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Thursday Dec 18, 2025 - Friday Dec 19, 2025 - 2 Adults. Showing 15 results.
Pet Friendly

2 The Quigley Room

Named for Thomas Quigley, an Irish immigrant who settled this land in 1765, The Quigley Room honors the perseverance and resilience of early settlers. Arriving in America wit...
Standard Rate
$249.00 / night
$249.00 Total
Pet Friendly

5 The Sidney Winslow Room

Named for Sidney Winslow Jr., a prominent businessman who played a key role in preserving this historic property, The Sidney Winslow Room reflects his vision of hospitality a...
Standard Rate
$249.00 / night
$249.00 Total
Pet Friendly

8 The Bryant Room

A tribute to Elias Parkman Bryant, whose family owned this land for over 113 years, The Bryant Room honors that legacy with timeless comfort and thoughtful design. Decorated ...
Standard Rate
$249.00 / night
$249.00 Total
Pet Friendly

Suite 2 The Crotched Mountain Three Bedroom Combo

The Inn on Crotched Mountain Three Bedroom Combo

A tribute to the inn’s historic past, The Inn on Crotched Mountain Combo offers a spacious and flexible three-bedroom setu...
Standard Rate
$457.00 / night
$457.00 Total
Pet Friendly

1 Caroline's Room

Named after Caroline True Wilson, a steadfast presence in the 1800s who helped run the farm and household with quiet strength, this room reflects her resilience and grace. Sh...
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Pet Friendly

10 Alice's Room

Named in honor of Alice Winslow, whose love for this land and its animals shaped its history, Alice’s Room is a cozy retreat with a special connection to the past. Alice ran ...
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Pet Friendly

11 The Storm Watch Room

Storm Watch Room
In 1815, the Great September Gale nearly destroyed James Wilson’s farm—but the family rebuilt, stronger than before. The Storm Watch Room honors that spirit...
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Pet Friendly

12 The Patriot's Rest

Dedicated to James Wilson and his fellow patriots, The Patriot’s Rest is a versatile and peaceful retreat, perfect for guests who need a quiet space to work or an extra sleep...
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Pet Friendly

1A The Bennington Twin Room

Located in a quiet alcove at the end of the hallway in our historic 1822 building, this room features two comfortable twin beds and a modern mini fridge for added convenience...
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Pet Friendly

1B The Bennington Queen Room

Tucked away in a quiet alcove at the end of the hallway in our historic 1822 building, this room features a cozy queen bed and a serene atmosphere perfect for relaxation. Gue...
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Pet Friendly

3 The Baldwin Room

A tribute to Alexander Wilson, a skilled orchardist whose Baldwin apples were once so prized they were shipped overseas, The Baldwin Room celebrates the property’s deep agric...
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Pet Friendly

4 Miriam's Room

Story has it that Miriam Winslow spent many peaceful days in this very room, propped up in bed and enjoying the warm sunshine that streams through the windows.

Located in...
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Pet Friendly

7 The Perry Room

Named after John and Rose Perry, who lovingly revived the inn in 1976, this cozy ground-floor retreat blends warmth, history, and modern comfort. Located in the East Wing, Th...
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Pet Friendly

9 The Prescott Room

Named for Frederick Adams Prescott, who transformed this farm into “The Mountain Inn,” The Prescott Room reflects his vision of hospitality and warmth. Prescott saw the poten...
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Pet Friendly

Suite 1 Bennington Suite

Tucked away in a peaceful alcove at the end of the hallway in our historic 1822 building, the Bennington Suite is an ideal setup for families or groups of friends. This two-b...
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1 Caroline's Room
10 Alice's Room
11 The Storm Watch Room
12 The Patriot's Rest
1A The Bennington Twin Room
1B The Bennington Queen Room
2 The Quigley Room
3 The Baldwin Room
4 Miriam's Room
5 The Sidney Winslow Room
7 The Perry Room
8 The Bryant Room
9 The Prescott Room
Suite 1 Bennington Suite
Suite 2 The Crotched Mountain Three Bedroom Combo
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