Middlefield Vacations from $611
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Your Middlefield Vacation
Our Middlefield vacation packages offer countless opportunities to indulge in new sights, sounds and smells. And with all the details worked out, you can breathe easy and enjoy your city getaway just like you deserve. Make your trip to Middlefield even more exciting by including some sightseeing. Glendale Falls, Skyline Trail and Chester Town Hall are some of the popular attractions you'll want to explore. Whatever your travel plans or budget, putting together the ultimate tailored Middlefield vacation is simple with Expedia.
The Latest Middlefield vacation packages
Price found within the past 48 hours. Click for updated prices.
Pondfront Gem Minutes From Hudsons Best Shops & Cafes The Stillwater House
$1,444
per person
Dec 25 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Albany (ALB)
6/10 (1 review)
The location of the house was very near for food and supplies,yet very private. The inside was very clean and well kept. We enjoyed the quietness and surrounding grounds with views of local wild life.
The things that we did not like was the musty - moldy smell when we first got there. Every time you used the water it smelled. Red light on fridge for changing filter. Bought spring water to use for drinking, coffee, and cooking. All reported to host upon departure.
Reviewed on Aug 23, 2025
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Skyline Trail
You can take time to visit Skyline Trail during your travels to Middlefield. Stroll along the area's lakeside, or simply savor its charming coffeehouses.
Middlefield Hotel Deals
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
$126 nightly
$140 total
Nov 18 - Nov 19
Total with taxes and fees
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$110 nightly
$123 total
Nov 18 - Nov 19
Total with taxes and fees
9/10 Wonderful! (1,213 reviews)
"This really is a great place and I will give it five stars, except the Wi-Fi is really crappy. We were on the fifth floor, but five MB/s is unacceptable in this day and age. The room was beautiful, and the kitchen was fabulous. One more nit is that they didn't make up the sofa bed. Most places make ..."
Reviewed on Oct 18, 2026
Hotel Northampton
36 King Street Northampton MA
Fully refundableReserve now, pay when you stay
$165 nightly
$184 total
Oct 27 - Oct 28
Total with taxes and fees
9.2/10 Wonderful! (1,005 reviews)
"Historic Hotel with an old tavern. Very comfortable bed & clean room. Check in & out went smoothly."
Reviewed on Oct 16, 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.
Find the Best Middlefield Vacation Packages
Middlefield Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 550 |
Max Temp Winter | 30ºF |
Max Temp Summer | 75ºF |
Top Sights | Glendale Falls, C.M. Gardner State Park and Skyline Trail |
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Frequently asked questions
How much does a Middlefield vacation package cost?
You'll find cheap prices from $611 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 vacation to Middlefield costs.
What are the cheapest months to go to Middlefield?
You're likely to find lower prices and better availability in January, October and December. Explore our cheap Middlefield vacation packages and you could get some excellent off-season deals.
How many days is enough for Middlefield?
With a well-planned itinerary, you can easily visit the main Middlefield sights in a handful of days. But if you'd like to explore off the beaten track or go on day tours, consider booking your Middlefield vacation for longer.
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 vacation package as early as possible.
Is it cheaper to book a Middlefield vacation as a package?
Expedia vacation 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 vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation 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 vacation.
Does Expedia offer Book Now, Pay Later Middlefield vacation packages?
Your Middlefield trip should be an escape from your daily routine, not a source of money worries. So to give you more flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.