Guide to book Bed & Breakfast in Chester, Massachusetts

Savings up to 60% Off!

Special Rates Available Call 855-516-1090



Chambery Inn

199 Main St, Lee MA - 1238

(855) 516-1090

14.38 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.

Read more
Federal House Inn

1560 Pleasant Street, South Lee MA - 1238

(855) 516-1090

15.91 miles

Rating - Federal House 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

(855) 516-1090

16.47 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.

Read more
Birchwood Inn

7 Hubbard Street, Lenox MA - 1240

(855) 516-1090

16.68 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.

Read more
The Cornell Inn, Lenox

203 Main St, Lenox MA - 1240

(855) 516-1090

16.75 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.

Read more
The Ellery

259 Elm Street, Northampton MA - 1060

(855) 516-1090

16.97 miles

Rating - The Ellery

Complimentary Breakfast, An Outdoor Pool And Rooms With Flat-Panel Tvs And Free Wi-Fi Help Our Guests Feel At Home At The Non-Smoking Autumn Inn. Renovated In 2010, The Two-Story, Non-Smoking Autumn Inn Offers 32 Rooms That Include Flat-Panel Tvs With Premium Cable, Complimentary Wi-Fi And Coffeemakers. The Hotel Serves A Free Continental Breakfast Each Morning In The Great Room. Guests May Stop By The Lobby To Check Email And Print Boarding Passes From The Computer Workstation Or, During Winter Months, Enjoy The Warmth Of The Large Fireplace. The Property Also Features A Seasonal Outdoor Pool. The Front Desk Is Open 24 Hours A Day For Added Convenience. The Autumn Inn Is Located In Central Northampton, A Few Blocks From The Campus Of Smith College. The Hotel'S Central Location Puts It A 15-Minute Walk From The Fort Hill Historic District, Childs Park And The Museum Of Art And The Botanic Garden At Smith College. There Are Numerous Parks And Conservation Areas Along The Connecticut River, 10 Minutes Away By Car, And The University Of Massachusetts Amherst Is Less Than 10 Miles Northeast. Bradley International Airport Is 35 Miles South. Hartford, Connecticut Is 45 Miles South Of The Property.

Read more
Eastgate Inn B&B

207 West Street, Lenox MA - 1240

(855) 516-1090

17.6 miles

Rating - Eastgate Inn B&B

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

Read more
Old Mill Inn

87 School St, Hatfield MA - 1038

(855) 516-1090

19.67 miles

Rating - Old Mill Inn

Old Mill Inn Is Located In A Historic Building In Hatfield, Right Next To A Waterfall. Free Wi-Fi Access Is Available.Rooms Here Will Provide You With A Private Bathroom With Shower Or Bathtub, Air Conditioning And Flat-Screen Cable Tv. Some Rooms Have A River View. Extras Include Linen And A Coffee Machine.At Old Mill Inn You Will Find A Garden And A Terrace. Free Parking Is Possible And Complimentary Breakfast Is Served Daily On Site.The Property Is 9 Km From Smith College And 49 Km From Bradley Airport. Several Dining Options Are Located Within 2 Km.

Read more
Shaker Mill Inn

2 Oak Street, West Stockbridge MA - 1266

(855) 516-1090

20.61 miles

Rating - Shaker Mill Inn

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

Read more
Harbour House Inn

725 North State Road, Cheshire MA - 1225

(855) 516-1090

22.18 miles

Rating - Harbour House Inn

A complimentary full breakfast is included.

Read more
Manor House Inn

69 Maple Ave, Norfolk CT - 6058

(855) 516-1090

23.15 miles

Rating - Manor House Inn

A Victorian Tudor Home With Tiffany Windows Built In 1898, The Sophisticated Manor House - Bed And Breakfast - Adults Only Now Offers Rooms Decorated With Antiques And Equipped With Two-Person Jetted Tubs And Other Indulgences. The Three-Story, Non-Smoking Bed-And-Breakfast Has Eight Rooms Featuring Private Baths With Two-Person Jetted Tubs, Plus Luxuries Like Plush Robes, Fluffy Towels And Crisp Bedding With Down Comforters. Some Rooms Have Wood-Burning Fireplaces; Others Are Furnished With Private Balconies Overlooking The Grounds, Garden And Gazebo. Spa Services, Including Massages, Facials And Body Treatments, Are Available With Reservations, And Made-To-Order Picnic Baskets May Be Requested For Al Fresco Dining. A Complimentary Hot Breakfast Is Served Daily. Parking Is Free. Please Note That Front Desk Hours Vary At Bed-And-Breakfast Properties. Guests Planning To Arrive Before Or After The 2Pm Check-In Time Should Contact The Inn For Special Instructions. The Inn, A 10-Minute Walk From The Downtown Area, Is Nine Miles From Falls Village, 11 Miles From Lime Rock Park And 12 Miles From Mohawk Mountain Ski Area. It'S 15 Miles To Butternut, 20 Miles To The Berkshires And 35 Miles To Bradley International Airport.

Read more
Blackberry River Inn

538 Greenwoods Road West, Norfolk CT - 6058

(855) 516-1090

23.65 miles

Rating - Blackberry River Inn

Cozy Rooms, Free Wi-Fi And Breakfast And An Outdoor Pool Make The Blackberry River Inn A Sweet Norfolk Getaway. The Two-Story Blackberry River Inn, Dating To The 19Th Century, Sits On 27 Acres And Offers 17 Uniquely Designed Rooms Featuring Free Wi-Fi And Cable Tv; Some Also Offer Wood Burning Fireplaces And Ipod Docks. Guests Can Dine On Complimentary Morning Goodies In The Sun-Bathed Breakfast Room And Take A Summertime Dip In The Seasonal Outdoor Pool. Warm Up By The Fireplace Or With Afternoon Tea In The Library. Front Desk Hours Are Limited At The Inn. Just Over Six Miles South Of The Massachusetts Border, The Blackberry River Inn Provides A Northwestern Connecticut Setting In Norfolk. In Less Than Five Minutes By Car, Guests Land In The Historic Heart Of Town, Home Of Infinity Hall And The Farmers' Market. A 10-Minute Drive North Leads Outdoor Lovers To The Waterfall At Campbell Falls State Park Reserve. Bradley International Airport Is Less Than 40 Miles East Of The Property.

