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Tonight Dec 14 - Dec 15
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Most Frequently Booked Windsor Hotels

$98
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.
 
$89
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.
 
$105
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


*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.