Dog Friendly, 3-Star Hotels, Vacation Homes, Apartments, B&Bs with Free Wi-Fi in Pittsfield MA

Berkshire Vacation Rentals: Chic Pittsfield Home With A View

Vacation Home in Pittsfield MA

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Vacation Home with Free Wi-Fi

3-Star Vacation Home

34 more hotels nearby!

Lenox House with Screened Patio and Mountain View 2.9 km from Pittsfield

Vacation Home in Lenox MA

$

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Dog Friendly Vacation Home

Vacation Home with Free Wi-Fi

3-Star Vacation Home

Charming Lenox Home View of October Mountain 2.9 km from Pittsfield

Vacation Home in Lenox MA

$

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Dog Friendly Vacation Home

Vacation Home with Free Wi-Fi

3-Star Vacation Home

Berkshire Retreat- A stone's throw to downtown Lenox 7.7 km from Pittsfield

Vacation Home in Stockbridge MA

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Dog Friendly Vacation Home

Vacation Home with Free Wi-Fi

3-Star Vacation Home

Spacious 3BR 3BA Sleeps 8 Ski On Off Jiminy Mountain Resort 8.1 km from Pittsfield

Vacation Home in Hancock MA

9.0

Excellent

$

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Dog Friendly Vacation Home

Vacation Home with Free Wi-Fi

3-Star Vacation Home

The Black Swan Lee - Lenox, Ascend Hotel Collection 8.1 km from Pittsfield

Hotel in Lee MA

8.3

Very Good

From $103

$

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Dog Friendly Hotel

Hotel with Free Wi-Fi

3-Star Hotel

Pet-Friendly Canaan Home Near Queechy Lake! 8.7 km from Pittsfield

Vacation Home in Canaan NY

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Vacation Home with Free Wi-Fi

3-Star Vacation Home

Iconic Yellow House On Main Street Sleeps 15 11.1 km from Pittsfield

Vacation Home in Stockbridge MA

$

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Dog Friendly Vacation Home

Vacation Home with Free Wi-Fi

3-Star Vacation Home

Historic Two Bedroom Downtown Stockbridge 11.1 km from Pittsfield

Apartment in Stockbridge MA

7.5

Good

$

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Dog Friendly Apartment

Apartment with Free Wi-Fi

3-Star Apartment

Historic Stockbridge On Main Street 3 Bedroom 11.1 km from Pittsfield

Apartment in Stockbridge MA

10

Excellent

$

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Dog Friendly Apartment

Apartment with Free Wi-Fi

3-Star Apartment

Holmes Suite PRIME Downtown Stockbridge 11.1 km from Pittsfield

Apartment in Stockbridge MA

8.0

Very Good

$

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Dog Friendly Apartment

Apartment with Free Wi-Fi

3-Star Apartment

Federal House Inn 11.2 km from Pittsfield

Bed & Breakfast in Lee MA

9.7

Excellent

From $150

$

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Dog Friendly Bed & Breakfast

Bed & Breakfast with Free Wi-Fi

3-Star Bed & Breakfast

Berkshire Vacation Rentals: Stonebridge Cabin: Modern Amenities Enjoy Nature 11.8 km from Pittsfield

Vacation Home in Lee MA

10

Excellent

$

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Dog Friendly Vacation Home

Vacation Home with Free Wi-Fi

3-Star Vacation Home

Berkshire Vacation Rentals: Loft Style Cabin In West Stockbridge Book Now 12.0 km from Pittsfield

Vacation Home in West Stockbridge MA

$

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Dog Friendly Vacation Home

Vacation Home with Free Wi-Fi

3-Star Vacation Home

Berkshire Vacation Rental: Stockbridge Home Come Experience The Berkshires 12.0 km from Pittsfield

Vacation Home in Stockbridge MA

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Dog Friendly Vacation Home

Vacation Home with Free Wi-Fi

3-Star Vacation Home

Berkshire Vacation Rentals: Spacious & Serene Berkshires Retreat In The Woods 13.2 km from Pittsfield

Vacation Home in West Stockbridge MA

$

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Dog Friendly Vacation Home

Vacation Home with Free Wi-Fi

3-Star Vacation Home

Berkshire Vacation Rentals: Private Cabin On Over 12 Acres Of Woods 13.9 km from Pittsfield

Vacation Home in Becket MA

$

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Dog Friendly Vacation Home

Vacation Home with Free Wi-Fi

3-Star Vacation Home

Massachusetts Vacation Rental with Deck and Grill 14.2 km from Pittsfield

Vacation Home in Cheshire MA

$

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Dog Friendly Vacation Home

Vacation Home with Free Wi-Fi

3-Star Vacation Home

Private Berkshires Home On 5+ Acres Rustic & Chic 15.1 km from Pittsfield

Vacation Home in Otis MA

$

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Dog Friendly Vacation Home

Vacation Home with Free Wi-Fi

3-Star Vacation Home

Berkshire Vacation Rentals: Pristine Home In Becket Woods 16.9 km from Pittsfield

Vacation Home in Becket MA

$

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Dog Friendly Vacation Home

Vacation Home with Free Wi-Fi

3-Star Vacation Home

Dog Friendly, 3-Star Hotels with Free Wi-Fi in Pittsfield MA