Chester Holidays
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Chester Holiday
Our pick of the best Chester Hotel Deals
Woodstock Inn & Resort
Fourteen The Green Woodstock VT
The price is NZ$683 per night from 19 Jan to 20 Jan
NZ$683
19 Jan - 20 Jan 2026
includes taxes & fees
9.2/10 Wonderful! (557 reviews)
Luxurious and friendly resort! Loved it
Reviewed on 18 Dec 2025
Pointe at Castle Hill Resort
2940 State Route 103 Cavendish VT
The price is NZ$270 per night from 19 Jan to 20 Jan
NZ$270
19 Jan - 20 Jan 2026
includes taxes & fees
8.6/10 Excellent! (928 reviews)
Good service
Reviewed on 18 Dec 2025
The Shire Woodstock
46 Pleasant St. Woodstock VT
Fully refundableReserve now, pay when you stay
8.6/10 Excellent! (891 reviews)
The staff was super nice and flexible! Location was great
Reviewed on 13 Dec 2025
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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- Hartland Hotels
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- Andover Hotels
- Visit Newfane
- Visit Perkinsville
- Visit Hartland
- Visit Rockingham
- Montshire Museum of Science
- Upper Valley Aquatic Center
- Calvin Coolidge Homestead
- Green Mountain National Golf Course
- Mount Snow
- Bear Mountain Quad Ski Lift
- Skyeship Express Gondola Stage I
- Dorsey Park
- Green Mountain National Forest
- Green Mountain Rock Climbing Center
- Fire Tower
- Woodstock Holidays
- Gifford Woods State Park
- Weston Priory
- Green Mountain Rock Climbing Center
- Merck Forest Farmland Center
- Hathaway Farm
- Black Dog Sports
- Brattleboro Farmers' Market
- Quechee State Park
- Rutland Holidays
- Pico Mountain at Killington Ski Resort
- Long Trail Brewing Company
- Baltimore Covered Bridge
- Viking Nordic Center
- Snowdon Triple Ski Lift
- Killington Peak
- Stratton Tennis School
- Sugar Shack
- Killington Golf Course
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
