Hancock Holidays

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Top hotels in Hancock

Club Wyndham Bentley Brook
Club Wyndham Bentley Brook
3 out of 5
1 Corey Road, Hancock, MA
9.2/10 Wonderful! (506 reviews)
"We came to ski and this place was perfect! It’s a time share so it is set up for longer stays but we only stayed the weekend. Our two bed / two bath suite seemed to be recently renovated and was clean. A huge plus is that there were a few electric chargers and so that made things extra convenient. ..."

Reviewed on 23 Feb,2025

Club Wyndham Bentley Brook
Jiminy Peak Mountain Resort
Jiminy Peak Mountain Resort
3 out of 5
37 Corey Rd, Hancock, MA
The price is S$218 per night from 1 Apr to 2 Apr
S$218
includes taxes & fees
1 Apr - 2 Apr
8.2/10 Very Good! (925 reviews)
"Staff was exceptionally helpful and friendly."

Reviewed on 14 Jan,2025

Jiminy Peak Mountain Resort
Life House Berkshires
Life House Berkshires
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is S$145 per night from 25 Mar to 26 Mar
S$145
includes taxes & fees
25 Mar - 26 Mar
9/10 Wonderful! (535 reviews)
"Motel style building with refreshed modern room. Very clean and the restaurant onsite was good but the breakfast is somewhat limited."

Reviewed on 22 Mar,2025

Life House Berkshires
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 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?

  1. Pick your dates: The things you want to do in Hancock and your preferred season can help you decide when to get away.
  2. 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.
  3. 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.
  4. 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.