Pet-friendly Hotels in Cheshire, Massachusetts

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Hotel On North

297 North Street, Pittsfield MA - 1201

(855) 516-1090

9.17 miles

Rating - Hotel On North

Free Wi-Fi, Boutique Rooms, Fine Dining And A Central Pittsfield Location A Block From The Amtrak Station Are The Attractions Of A Stay At The Non-Smoking Hotel On North. Opened In 2015, The Non-Smoking Hotel On North Has 45 Rooms In A Pair Of Four-Floor, 19Th-Century Buildings With Preserved Architectural Features Like Exposed Brick Walls And Tin Ceilings. The Interiors Feature Locally Crafted Furniture. Rooms Start At 300 Square Feet And Come With In-Room Safes, Mini-Bars, Coffee/Tea Makers, Free Filtered Water, Free Wi-Fi, Mp3 Plug-Ins And Bluetooth-Enabled Audio, Flat-Panel Hd Smart Tvs, Bathrobes And Plush Beds With Serta Pillowtop Mattresses And Mascioni Linens. Some Rooms Have Some Combination Of Gas Fireplaces, Wet Bars, Kitchenettes, Washers And Dryers, Sofa Beds, Mountain Views And Separate Tubs And Showers. You Can Order Room Service Or Dine In The Innovative Restaurant With Globally Inspired, Locally Sourced Cuisine. Mingle With Other Guests In The Lounge With Free Morning Coffee And Tea, Newspapers, Board Games, Vintage Puzzles And More. The Hotel Also Has A Cocktail Lounge, Atrium Sitting Area, Art Gallery, Fitness Room, Business Corner, Boutique Gift Shop, Free Overnight Shoeshine And On-Site Parking. The Hotel On North Is In Central Pittsfield Next To The Barrington Stage Company, A Block North Of The Amtrak Station. The Berkshire Museum Is A Little Less Than A Half-Mile South, The Colonial Theatre Is A Half-Mile South And Hancock Shaker Village Is Five Miles Southwest. If You'Re Coming From The Albany Area, The Hotel Is 38 Miles Southeast Of The City Center And 47 Miles Southeast Of Albany International Airport. Hotel On North Is A Boutique Berkshires Haven For Priceline Guests, Who Enjoy Charming Rooms, Free Wi-Fi And Excellent Dining.

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Williamstown Motel

295 Main Street, Williamstown MA - 1267

(855) 516-1090

9.83 miles

Rating - Williamstown Motel

Free Wi-Fi, In-Room Microwaves And Refrigerators, And A Location Near Skiing And Other Berkshires Attractions Are The Perks That Attract Guests To The Non-Smoking Williamstown Motel. The Single-Story, Non-Smoking Williamstown Motel Features 18 Rooms, Each Of Which Features A Flat-Panel Cable Tv, Air Conditioning, Microwave, Refrigerator And Free Wi-Fi Access. The Hotel Serves A Complimentary Continental Breakfast. The Front Desk Is Staffed 24-Hours, A Boon For Guests Arriving Late. Parking Is Free. The Williamstown Motel Is Two Miles From Downtown Williamstown And A Five-Minute Drive From Williams College. It'S Also Two Miles From The Clark Art Institute. Jiminy Peak Ski Resort Is A 20-Minute Drive From The Hotel. Albany International Airport Is 44 Miles Away.

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The Porches Inn

231 River Street, North Adams MA - 1247

(855) 516-1090

9.84 miles

Rating - The Porches Inn

Inspired By The Massachusetts Museum Of Contemporary Art And Known For Its Retro-Edgy Design, The Non-Smoking The Porches Inn At Mass Moca Features On-Site Art Exhibitions, Free Wi-Fi And An Outdoor Pool With Heated Pool Deck. Comprised Of A Row Of Restored Victorian Townhomes With A Retro Feel, The Non-Smoking The Porches Inn Is Is Home To 47 Rooms. Standard In-Room Features Include Free Wi-Fi, Eclectic Furnishings, Custom Window Treatments, Flat-Panel Tvs, Hairdryers, Minibars And Private Bathrooms With Slate Floors. Mornings Start With A Breakfast Buffet. Afterwards, Guests Take Advantage Of The Workout Room And Sauna. Some Of The Inn'S Most Distinct Features Are Found Outdoors, Including Its Year-Round Outdoor Heated Pool And Heated Deck, Hot Tub, Bonfire Pit, Gazebo And Native Woodland Garden. Pets Are Welcome For An Additional Fee. Parking Is Free. The Porches Inn Sits Directly Across The Street From The Massachusetts Museum Of Contemporary Art And Is A 15-Minute Walk From A Number Of Art Galleries. Williams College Museum Of Art Is Five Miles From The Inn, And Recreation At Mt. Greylock Is A 30-Minute Drive. Bradley International Airport Is 74 Miles Away.

