Guide to book Bed & Breakfast in Cheshire, Massachusetts

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Special Rates Available Call 855-516-1090



Harbour House Inn

725 North State Road, Cheshire MA - 1225

(855) 516-1090

1.03 miles

Rating - Harbour House Inn

A complimentary full breakfast is included.

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Topia Inn - An Organic Oasis

10 Pleasant Street, Adams MA - 1220

(855) 516-1090

4.4 miles

Rating - Topia Inn - An Organic Oasis

A complimentary full breakfast is served daily from 8:30 AM to 10 AM.

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Berkshire Mountain House

150 Berkshire Way, Stephentown NY - 12168

(855) 516-1090

11.43 miles

Rating - Berkshire Mountain House

A complimentary buffet breakfast is served daily from 8:30 AM to 10 AM.

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The Cornell Inn, Lenox

203 Main St, Lenox MA - 1240

(855) 516-1090

15.09 miles

Rating - The Cornell Inn, Lenox

Wi-Fi Is Free And The Views Are Stunning At The Non-Smoking Cornell Inn, Set On Four Acres Of Groomed Gardens. The Non-Smoking Cornell Inn Is Set In Three Period-Style Buildings That House 28 Rooms, All Uniquely Furnished And Outfitted With Free Wi-Fi, Cable Tv And Air Conditioning. There'S An Outdoor Deck With Mountain And Waterfall Views, And The Terrace And Garden Invite Restfulness And Daydreaming. Corporate Travelers Are Happy To Know The Inn Features A Business Center With Fax And Copy Services. The Property Is At The Base Of Kennedy Park, A Wooded Nature Preserve With Recreational Trails. It'S A Half-Mile From The Berkshire Equestrian Center And The Historic Village Of Lenox, Where You'Ll Find Art Galleries, Shops And Restaurants. Tanglewood Is Two Miles Away, And Both The Bousquet Ski Area And Berkshire Scenic Railroad Museum Are A 10-Minute Drive. Albany International Airport Is 51 Miles Away.

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Birchwood Inn

7 Hubbard Street, Lenox MA - 1240

(855) 516-1090

15.32 miles

Rating - Birchwood Inn

This Bed And Breakfast In The Scenic Berkshires Boasts Uniquely Styled Guest Rooms, Each With A Private Bathroom. Hiking And Bicycle Trails In Kennedy Park Are Just 1 Mile Away.Rooms At The Birchwood Inn Feature Free Wi-Fi Access And A Seating Area. They Are Decorated In Bright Colours, Wood Floors, And Plush Bedding. Select Rooms Have A Fireplace Or A Tv.Guests Can Relax On The Large Terrace Or In The Library At The Birchwood B&B. Conceirge Services And Daily Newspapers Are Also Available.Enjoy A Full Country Breakfast, Including Dishes Like Apple Pancakes, Fresh Fruit, And Homemade Breads, Served In The Dining Room. Afternoon Tea And Pastries Are Also Offered.Tanglewood Musical Center Is 5 Minutes’ Drive From The Inn. Edith Wharton’S Estate, The Mount, Is 2 Miles Away.

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Eastgate Inn B&B

207 West Street, Lenox MA - 1240

(855) 516-1090

16.34 miles

Rating - Eastgate Inn B&B

The recreational activities listed below are available either on site or nearby; fees may apply.

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Chambery Inn

199 Main St, Lee MA - 1238

(855) 516-1090

18.26 miles

Rating - Chambery Inn

Free Wi-Fi, Individually Decorated Rooms And Breakfast In Bed Are A Few Of The Special Touches At The Chambery Inn, A Historic Converted Building In Lee'S Charming Town Center. The Three-Story Converted Schoolhouse Has Nine Rooms Furnished In French-Inspired Style. The Former Parochial School Retains Many 19Th-Century Architectural Features, Such As Embossed Ceilings, Multiple Fireplaces And Even The Original Schoolhouse Chalkboards As A Nod To Its Past. Each Room Is Unique, With Canopy Beds, Fireplaces And Jetted Tubs Among The Features. Guests Have Access To Free Wi-Fi, But More Importantly, This Bed-And-Breakfast Brings Breakfast To Your Room For You To Enjoy In Private. Parking Is Free. The Bed-And-Breakfast Is On The Main Drag In The Center Of Lee, Making Up Part Of The Charm Of This Classic New England Town. There Are Restaurants Along Main Street As Well As Shopping; And Lee Premium Outlets Are A Mile Away, Including Brooks Brothers, Nike And Banana Republic. Tanglewood Musical Center Is A 10-Minute Drive Away, And Another Area Gem, The Berkshire Scenic Railroad Museum, Is Four Miles Away, Offering Area Tours On Vintage Trains. Bradley International Airport Is 53 Miles And Albany International Airport Is 56 Miles From The Inn.

