Middlefield Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Elizabeth Massa Peroulakis

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Your Middlefield Holiday

When a city stay is calling your name, answer it with a holiday package to Middlefield. With all your travel arrangements organised before you go, all you need to do here is focus on having the time of your life. Glendale Falls, Chester Town Hall and Skyline Trail are just some of the many attractions you'll want to check out during your trip to Middlefield. Your perfect Middlefield holiday is clicks away. Browse accommodation, flights and more on Expedia for a trip that's tailored just for you.

Middlefield Holiday

Middlefield Essential Information

Language
English
Currency
U.S dollars
Population
550
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC
Top Sights
Glendale Falls, C.M. Gardner State Park and Skyline Trail

Our pick of the best Middlefield Hotel Deals

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
The price is AU$203 per night from 27 Aug to 28 Aug
AU$203
27 Aug - 28 Aug
includes taxes & fees
8.6/10 Excellent! (1,952 reviews)
"Liked the fact there are 2 pools, an indoor and an outdoor."

Reviewed on 17 Aug. 2025

Vacation Village in the Berkshires
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 AU$148 per night from 7 Sept to 8 Sept
AU$148
7 Sept - 8 Sept
includes taxes & fees
8.8/10 Excellent! (573 reviews)
I’d stay there again
"Everything was nice expect the “last guests” socks we found tangled in the pull out sofa bed."

Reviewed on 17 Aug. 2025

Berkshire Mountain Lodge
Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
The price is AU$160 per night from 3 Sept to 4 Sept
AU$160
3 Sept - 4 Sept
includes taxes & fees
8.2/10 Very Good! (1,002 reviews)
"nice place"

Reviewed on 18 Aug. 2025

Quality Inn
See all 1,076 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

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.