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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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Green Valley Motel

1214 Simonds Rd, Williamstown MA - 1267

(855) 516-1090

12.89 miles

Rating - Green Valley Motel

The Freebies Include Wi-Fi, Parking And Local Calls At The Green Valley Motel In Williamstown, Where The Outdoor Pool Is Open Seasonally. The Two-Story, Exterior-Corridor Green Valley Motel Has 17 Budget-Friendly Rooms That All Include Free Wi-Fi, Cable Tv, Microwaves And Mini-Fridges. Non-Smoking Accommodations Are Available. Guests Cool Off In The Seasonal Outdoor Pool When The Sun'S Shining. Local Calls And Outdoor Parking Are Free, And Pets Are Allowed For A Small Fee. The Green Valley Motel Is In Rural Massachusetts, Just South Of The Vermont State Line. It'S Less Than Three Miles From The Center Of Williamstown And Williams College. An Hour'S Drive Lands Guests At The Famous Tanglewood Musical Center In Lenox Or The Norman Rockwell Museum In Stockbridge. Pittsfield Is A 35-Minute Drive And Offers A Variety Of Historic Attractions, Including The Home Of Herman Melville, Hancock Shaker Village And The Berkshire Museum. Jiminy Peak Mountain Resort Is A 20-Minute Drive. Albany International Airport Is 41 Miles West.

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Ladd Brook Inn

5939 Route 7, Pownal VT - 5261

(855) 516-1090

14.55 miles

Rating - Ladd Brook Inn

Whether You'Re Visiting The Green Mountains Or Berkshires For Business Or Pleasure, Ladd Brook Inn Offers Accommodations With In-Room Amenities. This Property Is Located 3.4 Km From The Massachusetts State Border And 8 Km From The New York State Border.A Cable Tv, Seating Area And Work Desk Are Included In All Rooms At The Ladd Brook Inn. The Hotel Staff Is Available Around The Clock At The 24-Hour Front Desk.A Continental Breakfast Is Served Each Morning At The Pownal Ladd Brook Inn.This Property Is Located 7.4 Km From Williams College, 7.2 Km From Williamstown Theater Festival And 7.5 Km From Williams College Museum Of Art.

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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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Seven Hills Inn

40 Plunkett Street, Lenox MA - 1240

(855) 516-1090

17 miles

Rating - Seven Hills Inn

Boasting A Seasonal Outdoor Swimming Pool, Seven Hills Inn Is Set In Lenox, 2.8 Km From Tanglewood. This 4-Star Inn Offers A Garden. Each Room Is Fitted With A Balcony With Garden Views.All Units In The Inn Are Equipped With A Flat-Screen Tv. The Rooms Are Equipped With A Private Bathroom, And Selected Rooms Come With A Patio. The Units At Seven Hills Inn Include Air Conditioning And A Desk.Tanglewood Musical Center Is 3.1 Km From The Accommodation. Albany International Airport Is 63 Km Away.

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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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Econo Lodge Lee - Great Barrington

980 Pleasant Street, Lee MA - 1238

(855) 516-1090

20.38 miles

Rating - Econo Lodge Lee - Great Barrington

Continental Breakfast And Wi-Fi Are Found At The Econo Lodge Lee, Where All Rooms Include The Convenience Of Microwaves And Mini-Fridges. The Low-Rise Hotel Has 23 Exterior-Corridor Rooms With Wi-Fi, Cable Tv, Mini-Fridges And Microwaves; Some Rooms Also Have Jetted Tubs. Brew A Cup Of Coffee From Your In-Room Machine Before Heading To The Continental Breakfast Each Morning, And Pick Up Snacks And Drinks Anytime At The On-Site Vending Machines. Parking Is Free, And Pets Can Stay For A Fee. The Hotel Is Two Miles From I-90 And The Lee Premium Outlets. It'S Five Miles From Historic Stockbridge, Home Of The Norman Rockwell Museum. Lee'S Charming Town Center, Two-And-A-Half-Miles North, Is Full Of Dining And Shopping Options. The Hotel Is 54 Miles From Bradley International Airport In Connecticut And 56 Miles From Albany International In New York State.

