Middlefield Holidays
Book a Hotel + Flight or Car together to unlock savings
Photo by Elizabeth Massa Peroulakis
Top hotels in Middlefield
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is 2.394.220 ₫ per night from 23 Mar to 24 Mar
2.394.220 ₫
3.261.887 ₫ total
23 Mar - 24 Mar
includes taxes & fees
9/10 Wonderful! (884 reviews)
This is our 3rd year staying here for my son’s birthday in March. Affordable and having the 2 rooms with a kitchen is so nice. My son’s favorite part is the pool which is always warm and clean, never smells too strong like some places. Hot tub feels amazing too. Will be back next year, or sooner ...
Reviewed on 22 Mar 2026
Berkshires Untold
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is 1.836.792 ₫ per night from 1 Apr to 2 Apr
1.836.792 ₫
2.051.697 ₫ total
1 Apr - 2 Apr
includes taxes & fees
9/10 Wonderful! (879 reviews)
This was a great stay! The room and hotel itself were up to date and was overall a great location to check out the Berkshires. We ate one night at the hotel too and the dinner was really good! I recommend the mushroom ravioli, would stay again.
Reviewed on 21 Mar 2026
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
190 Meadow Street South Lee MA
Fully refundable
The price is 2.958.750 ₫ per night from 23 Mar to 24 Mar
2.958.750 ₫
3.819.088 ₫ total
23 Mar - 24 Mar
includes taxes & fees
9/10 Wonderful! (855 reviews)
Room was awesome and very clean
Reviewed on 8 Mar 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.
Popular places to visit
Skyline Trail
You can take time to visit Skyline Trail during your travels to Middlefield. Stroll along the area's lakeside or simply savour its cosy cafes.
