
Windsor Vacations from $587
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Your Windsor Vacation
Enjoy amazing adventures when you reserve a Windsor vacation package. Whether you're a history buff, foodie or just a traveler who loves discovering new places, there's something for everyone in this awesome city. If seeing the sights is a priority during your trip to Windsor, make sure you swing by popular attractions like Wahconah Falls State Park and Bas Ridge Golf Course. No matter your travel plans or the size of your budget, organizing a tailored Windsor vacation is a walk in the park with Expedia.
The Latest Windsor vacation packages
Price found within the past 48 hours. Click for updated prices.

The Landing Hotel at Rivers Casino & Resort
Stockade Historic District
Price was $768, price is now $587 per person
$587
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
9/10 Wonderful! (1,004 reviews)
We came to hotel after complicated driving for 7 hours tired and were met by friendly staff. Check in was fast and easy. After all we got excellent warm chocolate cookies. Love the hotel !!
Reviewed on Sep 13, 2025


Gedney Farm
Price was $833, price is now $610 per person
$610
per person
Nov 10 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Albany (ALB)
9.2/10 Wonderful! (129 reviews)
Gedney Farms is very quiet, peaceful and rustic. Your stay is in a converted barn with towering ceilings, hard wood floors, and rustic reused furniture with no TV phones or radios. Note some rooms require stair climbing on winding stairs with sections without rails or handholds. Some bathtubs are very high. It would be helpful to talk to the location about the room accommodations if mobility is an issue.
The staff is very unobtrusive almost to the point of non existent. The breakfast was fresh and healthy with plain Greek yogurt, granola, fresh fruits, hard boiled eggs, muffins and bread to toast. The grounds are well tended but not fussy and offer beauty, peace and quiet. The location is an easy 30 minutes to Tanglewood and 15 minutes to Stockbridge. It is nearby Berkshire Botanical Gardens, Dr. Suess Museum, WEB DuBois statue and homestead, Norman Rockwell museum, Monument mountain, Housatonic river and many art stores, general stores, outdoor activities. This area is car dependent.
Reviewed on Aug 12, 2025


The Cornell Inn, Lenox & The Berkshires
Price was $755, price is now $596 per person
$596
per person
Nov 10 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Albany (ALB)
9/10 Wonderful! (1,000 reviews)
Very nice place. Quiet. The breakfasts are included and are upscale with excellent staff service.
Unless you are young and don't care, make sure you get a ground floor room - the upstairs rooms require a walk up a large staircase, and are inconvenient.
Would definitely return.
Reviewed on Sep 5, 2025
Windsor Hotel Deals

Vacation Village in the Berkshires
276 Brodie Mountain Rd, Williamstown, MA
Fully refundableReserve now, pay when you stay
$97 nightly
The price is $108 total per night from Oct 2 to Oct 3
$108 total
Oct 2 - Oct 3
Total with taxes and fees
8.6/10 Excellent! (2,004 reviews)
"Quiet, clean, beautifully landscaped- such a comfy bed!"
Reviewed on Sep 13, 2025

Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
$113 nightly
The price is $126 total per night from Sep 21 to Sep 22
$126 total
Sep 21 - Sep 22
Total with taxes and fees
8.8/10 Excellent! (640 reviews)
"Clean, bright, great value, love the hot tub and pool!"
Reviewed on Sep 15, 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
190 Meadow Street, South Lee, MA
Fully refundable
$142 nightly
The price is $158 total per night from Sep 23 to Sep 24
$158 total
Sep 23 - Sep 24
Total with taxes and fees
9/10 Wonderful! (727 reviews)
"Check-in and check-out was seamless, the room was spacious,clean, comfortable and well equipped. Swimming pools were well maintained and very clean. The stairs were a bit difficult for seniors…great stay!"
Reviewed on Sep 16, 2025
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.
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