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Paradise Inn

141 West Main Street, Bennington VT - 5201

(855) 516-1090

22.18 miles

Rating - Paradise Inn

Featuring An Outdoor Pool, Tennis, Shuffleboard, Pickleball Courts And A Restaurant, Paradise Inn Is Located In Bennington And Offers Free Wifi. All Rooms Have Splendid Pool And Garden Views.Providing A Tranquil Environment, The Rooms Here Feature Air Conditioning, Balconies, Patios And Private Bathrooms.Guests At Paradise Inn Are Welcome To Use The Onsite Laundry Services And Vending Machine. Free Parking Is Possible On Site.The Motel Is 1.9 Km From Bennington Center For The Arts, 2.1 Km From Bennington Battle Monument And 6.3 Km From North Bennington Historic District. Albany International Airport Is 51 Km Away.

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The Briarcliff Motel

506 Stockbridge Road, Great Barrington MA - 1230

(855) 516-1090

24.14 miles

Rating - The Briarcliff Motel

Surrounded By The Berkshires, This Motel Is 8 Km From Ski Butternut And Boasts Free Wi-Fi Access And Views Of Monument Mountain. The Norman Rockwell Museum Is 10 Minutes’ Drive Away.Each Room At The Briarcliff Features A Flat-Screen Tv, An Ipod Docking Station, And An En Suite Bathroom. They Are Decorated In Contemporary Design, Soft Colours, And Stylish Furnishings.Guests Can Relax In Air Conditioned Comfort At The Motel Briarcliff. Bicycles For Hire Are Available During Warm Weather Months, While Ski Storage Is Offered In The Winter. The Property Also Has An Outdoor Fire Pit.A Continental Breakfast Of Homemade Granola, Fruit, And Yogurt Is Served Every Morning.The Tanglewood Musical Center Is 15 Minutes’ Drive From The Motel. Enjoy The Fall Foliage At Fountain Pond Park, Just 1.6 Km Away.

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Travelodge by Wyndham Great Barrington Berkshires

400 Stockbridge Rd, Great Barrington MA - 1230

(855) 516-1090

24.91 miles

Rating - Travelodge by Wyndham Great Barrington Berkshires

Buffet Breakfast And Complimentary Wi-Fi Are On Offer At The Travelodge By Wyndham Great Barrington, Where There'S Also An Outdoor Pool, In A Location Right Outside Of Town. The Two-Story, 80-Room Hotel Has A Seasonal Outdoor Pool Where You Can Swim In The Fresh Mountain Air, And A Lounge Area To Sunbathe In. Rooms Have Desks Where You Can Set Up Your Laptop To Take Advantage Of The Free Wi-Fi; And There Are Mini-Fridges, Microwaves And Coffeemakers In Every Room. A Breakfast Buffet Is Served Daily, With Favorites Like Oatmeal, Pastries, Fresh Fruit And Bagels. Parking Is Free. The Hotel Is Less Than Two Miles From The Town'S Historic Center With Its Adorable Boutiques And Eateries. There Are Also A Number Of Restaurants And A Brewery Within Walking Distance Of The Hotel. Go Hiking At Monument Mountain Reservation, Two Miles North, Or Visit The Norman Rockwell Museum In Stockbridge, A 10-Minute Drive. Tanglewood Is 20 Minutes Away. Bradley International Airport Is 48 Miles Away, And Albany International Airport Is 53 Miles.

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Hotel On North

297 North Street, Pittsfield, MA - 1201

9.17 miles

Rating - Hotel On North

Free Wi-Fi, Boutique Rooms, Fine Dining And A Central Pittsfield Location A Block From The Amtrak Station Are The Attractions Of A Stay At The Non-Smoking Hotel On North. Opened In 2015, The Non-Smoki...

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Williamstown Motel

295 Main Street, Williamstown, MA - 1267

9.83 miles

Rating - Williamstown Motel

Free Wi-Fi, In-Room Microwaves And Refrigerators, And A Location Near Skiing And Other Berkshires Attractions Are The Perks That Attract Guests To The Non-Smoking Williamstown Motel. The Single-Story,...

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The Porches Inn

231 River Street, North Adams, MA - 1247

9.84 miles

Rating - The Porches Inn

Inspired By The Massachusetts Museum Of Contemporary Art And Known For Its Retro-Edgy Design, The Non-Smoking The Porches Inn At Mass Moca Features On-Site Art Exhibitions, Free Wi-Fi And An Outdoor P...

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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.

