Windsor, MA

Travel Guide

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
$122 nightly
The price is $136 total per night from Sep 27 to Sep 28
$136 total
Sep 27 - Sep 28
Total with taxes and fees
Book a stay at this family-friendly aparthotel in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful ...
Vacation Village in the Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
$109 nightly
The price is $121 total per night from Oct 1 to Oct 2
$121 total
Oct 1 - Oct 2
Total with taxes and fees
Book a stay at this golf aparthotel in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,153 reviews)
"One of the most important aspects of a good hotel is the smell of it when I first walk in the door. This lodge smelled clean and was clean. The second important thing is the customer service. This place was just okay. Polite but not very friendly. The third important aspect is the plumbing and that ..."

Reviewed on Sep 23, 2026

Berkshire Mountain Lodge
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
$109 nightly
The price is $122 total per night from Oct 25 to Oct 26
$122 total
Oct 25 - Oct 26
Total with taxes and 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 ...
9.2/10 Wonderful! (1,010 reviews)
"The staff was friendly and approachable. They were also very accommodating. I requested a room change upon check-in and a late check-out, and they made it happen. They do have a hiking trail and a pond behind the property, which was nice. While I was there, they were celebrating their housekeeping ..."

Reviewed on Sep 25, 2026

The Yankee Inn
See all 985 properties in Windsor
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.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
Book a stay at this family-friendly aparthotel in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful ...
Vacation Village in the Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Book a stay at this golf aparthotel in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,153 reviews)
"One of the most important aspects of a good hotel is the smell of it when I first walk in the door. This lodge smelled clean and was clean. The second important thing is the customer service. This place was just okay. Polite but not very friendly. The third important aspect is the plumbing and that ..."

Reviewed on Sep 23, 2026

Berkshire Mountain Lodge
The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
3 Foxhollow Drive Route 7 Lenox MA
Stay at this aparthotel in Lenox. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Tanglewood Music Center and The Mount are located ...
8.6/10 Excellent! (149 reviews)
"Our unit was very comfortable for 2 senior couples. We were only there for the weekend so we didn’t use any of the amenities but, the property is lovely."

Reviewed on Sep 4, 2026

The Ponds at Foxhollow
See all properties in Windsor
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.

Frequently asked questions

When is the best time to visit Windsor?
The best time to visit Windsor is from September through November, when the destination is most popular with travelers. For fewer crowds and potentially better value, consider visiting during the quieter months of December through February, which also mark the low season for lodging.
What cuisines can you find in Windsor?
In Windsor, you can find Thai cuisine, featuring popular dishes like Pad Thai, Green Curry, and Tom Yum Soup. Travelers can also enjoy a range of other options, including North American, Italian, and diverse Asian and Latin American dishes, as well as European and Mediterranean flavors.
Can I book a refundable hotel in Windsor?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Windsor by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Windsor with Expedia?
Expedia makes it easier to plan your Windsor trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Windsor?
The best choice depends on your travel style. Hotels in Windsor can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Windsor trip on Expedia?
Once you've booked your Windsor trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Windsor trip?
Expedia offers customer support before, during, and after your Windsor trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Windsor?
If it's your first trip to Windsor, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Windsor hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Windsor hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

Cities near Windsor

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Dalton

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Cheshire

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Hinsdale

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