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  1. World
  2. >North America
  3. >United States
  4. >Vermont
  5. >Rutland
  6. >Pittsfield

Small Hotels in Pittsfield

108 HOTELS IN AND AROUND PITTSFIELDRanking can be influenced by the commissions we receive.
Sleep Woodstock main photo
Sleep Woodstock
16.0 mi from Pittsfield
Motel in Woodstock VTUS flag
8.9
Excellent
From $153
$
+5
Info
Categories
Small
Sustainability Journey
Dog Friendly
Deer Brook Inn main photo
Deer Brook Inn
16.0 mi from Pittsfield
Bed & Breakfast in Woodstock VTUS flag
9.8
Excellent
Currently inactive on our platform.
$
+6
Info
Categories
Small
Ski
Dog Friendly
Dogs Stay Free
Farmhouse Inn at Robinson Farm main photo
Farmhouse Inn at Robinson Farm
16.1 mi from Pittsfield
Bed & Breakfast in Woodstock VTUS flag
0.0
From $215
$
+5
Info
Categories
Small
Ski
Free Wi-Fi
Lincoln Inn & Gallery main photo
Lincoln Inn & Gallery
17.0 mi from Pittsfield
Inn in Woodstock VTUS flag
7.9
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.
The Jackson main photo
The Jackson
17.2 mi from Pittsfield
Inn in Woodstock VTUS flag
8.4
Very Good
From $273
$
+5
Info
Categories
Small
Parking
Ski
The Woodstocker B&B main photo
The Woodstocker B&B
17.7 mi from Pittsfield
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.
The Blue Horse Inn main photo
The Blue Horse Inn
17.8 mi from Pittsfield
Bed & Breakfast in Woodstock VTUS flag
0.0
From $365
$
+8
Info
Categories
Small
Ski
Dog Friendly
The Buckmaster Inn main photo
The Buckmaster Inn
18.0 mi from Pittsfield
Bed & Breakfast in Shrewsbury VTUS flag
0.0
From $158
$
+5
Info
Categories
Small
Ski
Free Wi-Fi
The Vesper Woodstock main photo
The Vesper Woodstock
18.1 mi from Pittsfield
Bed & Breakfast in Woodstock VTUS flag
8.0
Very Good
$
+3
Info
Categories
Small
Ski
Free Wi-Fi
The Village Inn of Woodstock main photo
The Village Inn of Woodstock
18.2 mi from Pittsfield
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.
Stay At Jimmy's main photo
Stay At Jimmy's
18.2 mi from Pittsfield
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.
Mountain Views, Hot Tub, Trails, Waterfront main photo
Mountain Views, Hot Tub, Trails, Waterfront
18.9 mi from Pittsfield
Chalet in Plymouth VTUS flag
0.0
$
+3
Info
Categories
Small
Free Wi-Fi
Parking
Hot Tub & Firepit Near Ski Resorts & Cozy Modern Cabin main photo
Hot Tub & Firepit Near Ski Resorts & Cozy Modern Cabin
19.3 mi from Pittsfield
Chalet in Plymouth VTUS flag
0.0
$
+3
Info
Categories
Small
Free Wi-Fi
Parking
Kingswood 12H main photo
Kingswood 12H
19.8 mi from Pittsfield
Hotel in White River Junction VTUS flag
7.0
Good
Currently inactive on our platform.
$
+3
Info
Categories
Small
Ski
3 Star
Robert Frost Mountain Cabins main photo
Robert Frost Mountain Cabins
19.9 mi from Pittsfield
Lodge in Middlebury VTUS flag
10
Excellent
From $305
$
+7
Info
Categories
Small
Luxury
Ski
Dreamy Artist Chalet in Secluded Historic Village main photo
Dreamy Artist Chalet in Secluded Historic Village
21.1 mi from Pittsfield
Chalet in Warren VTUS flag
10
Excellent
$
+4
Info
Categories
Small
Dog Friendly
Free Wi-Fi
Spruce Moose Cottage main photo
Spruce Moose Cottage
21.6 mi from Pittsfield
Hotel in Hartland VTUS flag
0.0
Currently inactive on our platform.
$
+3
Info
Categories
Small
Ski
Dog Friendly
Echo Lake Inn main photo
Echo Lake Inn
21.6 mi from Pittsfield
Inn in Tyson VTUS flag
8.5
Very Good
From $184
$
+6
Info
Categories
Small
Ski
3 Star
Inn at Water's Edge main photo
Inn at Water's Edge
21.6 mi from Pittsfield
Bed & Breakfast in Ludlow VTUS flag
0.0
$
+4
Info
Categories
Small
Ski
Free Wi-Fi
Green Trails Inn main photo
Green Trails Inn
21.9 mi from Pittsfield
Inn in Brookfield VTUS flag
10
Excellent
$
+3
Info
Categories
Small
Free Wi-Fi
Parking
*Additional taxes or fees may apply. Please check the final price before completing your booking.Showing 81-100 out of 108 hotels in and around Pittsfield
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