7.3
Good
From $114
From $114
Info Categories
Dog Friendly Hotel

Hotel with Free Wi-Fi

Hotel with Spa

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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 Free Wi-Fi

Vacation Home with Parking

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

Motel with Free Wi-Fi

Motel Taking Steps Towards Sustainability

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76 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 Free Wi-Fi

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 Free Wi-Fi

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 Free Wi-Fi

Vacation Home with Parking

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

Villas with Free Wi-Fi

Villas with Parking

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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 Free Wi-Fi

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 Free Wi-Fi

Inn near Ski Resorts

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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 Free Wi-Fi

Vacation Home with Parking

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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 Free Wi-Fi

Vacation Home with Swimming Pool

Outdoor Pool  

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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 Free Wi-Fi

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 Free Wi-Fi

Vacation Home with Swimming Pool

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Shaker Mill Inn 9.0 km from Pittsfield
Bed & Breakfast in West Stockbridge MA
9.4
Excellent
From $144
From $144
Info Categories
Dog Friendly Bed & Breakfast

Bed & Breakfast with Free Wi-Fi

Boutique-style Bed & Breakfast

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Shaker Mill Inn 9.1 km from Pittsfield
Bed & Breakfast in West Stockbridge MA
9.4
Excellent
From $144
From $144
Info Categories
Dog Friendly Bed & Breakfast

Bed & Breakfast with Free Wi-Fi

Luxury Bed & Breakfast

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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 Free Wi-Fi

Family Friendly Apartment

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2 Bed Berkshire Getaway @ Stephentown Hotel 9.4 km from Pittsfield
Apartment in Stephentown NY
10
Excellent
Info Categories
Dog Friendly Apartment

Apartment with Free Wi-Fi

Family Friendly Apartment

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The entire Stephentown Hotel! 28 person occupancy 9.4 km from Pittsfield
Apartment in Stephentown NY
Info Categories
Dog Friendly Apartment

Apartment with Free Wi-Fi

Apartment with Parking

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The Stephentown Hotel 9.4 km from Pittsfield
Inn in Stephentown NY
Info Categories
Dog Friendly Inn

Inn with Free Wi-Fi

Family Friendly Inn

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Jacob's Tanglewood Ranch 10.1 km from Pittsfield
Guest House in Lee MA
9.1
Excellent
Info Categories
Dog Friendly Guest House

Guest House with Free Wi-Fi

Guest House near Ski Resorts

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