Southfield Vacation Rentals

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Check prices for these dates

In two weeks
Feb 6 - Feb 8
In two months
Mar 20 - Mar 22
In three months
Apr 17 - Apr 19
In four months
May 15 - May 17

Our top choices for Southfield vacation rentals

Property grounds

Apartment in Granby

Peaceful Meadow Retreat
2.0 star property
10.0 out of 10, Exceptional, (17 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.
$164 nightly
The price is $185
Jan 25 - Jan 26
Total with taxes and fees
Peaceful Meadow Retreat
Exterior

Apartment in Torrington

Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
9.2 out of 10, Wonderful, (5 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.
$292 nightly
The price is $334
Jan 22 - Jan 23
Total with taxes and fees
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
Exterior detail

Vacation Home in Goshen

CT Gate House Goshen CT, Gate House Goshen CT
2.5 star property
9.4 out of 10, Exceptional, (9 reviews)
"The property was great and the house was huge even for all 12 of us "
United States
Ryan L.
$627 nightly
The price is $643
Jan 22 - Jan 23
Total with taxes and fees
CT Gate House Goshen CT, Gate House Goshen CT
2 bedrooms, desk, free WiFi, bed sheets

Apartment in Torrington

Charming apartment 7 minute walk to downtown
10.0 out of 10, Exceptional, (16 reviews)
"Everything about our stay was great - Corin and Jen were wonderful hosts. The place is spotless, cozy, comfy. Love that they were right next to the Green Way Trail along the river. Will absolutely stay there again! "
United States
Kate B.
$213 nightly
The price is $241
Jan 22 - Jan 23
Total with taxes and fees
Charming apartment 7 minute walk to downtown
Smart TV, books

Vacation Home in Sherwood Forest

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
9.6 out of 10, Exceptional, (10 reviews)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
$339 nightly
The price is $379
Jan 25 - Jan 26
Total with taxes and fees
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Exterior

Apartment in Torrington

Cozy Modern Farmhouse Private Apt - 3 Beds
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.
$338 nightly
The price is $389
Jan 22 - Jan 23
Total with taxes and fees
Cozy Modern Farmhouse Private Apt - 3 Beds
Fridge, microwave, oven, stovetop

Vacation Home in Great Barrington

Home in Great Barrington
9.8 out of 10, Exceptional, (26 reviews)
"Great stay in a cool, new space, totally walkable to Railroad St. I would definitely go back to GB and would try to stay here again. "
United States
Cameron M.
$224 nightly
The price is $250
Jan 26 - Jan 27
Total with taxes and fees
Home in Great Barrington
Dining

Apartment in Torrington

Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
10.0 out of 10, Exceptional, (1 review)
"Good communication. Clean place in good location. Would stay again. "
United States
Jaimie S.
$338 nightly
The price is $389
Jan 22 - Jan 23
Total with taxes and fees
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
Property grounds

Cabin in Cornwall

Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
10.0 out of 10, Exceptional, (5 reviews)
"This cabin is so cute we had a relaxing time , will return"
United States
Candice S.
$492 nightly
The price is $557
Jan 22 - Jan 23
Total with taxes and fees
Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
Property grounds

Vacation Home in Russell

Big farmhouse in the foothills of the Berkshires
10.0 out of 10, Exceptional, (143 reviews)
"Perfect spot for a family celebration!"
United States
Kerry P.
$301 nightly
The price is $318
Jan 26 - Jan 27
Total with taxes and fees
Big farmhouse in the foothills of the Berkshires
Desk, iron/ironing board, WiFi, bed sheets

Apartment in Hillsdale

The Brooks Motel: Exceptional Suite
9.2 out of 10, Wonderful, (5 reviews)
"Clean, industrial, very comfy bed, easy to book and to check in and out. Would stay again."
United States
Deidre H.
$179 nightly
The price is $200
Jan 22 - Jan 23
Total with taxes and fees
The Brooks Motel: Exceptional Suite
Private kitchen

Vacation Home in Torrington

Litchfield Retreat, Wineries, Foliage & Skiing
2.0 star property
Litchfield Retreat, Wineries, Foliage & Skiing
Smart TV, books

Vacation Home in Lee

Sun Filled Lenox Retreat - Minutes to Tanglewood!
9.6 out of 10, Exceptional, (4 reviews)
"The house is in a great location and is very user friendly and well equipped. The only suggestion I would make is to put an air conditioner in the third bedroom. Overall, a lovely stay."
United States
Sarah D.
$412 nightly
The price is $460
Jan 26 - Jan 27
Total with taxes and fees
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Interior

Vacation Home in Housatonic

Sweet Cozy Victorian in Housatonic. Close to everything.
10.0 out of 10, Exceptional, (3 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.
$240 nightly
The price is $268
Feb 1 - Feb 2
Total with taxes and fees
Sweet Cozy Victorian in Housatonic. Close to everything.
Exterior

Vacation Home in Goshen

Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills
2.0 star property
$444 nightly
The price is $504
Jan 25 - Jan 26
Total with taxes and fees
Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills
Interior

Cabin in Sheffield

Guesthouse Cabin vacation rentals in Berkshire County
10.0 out of 10, Exceptional, (9 reviews)
"Great place. I highly recommend for a group or family. Amazing views! Beautiful property very private and quiet. Cabin was also very well stocked and had great outdoor space. "
United States
deborah d.
$616 nightly
The price is $688
Jan 25 - Jan 26
Total with taxes and fees
Guesthouse Cabin vacation rentals in Berkshire County
Interior

Vacation Home in Goshen

Whispering Estate Guest House - A Romantic Countryside Getaway
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful property and great location. A true retreat. "
United States
Andrea B.
$774 nightly
The price is $878
Jan 22 - Jan 23
Total with taxes and fees
Whispering Estate Guest House - A Romantic Countryside Getaway
Interior

Aparthotel in Spencertown

Suite 4 - Quiet and private accommodations in a country setting.
10.0 out of 10, Exceptional, (3 reviews)
"Happy to have found this lovely place, which is convenient to Tanglewood, pin-drop quiet, and super comfortable. Next time I will avoid VRBO, though, because of its extortionary fees, and book directly with the inn."
United States
jwnyc3
$243 nightly
The price is $272
Jan 25 - Jan 26
Total with taxes and fees
Suite 4 - Quiet and private accommodations in a country setting.
Interior

Vacation Home in Great Barrington

Family Ski Getaway in the Berkshires
9.2 out of 10, Wonderful, (7 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
$253 nightly
The price is $283
Jan 27 - Jan 28
Total with taxes and fees
Family Ski Getaway in the Berkshires
Interior

Vacation Home in Spencertown

Suite 3 - Quiet and private accommodations in a country setting.
10.0 out of 10, Exceptional, (1 review)
"Fantastic place to stay!"
United States
James
$243 nightly
The price is $272
Jan 25 - Jan 26
Total with taxes and fees
Suite 3 - Quiet and private accommodations in a country setting.
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

10/10 Excellent
"Staff was very friendly, room was clean. Overall great stay, thanks!"
Nathaniel 1-night trip
Posted 1 day ago
Days Inn by Wyndham Torrington

Find out more about Southfield

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 $250 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.

Explore a world of travel with Expedia

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 10 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.