Book Hotels in Windsor, MA

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Check prices in Windsor for tonight, Jul 5 - Jul 6
Jul 5 - Jul 6
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Check prices in Windsor for tomorrow night, Jul 6 - Jul 7
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Jul 11 - Jul 13

Top Windsor hotels

Hotel Downstreet, Ascend Hotel Collection

Hotel Downstreet, Ascend Hotel Collection

3 out of 5
40 Main St, North Adams, MA
Free Cancellation
Reserve now, pay when you stay
13.58 mi from city center
$144 nightly
The price is $160 total per night
$160 total
Aug 3 - Aug 4
Total includes taxes and fees
This hotel features an indoor pool and a 24-hour gym. Enjoy the hot tub and perks like free self parking and free WiFi. A communal living room, express check-out, and luggage storage are also on offer.
Pool
Hot Tub
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
Free Cancellation
Reserve now, pay when you stay
13.04 mi from city center
$117 nightly
The price is $131 total per night
$131 total
Jul 6 - Jul 7
Total includes taxes and fees
This condo features an outdoor pool and an indoor pool. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking and free WiFi.
Pool
Parking included
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
8.46 mi from city center
$71 nightly
The price is $80 total per night
$80 total
Jul 28 - Jul 29
Total includes taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the business center. The front desk is staffed around-the-clock and laundry facilities are on offer.
Parking included
Free WiFi
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street, Williamstown, MA
Free Cancellation
Reserve now, pay when you stay
16.04 mi from city center
$227 nightly
The price is $254 total per night
$254 total
Jul 13 - Jul 14
Total includes taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, conference center, and conference space. Free self parking, a coffee shop, and a terrace are also offered.
Pet friendly
Parking included
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 out of 5
190 Meadow Street, South Lee, MA
Free Cancellation
Reserve now, pay when you stay
19.96 mi from city center
$167 nightly
The price is $186 total per night
$186 total
Jul 9 - Jul 10
Total includes taxes and fees
This hotel features 2 outdoor pools, 2 indoor pools, and a poolside bar. There's fun for all ages with mini golf and a playground, and families will appreciate the picnic area. Enjoy the seasonal outdoor pool and conveniences like a coffee shop and barbecue grills.
Pool
Air conditioning
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 out of 5
1350 W Housatonic St, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
14.51 mi from city center
$109 nightly
The price is $122 total per night
$122 total
Jul 6 - Jul 7
Total includes taxes and fees
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Traveling for business? Take advantage of the 24-hour business center, express check-out, and conference space. There's a gym on site, and a 24-hour front desk and a snack bar/deli are also provided.
Breakfast included
Pet friendly
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

2 out of 5
462 Pittsfield Rd, Routes 7 and 20, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
13.41 mi from city center
$99 nightly
The price is $111 total per night
$111 total
Jul 6 - Jul 7
Total includes taxes and fees
An outdoor pool is featured at this motel, along with free self parking. WiFi in public areas is free. A garden and express check-out are also provided.
Pool
Parking included
Red Roof Inn PLUS+ South Deerfield – Amherst

Red Roof Inn PLUS+ South Deerfield – Amherst

2.5 out of 5
9 Greenfield Rd, South Deerfield, MA
Free Cancellation
Reserve now, pay when you stay
22.04 mi from city center
$89 nightly
The price is $99 total per night
$99 total
Jul 6 - Jul 7
Total includes taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. The front desk is staffed around-the-clock and laundry facilities are on offer.
Pet friendly
Parking included
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street, Pittsfield, MA
Free Cancellation
11.47 mi from city center
$123 nightly
The price is $137 total per night
$137 total
Jul 13 - Jul 14
Total includes taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
Pool
Pet friendly
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See all available properties in Windsor
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top hotels in Windsor for Extended Stay

The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook

The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook

Hancock
10/10 Exceptional! (4 reviews)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Seize your some day

Windsor Hotel & Travel Guide\n

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.

Windsor hotels essential information

Accommodation
970 hotels
Lowest Price
$80
Highest Price
$254
Popular hotels
Hotel Downstreet, Ascend Hotel Collection, Vacation Village in the Berkshires, FairBridge Inn Express, The Williams Inn, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, Best Western Plus Berkshire Hills Inn & Suites, Howard Johnson by Wyndham Lenox, Red Roof Inn PLUS+ South Deerfield – Amherst, Holiday Inn & Suites Pittsfield-Berkshires by IHG

Frequently asked questions

What are the top kid-friendly hotels in Windsor?
Family vacations are where treasured memories are made, but it's no secret that traveling with children can be a challenge. These kid-friendly Windsor hotels offer perks designed to keep adventurers of all ages comfortable and happy: Private Lakeside Carriage House in the Berkshires will help make your getaway the most memorable one yet. It comes with a range of conveniences geared toward families, such as childcare services and a playground. Alternatively, spend your Windsor trip at Picturesque Cottage with Sunroom on Ashmere Lake!. Take advantage of a nearby beach, a deck and more here.
Where can I find cheap hotels in Windsor?
At Travelocity you'll find really nice hotels in Windsor at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Windsor rather than in Windsor. We may find you even better rates, too.
How do I find the best Windsor hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Windsor then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Windsor?
The cheapest hotel in Windsor is $80. This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Windsor?
There are 970 hotels in Windsor on Travelocity.
What are the best hotels in Windsor?
Windsor has so many great hotels to choose from at Travelocity --- and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Windsor for you!
When is the best time to visit Windsor?
If you want the joy of a fun-filled trip in peak season, visit Windsor during February, March and May. If you'd prefer the peace of off-season, book a stay during quieter months, such as October, November and December.
When is the cheapest time to stay in Windsor?
Based on historic data is usually the cheapest month to visit Windsor. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Windsor?
There are multiple hotels in Windsor that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Windsor. We have plenty of kid-friendly hotels in Windsor to choose from on Travelocity!
Why book a hotel in Windsor through Travelocity?
Because we have the top hotels in Windsor! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Windsor on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Windsor hotel reviews by fellow wanderers

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

5 out of 5
Posted 23 hours ago
Travelocity Verified Review
"Helpful staff. Restful adirondack chairs scattered around the property. Good breakfast options. "
A verified traveler from barrington stayed at The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham

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