Southfield Holiday Rentals

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Holiday 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
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
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Pristine Home In Becket Woods
Fridge, microwave, oven, stovetop
Pristine Home In Becket Woods
10.0 out of 10, Exceptional, 8 reviews
"I really loved my stay at this beautiful property surrounded by nature and peacefulness in the Berkshire mountains. The owners were great too with communication and making things easy for check in and check out. Highly recommend this place!"
Pristine Home In Becket Woods
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 HK$1,242
HK$2,613 total
includes taxes & fees
30 Jun - 1 Jul
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Peace and quiet on the lake
Interior
Peace and quiet on the lake
9.6 out of 10, Exceptional, 186 reviews
"The house was clean and cozy. The kitchen was well stocked, especially important as we like to cook at home. Justin was responsive when I contacted him with questions. Love that the house was dog friendly with a fenced in back yard. The house has been updated inside but the deck needs some TLC, which I am sure are in the plans. A perfect get away!"
Peace and quiet on the lake
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
7 bedrooms, iron/ironing board, cots/infant beds, travel cot
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
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 HK$1,172
HK$2,114 total
includes taxes & fees
24 Jun - 25 Jun
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, 5 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
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
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
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....
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!
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.
Beautiful retreat to the woods to enjoy the winter season.
Aerial view
Beautiful retreat to the woods to enjoy the winter season.
10.0 out of 10, Exceptional, 31 reviews
"Very nice, well stocked and away from the hustle and bustle of city life. We had a great time."
Beautiful retreat to the woods to enjoy the winter season.
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, 21 reviews
"The rental property was just as described online. We had a very relaxing time. We also enjoyed playing all the games provided. This is a beautiful location and very quiet area. We loved sitting out in the hot tub at night looking up at the stars. Really special experience."
The Meadows House @ Otis Ridge w/ 7-person hot tub
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!
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!
Stockbridge Home, Come Experience The Berkshires!
Fridge, microwave, oven, stovetop
Stockbridge Home, Come Experience The Berkshires!
10.0 out of 10, Exceptional, 12 reviews
"we all loved it, especially the screened in porch...& my dog cooper also gives 5 stars"
Stockbridge Home, Come Experience The Berkshires!
Peaceful, Post and Beam Loft, Sleeps 9
TV, DVD player
Peaceful, Post and Beam Loft, Sleeps 9
10.0 out of 10, Exceptional, 8 reviews
"beautifully stay for couples."
Peaceful, Post and Beam Loft, Sleeps 9
Don't see what you're looking for?
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.

Other types of properties in Southfield you may be interested in

The Red Lion Inn
Outdoor pool, pool loungers
The Red Lion Inn
3.5 star property
8.8 out of 10, Excellent, 897 reviews
"The Red Lion Inn has been a mainstay for travelers since the 18th C. Staying there was an important experience for my visit to the Berkshires. The use of corridors to display art, as well as cabinets of collections by one of the previous owners as well as new installations was delightful."
The price is HK$1,398
HK$1,736 total
includes taxes & fees
18 Jun - 19 Jun
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, 1,003 reviews
"We liked that an Indian Cuisine was available on property. "
The price is HK$989
HK$1,105 total
includes taxes & fees
24 Jun - 25 Jun
The Black Swan Lee - Lenox, Ascend Hotel Collection
The Lenox Collection
Front of property
The Lenox Collection
3.5 star property
8.8 out of 10, Excellent, 219 reviews
"Friendly staff. Large attractive room with comfortable bed. Great continental breakfast Can walk to town. "
The price is HK$948
HK$1,059 total
includes taxes & fees
18 Jun - 19 Jun
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.

Search for holiday rentals in Southfield on Expedia! You can easily find your home rentals, villas, holiday apartments in Southfield using one of the methods below:

  • View our selection of featured holiday rentals in Southfield
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Look no further and take a look at our great range of rental properties in Southfield!

Frequently asked questions

Are there holiday rentals in Southfield?

Yes, there are holiday rentals close to the most popular sights in Southfield, or you can select a more secluded option if you're looking for a relaxing stay. Southfield is known for its parks.

What are some of the best holiday rentals that Southfield has to offer?

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

How many holiday rentals are there in Southfield?

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

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 wider area.

What’s a holiday rental in Southfield like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Southfield. Holiday rentals offer extras like kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a clean environment, holiday rentals can offer a sense of seclusion away from shared hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for a family trip.

Recent reviews of Southfield properties
Expedia verified reviews

Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington

5/5 Excellent
"Very clean and great shower pressure was great. Easy to check in and good parking. If you’re staying in Torrington, the best place to rest your head."
A verified traveller stayed at Days Inn by Wyndham Torrington
Posted 18 hours ago
Days Inn by Wyndham Torrington