Middlefield Vacations from $567

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Photo by Elizabeth Massa Peroulakis

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.
Hampton Inn Albany-Wolf Road (Airport)

Hampton Inn Albany-Wolf Road (Airport)

2.5 out of 5
Price was $677, price is now $567 per person
$567
per person
Jul 31 - Aug 2
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
8.8/10 Excellent! (1,015 reviews)
Very cosy and lovely hotel. Staff were great!

Reviewed on May 30, 2026

The Perch Hotel

The Perch Hotel

2 out of 5
Save 100% on your flight
Price was $1,058, price is now $750 per person
$750
per person
Jul 23 - Jul 26
found 8 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
9.6/10 Exceptional! (29 reviews)
This is a really charming hotel with amazing views and very friendly and helpful staff. We wish we could've stayed longer!

Reviewed on May 26, 2026

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
Price was $803, price is now $632 per person
$632
per person
Aug 5 - Aug 8
found 14 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Albany (ALB)
9/10 Wonderful! (949 reviews)
The room was clean and comfortable, the staff was friendly and helpful..only negative is that the furniture in the room is in serious need of replacement… veneers on end tables lifting, upholstered kitchen chairs all had rips…

Reviewed on May 27, 2026

Best Western Plus Franklin Square Inn Troy/Albany

Best Western Plus Franklin Square Inn Troy/Albany

2.5 out of 5
Price was $690, price is now $600 per person
$600
per person
Jul 31 - Aug 2
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
8.8/10 Excellent! (1,006 reviews)
The breakfast ran out of items at around. 9:30am which were not replenished ( oatmeal, sausage).

Reviewed on May 30, 2026

The Williams Inn

The Williams Inn

4 out of 5
Price was $874, price is now $763 per person
$763
per person
Aug 6 - Aug 8
found 14 hours ago
Roundtrip flight included
Los Angeles (LAX) to Albany (ALB)
9.6/10 Exceptional! (628 reviews)
Wonderful Inn with wonderful people in a wonderful town. One of my favorite places anywhere.

Reviewed on May 30, 2026

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Discover the most popular places to visit in Middlefield

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.

Skyline Trail

Middlefield Hotel Deals

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $145 total per night from May 31 to Jun 1
$145 total
May 31 - Jun 1
Total with taxes and fees
9/10 Wonderful! (960 reviews)
"Hot tub doesn’t go above 95 which is colder than you think, didn’t have any luggage carts available after asking 3 different people, but it’s a charming place to end on a positive note"

Reviewed on May 28, 2026

Berkshire Mountain Lodge
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
$128 nightly
The price is $143 total per night from May 31 to Jun 1
$143 total
May 31 - Jun 1
Total with taxes and fees
8.8/10 Excellent! (2,380 reviews)
"So after answering all questions that could only lead to a “decent” review here’s what happened. Check in was fine, it was a check in; friendly and we checked in. We get to the room and I leave to grab food for our dinner, my wife calls front desk because of awful noises upstairs, people stomping ..."

Reviewed on May 29, 2026

Vacation Village in the Berkshires
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $133 total per night from Jun 1 to Jun 2
$133 total
Jun 1 - Jun 2
Total with taxes and fees
9/10 Wonderful! (963 reviews)
"The converted motel has several appealing features — it was clean, the Le Labo products smelled wonderful, and the lobby bar is beautifully designed. Unfortunately, the level of service fell well below expectations. Two days before our arrival, I received a survey asking whether we’d like any additional ..."

Reviewed on May 27, 2026

Berkshires Untold
See all 1,063 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.

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 $567 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.