Middlefield Vacations from $559

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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 Landing Hotel at Rivers Casino & Resort

The Landing Hotel at Rivers Casino & Resort

4 out of 5
Nothside
Price was $755, price is now $559 per person
$559
per person
Apr 20 - Apr 24
found 20 hours ago
Roundtrip flight included
Charlotte (CLT) to Albany (ALB)
9.2/10 Wonderful! (1,001 reviews)
Shower was cold. No shower door or curtain to close to keep the heat in the shower. All the movies in the guide stated, unavailable! No coffee pot. Great warm cookie provided upon arrival. Staff very friendly. Room was clean and comfortable.

Reviewed on Mar 2, 2026

The Wiltwyck

The Wiltwyck

3.5 out of 5
Price was $725, price is now $583 per person
$583
per person
May 18 - May 22
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
9.4/10 Exceptional! (173 reviews)
It was an OK Inn. I felt it was overpriced.

Reviewed on Jan 29, 2026

Hotel Kinsley

Hotel Kinsley

3.5 out of 5
Stockade District
Price was $903, price is now $746 per person
$746
per person
May 18 - May 22
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
9/10 Wonderful! (344 reviews)
Very clean room and bathroom. Nice vibe. S

Reviewed on Feb 24, 2026

Marriott Albany

Marriott Albany

3.5 out of 5
Price was $1,196, price is now $1,003 per person
$1,003
per person
Apr 13 - Apr 17
found 20 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Albany (ALB)
8.4/10 Very Good! (870 reviews)
Room was VERY far from the parking garage. There was no internet or streaming available so the front desk asked if I wanted to cancel. I didn't, but was surprised they didn't offer a free pastry or muffin with their morning coffee(4 .00 dollars) as a trade. Especially since most places have these for FREE!! lol. Walk from garage to room was way too far. Will not stay again due to this.

Reviewed on Mar 5, 2026

Hutton Brickyards Riverfront Hotel + Venue

Hutton Brickyards Riverfront Hotel + Venue

3.5 out of 5
Price was $968, price is now $827 per person
$827
per person
May 18 - May 22
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
8.8/10 Excellent! (103 reviews)
Everything was perfect

Reviewed on Feb 17, 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
$119 nightly
The price is $133 total per night from Mar 8 to Mar 9
$133 total
Mar 8 - Mar 9
Total with taxes and fees
8.8/10 Excellent! (2,283 reviews)
Looks way better in person than the pictures. Still old and dated but not as spooky as the pictures seem. They don't tell you this at all, just expect you to read a packet - there is no housekeeping, no nothing. You are supposed to take your own trash out. They also do not really clean the room beforehand ...

Reviewed on Mar 7, 2026

Vacation Village in the Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$115 nightly
The price is $128 total per night from Apr 6 to Apr 7
$128 total
Apr 6 - Apr 7
Total with taxes and fees
9/10 Wonderful! (869 reviews)
The staff at the front desk was welcoming, the room was very nice. We enjoyed our stay. HOWEVER - on the day we were to arrive there was a major blizzard. There was no safe way to drive from the Boston area to Pittsfield. I called the hotel 2 days before to say that we would be arriving a day after ...

Reviewed on Mar 6, 2026

Berkshire Mountain Lodge
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
$93 nightly
The price is $103 total per night from Mar 15 to Mar 16
$103 total
Mar 15 - Mar 16
Total with taxes and fees
9.2/10 Wonderful! (1,008 reviews)
This is a well-kept and staffed property. It is quiet as it is set back from the highway. Conveniently located for our purposes. We stay here frequently due to business.

Reviewed on Mar 6, 2026

The Yankee, Trademark Collection by Wyndham
See all 1,056 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 $559 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.