Middlefield Vacations from $309

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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.
The Landing Hotel at Rivers Casino & Resort

The Landing Hotel at Rivers Casino & Resort

4 out of 5
Nothside
Price was $467, price is now $309 per person
$309
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
9.2/10 Wonderful! (1,005 reviews)
Very clean staff was very nice will return

Reviewed on Jan 12, 2026

Prospect Berkshires

Prospect Berkshires

3 out of 5
Price was $1,354, price is now $924 per person
$924
per person
Mar 14 - Mar 19
found 12 hours ago
Roundtrip non-stop flight included
Kansas City (MKC) to Albany (ALB)
9.4/10 Exceptional! (13 reviews)
Wow, just wow! My high school friend and I met up at Prospect Berkshires for a girls weekend. We had an incredible time relaxing by using all the amenities. The staff are so helpful and profession.

Reviewed on Nov 29, 2025

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
Manchester Village Historic District
Price was $1,371, price is now $994 per person
$994
per person
Mar 14 - Mar 20
found 14 hours ago
Roundtrip flight included
San Juan (SJU) to Albany (ALB)
7.4/10 Good! (567 reviews)
Was surprised at the dirty floors in common area and in my room one of the curtain sheers was ripped, other curtains were hanging off hokks, caulking at sink looked old, cracked, carpets in staircase dirty. I fear this beautiful hotel is in a downward spiral. One front desk person directed me to closed restaurants...

Reviewed on Jan 9, 2026

The Manchester View

The Manchester View

2.5 out of 5
Price was $1,049, price is now $776 per person
$776
per person
Mar 14 - Mar 20
found 14 hours ago
Roundtrip flight included
San Juan (SJU) to Albany (ALB)
9.4/10 Exceptional! (772 reviews)
For the price it is absolutely 10/10. Clean, easy to check in & out. Amazing value

Reviewed on Jan 11, 2026

The Dewey

The Dewey

3.5 out of 5
Price was $1,008, price is now $746 per person
$746
per person
Mar 14 - Mar 19
found 12 hours ago
Roundtrip non-stop flight included
Kansas City (MKC) to Albany (ALB)
8.6/10 Excellent! (329 reviews)
Great spot. Lots of history.

Reviewed on Sep 12, 2025

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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

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
$126 nightly
The price is $141 total per night from Jan 13 to Jan 14
$141 total
Jan 13 - Jan 14
Total with taxes and fees
8.6/10 Excellent! (2,202 reviews)
Clean rooms, chimney did not work

Reviewed on Jan 4, 2026

Vacation Village in the Berkshires
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
Fully refundable
$98 nightly
The price is $109 total per night from Jan 23 to Jan 24
$109 total
Jan 23 - Jan 24
Total with taxes and fees
8/10 Very Good! (1,004 reviews)
Another good 2 night stay. Did have a slow shower drain but reported that to maintenance and it was fixed right away. Good service. And also the restaurant is quite good featuring an American menu with a Southern emphasis. The parking garage demo is moving quickly by the way. More parking close to ...

Reviewed on Jan 7, 2026

Holiday Inn & Suites Pittsfield-Berkshires by IHG
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $113 total per night from Jan 20 to Jan 21
$113 total
Jan 20 - Jan 21
Total with taxes and fees
9/10 Wonderful! (1,001 reviews)
Everything was great!

Reviewed on Jan 8, 2026

The Yankee, Trademark Collection by Wyndham
See all 1,049 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 $309 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.