Southfield Vacation Rentals

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Vacation Rentals in Southfield

Romantic and Secluded Berkshire's Gem
Fridge, microwave, oven, stovetop
Romantic and Secluded Berkshire's Gem
10.0 out of 10, Exceptional, 9 reviews
"My friends and I had an amazing time staying in the cozy cabin. 9 of us slept comfortably, the place was spotless, and so cute. We hope to visit again."
Romantic and Secluded Berkshire's Gem
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
Interior
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
9.8 out of 10, Exceptional, 32 reviews
"We loved our time, very cozy cabin"
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
Pristine Home In Becket Woods
Fridge, microwave, oven, stovetop
Pristine Home In Becket Woods
10.0 out of 10, Exceptional, 7 reviews
"My wife and young daughters live in central CT, and the drive to Becket was both scenic and relatively short at around an hour and a half. The property offers great privacy in a remote wooded setting in the heart of the always beautiful Berkshires. We brought our dog along, and we all were able to relax by the fire, read our favorite books, as well as peruse interesting titles on the impressive bookshelf built into the living room wall—a book lover’s delight. We admired the openness and light...
Pristine Home In Becket Woods
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The Freeman - Newly Renovated 14K SF Estate on 40 Acres
7 bedrooms, iron/ironing board, cribs/infant beds, travel crib
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, 29 reviews
"We had a great time at The Freeman! The little touches like fresh fruit and a welcome basket made it even more special for our family getaway."
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Exterior
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
9.6 out of 10, Exceptional, 195 reviews
"We’ve stayed at the cabin with our dog four times and always enjoy our peaceful stay. It’s cozy, clean and private. Also, the Sherwood Shoppe - just down the road - is a wonderful place for breakfast, homemade chili and much more."
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Peace and quiet on the lake
Interior
Peace and quiet on the lake
9.6 out of 10, Exceptional, 184 reviews
"My husband and I had a very peaceful and relaxing long weekend at this lake house! It was very clean and has everything you need. We spent the majority of our time on the wonderful screened-in porch. The location was great and there was a little store/restaurant only a couple minutes walk up the street that was convenient and the food was really good! Overall, a great place to stay!"
Peace and quiet on the lake
Private Estate, Heated YEARROUND Outdoor Pool
Fridge, microwave, oven, stovetop
Private Estate, Heated YEARROUND Outdoor Pool
10.0 out of 10, Exceptional, 8 reviews
"The pictures simply do not do this place justice, it’s an incredible home. Our friend group was cozy all weekend! We loved the hot tub/pool, the really interesting artwork, the driving range mat and basketball hoop. Plenty of towels and kitchen supplies. The in law apartment (which we didn’t use as sadly part of our group was unable to join us) is attached to the main home and is so cute. We had a small issue upon arrival and the hosts were immediately responsive with us troubleshooting and...
Private Estate, Heated YEARROUND Outdoor Pool
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Exterior
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
9.8 out of 10, Exceptional, 7 reviews
"We had a great stay while skiing for 2 days at nearby Catamount ski resort. The kitchen and house were fully stocked with all essentials. Netflix access enabled us to enjoy a family movie after a long day of skiing. Cozy house and quiet area.......nice to wake up to hear birds chirping!!"
The price is $159
$334 total
includes taxes & fees
Jun 30 - Jul 1
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Property grounds
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
8.8 out of 10, Excellent, 3 reviews
"My family and I stayed and so enjoyed our time. The kitchen had everything we could have needed and the location was amazing to explore all neighboring towns. The beds were so comfortable and we even got out to enjoy the fire pit! Would absolutely come back again!"
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Private Island - Largest Fresh Water Reservoir in Mass....
Property grounds
Private Island - Largest Fresh Water Reservoir in Mass....
10.0 out of 10, Exceptional, 3 reviews
"So grateful to Bill for such a wonderful stay! The cottage was so lovely and had everything you could need for a weekend on the lake. Will definitely be returning in the future 😊"
Private Island - Largest Fresh Water Reservoir in Mass....
Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
Fridge, microwave, oven, stovetop
Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
6.0 out of 10, 2 reviews
"Be aware they will not proactively provide you with a local host name or contact info. It was very difficult to get Vacasa support to help me get this info to resolve wifi issue - like hours long to get them to just give me the property managers info and even then, they wouldn't give it to me, just had them contact me. Otherwise, amazing pool and great location. Outdated indoors but clean to the extent that it could be. Utensils were dirty and tons of flies in the house upon arrival - like 50...
Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
Perfect Vacation Get Away - Historical New Marlborough
Property grounds
Perfect Vacation Get Away - Historical New Marlborough
9.6 out of 10, Exceptional, 49 reviews
"This was our first stop on a long journey from VA to ME, traveling with 2 dogs. It was perfect, the dogs were safe with lots of freedom to roam. What a beautiful, peaceful village and sweet little cottage."
The price is $150
$272 total
includes taxes & fees
Jun 24 - Jun 25
Perfect Vacation Get Away - Historical New Marlborough
Serene Acreage - Pond - Hiking Trails Nearby
Property grounds
Serene Acreage - Pond - Hiking Trails Nearby
10.0 out of 10, Exceptional, 4 reviews
"Perfect place to relax and have dogs as part of a mini vacation. Very clean, organized, and provided helpful local information. Will definitely stay there again."
Serene Acreage - Pond - Hiking Trails Nearby
Berkshires Cabin 2 Mi to Appalachian Trail!
Interior
Berkshires Cabin 2 Mi to Appalachian Trail!
9.8 out of 10, Exceptional, 6 reviews
"My wife and I were looking for a nice little getaway within reasonable driving distance and came across this great property. As soon as we saw the big windows in the living room we were sold. Definitely getting added to our short list of places to go back to."
Berkshires Cabin 2 Mi to Appalachian Trail!
Tranquil 3-BR Waterfront Retreat
Exterior
Tranquil 3-BR Waterfront Retreat
10.0 out of 10, Exceptional, 7 reviews
"The house is immaculate! One of the cleanest properties we've stayed in. The house was the perfect size for my family of 4 (2 adults, 2 teens) with room for more. The beds are comfortable, and there were plenty of linens and towels. The linens and towels are high quality, very soft. The kids had fun fishing in the pond and made good use of the kayak (they caught some bass, pickerel and sun fish). The neighborhood is nice and quiet, dirt roads, no traffic...great for taking walks. We used the...
Tranquil 3-BR Waterfront Retreat
Fox Hollow Luxury Ranch Laurel Lake
Fridge, microwave, oven, stovetop
Fox Hollow Luxury Ranch Laurel Lake
9.4 out of 10, Exceptional, 12 reviews
"Generous facility, nicely located, accommodating host."
Fox Hollow Luxury Ranch Laurel Lake
Luxury Barn Retreat . Year-Round Paradise. OVER 100 5 STAR REVIEWS!!
Fridge, microwave, oven, stovetop
Luxury Barn Retreat . Year-Round Paradise. OVER 100 5 STAR REVIEWS!!
10.0 out of 10, Exceptional, 128 reviews
"Our stay at The Barn in New York was unforgettable. This luxury home, converted from a barn and situated at the end of a back road, is surrounded by 50 acres of picturesque fields and has every amenity. With many restaurants a short drive away and only 20 minutes to Great Barrington, MA, and Hudson, NY, we were never short on dining options and The Prairie Whale was our favorite and also dog friendly. The area offered endless adventures with hiking trails, antique stores, galleries, and outdoor...
Luxury Barn Retreat . Year-Round Paradise. OVER 100 5 STAR REVIEWS!!
The Meadows House @ Otis Ridge w/ 7-person hot tub
Property grounds
The Meadows House @ Otis Ridge w/ 7-person hot tub
9.8 out of 10, Exceptional, 20 reviews
"Relaxing get away. Great hot tub, table shuffleboard. 3 floors of comfort."
The Meadows House @ Otis Ridge w/ 7-person hot tub
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
TV, fireplace, DVD player, books
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
7.2 out of 10, Good, 39 reviews
"This house was the perfect get away house for out family! The place was clean and the kitchen well stocked! We had wonderful large family dinners and enjoyed heading into town for meals and fun too. We had the best hikes with are wonderful dog that we got to include, it was a very special week. Great location and the most peaceful and amazing views from the deck and the dock. Would stay here again for sure! Thank you for sharing your home."
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Quintessential 6-BR Berkshires Lodge
Exterior
Quintessential 6-BR Berkshires Lodge
10.0 out of 10, Exceptional, 4 reviews
"We had a great time. Place is amazing. Highly recommend. We had four different families and we never felt cramped. Lovely open main room allowed us to stay connected. Bedrooms were nice and spacious, good bed options. Nice decor."
Quintessential 6-BR Berkshires Lodge
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See all available 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.

