Housatonic Holidays

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to S$134 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in Housatonic

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is S$124 per night from 21 Sept to 22 Sept
S$124
21 Sept - 22 Sept
includes taxes & fees
8.8/10 Excellent! (582 reviews)
"Enjoyed the room, towels and kitchen. I can recommend."

Reviewed on 18 Aug, 2025

Berkshire Mountain Lodge
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is S$230 per night from 26 Aug to 27 Aug
S$230
26 Aug - 27 Aug
includes taxes & fees
9/10 Wonderful! (687 reviews)
"We loved everything! Josh was great at check in and with recommendations. Nick was truly fabulous bartending and giving us helpful suggestions and tips. Aurora was extremely helpful as well. 5 stat hotel in a great location with an awesome bar and restaurant. Hamburgers were off the chart. Thank ..."

Reviewed on 18 Aug, 2025

Berkshires Untold
Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
Fully refundableReserve now, pay when you stay
The price is S$133 per night from 7 Sept to 8 Sept
S$133
7 Sept - 8 Sept
includes taxes & fees
8.2/10 Very Good! (1,008 reviews)
"nice place"

Reviewed on 18 Aug, 2025

Quality Inn
See all 1,367 properties in Housatonic
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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.