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Top 12 Hotels near Windsor, Massachusetts, United States

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4 of 5 Stars

1 West Street, Pittsfield, MA 01201, USA

Top Among Hotels in the Berkshires of Massachusetts. Discerning travelers seeking full service hotels in the Berkshires of Western Massachusetts opt for the Crowne Plaza Hotel Pittsfield Berkshires. The hotel is located within minutes of area businesses including Berkshire Health Systems SABIC General Dynamics and major attractions ensuring...

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Approximately 10.9 Miles away from Windsor center
3 of 5 Stars

37 Corey Road, Hancock, MA 01237, USA

Jiminy Peak is located in the Berkshire Mountains in Hancock Massachusetts. Located at the base of the mountain is the all-suite Country Inn. The Country Inn features a heated outdoor pool indoor and outdoor Jacuzzi exercise room and John Harvards Restaurant and Brewery. The Country Inn Suites feature a master bedroom with a king bed living...

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Approximately 12.4 Miles away from Windsor center
2 of 5 Stars

462 Pittsfield Road, Lenox, MA 01240, USA

Book your next fun-filled family vacation at our hotel in the scenic Berkshire Mountains near restaurants, museums and outdoor adventures. Tear up the snow at Bousquet Ski Area just six minutes away, or enjoy zip lines and water slides during the summer. Music festivals at Tanglewood are just four miles away. Wake up to a free Rise and Dine...

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Approximately 13.0 Miles away from Windsor center
2 of 5 Stars

20 West Housatonic Street, Pittsfield, MA 01201, USA

25 Apartment Style Non-Smoking Suites in city setting. Property has three 2 story buildings. On site parking, mailboxes, and laundry facilities are some of the features that make this property unique. All Suites have separate bathrooms and bedrooms with either One King, One Queen or two Double Beds. A hallway leads to a living room/kitchen...

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Approximately 11.0 Miles away from Windsor center
1 of 5 Stars

525 Pittsfield Road, Lenox, MA 01240, USA

the lenox inn, a magnuson hotels affiliate, is a family-owned and operated hotel, located in the heart of the berkshires in lenox, massachusetts. The hotel offers easy access to some of the most popular attractions in the area, including the hancock shaker village the massachusetts museum of contemporary art the norman rockwell museum home...

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Approximately 12.7 Miles away from Windsor center

484 Pittsfield Road, Lenox, MA 01240, USA

Property Type Motel
Property Highlights Skiing Nearby
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Approximately 12.9 Miles away from Windsor center
1 of 5 Stars

16 Cheshire Road, Pittsfield, MA 01201, USA

The Econo Lodge hotel in Pittsfield, MA is centrally located in the heart of the Berkshires near several major highways including Interstate 90. We are near several restaurants and shops. Hotel amenities include free full breakfast, free high-speed Internet access, exercise room and business center. All guest rooms come with a microwave, refrigerator...

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Approximately 7.96 Miles away from Windsor center
1 of 5 Stars

475 South Main Street, Lanesborough, MA 01237, USA

Property Location Located in Lanesborough, The Weathervane Motel is within the vicinity of Mount Greylock State Reservation Visitor Center and Crane Museum of Papermaking. This motel is within the vicinity of Berkshire Athenaeum and Berkshire Museum. Rooms Make yourself at home in one of the 12 air-conditioned rooms featuring refrigerators...

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Approximately 9.12 Miles away from Windsor center
4 of 5 Stars

297 North Street, Pittsfield, 01201, USA

Hotel on North is a 45-room boutique hotel elegantly transformed within a pair of historic buildings. Filled with custom furniture from local artisans and craftspeople Hotel on North celebrates the creative and entrepreneurial spirit of downtown Pittsfield. We invite you to this thriving community with our own art gallery a restaurant from...

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Approximately 10.7 Miles away from Windsor center
1 of 5 Stars

150 West Housatonic Street, Pittsfield, MA 01201, USA

The Berkshire Inn is locally owned and operated. Downtown Pittsfield is within walking distance which is approximately 1/4 quarter mile from the Berkshire Inn. We offer different kinds of rooms for whatever your needs are. We invited you to stay at the Berkshire Inn and experience what the Beautiful Berkshires has to offer.

