Middlefield Holidays

Photo by Elizabeth Massa Peroulakis
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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit

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

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

Top hotels in Middlefield

Vacation Village in the Berkshires
Vacation Village in the Berkshires
3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
Fully refundableReserve now, pay when you stay
8.6/10 Excellent! (1,866 reviews)
"Wonderful property in an idyllic setting! Everything you need for a quality vacation with friends or family. One of the most relaxing getaways I've ever had."

Reviewed on 11 Jul, 2025

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Vacation Village in the Berkshires
Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites
2.5 out of 5
1350 W Housatonic St, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is S$181 per night from 15 Jul to 16 Jul
S$181
15 Jul - 16 Jul
includes taxes & fees
8.4/10 Very Good! (1,009 reviews)
"The staff was so friendly. And the place was extremely clean"

Reviewed on 10 Jul, 2025

Best Western Plus Berkshire Hills Inn & Suites
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$578 per night from 25 Jul to 26 Jul
S$578
25 Jul - 26 Jul
includes taxes & fees
9/10 Wonderful! (631 reviews)
"I’ve stayed at this property several times including before it changed management. We have always enjoyed everything about it. My only strong suggestion is that there is better signage out by the highway. You do not see the hotel or the sign until you get very close to the turn and it is a very busy ..."

Reviewed on 10 Jul, 2025

Berkshires Untold
See all 1,085 properties in Middlefield
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 Middlefield holiday package cost?
You'll find cheap prices on Expedia for your Middlefield break. However, a range of factors like the hotel choice, length of stay and season will influence how much your holiday to Middlefield costs.
What are the cheapest months to go to Middlefield?
You can generally find reduced prices and greater availability in January, February and November. Explore our cheap Middlefield holiday packages and you could land some excellent off-season deals.
How many days is enough for Middlefield?
The ideal length for your Middlefield holiday depends on what you'd like to see. Typically, a few days to a week will give you enough time to check out all the main sights and explore some hidden spots along the way.
How to find the best Middlefield package deals?
Use Expedia's filter tool to help you find some terrific Middlefield package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or search for Middlefield package deals in the off-season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to book your holiday package as early as possible.
Is it cheaper to book a Middlefield holiday as a package?
Expedia holiday packages are designed to make your money go further. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll usually snag a better deal than booking each component individually. And you'll still enjoy the freedom to create a tailored Middlefield holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday package to Middlefield?
Score incredible discounts by reserving your flights in advance with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Middlefield holiday.
How to plan a trip to Middlefield?

  1. Choose your dates: What you want to do in Middlefield and your preferred season will help you decide when to travel.
  2. Work out your budget: Ensure you have enough money to cover everything from transportation and food to activities and flights. Your hotel will likely be the largest expense during your trip to Middlefield.
  3. Decide how long to go away for: Now that you know more about Middlefield, you can figure out the ideal length of your break. Pull together a rough itinerary and give yourself enough time to get through everything on your must-do list.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a personalised Middlefield holiday package.

* 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.