Columbia County Vacations & Trips from $628
Book a Hotel + Flight or Car together to unlock savings
Photo by Barry Rowell
Your Columbia County Vacation
When adventure calls, answer it with a customized vacation package to Columbia County. Wherever your journey takes you and whatever you plan to do, prepare to experience a destination that'll make you feel alive. Start your trip to Columbia County with some time in Hudson visiting popular attractions like Olana State Historic Site and Thomas Cole National Historic Site. Canaan is another city that lures travelers from near and far. Bousquet Ski Area and The Mac-Haydn Theatre are two of the top places to see in this destination. Whether you plan to travel on a budget or in the lap of luxury, Expedia are here to help you tailor-make your next Columbia County vacation.
Top destinations in Columbia County
Hudson
New Lebanon
The Latest Columbia County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Prospect Berkshires
Save 100% on your flight
Price was $1,523, price is now $954 per person
$954
per person
Dec 31 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Albany (ALB)
18.8/10 Exceptional! (13 reviews)
Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay....
Reviewed on Oct 20, 2025
Pocketbook Hotel and Bath
Save 100% on your flight
Price was $1,838, price is now $1,168 per person
$1,168
per person
Dec 25 - Jan 2
found 4 hours ago
Roundtrip flight included
New York (JFK) to Albany (ALB)
17.6/10 Exceptional! (3 reviews)
The room was nice and clean, but the hotel itself was still under construction and it took 45 minutes for us to get in our room for check-in
I was able to ask for extended check out and we got two complementary drinks from the bar but overall they should have waited to open
Reviewed on Nov 12, 2025
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Save 100% on your flight
Price was $1,186, price is now $796 per person
$796
per person
Dec 31 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Albany (ALB)
18.4/10 Exceptional! (110 reviews)
It’s nice to come to this lovely setting and to be greeted by such a welcoming, smiling host! You cannot beat the ambiance, and the breakfast was marvelous. The entire cast and crew presented their masterpiece!!!
Reviewed on Oct 27, 2025
Find the Best Columbia County Vacation Packages
Columbia County Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Albany Intl. Airport (ALB) |
Top Sights | Lake Taghkanic State Park, Art Omi International Arts Center - Fields Sculpture Park and Kinderhook Lake |
Explore a world of travel with Expedia
Other vacations you might like
- Top cities in Columbia County
- Vacations and getaways similar to Columbia County
- Best vacation destinations by month
- January Vacations and Deals
- February Vacations and Deals
- March Vacations and Deals
- April Vacations and Deals
- May Vacations and Deals
- June Vacations and Deals
- July Vacations and Deals
- August Vacations and Deals
- September Vacations and Deals
- October Vacations and Deals
- November Vacations and Deals
- December Vacations and Deals
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.