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Shaker Mill Inn

2 Oak Street, West Stockbridge MA - 1266

(855) 516-1090

19.23 miles

Rating - Shaker Mill Inn

The recreational activities listed below are available either on site or nearby; fees may apply.

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Conroy's B&B

11 East Street (Route 7), Stockbridge MA - 1262

(855) 516-1090

19.54 miles

Rating - Conroy's B&B

Featuring An Outdoor Swimming Pool, Conroy'S B&B Is A Berkshires Farmhouse Located In Stockbridge, Massachusetts. Free Wi-Fi Access Is Available.Air Conditioning And A Fireplace Are Included In Each Room. Private Bathrooms Are Equipped With Free Toiletries. Ironing Facilities Are Also Provided.Conroy'S B&B Is Situated Across 3 Acres And Features A Garden And Shared Terrace. The Property Offers Free Parking.A Breakfast Including Fresh Fruit, Eggs, Coffee And More Is Served Each Morning.Norman Rockwell Museum Is 8 Minutes’ Drive From Conroy’S. Beartown State Forest Is 10 Minutes’ Drive.

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Federal House Inn

1560 Pleasant Street, South Lee MA - 1238

(855) 516-1090

20.82 miles

Rating - Federal House Inn

The recreational activities listed below are available either on site or nearby; fees may apply.

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The Four Chimneys Inn

21 West Road, Bennington VT - 5201

(855) 516-1090

22.29 miles

Rating - The Four Chimneys Inn

Morning Epicurean Feasts, Fireplaces, Bocce Ball And Easy Green Mountains Access Light The Way At The Four Chimneys Inn - Bed And Breakfast. Dating Its Roots To 1783, The Three-Story Four Chimneys Inn Sits On 11 Acres And Features 10 Rooms With High-Speed Internet, Cable Tv And Private Bathrooms. Some Include Jetted Tubs, Fireplaces Or Glassed-In Porches. A Complimentary Gourmet Breakfast Is Provided Daily. Guests Can Also Sip On A Libation In The Lounge And Feast On Dinner Treats In The Restaurant Each Evening. A Cozy Fireplace And Bocce Ball Sets Are Provided. Parking Is Free. Located Within The Shires Of Vermont, The Four Chimneys Inn Is Three Miles From The New York State Line. Williamstown, Mass., Is 12 Miles South. Guests Can Check Out The Local Culture A Half-Mile Away At The Bennington Museum Or Play A Round At Mt. Anthony Country Club Less Than One Mile North. Albany International Airport Is 40 Miles Southwest.

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Harbour House Inn

725 North State Road, Cheshire, MA - 1225

1.03 miles

Rating - Harbour House Inn

A complimentary full breakfast is included.

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Topia Inn - An Organic Oasis

10 Pleasant Street, Adams, MA - 1220

4.4 miles

Rating - Topia Inn - An Organic Oasis

A complimentary full breakfast is served daily from 8:30 AM to 10 AM.

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Berkshire Mountain House

150 Berkshire Way, Stephentown, NY - 12168

11.43 miles

Rating - Berkshire Mountain House

A complimentary buffet breakfast is served daily from 8:30 AM to 10 AM.

Read more
The Cornell Inn, Lenox

203 Main St, Lenox, MA - 1240

15.09 miles

Rating - The Cornell Inn, Lenox

Wi-Fi Is Free And The Views Are Stunning At The Non-Smoking Cornell Inn, Set On Four Acres Of Groomed Gardens. The Non-Smoking Cornell Inn Is Set In Three Period-Style Buildings That House 28 Rooms, A...

