Book Hotels in Windsor, MA

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Top Windsor hotels

The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street Williamstown MA
Fully refundableReserve now, pay when you stay
$186 nightly
The price is $208 total per night from Jan 11 to Jan 12
$208 total
Jan 11 - Jan 12
Total with 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 ...
The room was very nice

Reviewed on Jan 1, 2026

Opens in a new windowThe Williams Inn
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $113 total per night from Jan 11 to Jan 12
$113 total
Jan 11 - Jan 12
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy the seasonal outdoor pool ...
The room was clean, comfortable and spacious. The bathroom had enough space and was clean and well appointed.

Reviewed on Dec 30, 2025

Opens in a new windowThe Yankee, Trademark Collection by Wyndham
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $120 total per night from Feb 1 to Feb 2
$120 total
Feb 1 - Feb 2
Total with taxes and fees
This lodge features an indoor pool and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, ...
Clean and warm, very spacious and cozy. People here are very nice too! Very good experience here.

Reviewed on Dec 26, 2025

Opens in a new windowBerkshire Mountain Lodge
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
$131 nightly
The price is $146 total per night from Jan 4 to Jan 5
$146 total
Jan 4 - Jan 5
Total with taxes and fees
A restaurant and a bar/lounge are featured at this lodge. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a lobby ...
The hotel is very nice and the employees are wonderful. Thank you!

Reviewed on Dec 25, 2025

Opens in a new windowBerkshires Untold
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
$126 nightly
The price is $141 total per night from Jan 4 to Jan 5
$141 total
Jan 4 - Jan 5
Total with 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 ...
No frills stay with a kitchen and dishwasher (make sure your room has one— some do not!!!). Location is across the street from Jiminy Peak, so skiing can be accomplished almost as easy as staying on their property. This is our fourth time staying and it always serves its purpose.

Reviewed on Dec 30, 2025

Opens in a new windowVacation Village in the Berkshires
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
Fully refundable
$116 nightly
The price is $130 total per night from Feb 2 to Feb 3
$130 total
Feb 2 - Feb 3
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 2 conference rooms, free WiFi in public areas, and express ...
Courteous staff

Reviewed on Dec 19, 2025

Opens in a new windowHotel Downstreet, an Ascend Collection Hotel
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
Fully refundableReserve now, pay when you stay
$176 nightly
The price is $197 total per night from Jan 20 to Jan 21
$197 total
Jan 20 - Jan 21
Total with taxes and fees
This smoke-free hotel includes 3 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi ...
Wonderful stay in a winter wonderland that evening especially with use of the heated pool and hot tub being maintained! Loved it. Shops inside were lovely as well, bars & restaurant on-site were fun with quirky decor. Whole hotel is quirky, which is fun!

Reviewed on Dec 26, 2025

Opens in a new windowThe Red Lion Inn
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
Fully refundable
$93 nightly
The price is $104 total per night from Jan 4 to Jan 5
$104 total
Jan 4 - Jan 5
Total with 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 ...
Did not have breakfast. Wish it was free but the hotel staff was amazing and the valet was great too!

Reviewed on Dec 28, 2025

Opens in a new windowHoliday Inn & Suites Pittsfield-Berkshires by IHG
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
Fully refundableReserve now, pay when you stay
$85 nightly
The price is $95 total per night from Jan 5 to Jan 6
$95 total
Jan 5 - Jan 6
Total with 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 ...
They put a hold on my room for incidentals and never gave the money back to me. That charged me the hold! Terrible way to do business, don’t hide fees from your customers.

Reviewed on Dec 16, 2025

Opens in a new windowRed Roof Inn PLUS+ South Deerfield – Amherst
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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.

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.

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 $95. 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 Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

5 out of 5
Posted 18 hours ago
Travelocity Verified Review
"Clean"
A verified traveler stayed at The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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