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Chesterfield Bed and Breakfasts

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The Garden Gables Inn

Lenox, MA

Top-rated 15 room inn on 5 quiet, private acres steps from restaurants and shops of Lenox Village

from $220

4.6 (108)
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The Garden Gables Inn

The Garden Gables Inn

from $220

Lenox, MA

4.6 (108)

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Birchwood Inn

Lenox, MA

Enjoy 15% off January-April reservations. Best Breakfast in New England!

from $199

4.7 (37)
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Birchwood Inn

Birchwood Inn

from $199

Lenox, MA

4.7 (37)

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Inn at Stockbridge

Stockbridge, MA

Enjoy a beautiful 12 acre property convenient to all the Berkshire attractions.

from $170

4.4 (100)
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Inn at Stockbridge

Inn at Stockbridge

from $170

Stockbridge, MA

4.4 (100)

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Devonfield Inn, an English Country Estate

Lee, MA

Historic English Country Estate in the Heart of the Berkshires on 30 acre pastoral meadow

from $180

4.6 (205)
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Gateways Inn

Lenox, MA

Located in the heart of Lenox, Massachusetts, in the Berkshire Hills, the Gateways Inn offers a p...

from $180

4.2 (14)
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Gateways Inn

Gateways Inn

from $180

Lenox, MA

4.2 (14)

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Brook Farm Inn

Lenox, MA

A Victorian treasure near all Berkshires attractions;15 elegant rooms, fantastic breakfast.

from $159

4.5 (20)
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Brook Farm Inn

Brook Farm Inn

from $159

Lenox, MA

4.5 (20)

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Rookwood Inn

Lenox, MA

"Where Memories are Made"

from $185

4.6 (43)
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Rookwood Inn

Rookwood Inn

from $185

Lenox, MA

4.6 (43)

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Deerfield Inn

Deerfield, MA

Stay 3 nights for the price of 2 thru Aug 31! A National Historic Landmark Bed & Breakfast.

from $149

4.1 (2)
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Deerfield Inn

Deerfield Inn

from $149

Deerfield, MA

4.1 (2)

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Applegate Inn

Lee, MA

Recommended by: Frommer's, Karen Brown's Guides, Massachusetts, An explorer's Guide

from $160

4.5 (146)
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Applegate Inn

Applegate Inn

from $160

Lee, MA

4.5 (146)

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Inn At Richmond

Richmond, MA

The Inn at Richmond -- a Unique, Relaxing & Gracious Four Seasons Country Inn in The Berkshires

from $160

4.2 (39)
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Inn At Richmond

Inn At Richmond

from $160

Richmond, MA

4.2 (39)

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Whistlers Inn

Lenox, MA

Featured on National T.V. - The Travel Channel. An English Tudor mansion built in 1820 in the hea...

from $130

4.0 (81)
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Whistlers Inn

Whistlers Inn

from $130

Lenox, MA

4.0 (81)

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Berkshire's Chambery Inn

Lee, MA

A one of a kind Bed and Breakfast,Chateau Chambery Inn, circa 1885, with its French design and 9 ...

from $85

4.6 (47)
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The Barrington

Great Barrington,

Stylish, spacious, fully-renovated accommodation in the center of historic Great Barrington.

from $235

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The Barrington

The Barrington

from $235

Great Barrington,

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House On Main Street

Williamstown, MA

The charm of the Victorian era with the luxury of the 21st Century. This Quiet, cozy bed & breakf...

from $99

4.1 (21)
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House On Main Street

House On Main Street

from $99

Williamstown, MA

4.1 (21)

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Naomi's Inn Bed and Breakfast

Springfield,

Springfield's ONLY B&B offers upscale comfort, private en-suite baths, reasonable price

from $88

4.4 (28)
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Naomi's Inn Bed and Breakfast

Naomi's Inn Bed and Breakfast

from $88

Springfield,

4.4 (28)

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Cornell Inn Bed and Breakfast

Lenox, MA

You're gonna LOVE it here!

from $119

4.4 (315)
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The Birches at Steep Acres Farm

Williamstown, MA

The Birches Bed & Breakfast is located approximately two miles from Williams College and the cent...

from $125

4.7 (33)
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The Birches at Steep Acres Farm

The Birches at Steep Acres Farm

from $125

Williamstown, MA

4.7 (33)

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Hampton Terrace B&B

Lenox, MA

Described as "absolutely perfect" by Traditional Home Magazine. See our Specials Page!

from $199

4.6 (5)
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Hampton Terrace B&B

Hampton Terrace B&B

from $199

Lenox, MA

4.6 (5)

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1862 Seasons on Main Bed and Breakfast

Stockbridge, MA

An elegant boutique inn, built in 1862 and listed on the National Register of Historic Places

from $185

4.8 (1)
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1862 Seasons on Main Bed and Breakfast

1862 Seasons on Main Bed and Breakfast

from $185

Stockbridge, MA

4.8 (1)

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Seven Hills Inn

Lenox, MA

Hotel set in refurbished 1911 Tudor Mansion, blending modern comfort with antique furnishings.

from $100

4.8 (21)

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Seven Hills Inn

Seven Hills Inn

from $100

Lenox, MA

4.8 (21)

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The Stockbridge Country Inn

Stockbridge, MA

Closest Inn to The Norman Rockwell Museum, Chesterwood, Tanglewood & Berkshire Botannical Gardens!

from $139

4.7 (19)

