Southfield Vacations from $255

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Your Southfield Vacation

Say goodbye to the hassle of planning and hello to a Southfield vacation package. With the finer details organized before you go, you can focus on discovering every inch of this city, starting with Canann Village Historic District, which is great for dining, culture and shopping. Any trip to Southfield needs a well-crafted itinerary. Fill yours with attractions like Lake Buel, Magnolia Bluffs Casino and Les Trois Emme Winery. Expedia can help you escape the everyday. Tailor your vacation to Southfield to suit your travel style, whatever that may be.

The Latest Southfield 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
Price was $340, price is now $255 per person
$255
per person
May 7 - May 10
found 1 day ago
Roundtrip flight included
Raleigh (RDU) to Albany (ALB)
8.8/10 Excellent! (2,134 reviews)
Yes it was clean as usual.

Reviewed on Feb 21, 2026

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Save 100% on your flight
Price was $731, price is now $481 per person
$481
per person
May 7 - May 10
found 1 day ago
Roundtrip flight included
Raleigh (RDU) to Albany (ALB)
9/10 Wonderful! (1,002 reviews)
The rooms were beautiful and very comfortable. The cleanliness of the rooms was impeccable. Your complimentary breakfast was outstanding with service by the most pleasant staff. Lindsey and the cooks did an awesome job. Would recommend staying here. We surely will be returning. Thank you.

Reviewed on Feb 11, 2026

Prospect Berkshires

Prospect Berkshires

3 out of 5
Save 100% on your flight
Price was $1,056, price is now $727 per person
$727
per person
May 7 - May 10
found 1 day ago
Roundtrip flight included
Raleigh (RDU) to Albany (ALB)
9.4/10 Exceptional! (13 reviews)
The cabins are brand new, the property is gorgeous, restaurant features local and quality product and the staff is very responsive via text message. The lakeside sauna is private and easy to reserve. Great place!

Reviewed on Feb 20, 2026

Hilton Garden Inn Saratoga Springs

Hilton Garden Inn Saratoga Springs

3 out of 5
Save 100% on your flight
Price was $1,736, price is now $1,281 per person
$1,281
per person
May 13 - May 20
found 11 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Albany (ALB)
8/10 Very Good! (1,003 reviews)
The sink aerator is too powerful and it splashes water on your belly (or pants). You can't really adjust it. I get it that they are trying to save water, but they need to find a better model (or clean the one installed). There is no towel rack in easy reach of the shower. One of the dresser table lamps did not work.

Reviewed on Feb 16, 2026

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Discover the most popular places to visit in Southfield

Umpachene Falls Park

Explore the great outdoors at Umpachene Falls Park, a lovely green space in New Marlborough. Discover the area's breweries or seek out the hiking trails.

Umpachene Falls Park

Southfield Hotel Deals

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 refundable
$111 nightly
The price is $124 total per night from Mar 4 to Mar 5
$124 total
Mar 4 - Mar 5
Total with taxes and fees
9/10 Wonderful! (840 reviews)
Super clean spacious room!

Reviewed on Feb 15, 2026

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Quality Inn

Quality Inn

2.5 out of 5
372 Main Street Great Barrington MA
Fully refundableReserve now, pay when you stay
$66 nightly
The price is $74 total per night from Mar 23 to Mar 24
$74 total
Mar 23 - Mar 24
Total with taxes and fees
8.4/10 Very Good! (1,004 reviews)
Clean, breakfast was a nice option before heading to Butternut mountain nearby

Reviewed on Feb 20, 2026

Quality Inn
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
Fully refundableReserve now, pay when you stay
$197 nightly
The price is $221 total per night from Feb 22 to Feb 23
$221 total
Feb 22 - Feb 23
Total with taxes and fees
8.8/10 Excellent! (1,001 reviews)
great customer service

Reviewed on Feb 18, 2026

The Red Lion Inn
See all 1,068 properties in Southfield
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.

Find the Best Southfield Vacation Packages

Southfield Essential Information

Language
English
Currency
U.S dollars
Max Temp Winter
30ºF
Max Temp Summer
80ºF
Top Sights
Otis Ridge, Umpachene Falls Park and Mount Everett State Reservation

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Frequently asked questions

How much does a Southfield vacation package cost?
You'll find cheap prices from $255 on Expedia for your Southfield escape. However, factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Southfield costs.
What are the cheapest months to go to Southfield?
October, November and December are great times to search for cheap Southfield vacation packages. Traveling in less busy periods means you'll typically find better prices on flights and accommodations.
How many days is enough for Southfield?
With a well-organized itinerary, you can easily visit the top Southfield sights in a handful of days. But if you prefer to discover hidden spots or go on day trips, think about booking your Southfield vacation for longer.
How to find the best Southfield package deals?
Finding a cheap Southfield package deal is easy with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your budget, apply a few filters and browse what's available. You can tailor your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Order the results by "Price: low to high" to discover the most affordable Southfield package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Southfield vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging stays and flights individually. Better still, you can personalize your Southfield trip to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Southfield?
Secure amazing discounts by reserving your flights in advance with Expedia. If spontaneity is more your style, grab one of our last-minute deals for a spur-of-the-moment Southfield adventure.
Does Expedia offer Book Now, Pay Later Southfield vacation packages?
Set off on your dream trip to Southfield with Expedia's Book Now, Pay Later vacations. No need to save like crazy or wait for the next payday — we've teamed up with online lender Affirm to give you flexibility and choice. Our vacation packages with payment plans let you spread the cost over 3, 6 or 12 months. With no late payment fees or hidden charges, you can easily stick to your budget and snap up cheap deals before they disappear.

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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.