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Book Cheap Hotels in Windsor, Massachusetts

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Tonight Dec 14 - Dec 15
This weekend Dec 20 - Dec 22
Next weekend Dec 27 - Dec 29

Most Frequently Booked Windsor Hotels

Price for 1 night 2 adults*

$98

Dec 15 - Dec 16

Per night/room

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3.0 out of 5.0 276 Brodie Mountain Rd, Hancock, MA
4/5
(28 Reviews)
Free Cancellation
Reserve now, pay when you stay
This condo features an outdoor pool and an indoor pool. Enjoy the health club and perks like free self parking and free WiFi. A business center, a terrace, and a garden are also on offer.
 
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$89

Dec 25 - Dec 26

Per night/room

Holiday Inn & Suites Pittsfield-Berkshires

Holiday Inn & Suites Pittsfield-Berkshires

3.5 out of 5.0 One West Street, Pittsfield, MA
3.6/5
(22 Reviews)
Free Cancellation
This hotel features an indoor pool, a health club, and a restaurant. Traveling on business? Take advantage of the 10 conference rooms, as well as the 24-hour business center and free WiFi in public areas. Enjoy the sauna and perks like free self parking.
 
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$105

Dec 15 - Dec 16

Per night/room

The Red Lion Inn

The Red Lion Inn

3.5 out of 5.0 30 Main Street, Stockbridge, MA
3.9/5
(7 Reviews)
Free Cancellation
Reserve now, pay when you stay
This smoke-free hotel includes 3 restaurants, an outdoor pool, and a fitness center. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy perks like free self parking.
 
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How much is a hotel room in Windsor?

Hotels in Windsor start at $89 per night. Prices and availability subject to change. Additional terms may apply.

Windsor Hotel & Travel Guide

Unfortunately, Travelocity doesn't have any lodging options in Windsor itself, however, our extensive database provides an extensive range of places for you to base you trip that are not too far away. Appreciate your trip into Windsor, from any of the 74 short and long-term lodgings that are located within a 19-mile (30-kilometer) distance.

The nearest of our hotels is the Rookwood Inn, Massachusetts, which is 16 miles (26 kilometers) from the downtown precinct of Windsor. A different Travelocity-listed option is the Gateways Inn & Restaurant, situated in Massachusetts, about 16 miles (26 kilometers) from the downtown area of Windsor.

You could check out the Hampton Terrace Inn along with the Cranwell Spa and Golf Resort. The Hampton Terrace Inn is positioned 16 miles (26 kilometers) outside of the middle of Windsor. The Cranwell Spa and Golf Resort, is located just 16 miles (26 kilometers) away. Alternatively, book the Birchwood Inn or the Wyndham Bentley Brook.

If you can spare the time, enlightened travelers should explore the other scenic and cultural delights of Western Massachusetts. Western Massachusetts has mountains and rolling hills, and other popular sights include history museums. Common things to do in this area of United States of America include skiing, cross-country skiing and mountain biking.

Want more to do? Consider spending a few hours exploring Mount Greylock State Reservation Visitor Center and Skyline Country Club, which can be found in Lanesborough, 9 miles (15 kilometers) west of Windsor. Next time you visit Lanesborough, check out the rooms at the The Weathervane Motel and Lanesborough Country Inn. 14 miles (23 kilometers) northwest of Windsor, you'll also find Williamstown, which boasts the The Spring's Inn and Berkshire Hills Country Inn. The Williams College and Williams College Museum of Art are a couple of the most popular attractions to visit in Williamstown.

Get a serving of sport with a pilgrimage to Times Union Center, which you will find 35 miles (60 kilometers) to the west of Windsor. Book accommodation nearby to the action at the Hilton Albany or the TownePlace Suites by Marriott Albany Downtown/Medical Center.

When you're flying through Albany International Airport and need to find a room nearby, try Albany Marriott or Homewood Suites by Hilton Albany.

Recent Windsor Hotel Reviews By Fellow Wanderers

Berkshire Hills Country Inn

5.0 Travelocity Verified Review
The inn keepers were so hospitable! They even prepared breakfast 1/2 hour earlier to accommodate us. (10 people) I would add a bathroom rug or mat to cover the very cold floor. We would stay here again!
6 days ago by A verified traveler
Open Berkshire Hills Country Inn hotel guest reviews

Holiday Inn Berkshires

4.0 Travelocity Verified Review
Friendly and helpful employees. Quiet rooms. Great location for my visit to MASS MOCA.
1 week ago by A verified traveler
Open Holiday Inn Berkshires hotel guest reviews

Holiday Inn & Suites Pittsfield-Berkshires

5.0 Travelocity Verified Review
Easy to find right in the center of town. Fast check in
1 week ago by A verified traveler
Open Holiday Inn & Suites Pittsfield-Berkshires hotel guest reviews

Jiminy Peak Mountain Resort

5.0 Travelocity Verified Review
I loved my suite with kitchen, separate living room and bedroom with spectacular views. Gary, particularly was very helpful to me in finding transportation because I do not drive. However, overall the feeling was that the employees (all) truly want to be helpful and are friendly.
3 weeks ago by A verified traveler
Open Jiminy Peak Mountain Resort hotel guest reviews

Berkshire Valley Inn

5.0 Travelocity Verified Review
I needed to check in after hours. Was very convenient they left they key for my room. For one quick night this place was perfect
3 weeks ago by A verified traveler from Asbury, nj
Open Berkshire Valley Inn hotel guest reviews

The Orchards Hotel

4.0 Travelocity Verified Review
There's an old-world elegance to the place. I'd liken it to visiting the home of an elderly, well-off grandmother. A place with faded glory.
3 weeks ago by A verified traveler from Federal Way, WA
Open The Orchards Hotel hotel guest reviews

An Airport

An Attraction

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.