The Central Downtown Inn Suites
Hotel in Pittsfield MA
9.1
Excellent
From $136
From $136
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Dog Friendly Hotel

Hotel with Parking

Luxury Hotel

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Hotel on North
Hotel in Pittsfield MA
10
Excellent
From $322
From $322
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Dog Friendly Hotel

Hotel with Parking

Hotel with Rooms With Fireplace

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Berkshire Vacation Rentals: Chic Pittsfield Home With A View
Vacation Home in Pittsfield MA
Info Categories
Dog Friendly Vacation Home

Vacation Home with Parking

Vacation Home with Free Wi-Fi

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Heart of the Berkshires Motel
Motel in Pittsfield MA
6.6
Rated
From $82
From $82
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Dog Friendly Motel

Motel with Parking

Motel Taking Steps Towards Sustainability

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107 more hotels nearby!
Lenox House with Screened Patio and Mountain View 2.9 km from Pittsfield
Vacation Home in Lenox MA
Info Categories
Dog Friendly Vacation Home

Vacation Home with Parking

Vacation Home with Swimming Pool

Outdoor Pool  

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Charming Lenox Home View of October Mountain 2.9 km from Pittsfield
Vacation Home in Lenox MA
Info Categories
Dog Friendly Vacation Home

Vacation Home with Parking

Vacation Home with Swimming Pool

Outdoor Pool  

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Berkshire Beauty-Full Home 4.3 km from Pittsfield
Vacation Home in Richmond MA
10
Excellent
Info Categories
Dog Friendly Vacation Home

Vacation Home with Parking

Vacation Home with Free Wi-Fi

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Restored 1881 Farm House 4.7 km from Pittsfield
Vacation Home in Lenox MA
Info Categories
Dog Friendly Vacation Home

Vacation Home with Parking

Vacation Home near Ski Resorts

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Built for a US Secretary of State 13K SF in Lenox 6.0 km from Pittsfield
Villas in Lenox MA
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Dog Friendly Villas

Villas with Parking

Villas with Free Wi-Fi

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The Inn at Kenmore Hall 6.1 km from Pittsfield
Inn in Richmond MA
10
Excellent
From $430
From $430
Info Categories
Dog Friendly Inn

Inn with Parking

Inn where Extra Health & Safety Measures Have Been Taken

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The Cascades 6.9 km from Pittsfield
Inn in Canaan NY
8.0
Very Good
Info Categories
Dog Friendly Inn

Inn with Parking

Inn near Ski Resorts

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Walk to Tnglewd, Stckbrdg Bwl, Wheatleigh, HTd Pool, Hot Tub 6.9 km from Pittsfield
Vacation Home in Lenox MA
8.8
Excellent
From $612
From $612
Info Categories
Dog Friendly Vacation Home

Vacation Home with Parking

Luxury Vacation Home

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Wheatleigh 7.1 km from Pittsfield
Hotel in Lenox MA
9.2
Excellent
From $912
From $912
Info Categories
Dog Friendly Hotel

Hotel with Parking

EV charging stations  

Boutique-style Hotel

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Seven Hills Inn 7.2 km from Pittsfield
Inn in Lenox MA
7.2
Good
From $166
From $166
Info Categories
Dog Friendly Inn

Inn with Parking

Luxury Inn

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Berkshire Retreat- A stone's throw to downtown Lenox 7.7 km from Pittsfield
Vacation Home in Stockbridge MA
Info Categories
Dog Friendly Vacation Home

Vacation Home with Parking

Vacation Home with Free Wi-Fi

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Spacious 3BR 3BA Sleeps 8 Ski On Off Jiminy Mountain Resort 8.1 km from Pittsfield
Vacation Home in Hancock MA
9.0
Excellent
Info Categories
Dog Friendly Vacation Home

Vacation Home with Parking

Vacation Home with Swimming Pool

Outdoor Pool  

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Luxury Fox Hollow Home-Laurel Lake 8.1 km from Pittsfield
Villas in Lenox MA
9.7
Excellent
Info Categories
Dog Friendly Villas

Villas with Parking

Villas near Ski Resorts

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The Black Swan Lee - Lenox, Ascend Hotel Collection 8.1 km from Pittsfield
Hotel in Lee MA
8.3
Very Good
From $103
From $103
Info Categories
Dog Friendly Hotel

Hotel with Parking

Hotel near Ski Resorts

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Pet-Friendly Canaan Home Near Queechy Lake! 8.7 km from Pittsfield
Vacation Home in Canaan NY
Info Categories
Dog Friendly Vacation Home

Vacation Home with Parking

Vacation Home with Swimming Pool

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5 Bed / 3 bath Apt Near Jiminy Peak Berkshires 9.4 km from Pittsfield
Apartment in Stephentown NY
Info Categories
Dog Friendly Apartment

Apartment with Parking

Family Friendly Apartment

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*Additional taxes or fees may apply. Please check the final price before completing your booking.
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