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The Stockbridge Country Inn

The Stockbridge Country Inn

from $139

Stockbridge, MA

4.7 (19)

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1896 House Country Inn

Williamstown, MA

Set alongside a brook just a short drive from The Clark Museum, Williams College, and Jiminy Peak!

from $84

4.0 (57)
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1896 House Country Inn

1896 House Country Inn

from $84

Williamstown, MA

4.0 (57)

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Shaker Mill Inn

West Stockbridge, MA

Welcome to the Shaker Mill Inn! Nestled in the charming small town of West Stockbridge, MA, in th...

from $120

4.5 (13)
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Shaker Mill Inn

Shaker Mill Inn

from $120

West Stockbridge, MA

4.5 (13)

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Federal House Inn

South Lee, MA

"We have never experienced hospitality such as yours" The Gambles, Essex, England

from $165

4.6 (149)
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Federal House Inn

Federal House Inn

from $165

South Lee, MA

4.6 (149)

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Old Mill Inn

Hatfield, MA

Beautifully restored grist mill on the banks of the Mill River overlooking private dam and waterfall

from $149

4.6 (46)
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Old Mill Inn

Old Mill Inn

from $149

Hatfield, MA

4.6 (46)

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Centennial House Bed & Breakfast

Northfield, MA

Recognized for excellence, we offer comfort, charm and great food near WMass attractions

from $119

4.8 (35)
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Wainwright Inn

Great Barrington, MA

from $100

4.9 (2)

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Wainwright Inn

Wainwright Inn

from $100

Great Barrington, MA

4.9 (2)

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Conroy's B & B

Stockbridge, MA

from $120

4.3 (24)
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Conroy's B & B

Conroy's B & B

from $120

Stockbridge, MA

4.3 (24)

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from $135

4.9 (34)
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from $129

4.8 (10)
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Penrose Victorian Inn

Haydenville, MA

from $125

5 (1)
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Penrose Victorian Inn

Penrose Victorian Inn

from $125

Haydenville, MA

5 (1)

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from $160

4.5 (31)

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Sawyer Mansion B&B

Whitingham,

from $150

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Sawyer Mansion B&B

Sawyer Mansion B&B

from $150

Whitingham,

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from $135

4.8 (8)

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Candlelight Bed and Breakfast

Candlelight Bed and Breakfast

from $135

Jacksonville, VT

4.8 (8)

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from $195

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The Guest House at Field Farm

The Guest House at Field Farm

from $195

Williamstown, MA

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Journeys End Lodge

Williamstown, MA

from $165

4.9 (3)

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Journeys End Lodge

Journeys End Lodge

from $165

Williamstown, MA

4.9 (3)

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from $130

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Kemble Inn

Lenox, MA

from $335

4.9 (5)
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Kemble Inn

Kemble Inn

from $335

Lenox, MA

4.9 (5)

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Haflinger Haus

adams, MA

from $95

5 (1)

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Haflinger Haus

Haflinger Haus

from $95

adams, MA

5 (1)

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White Horse Inn B&B

Pittsfield, MA

from $100

4.6 (24)
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White Horse Inn B&B

White Horse Inn B&B

from $100

Pittsfield, MA

4.6 (24)

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Dancing Bear Guest House

Shelburne Falls, MA

from $99

4.5 (7)

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Dancing Bear Guest House

Dancing Bear Guest House

from $99

Shelburne Falls, MA

4.5 (7)

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from $160

4.2 (9)

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Poetry Ridge Bed and Breakfast

Poetry Ridge Bed and Breakfast

from $160

Greenfield, MA

4.2 (9)

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Berkshire Mountain House

Stephentown, NY

from $99

4.7 (55)

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Berkshire Mountain House

Berkshire Mountain House

from $99

Stephentown, NY

4.7 (55)

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Windflower Inn

Great Barrington, MA

from $100

5 (3)

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Windflower Inn

Windflower Inn

from $100

Great Barrington, MA

5 (3)

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The Acorn's Hope

Great Barrington, MA

from $125

4.3 (3)
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The Acorn's Hope

The Acorn's Hope

from $125

Great Barrington, MA

4.3 (3)

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Thornewood Inn

Great Barrington, MA

from $115

4.4 (1)

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Thornewood Inn

Thornewood Inn

from $115

Great Barrington, MA

4.4 (1)

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Topia Inn

Adams, MA

from $210

4.4 (32)
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Topia Inn

Topia Inn

from $210

Adams, MA

4.4 (32)

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Eastgate Inn B&B

Lenox, MA

from $95

Eastgate Inn B&B

Eastgate Inn B&B

from $95

Lenox, MA

The Inn at Sweet Water Farm

Great Barrington, MA

from $215

4.7 (5)

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The Inn at Sweet Water Farm

The Inn at Sweet Water Farm

from $215

Great Barrington, MA

4.7 (5)

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Stonover Farm

Lenox, MA

from $325

4.4 (1)

Stonover Farm

Stonover Farm

from $325

Lenox, MA

4.4 (1)

from $75

4.7 (37)
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Shaker Meadows Bed and Breakfast

Shaker Meadows Bed and Breakfast

from $75

New Lebanon,

4.7 (37)

from $95

4.6 (1)

Brookwood Bed and Breakfast

Brookwood Bed and Breakfast

from $95

Plainfield, MA

4.6 (1)

The Knoll

Florence, MA

from $95

4.2 (14)

The Knoll

The Knoll

from $95

Florence, MA

4.2 (14)

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Chesterfield B&B reviews

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