Pet-friendly Hotels in Windsor, Massachusetts

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Hotel On North

297 North Street, Pittsfield MA - 1201

(855) 516-1090

11.22 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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The Porches Inn

231 River Street, North Adams MA - 1247

(855) 516-1090

13.5 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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Williamstown Motel

295 Main Street, Williamstown MA - 1267

(855) 516-1090

14.82 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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Birchwood Inn

7 Hubbard Street, Lenox MA - 1240

(855) 516-1090

15.8 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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Berkshire Mountain House

150 Berkshire Way, Stephentown NY - 12168

(855) 516-1090

16.4 miles

Rating - Berkshire Mountain House

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

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Seven Hills Inn

40 Plunkett Street, Lenox MA - 1240

(855) 516-1090

17.05 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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Green Valley Motel

1214 Simonds Rd, Williamstown MA - 1267

(855) 516-1090

17.96 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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Econo Lodge Lee - Great Barrington

980 Pleasant Street, Lee MA - 1238

(855) 516-1090

19.52 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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Ladd Brook Inn

5939 Route 7, Pownal VT - 5261

(855) 516-1090

19.71 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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Shaker Mill Inn

2 Oak Street, West Stockbridge MA - 1266

(855) 516-1090

20.49 miles

Rating - Shaker Mill Inn

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

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Days Inn by Wyndham Greenfield

21 Colrain Road, Greenfield MA - 1301

(855) 516-1090

22.28 miles

Rating - Days Inn by Wyndham Greenfield

Freebies Like Parking And Wi-Fi And A Location With Quick Access To I-91 And A Variety Of Restaurants Make The Days Inn By Wyndham Greenfield A Sensible Choice For Our Guests. The Two-Story Days Inn By Wyndham Offers 57 Rooms With Flat-Panel Cable Tvs, Alarm Clocks, Coffeemakers, Microwaves And Refrigerators. Check Your Email Or Update Your Status With Free Wi-Fi. Work Off Breakfast In The Fitness Room Before You Take Off For The Day. Business Services Are Available. Parking Is Free. Pets Are Permitted, So You Don'T Have To Leave Your Four-Legged Best Friend Behind. Non-Smoking Rooms May Be Requested. The Hotel Is Located Off I-91, Within Walking Distance Of Mohawk Mall, Which Features A Variety Of Restaurants So You Don'T Have To Look Far For Food After A Long Day On The Road. The Center Of Greenfield Is One-And-A-Half Miles From The Hotel, And Historic Deerfield Is Five Miles Away. The Mohawk Trail Region Offers More Than 100 Miles Of Trails For Hiking And Biking Less Than 10 Minutes From The Hotel. Golfers Are Five Minutes From Meadows Golf Course. Bradley International Airport Is 58 Miles Away In Connecticut.

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Red Roof Inn PLUS+ South Deerfield - Amherst

9 Greenfield Rd, South Deerfield MA - 1373

(855) 516-1090

22.39 miles

Rating - Red Roof Inn PLUS+ South Deerfield - Amherst

An Indoor Pool, On-Site Arcade And Free Wi-Fi Are Perks Our Guests Appreciate At The Non-Smoking Red Roof Plus South Deerfield. Each Of The 122 Non-Smoking Rooms At This Two-Floor Red Roof Plus Has Cable Tv And Free Wi-Fi. Kid-Friendly Amenities Include A Game Room With Arcade Machines And An Indoor Pool. Guests Can Stop By The Lobby For Complimentary Coffee Or Keep Their Clothes Looking Sharp At The Laundry Facility. Pets Are Welcome And Parking Is Free. The Red Roof Plus Is Off I-91 In South Deerfield, 10 Miles North Of Amherst. Nearby Points Of Interest Include Magic Wings Butterfly Conservatory, University Of Massachusetts Amherst And The Emily Dickinson Museum — All Within 10 Miles. Guests Can Walk To Several Restaurants, Shops And A Brewing Company Within 15 Minutes. Boston And Albany, Ny, Are Both Two Hours Away By Car. Bradley International Airport, In Connecticut, Is 45 Miles South.

