Search Vacation Homes in Southfield

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Compare 312 Vacation Homes in Southfield with updated reviews, rates, and availability.

Peace and quiet on the lake

9.6 out of 10, Exceptional, (204)
"Such a cozy cabin for a perfect weekend stay with friends. Located close to multiple ski spots around the area, coming back to the cabin after to relax with hot cocoa and a fire going on. Right down the street is a shop that sells delicious sandwiches too. Owners of the property were super nice and quick to respond with any questions we had. Hoping to come back soon and check this place out during the summer time to enjoy the lake life!"
Peace and quiet on the lake

Spectacular views and close to Great Barrington.

10.0 out of 10, Exceptional, (1)
"A beautiful place for our grown family to congregate. Easy commute to Tanglewood, a pool to keep us cool, and a wonderful kitchen to cook in. There are lots of other houses within view but not bothersome. Had a great stay here."
Spectacular views and close to Great Barrington.

Beautiful Berkshire Farm House on 160+ Acres

10.0 out of 10, Exceptional, (37)
"The house was great. Plenty of bedrooms to fit our party of 16 (mix of kids and adults). Very comfortable hang out spaces and places to play games. The barn with the basketball court was awesome also! We got a lot of use out of that. The house was clean and everything worked well except that the dishwasher was broken. That was unfortunate, but these things happen, and we made due. The owner said that it would be fixed in a week or so, so hopefully not an issue for anyone else. Owner was...
Beautiful Berkshire Farm House on 160+ Acres

Berkshires Lakefront Retreat

10.0 out of 10, Exceptional, (5)
"I booked the weekend for my girlfriends birthday with a couple of her friends. The game room was a massive hit as was the propane fireplace outside. We also enjoyed watching the snow fall on the frozen lake. William was very responsive to messages and calls. We enjoyed our stay immensely and are hoping to come back in the summer"
Berkshires Lakefront Retreat

Amore Estate - beautiful room with many places to explore and relax in.

9.4 out of 10, Exceptional, (21)
"Fantastic, large house with tons of places to explore in the house and on the property. We came for a long weekend with 3 families and both the adults and kids felt quickly at home and really enjoyed our stay. We cannot wait to some back!"
Amore Estate - beautiful room with many places to explore and relax in.

COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

9.4 out of 10, Exceptional, (21)
"Well located and comfortable "
The price is AED 716
AED 1,380 total
includes taxes & fees
4 Feb - 5 Feb
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

The Goshen Glass Chalet

9.4 out of 10, Exceptional, (30)
"Nice and cozy property. The host has been very responsive. "
The Goshen Glass Chalet

Home in Great Barrington

10.0 out of 10, Exceptional, (18)
"Our family had a wonderful experience and stay. "
The price is AED 735
AED 1,173 total
includes taxes & fees
24 Feb - 25 Feb
Home in Great Barrington

BAGELS & SLOPES: Start Your Day Deliciously, Hit Powder Perfectly!

2.0 star property
8.8 out of 10, Excellent, (3)
"Property is lovely and very well maintained. We stayed for over 10 days and it was a perfect home away from home. Owners are very kind and accommodating — when I couldn’t find a hair dryer one was delivered to the house within a couple of hours. They also offered to relocate us if we were bothered by the nearby forest fire, which was not necessary. I hope we’ll have the opportunity to stay again."
BAGELS & SLOPES: Start Your Day Deliciously, Hit Powder Perfectly!

Hudson Valley and The Berkshires getaway

10.0 out of 10, Exceptional, (5)
"We loved our stay on Stone Ledge Rd in Hillsdale. We have stayed at Vrbo properties in Hillsdale two prior holiday weeks leading up to the New Year and this was by far the best set-up for us—gorgeous views through the wrap-around windows, easy and comfortable sleeping arrangements for the 6 of us, plenty of sofa space for reading, watching movies, just hanging out. Ben was very responsive when a mixture of drizzle and freezing temperatures made the driveway slippery and we were able to park in...
Hudson Valley and The Berkshires getaway

Pristine Home In Becket Woods

10.0 out of 10, Exceptional, (13)
"Pristine can mean several different things. My interpretation was to be “like new”. This dwelling did not quite live up to that standard, but was clean, sans the “mud room” and what appeared to be mold on the peak of the ceiling above the living room. The original listing stated firewood was provided by the host. Then, the checkin instructions stated guests provided their own. Not huge, just misstated in the listing (since changed). There was a power outage while we were there, thus no...
Pristine Home In Becket Woods

