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Our top choices for Chester vacation homes

Tranquil 3 bedroom Home with Hot Tub and Standby Generator in Andover

Tranquil 3 bedroom Home with Hot Tub and Standby Generator in Andover
Andover
The price is ¥35,921
¥90,834 total
includes taxes & fees
Jun 4 - Jun 5
Tranquil 3 bedroom Home with Hot Tub and Standby Generator in Andover

Charming Chester Farmhouse near Near VT Slopes

Charming Chester Farmhouse near Near VT Slopes
Chester Depot
9.6 out of 10, Exceptional, (20 reviews)
"We had a great stay! The house was clean, comfortable, and exactly as described. The location was perfect and the host was very responsive. We’d definitely stay here again and highly recommend it."
United States
Stephanie F.
The price is ¥31,611
¥65,265 total
includes taxes & fees
Jun 18 - Jun 19
Charming Chester Farmhouse near Near VT Slopes

Cozy Vermont Cabin · Mountain Views · Near Okemo

Cozy Vermont Cabin · Mountain Views · Near Okemo
Chester
10.0 out of 10, Exceptional, (4 reviews)
"Clean, spacous house, good location and great scenes of the mountains."
United States
pauline
The price is ¥86,067
¥161,123 total
includes taxes & fees
Jun 10 - Jun 11
Cozy Vermont Cabin · Mountain Views · Near Okemo

Perfect 2-bedroom in charming Newport

Perfect 2-bedroom in charming Newport
Newport
The price is ¥26,376
¥35,039 total
includes taxes & fees
Jun 16 - Jun 17
Perfect 2-bedroom in charming Newport

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, (41 reviews)
"This house has great hang out space and plenty of space for a big family!"
United States
Cheri V.
The price is ¥28,019
¥86,456 total
includes taxes & fees
Jun 8 - Jun 9
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

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, (85 reviews)
"Great proximity to mountain and Ludlow downtown area."
United States
Yasmine O.
The price is ¥21,553
¥53,561 total
includes taxes & fees
Jun 4 - Jun 5
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route

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, (108 reviews)
"Couldn’t have picked a better place! Warm and comfy and sooo close to okemo "
United States
Erica B.
The price is ¥21,553
¥53,561 total
includes taxes & fees
Jun 4 - Jun 5
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Lakefront Family Fun Retreat

Lakefront Family Fun Retreat
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 ¥31,132
¥80,722 total
includes taxes & fees
Jun 4 - Jun 5
Lakefront Family Fun Retreat

Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!

Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!
Mount Holly
10.0 out of 10, Exceptional, (11 reviews)
"We had a great time in this beautiful house for a family ski trip. It is located right off the main highway and 8min drive away from Okemo. It has all the amenities we wanted- including hot tub, cozy underground family entertainment room and parking garage. Heidi, the host was super prompt and all instructions about the house were very thorough. "
United States
Chi L.
The price is ¥30,864
¥124,668 total
includes taxes & fees
Jun 4 - Jun 5
Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!

Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (60 reviews)
"The host and her daughter were lovely and kind and very quick with all communication."
United States
Susan O.
The price is ¥28,935
¥52,472 total
includes taxes & fees
Jun 8 - Jun 9
Family Friendly Hilltop House In Putney Vermont

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, (3 reviews)
"Communication with the host was easy and the house was great. I would definitely book this home again if/when I come back to Keene."
United States
Jeremy S.
The price is ¥33,367
¥79,163 total
includes taxes & fees
Jun 16 - Jun 17
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!

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, (26 reviews)
"Easy booking, clean home, great location and the owner very easy to get in touch with."
United States
Chris M.
The price is ¥24,629
¥129,759 total
includes taxes & fees
Jun 10 - Jun 11
Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft

Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!

Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
Jamaica
9.6 out of 10, Exceptional, (29 reviews)
"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)."
United States
s w.
The price is ¥29,162
¥136,338 total
includes taxes & fees
Jun 9 - Jun 10
Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!

Modern Mount Snow Gnarvana - Balcony, Loft, Pets, Hiking

Modern Mount Snow Gnarvana - Balcony, Loft, Pets, Hiking
Dover
10.0 out of 10, Exceptional, (26 reviews)
"The hosts were very responsive, accommodating, and our family had a wonderful stay! "
United States
caroline m.
The price is ¥21,593
¥69,225 total
includes taxes & fees
Jun 4 - Jun 5
Modern Mount Snow Gnarvana - Balcony, Loft, Pets, Hiking

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Winhall
9.4 out of 10, Exceptional, (38 reviews)
"Our family had a wonderful time staying in this home."
United States
Meghan C.
The price is ¥31,507
¥105,851 total
includes taxes & fees
Jun 4 - Jun 5
Your Vermont Mountain Haven Pet Friendly home with Hot tub!

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 ¥30,334
¥88,332 total
includes taxes & fees
Jun 8 - Jun 9
Large Killington Area Home | Sleeps 7 | Game Room

Father's Day Special-Barrel Sauna, Game Room, Hot Tub, Fire Pit, Dogs Welcome!

Father's Day Special-Barrel Sauna, Game Room, Hot Tub, Fire Pit, Dogs Welcome!
Dover
10.0 out of 10, Exceptional, (9 reviews)
"We had a great family ski trip and stay in this cozy house. Good location close to town and was the perfect setup up to accommodate our two families of four. Beth and Jason were very responsive and easy to communicate with, would highly recommend! "
United States
James D.
The price is ¥29,954
¥90,591 total
includes taxes & fees
Jun 4 - Jun 5
Father's Day Special-Barrel Sauna, Game Room, Hot Tub, Fire Pit, Dogs Welcome!

The Navillus House: Hot Tub, Ski On/Ski Off, A/C. Discounted Ski Rentals.

The Navillus House: Hot Tub, Ski On/Ski Off, A/C. Discounted Ski Rentals.
Killington
10.0 out of 10, Exceptional, (63 reviews)
"Great stay, everything was clean and location was amazing."
United States
John D.
The price is ¥50,804
¥169,170 total
includes taxes & fees
Jun 4 - Jun 5
The Navillus House: Hot Tub, Ski On/Ski Off, A/C. Discounted Ski Rentals.

Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.

Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.
Bridgewater
8.0 out of 10, Very Good, (2 reviews)
"Great place for a ski weekend"
United States
Kathryn F.
The price is ¥37,150
¥114,694 total
includes taxes & fees
Jun 4 - Jun 5
Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.

RoundTop Chalet | Hot Tub, Fire Pit & Mountain Views near Killington & Okemo

RoundTop Chalet | Hot Tub, Fire Pit & Mountain Views near Killington & Okemo
Plymouth
9.0 out of 10, Wonderful, (2 reviews)
"Everything about the property was beautiful and relaxing. We loved our stay .... We did however run into one issue, while we were enjoying the property, someone claiming to be there to service the hot tub decided to let themselves in with the lock code unannounced while we were undressed and stood there listening to us and only when the dog ran down there did he announce himself. Not sure if simple sent them or if they showed up on their own accord but boy did we get quite the scare and hope...
United States
Adam S.
The price is ¥27,433
¥91,189 total
includes taxes & fees
Jun 8 - Jun 9
RoundTop Chalet | Hot Tub, Fire Pit & Mountain Views near Killington & Okemo
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
416
Accommodation
944 Vacation Homes
Lowest Price
¥35,039
Highest Price
¥169,170