Southfield Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 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
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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.
Top Southfield Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Berkshire Mountain Lodge
CA $920
per person
Oct 6 - Oct 11
found 19 hours ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
9/10 Wonderful! (1,077 reviews)
A convenient place to stay for Tanglewood events. Fully equipped kitchen, free laundry room and quiet. Sofa is uncomfortable.
Reviewed on Aug 23, 2026
Hideaway Inn Lenox
CA $1,358
per person
Sep 26 - Oct 2
found 6 hours ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
8/10 Very good! (39 reviews)
I am sorry to say that I cannot recommend. There is no staff on sight, no coffee, you have to buy everything from a vending machine.
The rooms are old and musty. we had to leave a day early because of the mustiness.
The mattresses are old as well.
The property has a lovely location but needs a lot of work to make it comfortable for guests.
Reviewed on Aug 23, 2026
Ready to book your vacation to Southfield?
Southfield Hotel Deals
The Red Lion Inn
30 Main Street Stockbridge MA
Fully refundableReserve now, pay when you stay
CA $204
CA $296 total
Sep 8 - Sep 9
includes taxes & fees
8.8/10 Excellent! (1,012 reviews)
"We loved our stay here. It’s not a modern cookie cutter experience. We loved the history and antique nature of the property."
Reviewed on Aug 22, 2026
Quality Inn Great Barrington
372 Main Street Great Barrington MA
Fully refundable
CA $127
CA $142 total
Sep 13 - Sep 14
includes taxes & fees
8.6/10 Excellent! (1,022 reviews)
"A nice little hotel. Friendly staff. Well-maintained. And the nice thing is the location - it's in downtown Great Barrington, so you can walk to restaurants and other attractions without having to get into your car. No more than 30 minutes from Tanglewood, Shakespeare and Co., and Jacob's Pillow. ..."
Reviewed on Aug 23, 2026
Holiday Inn Club Vacations Oak 'n Spruce Resort
190 Meadow Street South Lee MA
Fully refundable
CA $161
CA $207 total
Aug 31 - Sep 1
includes taxes & fees
9.2/10 Wonderful! (970 reviews)
"Oak’n’Spruce is a lovely resort in a wonderful area of the Berkshires. Very nice amenities, along with pools, tennis, mini golf, ping pong and other family activities. Best of all, it’s a short drive to the charming town of Stockbridge, a short drive to Tanglewood, and another short drive to Jacob’s ..."
Reviewed on Aug 23, 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.
Stay near popular Southfield attractions
Umpachene Falls Park
10.0/10 (1 review)
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.
Suter Farm
You can take time to visit Suter Farm during your travels to New Marlborough. While you're in the area, wander around the natural setting.
Rhodes Hill
Commune with nature and explore the great outdoors at Rhodes Hill during your travels in New Marlborough. While you're in the area, wander around the natural setting.
Benton Hill
Commune with nature and explore the great outdoors at Benton Hill during your travels in New Marlborough. While you're in the area, wander around the natural setting.
Frequently asked questions
How much does a Southfield vacation package cost?
Offering excellent value package deals from CA $788 on Expedia, you'll be surprised at how little a vacation to Southfield costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Southfield?
You're likely to find lower rates and better availability in January, February and March. Check out our cheap Southfield vacation packages and you could land some great off-season discounts.
How many days is enough for Southfield?
With a well-organized travel plan, you can easily tick off the main Southfield sights in a handful of days. But if you prefer to explore off the beaten track or go on day trips, consider booking your Southfield vacation for longer.
How to find the best Southfield package deals?
Begin your search for a Southfield package deal by entering your preferred travel dates and destination under our "Packages" tab. Then apply a few filters, like "Popular locations" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the ideal Southfield package deal right away, just switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Southfield adventure underway.
Is it cheaper to book a Southfield vacation as a package?
You can enjoy significant savings on your next Southfield break by booking a personalized vacation package. Check the "Package" heading, then select your travel dates and destination to view some great hotel prices and airfares. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Southfield?
Enjoy fantastic discounts by booking your flights ahead of time with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for a spur-of-the-moment Southfield trip.
How to plan a trip to Southfield?
- Choose when to get away: Check your schedule and pack your bags. Your favourite season and the type of activities available will also help you decide when to visit Southfield.
- Calculate your budget: Ensure you have enough money to cover everything from food and transportation to airfares and activities. Your hotel will probably be the biggest expense during your trip to Southfield.
- Set the duration of your trip: Start by listing all the attractions you want to get to in Southfield. Then, estimate how long you'll need at each, along with any travel time.
- Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a personalized Southfield vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
