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Southfield Vacation Rentals

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Dates

November 2026

December 2026

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Top Southfield Hotel Reviews

A white two-story house with a front door, windows, and a chimney.

The Old Inn On The Green

Great Barrington

10/10 Excellent

Rishi

A cozy living room with a fireplace, leather armchairs, a coffee table with fruit, and a bookshelf.

Blackberry River Inn

Norfolk

10/10 Excellent

Brandon

A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Great Barrington

10/10 Excellent

We were greeted by extremely friendly staff. Check in and check out was seamless. Room was very nice and immaculate. We especially liked the bathroom design - didn't have to trip over the toilet to get in the shower as in most hotels! Free breakfast was the usual fare, but in a very pleasant and uncrowded room. Appreciated the free US News and NY Times Beautiful indoor pool - wish we'd brought our bathing suits!

Anonymous traveler

Wilder House Berkshires

Sheffield

10/10 Excellent

Liliana

A spacious indoor area with a reception desk, multiple seating arrangements, and a view of the outdoors through large windows.

Quality Inn Great Barrington

Downtown Great Barrington

10/10 Excellent

Andrew

A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.

Monument Mountain Motel

Great Barrington

10/10 Excellent

We have stayed here a half dozen times, and if you are simply looking for a clean place to lay your head for the night with no frills, then this place is perfect! The rooms have always been clean and everything in good working order. So what that they don't have breakfast...there is an AMAZING breakfast spot right across the street. Take HALF the money you saved by avoiding big name hotels and you'll get a much better breakfast! We've never had noise issues, never felt "unsafe", and the staff is...

Anthony

A covered porch with white railings and rocking chairs.

Locust Tree Bed and Breakfast LLC

East Canaan

10/10 Excellent

rose

A tranquil stream with rocks and trees, a building with balconies and a red railing, and a clear sky.

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

South Lee

10/10 Excellent

I love this place and have stayed here before. Even with the precautions for COVID-19, my kids and I still had a great time. The check-in was smooth and safe. The room was clean and sanitized. In fact, we had to "break the seal" on the door to enter and the seal was evidence of the cleaning that was done. Of course, the arcade and movie theatre were closed, but that was no surprise. The pools were open and reservations required to ensure everyone could be safe and still have fun. Lots of...

David

A large house with a balcony and a grassy yard.

The Little Lion

Great Barrington

10/10 Excellent

Hong

A house with a stone patio and wooden stools.

Little Cat Lodge

Copake Falls

10/10 Excellent

Elisabeth

A large, two-story house with a porch and multiple windows, surrounded by a well-maintained lawn.

The White Hart

Salisbury

10/10 Excellent

We enjoyed our stay at the White Hart. We got a room in the back of the building overlooking a garden. We loved sitting out there and relaxing. The room was a nice size and comfortable. The complementary breakfast provided a good selection and was tasty. The lobby is a nice place to have coffee or wine. The chairs are everywhere and make it a nice place to relax. Service was friendly and attentive and Provisions provides excellent sandwiches. We were also able to park right outside our...

thomas

A lodge with a large building and a dock by a lake, surrounded by forest.

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

10/10 Excellent

Sheila

A straw hat, sunglasses, and two drinks on a striped towel by a body of water.

The Red Lion Inn

Stockbridge

10/10 Excellent

Michael

Quality Inn Lee - Lenox South

Lee

10/10 Excellent

Anonymous traveler

Shaker Mill Inn

West Stockbridge

10/10 Excellent

This was the most comfortable B&B I have every heard of let alone stayed at. It does not have the awkwardness of eating breakfast in a community room of strangers. All the breakfast amenities are in you room, including the food that is stock daily by the inn keepers, so you get to enjoy in the comforts of your room (which is a cozy as home). The room was so spacious and well kept. Every detail is thought of by the innkeepers and if they forgot something they are accessible and gracious to...

Joe

Find out more about Southfield

Everything you need to know about Southfield vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Southfield vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Southfield vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Southfield vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Southfield. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Southfield in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $115 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Southfield rentals

At Expedia, we put the best Southfield vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Southfield rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Southfield vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Southfield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Are there vacation rentals in Southfield?

Yes, there are vacation rentals close to the most popular sights in Southfield, or you can go with a more secluded option if you want a relaxing place to stay. Southfield is known for its parks.

What's the top vacation rental that Southfield has to offer?

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This vacation home rental outside of Southfield is located near skiing and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals are there in Southfield?

Choose from 10 Expedia vacation rentals in Southfield for a memorable vacation.

What’s there to see and do in Southfield?

Umpachene Falls Park and Rhodes Hill are a couple of lovely local spots to get outside and enjoy nature. Suter Farm and Benton Hill are other places to visit while you're in town.

What’s a vacation rental in Southfield like?

Vacation rentals are private properties you can stay in for a few weeks or just a few days in Southfield. Vacation rentals offer extras like WiFi and washers and dryers so you'll feel right at home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of privacy away from shared hotel elevators and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for family gatherings.

Southfield Vacation Rentals

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Find vacation rentals that suit your style

Top Southfield Hotel Reviews

The Old Inn On The Green

10/10 Excellent

Find out more about Southfield

Everything you need to know about Southfield vacation rentals

Southfield vacation rentals: An excellent choice for every season

How to find incredible deals on Southfield rentals

Frequently Asked Questions

Are there vacation rentals in Southfield?

What's the top vacation rental that Southfield has to offer?

How many vacation rentals are there in Southfield?

What’s there to see and do in Southfield?

What’s a vacation rental in Southfield like?

Explore a world of travel with Expedia