Southfield Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Southfield

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 2.458.332 ₫ per night from 2 Sept to 3 Sept
2.458.332 ₫
3.111.859 ₫ total
2 Sept - 3 Sept
includes taxes & fees
9/10 Wonderful! (689 reviews)
"This was our third year of two summer weeks at Oak 'n' Spruce. The accommodations are comfortable and convenient, and the staff is wonderful. We hope to be back next summer."

Reviewed on 10 Aug 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
The price is 4.956.525 ₫ per night from 18 Aug to 19 Aug
4.956.525 ₫
6.708.172 ₫ total
18 Aug - 19 Aug
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
We loved the sunny Stevens room
"We love the Red Lion. And had two excellent meals around our trips to Tanglewood concerts. We stayed at the Stevens house room 184. Sunny, sweet, fridge downstairs was helpful to store picnic items/wine. But the bed is soft and the bathtub was plastic insert which was unexpected for the cost per ..."

Reviewed on 9 Aug 2025

The Red Lion Inn
Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
Fully refundableReserve now, pay when you stay
The price is 2.429.746 ₫ per night from 2 Sept to 3 Sept
2.429.746 ₫
2.714.027 ₫ total
2 Sept - 3 Sept
includes taxes & fees
8.2/10 Very Good! (1,003 reviews)
"Good"

Reviewed on 8 Aug 2025

Quality Inn
See all 1,060 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.

Popular places to visit

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

Frequently asked questions

How much does a Southfield holiday package cost?
You'll find cheap prices 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 holiday to Southfield costs.
What are the cheapest months to go to Southfield?
You're likely to find lower rates and greater availability in January, February and March. Take a look at our cheap Southfield holiday packages and you could get some great off-season deals.
How many days is enough for Southfield?
With a well-planned itinerary, you can easily visit the top Southfield attractions in a handful of days. But if you'd like to explore off the beaten track or go on day tours, consider booking your Southfield holiday 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," "Traveller 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 holiday as a package?
An Expedia holiday package could land you considerable savings when compared to arranging stays and flights individually. Better still, you can personalise 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 holiday 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.
How to plan a trip to Southfield?

  1. Choose the right time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to travel to Southfield.
  2. Plan your budget wisely: In addition to the price of your stay, you should factor in other expenses. These include transportation, flights and food. Also, set aside some extra funds for unexpected expenses that may come up during your trip to Southfield.
  3. Decide how long to go for: Now that you're more familiar with Southfield, you can figure out the perfect length of your holiday. Put together a rough itinerary and give yourself enough time for all the things you want to do.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. Now all that's left is to pick a Southfield holiday package that brings all your bookings together.