Middlefield Vacations from $352

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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
Save 100% on your flight
per person
Oct 17 - Oct 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
8.6/10 Excellent! (1,862 reviews)
The unit has everything you need and is very clean. It would benefit from a step stool in the kitchen area because you can't reach the dishes without standing on a chair. Also it says you MUST use a convention pan to use the cooktop but there isn't one. Parking is difficult -- the spaces area too short for many vehicles leaving them partly in the road.

Reviewed on Aug 3, 2025

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
Save 100% on your flight
per person
Oct 17 - Oct 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
8.8/10 Excellent! (507 reviews)
Great location to stay between Tanglewood concerts. Will come again.

Reviewed on Aug 2, 2025

The Dewey

The Dewey

3.5 out of 5
Save 100% on your flight
per person
Oct 17 - Oct 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
8.8/10 Excellent! (314 reviews)
Old world charm building with high ceilings and period features. Comfortable bed with nice bedding. En suite bathroom could use some love. One lightbulb was out and the toiletries weren’t fully stocked. Some visible mildew. Overall, a pleasant experience for our overnight stay.

Reviewed on Jul 30, 2025

River House by Avantstay Historic & Secluded Estate on the Hudson River w/ Pool Sleeps 24!

River House by Avantstay Historic & Secluded Estate on the Hudson River w/ Pool Sleeps 24!

3.5 out of 5
Save 100% on your flight
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
No reviews
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
Save 100% on your flight
per person
Sep 23 - Sep 27
found 6 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
7.4/10 Good! (491 reviews)
Beautiful setting! Comfortable rooms

Reviewed on Jul 25, 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
$106 nightly
The price is $119 total per night from Aug 25 to Aug 26
$119 total
Aug 25 - Aug 26
Total includes taxes and fees
8.6/10 Excellent! (1,921 reviews)
"Excellent"

Reviewed on Aug 2, 2025

Vacation Village in the Berkshires
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road, Pittsfield, MA
Fully refundableReserve now, pay when you stay
$70 nightly
The price is $79 total per night from Aug 12 to Aug 13
$79 total
Aug 12 - Aug 13
Total includes taxes and fees
5.2/10 (756 reviews)
"Well the little fridge they had in the room hummed loudly all the time the freezer needed to be defrosted I bought a couple of frozen dinners and couldn't get both of them in the freezer. One of the draws on the side tables when I pulled open the drawer one side of the handle came loose I was able ..."

Reviewed on Jul 28, 2025

FairBridge Inn Express
Quality Inn & Suites Northampton - Amherst

Quality Inn & Suites Northampton - Amherst

2.5 out of 5
117 Conz St, Northampton, MA
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $151 total per night from Aug 6 to Aug 7
$151 total
Aug 6 - Aug 7
Total includes taxes and fees
7/10 Good! (1,000 reviews)
"This hotel offered great comfort and service at a reasonable price. Staff was super friendly and accommodating. Continental breakfast offered various options."

Reviewed on Jul 29, 2025

Quality Inn & Suites Northampton - Amherst
See all 1,076 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.

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Frequently asked questions

How much does a Middlefield vacation package cost?
You'll find cheap prices from $352 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.