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Check prices for these dates

Next weekend
27 Jun - 29 Jun
In two weeks
4 Jul - 6 Jul
In one month
18 Jul - 20 Jul
In two months
15 Aug - 17 Aug

Vacation 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)
"The room was really cozy and the community area was quaint and comfortable. "
The price is SAR 371
SAR 626 total
includes taxes & fees
22 Jun - 23 Jun
Whimsical Room & Private Bathroom in Historic Inn
Charming Chester Farmhouse – peaceful and close to everything!
Terrace/patio

Charming Chester Farmhouse – peaceful and close to everything!

9.4 out of 10, Exceptional, (10)
"Great location. Beautiful house. All the amenties. We came up for a ski trip and it was perfect. "
The price is SAR 784
SAR 1,593 total
includes taxes & fees
22 Jun - 23 Jun
Charming Chester Farmhouse – peaceful and close to everything!
WhiSki Cabin - 12 Acres With a Mountain View!
Interior

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 SAR 2,023
SAR 3,690 total
includes taxes & fees
20 Jun - 21 Jun
WhiSki Cabin - 12 Acres With a Mountain View!
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, (4)
"Online info was accurate. Nice spot to rent with family."
The price is SAR 1,328
SAR 2,198 total
includes taxes & fees
23 Jun - 24 Jun
Cozy Home Near Downtown, Shops, and Restaurants.
Lake Front Family Friendly Escape
Fridge, microwave, oven, stovetop

Lake Front Family Friendly Escape

10.0 out of 10, Exceptional, (2)
"My husband and 3 teens were more than comfortable in this gorgeous lakeside home. We skied at Mt. Sunapee (about 25 min drive) and made our meals at home in the evening. The house is new and welcoming. We were always warm enough and slept well. The view from the Master BR is breathtaking. I would recommend eye shades for the morning as the sun is bright through the bedroom windows. The caretakers are kind and very responsive. I would return next year and recommend this home."
The price is SAR 652
SAR 1,603 total
includes taxes & fees
26 Jun - 27 Jun
Lake Front Family Friendly Escape
Family Friendly Hilltop House In Putney Vermont
Exterior

Family Friendly Hilltop House In Putney Vermont

9.4 out of 10, Exceptional, (55)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
The price is SAR 732
SAR 1,282 total
includes taxes & fees
2 Jul - 3 Jul
Family Friendly Hilltop House In Putney Vermont
Cozy Cavendish Bunk minutes to Okemo
Interior

Cozy Cavendish Bunk minutes to Okemo

9.8 out of 10, Exceptional, (6)
"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 SAR 473
SAR 891 total
includes taxes & fees
22 Jun - 23 Jun
Cozy Cavendish Bunk minutes to Okemo
Sleep Woodstock - 2 Double Beds - Dog Friendly
Aerial view

Sleep Woodstock - 2 Double Beds - Dog Friendly

The price is SAR 429
SAR 619 total
includes taxes & fees
1 Jul - 2 Jul
Sleep Woodstock - 2 Double Beds - Dog Friendly
Sleep Woodstock - Dog Friendly King Suite
Miscellaneous

Sleep Woodstock - Dog Friendly King Suite

The price is SAR 583
SAR 809 total
includes taxes & fees
1 Jul - 2 Jul
Sleep Woodstock - Dog Friendly King Suite
Sleep Woodstock Mobility Impaired Accessible Suite
Iron/ironing board, travel crib, WiFi, bed sheets

Sleep Woodstock Mobility Impaired Accessible Suite

The price is SAR 351
SAR 528 total
includes taxes & fees
24 Jun - 25 Jun
Sleep Woodstock Mobility Impaired Accessible Suite
Sleep Woodstock - Deluxe Suite
TV

Sleep Woodstock - Deluxe Suite

2.0 star property
Sleep Woodstock - Deluxe Suite
A charming 1820's farmhouse
Interior

A charming 1820's farmhouse

10.0 out of 10, Exceptional, (26)
"5 families getting together once a year for a winter adventure weekend. Carmen is a fantastic host. The home is lovely, and we had a great time. Carmen makes sure if we need something, she is a phone call away.Would highly recommend this VRBO."
The price is SAR 2,364
SAR 4,212 total
includes taxes & fees
23 Jun - 24 Jun
A charming 1820's farmhouse
A vacation destination in Southern Vermont
Fridge, microwave, oven, stovetop

A vacation destination in Southern Vermont

10.0 out of 10, Exceptional, (69)
"Super comfortable cabin in a great location."
The price is SAR 1,313
SAR 2,870 total
includes taxes & fees
11 Jul - 12 Jul
A vacation destination in Southern Vermont
The Bridgewater House | Game Room | Hiking | Golf
Fridge, microwave, oven, stovetop

The Bridgewater House | Game Room | Hiking | Golf

9.4 out of 10, Exceptional, (6)
"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."
The price is SAR 773
SAR 2,105 total
includes taxes & fees
23 Jun - 24 Jun
The Bridgewater House | Game Room | Hiking | Golf
Beautifully Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Exterior

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

9.8 out of 10, Exceptional, (84)
"We had a great stay at this home for a long weekend skiing at Okemo. "
The price is SAR 687
SAR 1,482 total
includes taxes & fees
22 Jun - 23 Jun
Beautifully Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (99)
"Great location and house was very nice."
The price is SAR 687
SAR 1,482 total
includes taxes & fees
22 Jun - 23 Jun
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Okemo's Back Room - in the heart of the village on the shuttle route!
Interior

Okemo's Back Room - in the heart of the village on the shuttle route!

9.6 out of 10, Exceptional, (14)
"Perfect location. Charming place to stay. Very clean. Great view of the creek."
The price is SAR 375
SAR 1,189 total
includes taxes & fees
22 Jun - 23 Jun
Okemo's Back Room - in the heart of the village on the shuttle route!
Briggs Ski House | Group Ski Fun | 6 bdrm 4 bath
Fridge, microwave, oven, stovetop

Briggs Ski House | Group Ski Fun | 6 bdrm 4 bath

10.0 out of 10, Exceptional, (1)
"We booked this for a last minute trip to Okemo and it was perfect for our group. It is only a couple minutes from Okemo base and a couple minutes from the cute downtown and a supermarket and craft beer store. The host was easy to talk to and extremely available, and very friendly and helpful! The house was in great condition, clean, and updated."
The price is SAR 1,985
SAR 4,078 total
includes taxes & fees
20 Jun - 21 Jun
Briggs Ski House | Group Ski Fun | 6 bdrm 4 bath
New Ludlow Village Home with Stunning Okemo Mountain View
Fridge, microwave, oven, stovetop

New Ludlow Village Home with Stunning Okemo Mountain View

10.0 out of 10, Exceptional, (6)
"Beautiful and clean place near Okemo with everything you need. "
The price is SAR 1,344
SAR 2,623 total
includes taxes & fees
20 Jun - 21 Jun
New Ludlow Village Home with Stunning Okemo Mountain View
NEW Hot Tub/Lakeview/Pool Table/Okemo Ski House
Outdoor dining

NEW Hot Tub/Lakeview/Pool Table/Okemo Ski House

The price is SAR 1,501
SAR 3,273 total
includes taxes & fees
22 Jun - 23 Jun
NEW Hot Tub/Lakeview/Pool Table/Okemo Ski House
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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