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Approximately 11.3 Miles away from Windsor center
3 of 5 Stars

1032 South Street , Pittsfield, MA 01201, USA

Enjoy our full service restaurant on site serving breakfast and dinner daily. Breakfast buffet is USD 11.95 per person children 6 and under are free. Hilton Garden Inn Lenox Pittsfield offers you a great location and convenient amenities to help make your stay a memorable one. Our hotel features -Complimentary WiFi -Restaurant and bar onsite...

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Approximately 12.7 Miles away from Windsor center
1 of 5 Stars

474 Pittsfield Road, Lenox, MA 01240, USA

The Hotel was constructed in 1972 and was remodeled in 2005. Surrounded by the scenic Berkshire Mountains, Knights Inn Lenox is minutes away from Mass Pike, Exit-2 and conveniently located on Routes 20 and 7 in Lenox, MA. Visit nearby museums, theaters, ski areas -Jiminy Peak and Brodie Mountain, cross-country skiing, shopping, scenic bike...

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Approximately 12.9 Miles away from Windsor center
Best Windsor Hotels - Map View
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Windsor Frequently Asked Questions

Question: How's the seasonal weather in Windsor?

Answer: Windsor Seasonal temperature break down - The average median temperature March through May is approximately 44°F with highs averaging at 57°F and lows averaging at 33°F. June through August has an approximate average median temperature of 68°F with highs averaging at 81°F, lows typically average at 55°F. Average median temperatures September through November average out at 48°F, high temperatures average out at 60°F and lows average at 37°F. The average median temperature December through February is approximately 25°F with highs averaging at 35°F, lows average out at 15°F. The average Windsor annual median temperature averages out at approximately 46°F. The coldest month in Windsor is January with a median temperature of 22°F, the average high for the month of January is 31°F with an average low of 10°F. The hottest month in Windsor is July with an approximate median temperature of 71°F, the average high for the month of July is 85°F with an average low of 59°F.

Question: What type of clothing should I pack for my trip to Windsor?

Answer: If you plan on traveling to Windsor from March through May you will want to pack a couple of lightweight long sleeve shirts and lightweight jeans or pants. You will also want to think about packing a lightweight jacket or a lightweight sweater for the cooler days or nights. Those of you who will be traveling to Windsor from June through August should think about packing some short sleeve shirts and shorts. You may also want to pack a tank top as it can sometimes get pretty hot during the day. You should also consider packing a lightweight long sleeve shirt and jeans as there's a possibility you can run into a cooler night. Folks that will be traveling to Windsor September through November may want to consider packing a couple of long sleeve shirts and jeans, you will also want to consider packing a lightweight jacket. Those of you that will be traveling to Windsor from December through February will want to pack a number of heavy sweaters, long sleeve shirts, jeans, gloves, a heavy jacket, ear muffs will also be a good idea.

Sightseeing - Places to Visit During Your Stay in Windsor

Windsor James State Park - Park - Windsor

Top 12 hotels in Windsor - Map View

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Crowne Plaza Pittsfield
Crowne Plaza Pittsfield
$99
Jiminy Peak
Jiminy Peak
$115
Howard Johnson Lenox
Howard Johnson Lenox
$56
The Yankee Suites Extend Stay
The Yankee Suites Extend Stay
$104
Lenox Inn
Lenox Inn
$50
Wagon Wheel Inn
Wagon Wheel Inn
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Econo Lodge Pittsfield
Econo Lodge Pittsfield
$55
The Weathervane Motel
The Weathervane Motel
$40
Hotel on North
Hotel on North
$175
Berkshire Inn
Berkshire Inn
$65
Hilton Garden Inn Lenox-Pittsfield
Hilton Garden Inn Lenox-Pittsfield
$110
Knights Inn Lenox MA
Knights Inn Lenox MA
$45
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