"EXCELLENT location managed by an amazing host who was very communicative and helpful!Hottub was perfect, plenty of sleeping and activities available at the house and in the immediate area (local food was AWESOME)."
The price is AU$867
includes taxes & fees
11 Sept - 12 Sept
Mountain Oasis - Hot Tub, Sauna, Fire Pit, & MORE!
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

Find out more about Chester

Chester Holiday Homes information

Number of reviews
Accommodation
1139 Holiday Homes
Lowest Price
AU$373
Highest Price
AU$1,317

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