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Check prices in Windsor for tonight, Jun 29 - Jun 30
Jun 29 - Jun 30
Tomorrow night
Check prices in Windsor for tomorrow night, Jun 30 - Jul 1
Jun 30 - Jul 1
This weekend
Check prices in Windsor for this weekend, Jul 3 - Jul 5
Jul 3 - Jul 5
Next weekend
Check prices in Windsor for next weekend, Jul 10 - Jul 12
Jul 10 - Jul 12

Most frequently booked Windsor hotels

The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
Free cancellation
Reserve now, pay when you stay
21.65 km from city centre
The price is CA $181 per night
CA $181
CA $202 total
Jul 6 - Jul 7
includes taxes & fees
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Tanglewood Music Center and Guido's Marketplace are located nearby.
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
20.99 km from city centre
The price is CA $166 per night
CA $166
CA $201 total
Jul 6 - Jul 7
includes taxes & fees
Book a stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster are located nearby.
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Free cancellation
Reserve now, pay when you stay
20.85 km from city centre
The price is CA $199 per night
CA $199
CA $254 total
Jul 28 - Jul 29
includes taxes & fees
Book a stay at this golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tanglewood Music Center and Guido's Marketplace are located nearby.
Pool
Hot tub
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
Free cancellation
Reserve now, pay when you stay
33.37 km from city centre
The price is CA $210 per night
CA $210
CA $298 total
Jul 6 - Jul 7
includes taxes & fees
Book a stay at this historic hotel in Stockbridge. Enjoy free WiFi, free parking, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions National Shrine of the Divine Mercy and Tanglewood Music Center are located nearby.
Pool
Spa
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
35.49 km from city centre
The price is CA $140 per night
CA $140
CA $157 total
Jul 2 - Jul 3
includes taxes & fees
Stay at this hotel in South Deerfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Yankee Candle Village and Mount Sugarloaf State Reservation are located nearby.
Pet-friendly
Parking included
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Free cancellation
Reserve now, pay when you stay
23.14 km from city centre
The price is CA $214 per night
CA $214
CA $239 total
Jul 1 - Jul 2
includes taxes & fees
Stay at this lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tanglewood Music Center and Kennedy Park are located nearby.
Pet-friendly
Parking included
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

2.5 out of 5
1055 South Street Pittsfield MA
Free cancellation
21.11 km from city centre
The price is CA $243 per night
CA $243
CA $271 total
Jul 6 - Jul 7
includes taxes & fees
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Guido's Marketplace are located nearby.
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

2.5 out of 5
170 Housatonic Street Lee MA
Free cancellation
Reserve now, pay when you stay
28.28 km from city centre
The price is CA $192 per night
CA $192
CA $214 total
Jul 27 - Jul 28
includes taxes & fees
Book a stay at this business-friendly hotel in Lee. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions National Shrine of the Divine Mercy and Tanglewood Music Center are located nearby.
Hotel On North

Hotel On North

3.5 out of 5
297 North Street Pittsfield MA
Free cancellation
Reserve now, pay when you stay
18.1 km from city centre
The price is CA $353 per night
CA $353
CA $395 total
Jul 7 - Jul 8
includes taxes & fees
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Barrington Stage Company and Lichtenstein Center for the Arts are located nearby.
Pet-friendly
Parking included
Don't see what you're looking for?
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 MA
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.

Windsor hotels essential information

Accommodation
974 hotels
Lowest Price
CA $157
Highest Price
CA $395
Popular hotels
The Yankee Inn, Vacation Village in the Berkshires, Berkshire Mountain Lodge, The Red Lion Inn, Red Roof Inn PLUS+ South Deerfield – Amherst, Berkshires Untold, Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG, Quality Inn Lee - Lenox South, Hotel On North

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 CA $157 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 974 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 Inn

The Yankee Inn

4 out of 5
Posted less than an hour ago
Travelocity Verified Review
"The room was spacious with 2 queen beds. The AC worked well and kept the room cool. We had a glass sliding door to the back of the building that was operational and we could use it to get fresh air or go in and out of. The bathroom was clean and large. The bedding was comfortable and the towels were ok quality. The refrigerator was a good size so that we could fit a lot of stuff in it which was great. The staff were helpful. There is a fire pit out front where people sat and read or chatted. I did not go into the bar. The breakfast is standard fare. Cereals, powdered eggs, hard boiled eggs, make your own waffle, fresh fruit, very very watery oatmeal, assorted breads. The coffee was good. it is expensive for what you get but it is high season in the berkshires. the location is ok. It is close to downtown Lenox. 10 minutes from Pittsfield. 30 minutes from Great Barrington. 15 minutes from Tangelwood."
A verified traveller stayed at The Yankee Inn
The Yankee Inn