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The Briarcliff Motel

506 Stockbridge Road, Great Barrington MA - 1230

(855) 516-1090

23.86 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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The Ellery

259 Elm Street, Northampton MA - 1060

(855) 516-1090

24.47 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.

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Travelodge by Wyndham Great Barrington Berkshires

400 Stockbridge Rd, Great Barrington MA - 1230

(855) 516-1090

24.61 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

11.22 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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The Porches Inn

231 River Street, North Adams, MA - 1247

13.5 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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Williamstown Motel

295 Main Street, Williamstown, MA - 1267

14.82 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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Birchwood Inn

7 Hubbard Street, Lenox, MA - 1240

15.8 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 ...

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Berkshire Mountain House

150 Berkshire Way, Stephentown, NY - 12168

16.4 miles

Rating - Berkshire Mountain House

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

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Seven Hills Inn

40 Plunkett Street, Lenox, MA - 1240

17.05 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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Green Valley Motel

1214 Simonds Rd, Williamstown, MA - 1267

17.96 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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Econo Lodge Lee - Great Barrington

980 Pleasant Street, Lee, MA - 1238

19.52 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, ...

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Ladd Brook Inn

5939 Route 7, Pownal, VT - 5261

19.71 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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Shaker Mill Inn

2 Oak Street, West Stockbridge, MA - 1266

20.49 miles

Rating - Shaker Mill Inn

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

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Days Inn by Wyndham Greenfield

21 Colrain Road, Greenfield, MA - 1301

22.28 miles

Rating - Days Inn by Wyndham Greenfield

Freebies Like Parking And Wi-Fi And A Location With Quick Access To I-91 And A Variety Of Restaurants Make The Days Inn By Wyndham Greenfield A Sensible Choice For Our Guests. The Two-Story Days Inn B...

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Red Roof Inn PLUS+ South Deerfield - Amherst

9 Greenfield Rd, South Deerfield, MA - 1373

22.39 miles

Rating - Red Roof Inn PLUS+ South Deerfield - Amherst

An Indoor Pool, On-Site Arcade And Free Wi-Fi Are Perks Our Guests Appreciate At The Non-Smoking Red Roof Plus South Deerfield. Each Of The 122 Non-Smoking Rooms At This Two-Floor Red Roof Plus Has Ca...

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The Briarcliff Motel

506 Stockbridge Road, Great Barrington, MA - 1230

23.86 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
The Ellery

259 Elm Street, Northampton, MA - 1060

24.47 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
Travelodge by Wyndham Great Barrington Berkshires

400 Stockbridge Rd, Great Barrington, MA - 1230

24.61 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 Windsor Pet-friendly Hotels

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


Weather Forecast for Windsor, Massachusetts

Traveling to Windsor, 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 9:44 AM and don’t miss the sunset at 11:55 PM. Today’s winds are traveling west-southwest at a speed of 15 MPH. The temperature feels like 57 with a humidity level of 67. Cloud coverage is 36 percent with 11.7 percent visibility. Today’s UV index is 9 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
Today 5/2
Scattered clouds

Thursday 5/2 Weather forecast for Windsor, Massachusetts, Scattered clouds
57°F
High: 66°F
Low: 46°F
Precipitation: 10%
Friday 5/3
Broken clouds

Friday 5/3 Weather forecast for Windsor, Massachusetts, Broken clouds
52°F
High: 62°F
Low: 43°F
Precipitation: 0%
Saturday 5/4
Broken clouds

Saturday 5/4 Weather forecast for Windsor, Massachusetts, Broken clouds
52°F
High: 61°F
Low: 42°F
Precipitation: 20%
Sunday 5/5
Light rain

Sunday 5/5 Weather forecast for Windsor, Massachusetts, Light rain
46°F
High: 53°F
Low: 46°F
Precipitation: 80%
Monday 5/6
Broken clouds

Monday 5/6 Weather forecast for Windsor, Massachusetts, Broken clouds
55°F
High: 67°F
Low: 48°F
Precipitation: 40%
Tuesday 5/7
Scattered clouds

Tuesday 5/7 Weather forecast for Windsor, Massachusetts, Scattered clouds
56°F
High: 72°F
Low: 56°F
Precipitation: 0%

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