
Windsor Vacations from $483
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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.

Berkshire Mountain Lodge
Price was $647, price is now $483 per person
$483
per person
May 18 - May 25
found 24 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
9/10 Wonderful! (870 reviews)
Clean, quiet, spacious, comfortable, and lovely furnishings! It was a very relaxing overnight.
Reviewed on Mar 31, 2026

Hotel Brookmere & Arbor Spa
Price was $720, price is now $514 per person
$514
per person
May 14 - May 17
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
9.2/10 Wonderful! (271 reviews)
Located by the elevator was a bit noisy. Other than that, wonderful stay!
Reviewed on Mar 11, 2026

Vacation Village in the Berkshires
Price was $744, price is now $534 per person
$534
per person
May 18 - May 25
found 24 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
8.8/10 Excellent! (2,318 reviews)
I recently stayed in a one bedroom suite at this villa property and unfortunately the experience was disappointing, especially for business travel.
When I booked the reservation, I expected the main amenities such as the clubhouse to be easily accessible. In reality, the clubhouse sits on top of a hill. While there is temporary parking directly in front of the entrance, the designated guest parking is located at the bottom of the hill. This means guests either have to walk up a steep hill or climb several flights of stairs to reach the clubhouse. This setup is very inconvenient, particularly in cold weather or when carrying items for activities like swimming.
I also experienced maintenance issues in the unit. I reported a clogged faucet and maintenance came to address it, but the problem was not actually fixed. Instead, the clog appeared to shift from one side of the sink to the other, eventually causing unpleasant debris to come back up through the drain, which was unsanitary and frustrating.
The location is also quite isolated with limited nearby restaurant or dining options. While the condominium setup may work for guests planning to cook, it is not ideal for business travelers who need convenience and easy access to food and services.
Overall, I would not recommend this property for corporate travel.
Reviewed on Apr 2, 2026

Hilton Garden Inn Saratoga Springs
Price was $820, price is now $609 per person
$609
per person
May 14 - May 17
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
8/10 Very Good! (1,005 reviews)
Bar and restaurant not open on the Dunday I was there
Reviewed on Mar 30, 2026

Windsor Hotel Deals

Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
$126 nightly
The price is $141 total per night from Apr 5 to Apr 6
$141 total
Apr 5 - Apr 6
Total with taxes and fees
8.8/10 Excellent! (2,322 reviews)
I recently stayed in a one bedroom suite at this villa property and unfortunately the experience was disappointing, especially for business travel. When I booked the reservation, I expected the main amenities such as the clubhouse to be easily accessible. In reality, the clubhouse sits on top of ...
Reviewed on Apr 2, 2026

Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
Fully refundable
$131 nightly
The price is $146 total per night from May 3 to May 4
$146 total
May 3 - May 4
Total with taxes and fees
8.8/10 Excellent! (1,000 reviews)
Great location. Within walking distance to MOCA, and a few restaurants that were open during our stay. The town is post industrial and post manufacturing. Walking around MOCA is a wonderful experience in itself as much of the history of the building and surrounding area comes alive and is fascinating.The ...
Reviewed on Mar 22, 2026

Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $120 total per night from May 3 to May 4
$120 total
May 3 - May 4
Total with taxes and fees
9/10 Wonderful! (893 reviews)
Clean, quiet, spacious, comfortable, and lovely furnishings! It was a very relaxing overnight.
Reviewed on Mar 31, 2026
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.
Find the Best Windsor Vacation Packages
Windsor Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 890 |
Max Temp Winter | 30ºF |
Max Temp Summer | 75ºF |
Top Sights | Colonial Theater, Barrington Stage Company and Berkshire Museum |
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.



















