Holiday Rentals in Southfield

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Holiday Rentals in Southfield

Romantic and Secluded Berkshire's Gem

9.8 out of 10, Exceptional, (14)
"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

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (121)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
The Ponds at Foxhollow

Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

9.2 out of 10, Wonderful, (18)
"We had a wonderful time at the cabin by the lake. Beautiful views in the Morning!! Loved it."
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

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

9.6 out of 10, Exceptional, (41)
"We had a wonderful stay. The cabin was clean and comfortable! "
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

10.0 out of 10, Exceptional, (13)
"Host was extremely accommodating and house was as-advertised. Great spot to explore great Barrington and surrounding towns! Wood burning stove and fireplaces are a real highlight! Fire pit is not advertised on listing but there is one. Would recommend highly"
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

7.2 out of 10, Good, (44)
"The property was great overall. I was not impressed with finding cobwebs around furniture, or with the hair in the shower and the toothpaste on the sink, mirror mirrorandbehind behind"
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

The Kemble- Built by a US Secretary of State in Lenox

10.0 out of 10, Exceptional, (17)
"Loved the property. Perfect for our gathering."
The Kemble- Built by a US Secretary of State in Lenox

Spacious 5-bedroom house in charming Lee with WiFi

The price is €753
includes taxes & fees
17 Jul - 18 Jul
Spacious 5-bedroom house in charming Lee with WiFi

Deluxe Queen Room with 2 Queen Beds

2.0 star property
2.0 out of 10, (1)
"Wrote to them asking for early check in around 1pm for 3pm check in, no reply. Not a problem, early check in isn’t a guarantee. Get to the property 10 mins before check in and no one is there, wait around for 30 mins, no one there, no one answering in the app, no one picking up the phone. By 340 called Vrbo who canceled my reservation around 4pm the property called asked if I left, I said I did and booked somewhere else, no apology, no reasoning, just “ok” and hung up. Thankfully there was...
The price is €127
includes taxes & fees
10 Aug - 11 Aug
Deluxe Queen Room with 2 Queen Beds

Big farmhouse in the foothills of the Berkshires

10.0 out of 10, Exceptional, (138)
"This was the perfect place to stay while we visited family in Massachusetts. The place was kept beautifully and had all of the amenities to make our visit comfortable. We will definitely book this place in the future."
The price is €313
includes taxes & fees
27 Jul - 28 Jul
Big farmhouse in the foothills of the Berkshires

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

10.0 out of 10, Exceptional, (7)
"Elise was an excellent host and super easy to work with. The property was even bigger, nicer, and cleaner than we expected. Plenty of room for a family getaway. "
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

Peace and quiet on the lake

9.6 out of 10, Exceptional, (216)
"This property was in an incredible location with a nice cozy feel. It was perfect for my family of 6. I highly recommend this place!"
Peace and quiet on the lake

Exclusive Estate, Heated Yearround Outdoor Pool

9.6 out of 10, Exceptional, (19)
"Lovely horse farm in the woods but not too far from useful shops. We had a great experience."
Exclusive Estate, Heated Yearround Outdoor Pool

Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

The price is €355
includes taxes & fees
28 Jul - 29 Jul
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

Quintessential 6-BR Berkshires Lodge

10.0 out of 10, Exceptional, (14)
"The house was perfect for our group of couples and young kids. Large bedrooms and beautiful property "
Quintessential 6-BR Berkshires Lodge

CT Gate House Goshen CT, Gate House Goshen CT

2.5 star property
The price is €739
includes taxes & fees
14 Jul - 15 Jul
CT Gate House Goshen CT, Gate House Goshen CT

Lakefront Bungalow

9.6 out of 10, Exceptional, (9)
"Nice location on water, clean, kitchen had all our needs--would stay there again."
Lakefront Bungalow

Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

9.4 out of 10, Exceptional, (63)
"Cute and comfy place, great location. We walked to dinner twice and enjoyed how convenient this place was to all of the Berkshires. "
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

Private Island - Largest Fresh Water Reservoir in Mass....

9.0 out of 10, Wonderful, (7)
"We had a great time. The owner Bill was a great host."
Private Island - Largest Fresh Water Reservoir in Mass....

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

9.0 out of 10, Wonderful, (38)
"My husband, dog and I enjoyed a long weekend here to celebrate our 8th wedding anniversary- the property was beautiful and quaint! Perfect for exploring on walks, or nearby to the Norman Rockwell museum. Would stay here again."
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
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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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?

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT: This holiday home rental outside of Southfield is located in a rural location, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

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 Cookson State Forest are a couple of lovely local spots to get outside and enjoy nature. Campbell Falls State Park and Suter Farm are other places to visit while you're in town.

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.