Middlefield Vacations

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Find the Best Middlefield Vacation Packages

Middlefield Hotel Deals

Life House Berkshires
Life House Berkshires
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is AED 474 per night from Apr 21 to Apr 22
AED 474
AED 529 total
includes taxes & fees
21 Apr - 22 Apr
9/10 Wonderful! (557 reviews)
"The hotel is cozy and charming. The rooms are well-appointed. The staff was great. Easy check-in, check-out. The bar is well stocked and they offer free (real) coffee in the morning!"

Reviewed on 14 April 2025

Life House Berkshires
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 out of 5
190 Meadow Street, South Lee, MA
Fully refundableReserve now, pay when you stay
The price is AED 393 per night from Apr 28 to Apr 29
AED 393
AED 491 total
includes taxes & fees
28 Apr - 29 Apr
9/10 Wonderful! (620 reviews)
"Great deal for villa resort suite. Lots of space, great condition, great amenities, great location."

Reviewed on 12 April 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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
The price is AED 356 per night from Apr 28 to Apr 29
AED 356
AED 398 total
includes taxes & fees
28 Apr - 29 Apr
9/10 Wonderful! (1,002 reviews)
"This place was being remodeled and had I known I would have stayed elsewhere."

Reviewed on 16 April 2025

The Yankee, Trademark Collection by Wyndham
See all 1,045 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.

Frequently asked questions

How much does a Middlefield vacation package cost?
You’ll find cheap prices 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 can generally find reduced prices and greater availability in January, February and November. Explore our cheap Middlefield vacation packages and you could land some excellent off-season deals.
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.
How to plan a trip to Middlefield?

  1. Choose your dates: What you want to do in Middlefield and your preferred season will help you decide when to travel.
  2. Work out your budget: Ensure you have enough money to cover everything from transportation and food to activities and flights. Your hotel will likely be the largest expense during your trip to Middlefield.
  3. Decide how long to go away for: Now that you know more about Middlefield, you can figure out the ideal length of your break. Pull together a rough itinerary and give yourself enough time to get through everything on your must-do list.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a personalized Middlefield vacation package.

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