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Compare 382 Vacation Homes in Southfield with updated reviews, rates, and availability.

Peace and quiet on the lake

9.6 out of 10, Exceptional, (211)
"Property was very nice. Quite area. Host was fantastic. "
Peace and quiet on the lake

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

10.0 out of 10, Exceptional, (45)
"We had an amazing long ski weekend at the Great Escape Ski Cottage. The listing is very accurate. Great communication with Shay. The house was immaculate upon arrival. The layout of the house was perfect for our family (6 adults and 4 children aged 4-9). One beautiful Master Bedroom on the first floor. Two of the other equally beautiful bedrooms are on the second floor. The linens were hotel quality! The "Kid's Quarters" was located off of the kitchen/laundry room. A playroom with multiple games...
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

Mountain View Getaway

10.0 out of 10, Exceptional, (49)
"Such a magical place…always enjoy our stay. The home is so comfy - the hosts are amazing. "
Mountain View Getaway

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.

Laurel Lake Luxury 4BR, 4.5 Bath, Ranch on Fox Hollow Estate

10.0 out of 10, Exceptional, (1)
"My friends and I stayed at this adorable and HUGE home in this lovely condo complex to spend the weekend at Ski Butternut which was only like 10 minutes away. The host even left us 2 bottles of wine! It had FIVE bathrooms which is unheard of, like anywhere, and the beds were the fancy adjustable kinds. TVs and cable in every bedroom. The fireplace was so luxurious. When the living room TV was giving us some connection issues I think it was a total of like 7 minutes to contact the host/co-host...
Laurel Lake Luxury 4BR, 4.5 Bath, Ranch on Fox Hollow Estate

Heart of Lenox Walk to Town Cozy Cottage!

10.0 out of 10, Exceptional, (69)
"Tom’s cottage was the perfect place for us to stay to enjoy the new year in quiet Lenox. It was centrally located which made exploring town easy and convenient. The check in and out process was super simple and Tom made himself easily accessible throughout the stay. "
Heart of Lenox Walk to Town Cozy Cottage!

Berkshires Lakefront Retreat

10.0 out of 10, Exceptional, (6)
"Outfitted with everything a guest could want or need, from a fully equipped kitchen, linens, and cozy afghans to marshmallows for the hot chocolate. Spacious house with lots of places to gather or spread out. Beautiful setting—snow covered frozen lake. We would love to return in warm weather to make use of the lakefront. Very responsive and considerate host. "
Berkshires Lakefront Retreat

Perfect Nature Retreat In Great Barrington

2.0 star property
10.0 out of 10, Exceptional, (2)
"We had a great time at the house. We had everything we needed. It was close to town. The space is very comfortable."
Perfect Nature Retreat In Great Barrington

Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

9.4 out of 10, Exceptional, (8)
"The location was great and just a short walk to downtown. We thought the pictures on the site were a bit misleading. The house looked a little more open than it actually was, especially in the kitchen. The outside fire pit area was a little run down. A chair was broken and the string lights were down on the ground, water filled and no outlet to plug into. Plenty of bed space for everyone to sleep and beds were comfortable. Plenty of extra sheets and towels and the kitchen was well equipped. We...
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

Remodeled Lakefront retreat!! Come join us for Ski Season!!

9.8 out of 10, Exceptional, (6)
"Lovely lake house. Had a wonderful time! The kitchen is great and second stove is a bonus too! "
Remodeled Lakefront retreat!! Come join us for Ski Season!!

4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi

10.0 out of 10, Exceptional, (149)
"The location is beautiful and there are lots of places to visit in the area. The house is nice; great view of Otis Reservoir. It took us a while to figure out the multiple thermostats, but it was a good Christmas house. The owner was nice enough to allow us to have a Christmas tree, and had someone make an extra trash pick up for us after Christmas.The one thing we were disappointed in was the cleanliness. Shower curtains were moldy, some of the dishes weren't very clean, expired condiments...
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi

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, (120)
"Fantastic home! Clean, well stocked and very comfortable. We had a great time and will be back. The owner was kind, considerate and appreciative of our stay. Thanks again! "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

The Goshen Glass Chalet

9.6 out of 10, Exceptional, (33)
"Went there for a weekend with a friend to hole up and relax in February and it was lovely. Listing is accurate and Cindy was very easy to communicate with. Hot tub was great!"
The Goshen Glass Chalet

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

9.0 out of 10, Wonderful, (23)
"The property is great for a group of people lots of bedrooms. Lots of sitting rooms. The kitchen is great for a culinary event - we had a private chef one night. The upstairs den was very cozy-It was a cold weekend with lots of snow- we didn’t want to leave the house !And close to Lenox -and Miraval spaWe would definitely come back next year. "
Amore Estate - beautiful room with many places to explore and relax in.

Beautiful Berkshire Farm House on 160+ Acres

10.0 out of 10, Exceptional, (39)
"We had a wonderful time -- the bedrooms were so comfortable, the kitchen had everything we needed, and when we got snowed in, the owners and neighbors were incredibly helpful. Thank you!"
Beautiful Berkshire Farm House on 160+ Acres

Home in Great Barrington

9.6 out of 10, Exceptional, (19)
"Our family had a wonderful experience and stay. "
The price is SAR 806
SAR 1,253 total
includes taxes & fees
23 Mar - 24 Mar
Home in Great Barrington

Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.

10.0 out of 10, Exceptional, (120)
"Really enjoyed our stay. Open-plan downstairs with spacious kitchen, two dining areas, amazing sectional that fit all of us for movie night. Great fireplace where we enjoyed a couple fires."
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.

Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

10.0 out of 10, Exceptional, (3)
"Our group of 8 were happy in this comfy home. The kitchen was well appointed with everything we needed. The bedding, towels and toiletries provided were very much appreciated. The cozy living room with the pellet stove has a beautiful view for morning coffee. "
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

Monterey Home w/ Hot Tub, Pool & Game Room!

9.0 out of 10, Wonderful, (2)
"Beautiful property. Lovely grounds. Clean and so much fun for the little ones. Communication and service were excellent. "
Monterey Home w/ Hot Tub, Pool & Game Room!
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.
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Other property types in Southfield

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The Ponds at Foxhollow

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

9.6 out of 10, Exceptional, (39)
"A nice cabin in the woods. Only issue was rodents at the property. We had four sighting in three days. Would stay again if they resolved the mouse problem."
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

9.4 out of 10, Exceptional, (15)
"Great location. "
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
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.