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Green Valley Motel

1214 Simonds Rd, Williamstown, MA - 1267

12.89 miles

Rating - Green Valley Motel

The Freebies Include Wi-Fi, Parking And Local Calls At The Green Valley Motel In Williamstown, Where The Outdoor Pool Is Open Seasonally. The Two-Story, Exterior-Corridor Green Valley Motel Has 17 Bud...

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Ladd Brook Inn

5939 Route 7, Pownal, VT - 5261

14.55 miles

Rating - Ladd Brook Inn

Whether You'Re Visiting The Green Mountains Or Berkshires For Business Or Pleasure, Ladd Brook Inn Offers Accommodations With In-Room Amenities. This Property Is Located 3.4 Km From The Massachusetts ...

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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
Seven Hills Inn

40 Plunkett Street, Lenox, MA - 1240

17 miles

Rating - Seven Hills Inn

Boasting A Seasonal Outdoor Swimming Pool, Seven Hills Inn Is Set In Lenox, 2.8 Km From Tanglewood. This 4-Star Inn Offers A Garden. Each Room Is Fitted With A Balcony With Garden Views.All Units In T...

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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.

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Econo Lodge Lee - Great Barrington

980 Pleasant Street, Lee, MA - 1238

20.38 miles

Rating - Econo Lodge Lee - Great Barrington

Continental Breakfast And Wi-Fi Are Found At The Econo Lodge Lee, Where All Rooms Include The Convenience Of Microwaves And Mini-Fridges. The Low-Rise Hotel Has 23 Exterior-Corridor Rooms With Wi-Fi, ...

Read more
Paradise Inn

141 West Main Street, Bennington, VT - 5201

22.18 miles

Rating - Paradise Inn

Featuring An Outdoor Pool, Tennis, Shuffleboard, Pickleball Courts And A Restaurant, Paradise Inn Is Located In Bennington And Offers Free Wifi. All Rooms Have Splendid Pool And Garden Views.Providing...

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The Briarcliff Motel

506 Stockbridge Road, Great Barrington, MA - 1230

24.14 miles

Rating - The Briarcliff Motel

Surrounded By The Berkshires, This Motel Is 8 Km From Ski Butternut And Boasts Free Wi-Fi Access And Views Of Monument Mountain. The Norman Rockwell Museum Is 10 Minutes’ Drive Away.Each Room At The B...

Read more
Travelodge by Wyndham Great Barrington Berkshires

400 Stockbridge Rd, Great Barrington, MA - 1230

24.91 miles

Rating - Travelodge by Wyndham Great Barrington Berkshires

Buffet Breakfast And Complimentary Wi-Fi Are On Offer At The Travelodge By Wyndham Great Barrington, Where There'S Also An Outdoor Pool, In A Location Right Outside Of Town. The Two-Story, 80-Room Hot...

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Map of Cheshire Pet-friendly 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 11:53 AM. The temperature feels like 32.15 with a humidity level of 79 so dress accordingly. Cloud coverage is 81 percent with visibility at 8.5 percent. Today’s UV index is 2, don’t forget the sunscreen if you need it! Today’s winds are traveling west-northwest at a speed of 12 MPH. At the end of the day don’t miss the sunset at 9:23 PM.


Fahrenheit / Celsius
Saturday 11/23
Light rain

Saturday 11/23 Weather forecast for Cheshire, Massachusetts, Light rain
39°F
High: 45°F
Low: 34°F
Precipitation: 75%
Today 11/24
Broken clouds

Sunday 11/24 Weather forecast for Cheshire, Massachusetts, Broken clouds
38°F
High: 45°F
Low: 29°F
Precipitation: 0%
Monday 11/25
Scattered clouds

Monday 11/25 Weather forecast for Cheshire, Massachusetts, Scattered clouds
37°F
High: 48°F
Low: 34°F
Precipitation: 20%
Tuesday 11/26
Mix snow/rain

Tuesday 11/26 Weather forecast for Cheshire, Massachusetts, Mix snow/rain
41°F
High: 50°F
Low: 31°F
Precipitation: 85%
Wednesday 11/27
Mix snow/rain

Wednesday 11/27 Weather forecast for Cheshire, Massachusetts, Mix snow/rain
36°F
High: 42°F
Low: 27°F
Precipitation: 20%
Thursday 11/28
Flurries

Thursday 11/28 Weather forecast for Cheshire, Massachusetts, Flurries
32°F
High: 37°F
Low: 31°F
Precipitation: 10%

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