Southfield Vacation Rental Travel Info

Number of vacation rentals
5
Popular accommodation
Southfield private vacation homes
Known landmarks
Les Trois Emme Winery, Umpachene Falls Park and Magnolia Bluffs Casino
International airports
Hartford, CT (BDL-Bradley Intl.), Hartford, CT (HFD-Hartford - Brainard) and Albany, NY (ALB-Albany Intl.)

Other types of properties in Southfield you may be interested in

The Red Lion Inn
Outdoor pool, sun loungers
The Red Lion Inn
3.5 star property
8.8 out of 10, Excellent, 889 reviews
"Always a great HISTORIC INN "
The price is $152
$193 total
includes taxes & fees
Jun 17 - Jun 18
The Red Lion Inn
The Black Swan Lee - Lenox, Ascend Hotel Collection
Exterior
The Black Swan Lee - Lenox, Ascend Hotel Collection
3.0 star property
9.0 out of 10, Wonderful, 1,006 reviews
"Staff was great, view is beautiful, it was very clean."
The price is $127
$141 total
includes taxes & fees
Jun 16 - Jun 17
The Black Swan Lee - Lenox, Ascend Hotel Collection
The Lenox Collection
Front of property
The Lenox Collection
3.5 star property
8.6 out of 10, Excellent, 213 reviews
"This was the best stay we have had in a hotel in a very long time. We were at The Constance for four nights. May 13th with checkout Friday morning, May 17, 2024. The building is very old, and it had a lot of charm and character. Comfortable front porch with plenty of seating, and tables and chairs for your use. There was also a quaint parlor with chairs, couches, fireplace, and piano to the right of the front desk where we spent a rainy afternoon catching up on our reading. The rooms were very...
The price is $98
$109 total
includes taxes & fees
Jun 17 - Jun 18
The Lenox Collection
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.

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 $150 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?

Peace and quiet on the lake: This vacation home rental outside of Southfield is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals are there in Southfield?

Choose from 8 Expedia vacation rentals in Southfield for a memorable vacation.

What’s there to see and do in Southfield?

Umpachene Falls Park and Campbell Falls State Park are a couple of lovely local spots to get outside and enjoy nature. Ski Butternut and Infinity Music Hall and Bistro are a couple of places you'll find in the larger area.

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.

Recent reviews of Southfield properties
Expedia verified reviews

Quality Inn

Quality Inn

5/5 Excellent
Birthday Trip
"Our stay was excellent. I greatly appreciated the refrigerator and microwave in the room. The proximity to everything in Lee was marvelous."
A verified traveler stayed at Quality Inn
Posted 1 day ago
Quality Inn