Housatonic Vacations from $643
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Your Housatonic Vacation
Enjoy amazing adventures when you lock in a vacation package to Housatonic. Whether you're a history buff, art enthusiast or just a traveler who loves discovering new places, there's something for everyone in this vibrant city. Make your trip to Housatonic even more fun by including some sightseeing. National Shrine of the Divine Mercy, Norman Rockwell Museum and Naumkeag Museum are among the major attractions worth exploring. Your perfect Housatonic vacation is a few clicks away. Explore accommodations, flights and more on Expedia for a getaway that's tailored to suit your style.
The Latest Housatonic vacation packages
Price found within the past 48 hours. Click for updated prices.
Hotel Vienna
Price was $774, price is now $643 per person
$643
per person
Aug 11 - Aug 15
found 17 hours ago
Roundtrip flight included
Jacksonville (JAX) to Hudson (HCC)
9.4/10 Exceptional! (799 reviews)
Cute, family run eclectic hotel. Staff was friendly and helpful.
The pool, sauna, breakfast, and location to town, the hiking trails, and ski slopes was perfect. Great value. Would definitely recommend and stay here again.
Reviewed on May 31, 2026
Mountainview Estate - Main House by Avantstay Pool + Hot Tub + Canoe + Outdoor Dining + Game Room Near Windham Mountain
Save 100% on your flight
Price was $14,501, price is now $9,969 per person
$9,969
per person
Aug 11 - Aug 15
found 17 hours ago
Roundtrip flight included
Jacksonville (JAX) to Hudson (HCC)
No reviews
The Haüs Windham
Price was $1,018, price is now $812 per person
$812
per person
Aug 11 - Aug 15
found 17 hours ago
Roundtrip flight included
Jacksonville (JAX) to Hudson (HCC)
7.8/10 Good! (28 reviews)
I stayed in the mirror cabin everything was great just prepare to have no microwave and or a burner. So you cannot cook or heat anything up. I was able to make it work by just getting stuff that can be eaten cold and then going out to dinner which was fine. Also because the cabin is mirror please note birds constantly fly into it on purpose. It was one bird that every day i was there from morning to night was hitting the glass and it did get very annoying.
Reviewed on Apr 20, 2026
Wylder Hotel Windham
Price was $1,016, price is now $850 per person
$850
per person
Aug 11 - Aug 15
found 17 hours ago
Roundtrip flight included
Jacksonville (JAX) to Hudson (HCC)
8.8/10 Excellent! (98 reviews)
Family Weekend Getaway.
This is our 4th time at this property. Our first time was a year ago during Memorial Day Weekend. Although it was a very droopy weekend, Wylder made it an unforgettable moment . Enough to come back several times. May 16 weekend was one if the best, the weather was perfect, the food as always delicious and the staff amazing. Wylder will always be a perfect location with or without kids/furry babies . I am all ready looking for our next weekend getaway.
Reviewed on May 18, 2026
Housatonic Hotel Deals
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$155 nightly
The price is $173 total per night from Jun 2 to Jun 3
$173 total
Jun 2 - Jun 3
Total with taxes and fees
9/10 Wonderful! (960 reviews)
"Hot tub doesn’t go above 95 which is colder than you think, didn’t have any luggage carts available after asking 3 different people, but it’s a charming place to end on a positive note"
Reviewed on May 28, 2026
Berkshires Untold
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $133 total per night from Jun 2 to Jun 3
$133 total
Jun 2 - Jun 3
Total with taxes and fees
9/10 Wonderful! (966 reviews)
"From the time we showed up and told that they had no reservation for us, when we paid in full for a king suite, until we left, this experience was frustrating and full of problems. All king suites were sold out, including the one we paid for! We were told we would receive a 50% credit back to our ..."
Reviewed on Jun 1, 2026
The Yankee Inn
461 Pittsfield Rd Lenox MA
$120 nightly
The price is $134 total per night from Jun 2 to Jun 3
$134 total
Jun 2 - Jun 3
Total with taxes and fees
9.2/10 Wonderful! (1,002 reviews)
"Beautiful and well maintained and close to shipping and food"
Reviewed on May 29, 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 Housatonic Vacation Packages
Housatonic Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 1,100 |
Top Sights | Norman Rockwell Museum, Ski Butternut and Bousquet Ski Area |
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Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
