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Canaan Bed and Breakfasts

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1800 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 (181)
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Birchwood Inn

Lenox, MA

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

from $199

4.8 (25)
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Birchwood Inn

Birchwood Inn

from $199

Lenox, MA

4.8 (25)

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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 (104)
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The Garden Gables Inn

The Garden Gables Inn

from $220

Lenox, MA

4.6 (104)

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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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Applegate Inn

Lee, MA

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

from $150

4.5 (124)
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Applegate Inn

Applegate Inn

from $150

Lee, MA

4.5 (124)

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Brook Farm Inn

Lenox, MA

There is poetry here. Brook Farm Inn welcomes you to the grace of its past and the comforts of th...

from $159

4.6 (12)
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Brook Farm Inn

Brook Farm Inn

from $159

Lenox, MA

4.6 (12)

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Rookwood Inn

Lenox, MA

"Where Memories are Made"

from $185

4.6 (42)
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Rookwood Inn

Rookwood Inn

from $185

Lenox, MA

4.6 (42)

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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 (98)
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Inn at Stockbridge

Inn at Stockbridge

from $170

Stockbridge, MA

4.4 (98)

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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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Cornell Inn, Lenox

Lenox, MA

You're gonna LOVE it here!

from $99

4.3 (245)
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Cornell Inn, Lenox

Cornell Inn,  Lenox

from $99

Lenox, MA

4.3 (245)

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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 $90

4.0 (78)
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Whistlers Inn

Whistlers Inn

from $90

Lenox, MA

4.0 (78)

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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 (12)
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House On Main Street

House On Main Street

from $99

Williamstown, MA

4.1 (12)

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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 (43)
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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 Post Cottage

Catskill, NY

Spacious and luxurious Shingle Style house in Catkill close to all Catskill attractions

from $220

4.9 (18)
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The Post Cottage

The Post Cottage

from $220

Catskill, NY

4.9 (18)

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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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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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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 (32)
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The Birches at Steep Acres Farm

The Birches at Steep Acres Farm

from $125

Williamstown, MA

4.7 (32)

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B&B at Howden Farm

Sheffield, MA

Howden Farm is a 250 acre working farm in the Berkshires. We grow blueberries, raspberries and s...

from $119

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B&B at Howden Farm

B&B at Howden Farm

from $119

Sheffield, MA

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Federal House Inn

South Lee, MA

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

from $150

4.6 (133)
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Federal House Inn

Federal House Inn

from $150

South Lee, MA

4.6 (133)

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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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Inn at Silver Maple Farm

East Chatham, NY

Elegant simplicity minutes from Hudson, Lenox, Stockbridge, Lee and Chatham.

from $130

4.9 (3)
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Inn at Silver Maple Farm

Inn at Silver Maple Farm

from $130

East Chatham, NY

4.9 (3)

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Front Street Guest House

Hudson, NY

Super comfy beds w/ the best of linens, Tivoli radios, free wifi, flat screens in every room

from $139

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Inn At Richmond

Richmond, MA

The Inn at Richmond, a Relaxing and Gracious Four Season Country Inn in the Berkshires

from $160

4.2 (36)
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Inn At Richmond

Inn At Richmond

from $160

Richmond, MA

4.2 (36)

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The Inn at Ca' Mea

Hudson, NY

Book online at our website innatcamea or camearestaurant It makes no difference what time of yea...

from $120

4.7 (5)

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The Inn at Ca' Mea

The Inn at Ca' Mea

from $120

Hudson, NY

4.7 (5)

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Mount Merino Manor

Hudson, NY

Enjoy the comfort of Mount Merino Manor, an elegant Bed and Breakfast in a private country setting

from $135

5.0 (4)

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Mount Merino Manor

Mount Merino Manor

from $135

Hudson, NY

5.0 (4)

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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 ...

from $109

4.4 (12)
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Shaker Mill Inn

Shaker Mill Inn

from $109

West Stockbridge, MA

4.4 (12)

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A Mountain View Retreat

Germantown, NY

A Former Small Hunting Lodge Renovated into a Posh, Exclusive B&B on 20 Beautiful Wooded Acres

The Croff House Bed & Breakfast

Hudson, NY

The Croff House combines the personalized service of a B&B and the luxury of a boutique hotel.

from $170

4.7 (195)

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The Croff House Bed & Breakfast

The Croff House Bed & Breakfast

from $170

Hudson, NY

4.7 (195)

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Hudson City Bed and Breakfast

Hudson, NY

Step back in time to the comfort and fine accommodations of 19th Century Victorian America. We of...

from $100

4.5 (6)

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Hudson City Bed and Breakfast

Hudson City Bed and Breakfast

from $100

Hudson, NY

4.5 (6)

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The Berkshire 1802 House B&B

Sheffield, MA

Enjoy a delicious breakfast while relaxing in a quintessential country setting.

from $95

4.9 (6)
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The Berkshire 1802 House B&B

The Berkshire 1802 House B&B

from $95

Sheffield, MA

4.9 (6)

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The Briarcliff Motel

Great Barrington, MA

Classic 60s motor lodge, transformed into a friendly, contemporary 16-room hotel.