Quintessential 6-BR Berkshires Lodge

10.0 out of 10, Exceptional, (11)
"The house was perfect for us. Spacious, clean, comfortable. Beds comfortable. Bathrooms really nice. The road in the development is dirt, a 4wd is needed as stated. It was muddy and rutty on arrival, then snow and ice , but do-able. Great house. Would recommend "
Quintessential 6-BR Berkshires Lodge

Wellspring by AvantStay | Indoor Pool + Views

10.0 out of 10, Exceptional, (10)
"We all enjoyed our stay. The house and indoor pool were wonderful. There are plenty of comfortable places to sit and enjoy the gorgeous views. We loved the location which is both close to Lenox restaurants, as well as, the southern Berkshires for food markets and activities for kids. The property manager was attentive, and the owner was very responsive. We loved our week at this family friendly property and highly recommend it. "
Wellspring by AvantStay | Indoor Pool + Views

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

10.0 out of 10, Exceptional, (118)
"Property as described. Great location to towns. Larger interior space than anticipated. Great Kitchen for a group of 5 to cook, chat and enjoy! Overall a warm and spacious home for old college friends to reunite. "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

5 Minutes from Catamount Ski Area

9.0 out of 10, Wonderful, (21)
"Cozy spot after skiing. "
5 Minutes from Catamount Ski Area

Butternut SKI 4miles!! Ranch Sleeps 10 & 0.7 mi to GB Main St.Wi-Fi + HOT TUB.

10.0 out of 10, Exceptional, (20)
"We were a group of 4 long time girlfriends on a Girls' Weekend. This house was perfect for us. The house is set fairly far back from the road which gives you an abundance of privacy. There are 3 bedrooms (king, king, and 2 full beds). If you don't mind sharing a room with one of your besties, then this completely updated home is for you! We selected the home for the hot tub and firepit. We used the hot tub both nights of our weekend stay! We loved the lights in the trees...was so relaxing...
Butternut SKI 4miles!! Ranch Sleeps 10 & 0.7 mi to GB Main St.Wi-Fi + HOT TUB.

Peaceful, Post and Beam Loft, Sleeps 9

10.0 out of 10, Exceptional, (15)
"We enjoyed our stay in this lovely, remote location. The home was welcoming and inviting. The property is large with nice views. It is a bit of a drive to reach stores and restaurants but that is what we like! The upstairs loft is one wide-open space with several beds so you need to be okay with sharing the space. "
Peaceful, Post and Beam Loft, Sleeps 9

Antique Farmhouse Totally Restored

9.8 out of 10, Exceptional, (85)
"Place is great. Has a old farmhouse feel with an update. Lots of spots within the house for people to hang out. We did a family birthday get together and had a great time. "
Antique Farmhouse Totally Restored

Stunning lake views and privacy only mins. to downtown Lenox, Stockbridge, Lee.

10.0 out of 10, Exceptional, (22)
"This was our third year in a row staying at this house for our annual ski trip with 4 adults and 6 kids. It is always immaculate and has great common rooms for all of us. Kari and Glenn think of everything and Glenn even came to shovel the walkway and driveway for us during a snow storm (without even having to enter the house). We look forward to our time at this beautiful property every year! "
Stunning lake views and privacy only mins. to downtown Lenox, Stockbridge, Lee.

Large Barn styled vacation home that fits groups with space to spare.

9.8 out of 10, Exceptional, (57)
"Everything was ideal for our Thanksgiving get together. Setting and views were perfect, made even more so with a timely blanket of fresh snow. An amazing amount of cooking provisions allowed us to cook as if we were in our own kitchen. Lots of options for keeping a large group entertained, and sleeping accomodations that pleased everyone. Host was very helpful with check-in communications and gracious with check in and out times without other bookings adjacent to ours. All in all a very special...
Large Barn styled vacation home that fits groups with space to spare.
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.
Don't see what you're looking for?
See all available properties in Southfield
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Southfield

Romantic and Secluded Berkshire's Gem

9.8 out of 10, Exceptional, (13)
"This was a perfect meet up spot for us and our friends from Westchester. It was cozy and clean and warm! A perfect spot to enjoy skiing at Butternut and to stay warm during and play in the snow during a snowstorm!"
Romantic and Secluded Berkshire's Gem

The Ponds at Foxhollow by Capital Vacations

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The price is AED 879
AED 981 total
includes taxes & fees
14 Feb - 15 Feb
The Ponds at Foxhollow by Capital Vacations

Private Estate, Heated Yearround Outdoor Pool

10.0 out of 10, Exceptional, (16)
"The home was beautiful and it was a gorgeous property too. It had all the right amenities in the kitchen. "
The price is AED 6,178
AED 10,531 total
includes taxes & fees
19 Feb - 20 Feb
Private Estate, Heated Yearround Outdoor Pool
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.