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Southfield Vacation Rentals

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Check prices for these dates

In two weeks
4 Sep - 6 Sep
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Southfield vacation rentals

Coffee/tea maker, fridge, microwave, oven

1. Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
9.0 out of 10, Wonderful, (2 reviews)
"great location , berkshires are awesome . very clean , host is excellent ."
United States
bob i.
The price is AED 380
AED 568 total
includes taxes & fees
24 Aug - 25 Aug
Cozy 1-bedroom studio in serene Great Barrington with AC
Terrace/patio

2. Enjoy a restful stay with fast internet, smart TV and the company of your pet.

Enjoy a restful stay with fast internet, smart TV and the company of your pet.
winsted
9.4 out of 10, Exceptional, (51 reviews)
"Fantastic hosts and great facilities would highly recommend"
United States
Steve
The price is AED 466
AED 793 total
includes taxes & fees
24 Aug - 25 Aug
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Interior

3. Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is AED 235
AED 1,116 total
includes taxes & fees
13 Sep - 14 Sep
Real Estate: Therapy - Lake, Laundry, Love it
Coffee/tea maker, fridge, microwave, oven

4. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (38 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is AED 992
AED 1,493 total
includes taxes & fees
24 Aug - 25 Aug
Home in Great Barrington
Beach nearby, sun loungers, beach towels

5. Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake

Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Great Barrington
10.0 out of 10, Exceptional, (3 reviews)
"We had a wonderful visit. They were so accommodating and great location to downtown. We’ll stay again!"
United States
Kristin O.
The price is AED 696
AED 1,003 total
includes taxes & fees
15 Sep - 16 Sep
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Interior

6. Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.6 out of 10, Exceptional, (23 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
The price is AED 702
AED 1,105 total
includes taxes & fees
15 Sep - 16 Sep
Cozy Riverside Berkshires Retreat
Property grounds

7. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (43 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is AED 907
AED 1,908 total
includes taxes & fees
7 Sep - 8 Sep
Cheerful 3-bedroom cottage with woodstove
Outdoor spa tub

8. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (16 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is AED 621
AED 1,498 total
includes taxes & fees
25 Aug - 26 Aug
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
TV

9. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "
United States
Samantha G.
The price is AED 1,043
AED 2,131 total
includes taxes & fees
16 Sep - 17 Sep
Treetop Hideaway in Tyringham
Interior

10. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (6 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AED 632
AED 1,510 total
includes taxes & fees
9 Sep - 10 Sep
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Desk, iron/ironing board, WiFi, bed sheets

11. The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
7.2 out of 10, Good, (5 reviews)
"Close to the competition I was in"
United States
Joan
The price is AED 551
AED 699 total
includes taxes & fees
18 Aug - 19 Aug
The Brooks Motel: Exceptional Suite
Interior

12. Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (9 reviews)
"The host did a great job of prepping the place and being welcoming to us. It was clean and thoughtfully designed. So happy we found this spot!"
United States
Peter S.
The price is AED 643
AED 1,173 total
includes taxes & fees
1 Sep - 2 Sep
Sweet Cozy Victorian in Housatonic. Close to everything.
2 bedrooms, WiFi (free), bed sheets

13. Peaceful and cozy 1 bed 1 bath in quaint Winchester

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
The price is AED 456
AED 824 total
includes taxes & fees
30 Aug - 31 Aug
Peaceful and cozy 1 bed 1 bath in quaint Winchester
Smart TV

14. stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
9.0 out of 10, Wonderful, (4 reviews)
"Property was just as described, clean and well equipped. Had excellent communication with the host. Would highly recommend staying here."
United States
Donna K.
The price is AED 595
AED 1,415 total
includes taxes & fees
15 Sep - 16 Sep
stylish Berkshires Retreat
Property grounds

15. Peaceful Meadow Retreat

Peaceful Meadow Retreat
Granby
10.0 out of 10, Exceptional, (24 reviews)
"Great location, quite country yet close to MA and airport."
United States
Todd R.
The price is AED 419
AED 770 total
includes taxes & fees
11 Sep - 12 Sep
Peaceful Meadow Retreat
Exterior

16. Cozy Attic 10 min to Llitchfield

Cozy Attic 10 min to Llitchfield
Torrington
9.4 out of 10, Exceptional, (6 reviews)
"A couple of the surfaces were not clean but mostly a clean comfy space. The bed was very comfortable and the bathroom was spacious and clean.The stairs are not for the faint of heart. A nice cozy place to stay once the luggage and groceries are up there."
United States
Rhonda H.
The price is AED 336
AED 1,030 total
includes taxes & fees
18 Aug - 19 Aug
Cozy Attic 10 min to Llitchfield
Dining

17. Art House 3 Beds Close to Warner Theater

Art House 3 Beds Close to Warner Theater
Torrington
10.0 out of 10, Exceptional, (2 reviews)
"Place was perfectly located for where we needed to be. The host was amazing, would stay again. Unit was comfy and cozy with perfect little homey touches. "
United States
Brittany M.
The price is AED 516
AED 1,595 total
includes taxes & fees
15 Sep - 16 Sep
Art House 3 Beds Close to Warner Theater
Exterior

18. Cozy Modern Farmhouse Private Apt - 3 Beds

Cozy Modern Farmhouse Private Apt - 3 Beds
Torrington
10.0 out of 10, Exceptional, (4 reviews)
"My husband and I came down from Boston for Christmas to see family and couldn’t find one decent hotel in the area. We were relieved to find this place. Cute, comfortable, clean environment and just what we needed. "
United Kingdom
Louisa A.
The price is AED 474
AED 1,238 total
includes taxes & fees
18 Aug - 19 Aug
Cozy Modern Farmhouse Private Apt - 3 Beds
Property grounds

19. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (149 reviews)
"Great location"
United States
Will G.
The price is AED 698
AED 1,308 total
includes taxes & fees
23 Aug - 24 Aug
Big farmhouse in the foothills of the Berkshires
3 bedrooms, iron/ironing board, WiFi, bed sheets

20. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (2 reviews)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
The price is AED 1,198
AED 2,093 total
includes taxes & fees
31 Aug - 1 Sep
Cozy. Clean. Free bagel shop. 3 Fireplaces.
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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Top Southfield Hotel Reviews

Americas Best Value Inn Torrington CT

Americas Best Value Inn Torrington CT

10/10 Excellent
"All the staff members I met were cheerful & helpful. I asked for a ground floor room, upon arrival, got a very nice one at no extra charge. I was in the area for a music festival, plan on booking a stay again , next year."
Peter 2-night trip
Posted 7 hours ago
Americas Best Value Inn Torrington CT

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?

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This vacation home rental outside of Southfield is located near skiing and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals are there in Southfield?

Choose from 9 Expedia vacation rentals in Southfield for a memorable vacation.

What’s there to see and do in Southfield?

Umpachene Falls Park and Rhodes Hill 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 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.