Middlefield Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
Photo by Elizabeth Massa Peroulakis
- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Middlefield Hotel Deals
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
The price is CA $142 per night from Feb 8 to Feb 9
CA $142
CA $174 total
Feb 8 - Feb 9
includes taxes & fees
8.6/10 Excellent! (2,227 reviews)
Spacious 2 bed 2 bath!
Reviewed on Feb 3, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is CA $135 per night from Feb 8 to Feb 9
CA $135
CA $181 total
Feb 8 - Feb 9
includes taxes & fees
9/10 Wonderful! (825 reviews)
We had a lovely extended family weekend here. The staff was outstanding, every staff member was helpful, friendly and courteous. The large room in back of the lobby was especially helpful for our large group to hang out in and be comfortable. Everyone enjoyed the pool and hot tub despite it being ...
Reviewed on Feb 1, 2026
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is CA $134 per night from Feb 8 to Feb 9
CA $134
CA $150 total
Feb 8 - Feb 9
includes taxes & fees
9/10 Wonderful! (1,010 reviews)
The staff is very helpful, and always willing to assist with any inquiries. The room was definitely clean and well-stocked throughout our entire stay.
Reviewed on Feb 5, 2026
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