The Briarcliff Motel

The Briarcliff Motel

from $90

Great Barrington, MA

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26 warren B & B

hudson, NY

from $160

4.7 (14)
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26 warren B & B

26 warren B & B

from $160

hudson, NY

4.7 (14)

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from $175

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Westcott House B & B

Westcott House B & B

from $175

Hudson, NY

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Kemble Inn

Lenox, MA

from $115

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Kemble Inn

Kemble Inn

from $115

Lenox, MA

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Greenville Arms 1889 Inn

Greenville, NY

from $115

4.1 (26)
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Greenville Arms 1889 Inn

Greenville Arms 1889 Inn

from $115

Greenville, NY

4.1 (26)

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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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from $55

4.6 (35)
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Olde Judge Mansion

Olde Judge Mansion

from $55

Troy, NY

4.6 (35)

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Berkshire Mountain House

Stephentown, NY

from $99

4.7 (52)

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Berkshire Mountain House

Berkshire Mountain House

from $99

Stephentown, NY

4.7 (52)

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from $100

4.1 (218)

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Union Street Guest House

Union Street Guest House

from $100

Hudson, NY

4.1 (218)

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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 (21)
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White Horse Inn B&B

White Horse Inn B&B

from $100

Pittsfield, MA

4.6 (21)

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VanWinkle Inn

Greenville, NY

from $139

4.6 (12)
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VanWinkle Inn

VanWinkle Inn

from $139

Greenville, NY

4.6 (12)

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from $135

4.7 (2)
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The Morgan State House

The Morgan State House

from $135

Albany, NY

4.7 (2)

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Inn At Green River

Hillsdale, NY

from $139

4.5 (42)

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Inn At Green River

Inn At Green River

from $139

Hillsdale, NY

4.5 (42)

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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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Van Schaack House

Kinderhook, NY

from $150

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Van Schaack House

Van Schaack House

from $150

Kinderhook, NY

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from $175

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The Guest House at Field Farm

The Guest House at Field Farm

from $175

Williamstown, MA

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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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1896 House

Williamstown, MA

from $179

4.5 (65)
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1896 House

1896 House

from $179

Williamstown, MA

4.5 (65)

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Mile Hill B&B

Kinderhook, NY

from $100

4.9 (9)

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Mile Hill B&B

Mile Hill B&B

from $100

Kinderhook, NY

4.9 (9)

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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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The Inn on East Main Street

North Adams, MA

from $180

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The Inn on East Main Street

The Inn on East Main Street

from $180

North Adams, MA

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from $140

4.5 (20)

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Thyme in the Country

Thyme in the Country

from $140

Hudson, NY

4.5 (20)

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from $100

4.9 (20)

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Angel Wing Hollow Bed & Breakfast

Angel Wing Hollow Bed & Breakfast

from $100

Niverville, NY

4.9 (20)

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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 $160

4.6 (28)

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from $100

4.6 (1)

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THE COUNTRY SQUIRE B&B

THE COUNTRY SQUIRE B&B

from $100

Hudson, NY

4.6 (1)

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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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Blackinton Manor

North Adams, MA

from $120

4.0 (3)

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Blackinton Manor

Blackinton Manor

from $120

North Adams, MA

4.0 (3)

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from $95

Brookwood Bed and Breakfast

Brookwood Bed and Breakfast

from $95

Plainfield, MA

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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Pine Haven B&B

Albany, NY

from $69

2.4 (1)

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Pine Haven B&B

Pine Haven B&B

from $69

Albany, NY

2.4 (1)

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Eastgate Inn B&B

Lenox, MA

from $95

Eastgate Inn B&B

Eastgate Inn B&B

from $95

Lenox, MA

Stonover Farm

Lenox, MA

from $325

4.4 (1)

Stonover Farm

Stonover Farm

from $325

Lenox, MA

4.4 (1)

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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Canaan B&B reviews

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The Canaan B&B review score is based on feedback from travelers from around the world. See property page for full, detailed reviews by real travelers.

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