Read more
The Windflower Inn

684 South Egremont Road, Great Barrington MA - 1230

(855) 516-1090

23.72 miles

Rating - The Windflower Inn

A complimentary full breakfast is served daily.

Read more
Topia Inn - An Organic Oasis

10 Pleasant Street, Adams MA - 1220

(855) 516-1090

24.4 miles

Rating - Topia Inn - An Organic Oasis

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

Read more
Chambery Inn

199 Main St, Lee, MA - 1238

14.38 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
Federal House Inn

1560 Pleasant Street, South Lee, MA - 1238

15.91 miles

Rating - Federal House 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

16.47 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...

Read more
Birchwood Inn

7 Hubbard Street, Lenox, MA - 1240

16.68 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
The Cornell Inn, Lenox

203 Main St, Lenox, MA - 1240

16.75 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
The Ellery

259 Elm Street, Northampton, MA - 1060

16.97 miles

Rating - The Ellery

Complimentary Breakfast, An Outdoor Pool And Rooms With Flat-Panel Tvs And Free Wi-Fi Help Our Guests Feel At Home At The Non-Smoking Autumn Inn. Renovated In 2010, The Two-Story, Non-Smoking Autumn I...

Read more
Eastgate Inn B&B

207 West Street, Lenox, MA - 1240

17.6 miles

Rating - Eastgate Inn B&B

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

Read more
Old Mill Inn

87 School St, Hatfield, MA - 1038

19.67 miles

Rating - Old Mill Inn

Old Mill Inn Is Located In A Historic Building In Hatfield, Right Next To A Waterfall. Free Wi-Fi Access Is Available.Rooms Here Will Provide You With A Private Bathroom With Shower Or Bathtub, Air Co...

Read more
Shaker Mill Inn

2 Oak Street, West Stockbridge, MA - 1266

20.61 miles

Rating - Shaker Mill Inn

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

Read more
Harbour House Inn

725 North State Road, Cheshire, MA - 1225

22.18 miles

Rating - Harbour House Inn

A complimentary full breakfast is included.

Read more
Manor House Inn

69 Maple Ave, Norfolk, CT - 6058

23.15 miles

Rating - Manor House Inn

A Victorian Tudor Home With Tiffany Windows Built In 1898, The Sophisticated Manor House - Bed And Breakfast - Adults Only Now Offers Rooms Decorated With Antiques And Equipped With Two-Person Jetted ...

Read more
Blackberry River Inn

538 Greenwoods Road West, Norfolk, CT - 6058

23.65 miles

Rating - Blackberry River Inn

Cozy Rooms, Free Wi-Fi And Breakfast And An Outdoor Pool Make The Blackberry River Inn A Sweet Norfolk Getaway. The Two-Story Blackberry River Inn, Dating To The 19Th Century, Sits On 27 Acres And Off...

Read more
The Windflower Inn

684 South Egremont Road, Great Barrington, MA - 1230

23.72 miles

Rating - The Windflower Inn

A complimentary full breakfast is served daily.

Read more
Topia Inn - An Organic Oasis

10 Pleasant Street, Adams, MA - 1220

24.4 miles

Rating - Topia Inn - An Organic Oasis

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

Read more

Map of Chester Bed & Breakfast Hotels

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


Weather Forecast for Chester, Massachusetts

Traveling to Chester, Massachusetts? Here is your 6-day weather forecast in the area. Whether it is a warm weather destinations or cold climate don’t forget to consider weather, while you pack your bags for this trip. Start your day when the sunrises at 11:47 AM and don’t miss the sunset at 9:26 PM. Today’s winds are traveling west-northwest at a speed of 10 MPH. The temperature feels like 45 with a humidity level of 67. Cloud coverage is 31 percent with 13.9 percent visibility. Today’s UV index is 2 make sure to prepare properly. Make sure to plan your travel itinerary to match your travel weather forecast to make the most of your vacation with Reservations.com.


Fahrenheit / Celsius
Monday 11/18
Scattered clouds

Monday 11/18 Weather forecast for Chester, Massachusetts, Scattered clouds
47°F
High: 55°F
Low: 35°F
Precipitation: 0%
Today 11/19
Few clouds

Tuesday 11/19 Weather forecast for Chester, Massachusetts, Few clouds
42°F
High: 52°F
Low: 34°F
Precipitation: 0%
Wednesday 11/20
Broken clouds

Wednesday 11/20 Weather forecast for Chester, Massachusetts, Broken clouds
43°F
High: 54°F
Low: 39°F
Precipitation: 20%
Thursday 11/21
Heavy rain

Thursday 11/21 Weather forecast for Chester, Massachusetts, Heavy rain
42°F
High: 46°F
Low: 33°F
Precipitation: 90%
Friday 11/22
Mix snow/rain

Friday 11/22 Weather forecast for Chester, Massachusetts, Mix snow/rain
37°F
High: 44°F
Low: 32°F
Precipitation: 80%
Saturday 11/23
Overcast clouds

Saturday 11/23 Weather forecast for Chester, Massachusetts, Overcast clouds
38°F
High: 44°F
Low: 35°F
Precipitation: 35%

Loading...