Middlefield Vacations from $425

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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.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was $567, price is now $425 per person
$425
per person
Feb 19 - Feb 23
found 14 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Albany (ALB)
8.8/10 Excellent! (2,134 reviews)
Clean rooms, chimney did not work

Reviewed on Jan 4, 2026

Prospect Berkshires

Prospect Berkshires

3 out of 5
Price was $799, price is now $429 per person
$429
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip flight included
Miami (MIA) 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
Save 100% on your flight
Price was $1,384, price is now $924 per person
$924
per person
Feb 13 - Feb 15
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
7.4/10 Good! (567 reviews)
I really wanted to love the Equinox and it is charming. However many aspects were disappointing. Service atvthecrestaurants was impossibly slow. It took over an hour to get breakfast - and not because there was a line waiting. Coffee is promised from 7 am to noon in the lobby (there is no coffee in the room), but they were out by 9:30. Their virtual person who answers the phone promised a Keurig and frig in the room, but there was none. The fireplaces were not kept going (we were told to avoid making it smoky, but still disappointing on a cold winter night). Staff seemed nice, but overwhelmed. It was a fine trip, but not great for those reasons.

Reviewed on Jan 4, 2026

The Manchester View

The Manchester View

2.5 out of 5
Price was $1,011, price is now $702 per person
$702
per person
Feb 13 - Feb 18
found 5 hours ago
Roundtrip non-stop flight included
New York (JFK) to Albany (ALB)
9.4/10 Exceptional! (772 reviews)
The place is great. Especially the wood burning stove in the room.

Reviewed on Jan 7, 2026

Aspen At Manchester

Aspen At Manchester

2.5 out of 5
Price was $896, price is now $692 per person
$692
per person
Feb 12 - Feb 16
found 23 hours ago
Roundtrip non-stop flight included
New York (NYC) to Albany (ALB)
8.8/10 Excellent! (600 reviews)
Everything was good, The refrigerator was barely working, so we had to take the food outside.

Reviewed on Jan 7, 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

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 11 to Jan 12
$141 total
Jan 11 - Jan 12
Total with taxes and fees
8.6/10 Excellent! (2,200 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! (1,007 reviews)
Everyone that works here is so nice! I’ve stayed here twice and had such a nice time. Thank youN

Reviewed on Jan 4, 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 19 to Jan 20
$113 total
Jan 19 - Jan 20
Total with taxes and fees
9/10 Wonderful! (1,010 reviews)
All of the above!

Reviewed on Jan 3, 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 $425 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.