Middlefield Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Elizabeth Massa Peroulakis

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, 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.

Top Middlefield Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
Price was CA $1,248, price is now CA $1,091 per person
CA $1,091
per person
Oct 3 - Oct 6
found 14 hours ago
Roundtrip flight included
Edmonton (YEG) to Albany (ALB)
9/10 Wonderful! (542 reviews)
Enjoyed the room, towels and kitchen. I can recommend.

Reviewed on Aug. 18, 2025

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Price was CA $1,799, price is now CA $1,490 per person
CA $1,490
per person
Oct 3 - Oct 6
found 14 hours ago
Roundtrip flight included
Edmonton (YEG) to Albany (ALB)
9/10 Wonderful! (1,000 reviews)
We have stayed at the Cornell Inn in the past. Always a comfortable, convenient and friendly stay. The food, staff and accommodations are perfect.

Reviewed on Aug. 19, 2025

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was CA $1,264, price is now CA $1,096 per person
CA $1,096
per person
Oct 3 - Oct 6
found 14 hours ago
Roundtrip flight included
Edmonton (YEG) to Albany (ALB)
8.6/10 Excellent! (1,931 reviews)
A rare, affordable place in the Berkshires! The scenery is stunning, and we loved the pools (both indoor and out) and fire pit. The staff was friendly, and our room was spacious but dated: the blinds were broken, the doors stuck, the walls were paper thin and our king-size mattress had clearly seen better days (so uncomfortable!) But we were glad to have enough space for three, plus a terrace overlooking the woods and close by the outdoor pool. Fully stocked kitchen as well. We will be back.

Reviewed on Aug. 18, 2025

Berkshires Untold

Berkshires Untold

3.5 out of 5
Price was CA $1,576, price is now CA $1,416 per person
CA $1,416
per person
Oct 3 - Oct 6
found 14 hours ago
Roundtrip flight included
Edmonton (YEG) to Albany (ALB)
9.2/10 Wonderful! (659 reviews)
Terrific property. The lobby is outstanding for relaxing. Rooms are small but met all needs including a fridge. Linens were very high end, as were the toiletries. Very comfortable bed and pillows. Very clean and neat, all felt new and well maintained. Lots of parking. Very easy and tech heavy checkin and checkout. Easy checkout extension granted until 12pm.

Reviewed on Aug. 18, 2025

Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

2.5 out of 5
Price was CA $1,276, price is now CA $1,186 per person
CA $1,186
per person
Oct 3 - Oct 6
found 14 hours ago
Roundtrip flight included
Edmonton (YEG) to Albany (ALB)
8.4/10 Very Good! (1,001 reviews)
The only thing I don’t like is their coffee. It’s doesn’t taste good at all. Some staff at the front desk could use an attitude adjustment. Otherwise this hotel has become our go to for the Albany area.

Reviewed on Aug. 18, 2025

Ready to book your vacation to Middlefield?

 

Choose your dates

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
The price is CA $150 per night from Aug 27 to Aug 28
CA $150
CA $183 total
Aug 27 - Aug 28
includes taxes & fees
8.6/10 Excellent! (1,952 reviews)
"Liked the fact there are 2 pools, an indoor and an outdoor."

Reviewed on Aug. 17, 2025

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
The price is CA $91 per night from Sep 7 to Sep 8
CA $91
CA $133 total
Sep 7 - Sep 8
includes taxes & fees
8.8/10 Excellent! (578 reviews)
"Enjoyed the room, towels and kitchen. I can recommend."

Reviewed on Aug. 18, 2025

Berkshire Mountain Lodge
Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
The price is CA $128 per night from Sep 3 to Sep 4
CA $128
CA $144 total
Sep 3 - Sep 4
includes taxes & fees
8.2/10 Very Good! (1,007 reviews)
"I'd say the property was adequate. The property is pretty dated, but it met our needs for a brief stay. Our unit was clean and our stay was comfortable."

Reviewed on Aug. 17, 2025

Quality Inn
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Middlefield vacation package cost?
You'll find cheap prices from CA $1,091 on Expedia for your Middlefield escape. However, a range of factors like the length of stay, the season and your choice of hotel will influence how much your vacation to Middlefield costs.
What are the cheapest months to go to Middlefield?
January, February and November are the best times to search for cheap Middlefield vacation packages. Opting to travel in quieter months means you can generally find lower prices on flights and hotels.
How many days is enough for Middlefield?
The ideal duration of your Middlefield vacation depends on what you'd like to do. Usually, a few days to a week will give you enough time to check out all the main sights and discover some hidden treasures along the way.
How to find the best Middlefield package deals?
Start your search for a Middlefield package deal by entering your destination and preferred travel dates under our "Packages" tab. Then add a few filters, like "Guest rating" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Middlefield package deal straight away, just change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Middlefield escape off to a flying start.
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 enjoy significant savings. You'll usually snag a better deal than booking each component separately. And you'll still have the flexibility to create a personalized Middlefield vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Middlefield?
If you're planning an impromptu Middlefield vacation, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can find awesome deals on your hotels and flights by booking well in advance.
How to plan a trip to Middlefield?

  1. Choose your dates: The things you plan to do in Middlefield and your preferred season can help you decide when to go.
  2. Set your budget: Consider expenses such as food, flights and transportation when calculating how much to set aside for your trip to Middlefield. Then, select a hotel that fits your budget, whether that's a wallet-friendly stay or a swankier retreat.
  3. Set the duration of your trip: Start by listing all the activities and sights you'd like to experience in Middlefield. Then, estimate how long you'll need for each, including any travel time.
  4. Combine your accommodations and airfare: Once you've settled on your trip dates and duration, lock in the ideal Middlefield vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.