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  2. >North America
  3. >United States
  4. >Vermont
  5. >Windsor

Small Hotels in Windsor

47 HOTELS IN WINDSOR
Most popular user searches in Windsor: boutique-style hotels.
Ranking can be influenced by the commissions we receive.
The Governor's Inn main photo
The Governor's Inn
Bed & Breakfast in Ludlow VTUS flag
9.7
Excellent
$
+4
Small
AI-generatedThis bed and breakfast offers a charming and intimate experience. It provides a cozy atmosphere with personalized service, making it ideal for guests seeking a unique and memorable stay.
The Village Inn of Woodstock main photo
The Village Inn of Woodstock
Bed & Breakfast in Woodstock VTUS flag
9.3
Excellent
From $283
$
+2
Small
AI-generatedLocated on Pleasant Street, this bed and breakfast offers a charming and convenient stay. The cozy atmosphere and proximity to Woodstock's attractions make it a great choice for a relaxing visit.
Golden Stage Inn main photo
Golden Stage Inn
Bed & Breakfast in Proctorsville VTUS flag
9.7
Excellent
From $269
$
+4
Small
AI-generatedThis inn offers a historic and charming setting with well-appointed rooms. Its serene location and personalized service ensure a cozy and memorable stay.
Inn Victoria main photo
Inn Victoria
Inn in Chester VTUS flag
9.6
Excellent
From $437
$
+4
Small
AI-generatedThis inn offers a charming and intimate experience with its well-appointed rooms and personalized service. Its location on Main Street provides easy access to local attractions, making it ideal for a cozy getaway.
Franklyn Farm Inn main photo
Franklyn Farm Inn
Bed & Breakfast in Chester VTUS flag
9.8
Excellent
$
+3
Small
AI-generatedThis bed and breakfast provides a rustic and cozy farm stay experience. Guests can enjoy the peaceful surroundings and the charm of a traditional Vermont farm.
Woodbridge Inn Bed & Breakfast main photo
Woodbridge Inn Bed & Breakfast
Bed & Breakfast in Woodstock VTUS flag
9.4
Excellent
From $273
$
+3
Info
Categories
Small
Ski
3 Star
The Vesper Woodstock main photo
The Vesper Woodstock
Bed & Breakfast in Woodstock VTUS flag
8.1
Very Good
$
+3
Info
Categories
Small
Ski
Free Wi-Fi
Stone Hearth Inn and Eatery main photo
Stone Hearth Inn and Eatery
Bed & Breakfast in Chester VTUS flag
9.0
Excellent
From $216
$
+3
Small
AI-generatedThis inn offers a cozy and welcoming atmosphere with its on-site eatery. Guests can enjoy comfortable accommodations and delicious meals in a relaxed setting.
The Woodstocker B&B main photo
The Woodstocker B&B
Bed & Breakfast in Woodstock VTUS flag
9.6
Excellent
From $350
$
+2
Small
AI-generatedLocated on River Street, this bed and breakfast provides a cozy and convenient stay. Its charming ambiance and proximity to Woodstock's attractions make it a great choice.
Stay At Jimmy's main photo
Stay At Jimmy's
Bed & Breakfast in Woodstock VTUS flag
9.4
Excellent
$
+5
Small
AI-generatedThis bed and breakfast offers a comfortable and personalized experience. Its location on Pleasant Street provides easy access to local amenities and attractions.
Lincoln Inn & Gallery main photo
Lincoln Inn & Gallery
Inn in Woodstock VTUS flag
7.8
Good
$
Small
AI-generatedLocated on West Woodstock Road, this inn combines accommodation with an art gallery. The unique setting and cozy rooms provide a memorable and intimate stay.
Chester Inn main photo
Chester Inn
Inn in Chester VTUS flag
8.5
Very Good
From $154
$
+4
Info
Categories
Small
Ski
Free Wi-Fi
Sleep Woodstock main photo
Sleep Woodstock
Motel in Woodstock VTUS flag
8.8
Excellent
From $153
$
+5
Info
Categories
Small
Sustainability Journey
Dog Friendly
Solitude Village at Okemo main photo
Solitude Village at Okemo
Aparthotel in Ludlow VTUS flag
9.3
Excellent
From $165
$
+11
Info
Categories
Small
Ski In Ski Out
Ski
Solitude Village at Okemo by Vail Resorts main photo
Solitude Village at Okemo by Vail Resorts
Resort in Ludlow VTUS flag
7.5
Good
From $165
$
+9
Info
Categories
Small
Ski
Parking
Deer Brook Inn main photo
Deer Brook Inn
Bed & Breakfast in Woodstock VTUS flag
9.8
Excellent
From $502
$
+6
Info
Categories
Small
Ski
Dog Friendly
Dogs Stay Free
Echo Lake Inn main photo
Echo Lake Inn
Inn in Tyson VTUS flag
8.7
Very Good
From $184
$
+6
Info
Categories
Small
Ski
3 Star
Pomfret Bungalow main photo
Pomfret Bungalow
Hotel in Woodstock VTUS flag
9.6
Excellent
$
+4
Info
Categories
Small
Golf
Ski
The Weston Hotel main photo
The Weston Hotel
Hotel in Weston VTUS flag
9.8
Excellent
$
+8
Info
Categories
Small
Free Wi-Fi
Accessible
Winterplace at Okemo, A Vail Resorts Property main photo
Winterplace at Okemo, A Vail Resorts Property
Resort in Ludlow VTUS flag
8.0
Very Good
From $191
$
+6
Info
Categories
Small
Ski
Family
*Additional taxes or fees may apply. Please check the final price before completing your booking.Showing 1-20 out of 47 hotels in Windsor
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