Middlefield Vacations from $612

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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.
The Motel Montreal

The Motel Montreal

2 out of 5
Save 100% on your flight
Price was $875, price is now $612 per person
$612
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
7.2/10 Good! (502 reviews)
Very good for the price. A+

Reviewed on Jul 12, 2026

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Save 100% on your flight
Price was $1,363, price is now $907 per person
$907
per person
Sep 18 - Sep 21
found 24 hours ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
9.2/10 Wonderful! (1,002 reviews)
So welcoming and peaceful. Lovely property.

Reviewed on Jul 13, 2026

Lodges At Cresthaven

Lodges At Cresthaven

4 out of 5
Save 100% on your flight
Price was $1,994, price is now $1,413 per person
$1,413
per person
Sep 20 - Sep 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
9.4/10 Exceptional! (616 reviews)
what a beautiful and special place! Theres a fantastic pool for kids/family overlooking the beautiful lake. I wish we were able to stay longer. It was really one of the most beautiful places I have stayed. The Cabin lodging, the rooms, the bathrooms, everything was just great! Check out is at 10am, I wish it was maybe till noon for what you pay for but I understand because the cabins need to be cleaned. It was great!

Reviewed on Jul 9, 2026

The Lake George Inn

The Lake George Inn

2 out of 5
Save 100% on your flight
Price was $1,262, price is now $900 per person
$900
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
5.6/10 (8 reviews)
Quick overnight trip crazy tho to charge for 2 people extra

Reviewed on Oct 25, 2025

Brook Bound Inn

Brook Bound Inn

2 out of 5
Save 100% on your flight
Price was $1,630, price is now $1,168 per person
$1,168
per person
Aug 29 - Sep 5
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Albany (ALB)
9.2/10 Wonderful! (17 reviews)
The cabin and grounds are well-maintained. The pool was crystal clear and the slide was a nice addition. Gorgeous views!

Reviewed on Jun 28, 2026

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Stay near popular Middlefield attractions

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.
See properties

Middlefield Hotel Deals

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
$145 nightly
The price is $162 total per night from Jul 16 to Jul 17
$162 total
Jul 16 - Jul 17
Total with taxes and fees
Vacation Village in the Berkshires
Quality Inn Great Barrington

Quality Inn Great Barrington

2.5 out of 5
372 Main Street Great Barrington MA
$118 nightly
The price is $132 total per night from Aug 6 to Aug 7
$132 total
Aug 6 - Aug 7
Total with taxes and fees
8.6/10 Excellent! (1,000 reviews)
"Comfortable rooms within walking distance to Great Barrington."

Reviewed on Jul 13, 2026

Quality Inn Great Barrington
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
$189 nightly
The price is $211 total per night from Jul 16 to Jul 17
$211 total
Jul 16 - Jul 17
Total with taxes and fees
9.2/10 Wonderful! (1,016 reviews)
"I still suffer from bed bugs bite and mosquito, we were placed in the old room, old carpet and smelly room. The staff were nice and the cleaners too. I just wish we could have stayed in the main building."

Reviewed on Jul 15, 2026

The Yankee Inn
See all 1,061 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 $612 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.