Hancock 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 Hancock
Jiminy Peak Mountain Resort
37 Corey Rd Hancock MA
Fully refundableReserve now, pay when you stay
S$224
14 Sept - 15 Sept
includes taxes & fees
8.2/10 Very good! (1,007 reviews)
"Only problem was the stairs. I hadn't realized that there was such a long climb to our condo or I would have asked for something a little friendlier to a 75 year old."
Reviewed on 13 Aug, 2026
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
S$138
31 Aug - 1 Sept
includes taxes & fees
8.8/10 Excellent! (2,529 reviews)
"The room was clean, beds, sheets and towels, kitchen also nice and clean with all the things we needed to stay for a few days to cook. Is is like a small apartment. We really enjoyed."
Reviewed on 14 Aug, 2026
The Yankee Inn
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
S$226
14 Sept - 15 Sept
includes taxes & fees
9.2/10 Wonderful! (1,002 reviews)
"Seamless stay from check in to check out. All the important things like cleanliness and updated bathroom with working faucets, great shower, lots of towels, etc. and unusual amenities like “two” swimming pools as well as hiking (walking) trail and ponds in the rear of the hotel property. Breakfast ..."
Reviewed on 14 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.
Stay near popular Hancock attractions
Jiminy Peak Mountain Resort
8.8/10 (311 reviews)
Southern New England's largest ski resort transforms into a summer playground with thrilling attractions. Glide down 45 winter trails or ride the Mountain Coaster through Berkshire Mountain scenery.
Mountain Coaster
Experience the East Coast's first alpine coaster as you twist through scenic Berkshire Mountain forests. Control your own speed up to 23 mph for either a thrilling ride or a leisurely descent through seasonal landscapes.
Alpine Super Slide
Glide down the 2,890-foot Alpine Super Slide, controlling your speed through tunnels and curves. Begin with a scenic chairlift ride offering panoramic Berkshire Mountain views before your thrilling descent.
Frequently asked questions
How much does a Hancock holiday package cost?
You'll find cheap prices on Expedia for your Hancock getaway. However, factors like the season, length of stay and your choice of hotel will influence how much your holiday to Hancock costs.
What are the cheapest months to go to Hancock?
March, April and May are the best times to search for cheap Hancock holiday packages. Travelling in quieter periods means you'll typically find better prices on flights and hotels.
How many days is enough for Hancock?
The ideal duration for your Hancock holiday depends on what you'd like to do and see. Usually, a few days to a week will give you plenty of time to check out all the top attractions and explore some hidden gems along the way.
How to find the best Hancock package deals?
Start your search for a Hancock package deal by entering your travel dates and destination under our "Packages" tab. Then apply some filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the perfect Hancock package deal right away, just play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Hancock escape underway.
Is it cheaper to book a Hancock holiday as a package?
Expedia holiday packages are designed to give you more bang for your buck. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll generally score a better deal than booking each component separately. And you'll still have the flexibility to create a customised Hancock holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday package to Hancock?
Enjoy incredible bargains by booking your flights in advance with Expedia. If spontaneity is more your style, grab one of our last-minute deals for an impromptu Hancock break.
How to plan a trip to Hancock?
- Pick your dates: The things you want to do in Hancock and your preferred season can help you decide when to get away.
- Budget wisely: In addition to the price of your accommodation, you'll need to factor in other expenses. These include food, transportation and flights. Also, put aside some extra funds for unexpected expenses that could crop up during your trip to Hancock.
- Decide how long to go away for: Now that you know more about Hancock, you can figure out the right length of your break. Pull together a draft plan and give yourself enough time to get through everything on your must-do list.
- Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to find a Hancock 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.
