Housatonic Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Housatonic
The Yankee Inn
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
S$226
14 Sept - 15 Sept
includes taxes & fees
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
S$164
31 Aug - 1 Sept
includes taxes & fees
9/10 Wonderful! (1,077 reviews)
"The rooms were spotless and a good size. And is not far from Lenox which was our focus. I’d suggest that guests bring some food with them and there is a supermarket nearby. There is not a morsel of food in the ‘resort’. The tv is complicated and I’m not sure why it is set up the way it is. Check ..."
Reviewed on 17 Aug, 2026
Berkshires Untold
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
S$183
9 Sept - 10 Sept
includes taxes & fees
9/10 Wonderful! (1,009 reviews)
"Pleasant stay and Sarah made a bouquet of flowers for my daughter’s birthday..a fellow Leo!"
Reviewed on 17 Aug, 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.
Frequently asked questions
How much does a Housatonic holiday package cost?
You can grab a holiday package to this popular destination on Expedia. But how much your holiday to Housatonic costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Housatonic?
To score cheap Housatonic holiday packages, plan your trip outside of busy periods such as public holidays. You'll typically find better availability and lower prices when it's less busy.
How many days is enough for Housatonic?
With a well-planned schedule, you can easily visit the top Housatonic sights in a handful of days. But if you want to discover lesser-known spots or take day trips, consider booking your Housatonic holiday for longer.
How to find the best Housatonic package deals?
Bagging a cheap Housatonic package deal is a breeze with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your maximum budget, apply some filters and see what's available. You can tweak your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to discover the most wallet-friendly Housatonic package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Housatonic holiday as a package?
An Expedia holiday package could land you great savings when compared to arranging flights and stays separately. Better still, you can tailor your Housatonic getaway to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a holiday package to Housatonic?
Land incredible bargains by booking your flights ahead of time with Expedia. If spontaneity is more your style, grab one of our last-minute deals for an impromptu Housatonic trip.
How to plan a trip to Housatonic?
- Pick the right time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to go to Housatonic.
- Plan your budget wisely: Besides the cost of your hotel, you should factor in other expenses. These include flights, food and transportation. Also, set aside some extra funds for unexpected expenses that may arise during your trip to Housatonic.
- Determine how many days away: Start by compiling a list of the activities and attractions you'd like to get to in Housatonic. Then, estimate how long you'll need for each, including any travel time.
- Combine your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to pick a Housatonic holiday package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
