Southfield Vacation Rentals

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Check prices for these dates

In two weeks
May 15 - May 17
In two months
Jun 26 - Jun 28
In three months
Jul 24 - Jul 26
In four months
Aug 21 - Aug 23

Our top choices for Southfield vacation rentals

Private kitchen

Litchfield Retreat, Wineries, Foliage & Skiing

Litchfield Retreat, Wineries, Foliage & Skiing
Torrington
The price is ￥41,648
￥63,134 total
includes taxes & fees
May 5 - May 6
Litchfield Retreat, Wineries, Foliage & Skiing
Property grounds

Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (145 reviews)
"The house is absolutely charming and cozy. It was very clean as well. "
United States
Amanda C.
The price is ￥29,520
￥55,153 total
includes taxes & fees
May 4 - May 5
Big farmhouse in the foothills of the Berkshires
Property grounds

Peaceful Meadow Retreat

Peaceful Meadow Retreat
Granby
10.0 out of 10, Exceptional, (22 reviews)
"We stayed here as a quick overnight trip for events in the area. We really enjoyed the property, reading through the guestbook, and the local pizza place La Figata. "
United States
Kaleigh L.
The price is ￥14,140
￥28,686 total
includes taxes & fees
May 5 - May 6
Peaceful Meadow Retreat
Smart TV, books

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, (14 reviews)
"Very nice cabin, responsive host."
United States
Nick R.
The price is ￥25,563
￥62,953 total
includes taxes & fees
May 3 - May 4
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Smart TV

Pristine Cozy Walkable Downtown 2BR Getaway

Pristine Cozy Walkable Downtown 2BR Getaway
Torrington
10.0 out of 10, Exceptional, (18 reviews)
"What a comfortable and welcoming place to stay! Great communication with the hosts, and the space had all the amenities we needed, as well as many thoughtful extra touches. Home was spotless, and tastefully decorated. Quiet neighborhood, and super easy access to downtown. Would absolutely stay here again!"
United States
Kathryn A.
The price is ￥26,329
￥44,839 total
includes taxes & fees
May 11 - May 12
Pristine Cozy Walkable Downtown 2BR Getaway
Exterior

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (36 reviews)
"Charming house in a wonderful setting in the Berkshires. "
United States
Mark Cristen J.
The price is ￥57,286
￥115,856 total
includes taxes & fees
May 4 - May 5
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Private kitchen

Art House 3 Beds Close to Warner Theater

Art House 3 Beds Close to Warner Theater
Torrington
10.0 out of 10, Exceptional, (1 review)
"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 ￥19,480
￥63,998 total
includes taxes & fees
May 5 - May 6
Art House 3 Beds Close to Warner Theater
Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.2 out of 10, Wonderful, (14 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is ￥32,313
￥50,531 total
includes taxes & fees
May 13 - May 14
Cozy Riverside Berkshires Retreat
Interior

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, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is ￥23,265
￥59,853 total
includes taxes & fees
May 6 - May 7
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Exterior

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 ￥23,457
￥67,465 total
includes taxes & fees
May 5 - May 6
Cozy Modern Farmhouse Private Apt - 3 Beds
Desk, iron/ironing board, WiFi, bed sheets

The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
7.0 out of 10, Good, (4 reviews)
"Location was good for what we wanted. The people involved responded quickly. The bed was very comfortable. Reasonably clean, the coffee pot had leftover coffee in it and a dirty spoon on the counter. The biggest issue was the musty odor."
United States
John P.
The price is ￥23,936
￥30,383 total
includes taxes & fees
May 3 - May 4
The Brooks Motel: Exceptional Suite
Property grounds

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (42 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is ￥37,818
￥80,565 total
includes taxes & fees
May 6 - May 7
Cheerful 3-bedroom cottage with woodstove
Fridge, microwave, oven, stovetop

Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi
Lee
8.8 out of 10, Excellent, (3 reviews)
"House was clean and made our Thanksgiving great with it's size and amenities. "
United States
Khalil S.
The price is ￥75,796
￥136,176 total
includes taxes & fees
May 13 - May 14
Spacious 5-bedroom house in charming Lee with WiFi
Dining

Whispering Estate Guest House - Countryside Getaway

Whispering Estate Guest House - Countryside Getaway
Goshen
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful property and great location. A true retreat. "
United States
Andrea B.
The price is ￥86,168
￥139,704 total
includes taxes & fees
May 2 - May 3
Whispering Estate Guest House - Countryside Getaway
TV

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!"
United States
Sarah B.
The price is ￥42,924
￥89,729 total
includes taxes & fees
May 6 - May 7
Treetop Hideaway in Tyringham
3 bedrooms, iron/ironing board, WiFi, bed sheets

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (1 review)
"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 ￥47,871
￥85,199 total
includes taxes & fees
May 3 - May 4
Cozy. Clean. Free bagel shop. 3 Fireplaces.
TV, fireplace, printers

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (4 reviews)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is ￥90,476
￥212,105 total
includes taxes & fees
May 13 - May 14
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Dining

Classy Private Apt - 3 Beds 2nd Flr - Near Downtown

Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
Torrington
10.0 out of 10, Exceptional, (1 review)
"Good communication. Clean place in good location. Would stay again. "
United States
Jaimie S.
The price is ￥52,774
￥109,042 total
includes taxes & fees
May 7 - May 8
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
Interior

Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (6 reviews)
"Emma's property is adorable! Clean, well appointed with fresh flowers on the table to great us. Smooth and easy communication from start to finish. Really close to Tanglewood and all the activities Western Massachusetts has to offer."
United States
Cheryl F.
The price is ￥21,542
￥42,778 total
includes taxes & fees
May 3 - May 4
Sweet Cozy Victorian in Housatonic. Close to everything.
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

Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington

4/10 Poor
"Bedspread had stain marks. Made me sick because it was human fluid. Room can be upgraded. Staff was friendly. Parking was ok. Breakfast not appetizing. Too much bread not real breakfast. "
Viola 2-night trip
Posted 15 hours ago
Days Inn by Wyndham Torrington

Find out more about Southfield

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:

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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 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?

Cozy Riverside Berkshires Retreat: This vacation home rental outside of Southfield is located on a river and has a fireplace, a garden, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and kitchenware, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like 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 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 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.