Read more
Birchwood Inn

7 Hubbard Street, Lenox, MA - 1240

15.32 miles

Rating - Birchwood Inn

This Bed And Breakfast In The Scenic Berkshires Boasts Uniquely Styled Guest Rooms, Each With A Private Bathroom. Hiking And Bicycle Trails In Kennedy Park Are Just 1 Mile Away.Rooms At The Birchwood ...

Read more
Eastgate Inn B&B

207 West Street, Lenox, MA - 1240

16.34 miles

Rating - Eastgate Inn B&B

The recreational activities listed below are available either on site or nearby; fees may apply.

Read more
Chambery Inn

199 Main St, Lee, MA - 1238

18.26 miles

Rating - Chambery Inn

Free Wi-Fi, Individually Decorated Rooms And Breakfast In Bed Are A Few Of The Special Touches At The Chambery Inn, A Historic Converted Building In Lee'S Charming Town Center. The Three-Story Convert...

Read more
Shaker Mill Inn

2 Oak Street, West Stockbridge, MA - 1266

19.23 miles

Rating - Shaker Mill Inn

The recreational activities listed below are available either on site or nearby; fees may apply.

Read more
Conroy's B&B

11 East Street (Route 7), Stockbridge, MA - 1262

19.54 miles

Rating - Conroy's B&B

Featuring An Outdoor Swimming Pool, Conroy'S B&B Is A Berkshires Farmhouse Located In Stockbridge, Massachusetts. Free Wi-Fi Access Is Available.Air Conditioning And A Fireplace Are Included In Each R...

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Federal House Inn

1560 Pleasant Street, South Lee, MA - 1238

20.82 miles

Rating - Federal House Inn

The recreational activities listed below are available either on site or nearby; fees may apply.

Read more
The Four Chimneys Inn

21 West Road, Bennington, VT - 5201

22.29 miles

Rating - The Four Chimneys Inn

Morning Epicurean Feasts, Fireplaces, Bocce Ball And Easy Green Mountains Access Light The Way At The Four Chimneys Inn - Bed And Breakfast. Dating Its Roots To 1783, The Three-Story Four Chimneys Inn...

Read more

Map of Cheshire Bed & Breakfast Hotels

View all Cheshire, Massachusetts hotels, motels, lodging and attractions on Cheshire, Massachusetts location map.


Weather Forecast for Cheshire, Massachusetts

If you planning to travel to Cheshire, Massachusetts, here is your 6-day travel weather forecast to make sure you have all the essentials needed during your stay. Start your day when the sunrises at 12:18 PM. The temperature feels like 9.5 with a humidity level of 66 so dress accordingly. Cloud coverage is 75 percent with visibility at 11.8 percent. Today’s UV index is 1, don’t forget the sunscreen if you need it! Today’s winds are traveling north-northwest at a speed of 9 MPH. At the end of the day don’t miss the sunset at 9:23 PM.


Fahrenheit / Celsius
Saturday 12/21
Overcast clouds

Saturday 12/21 Weather forecast for Cheshire, Massachusetts, Overcast clouds
20°F
High: 24°F
Low: 2°F
Precipitation: 0%
Today 12/22
Few clouds

Sunday 12/22 Weather forecast for Cheshire, Massachusetts, Few clouds
9°F
High: 16°F
Low: 1°F
Precipitation: 0%
Monday 12/23
Scattered clouds

Monday 12/23 Weather forecast for Cheshire, Massachusetts, Scattered clouds
15°F
High: 26°F
Low: 18°F
Precipitation: 0%
Tuesday 12/24
Light snow

Tuesday 12/24 Weather forecast for Cheshire, Massachusetts, Light snow
26°F
High: 34°F
Low: 15°F
Precipitation: 90%
Wednesday 12/25
Broken clouds

Wednesday 12/25 Weather forecast for Cheshire, Massachusetts, Broken clouds
24°F
High: 34°F
Low: 18°F
Precipitation: 0%
Thursday 12/26
Broken clouds

Thursday 12/26 Weather forecast for Cheshire, Massachusetts, Broken clouds
25°F
High: 39°F
Low: 21°F
Precipitation: 0%

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