Southfield Holiday Rentals

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Check prices for these dates

In two weeks
27 Mar - 29 Mar
In two months
8 May - 10 May
In three months
5 Jun - 7 Jun
In four months
3 Jul - 5 Jul

Our top choices for Southfield holiday rentals

Property grounds

Apartment in Granby

Peaceful Meadow Retreat
10.0 out of 10, Exceptional, (18 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 HK$662
HK$1,368 total
includes taxes & fees
19 Mar - 20 Mar
Peaceful Meadow Retreat
Private kitchen

Holiday Home in Torrington

Litchfield Retreat, Wineries, Foliage & Skiing
The price is HK$2,041
HK$3,102 total
includes taxes & fees
12 Mar - 13 Mar
Litchfield Retreat, Wineries, Foliage & Skiing
Property grounds

Holiday 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.
The price is HK$1,564
HK$2,843 total
includes taxes & fees
13 Mar - 14 Mar
Big farmhouse in the foothills of the Berkshires
Interior

Apartment in Torrington

Pristine, Walkable downtown, Entire 2 Bedroom apartment
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.
The price is HK$1,251
HK$2,174 total
includes taxes & fees
12 Mar - 13 Mar
Pristine, Walkable downtown, Entire 2 Bedroom apartment
Smart TV, books

Holiday Home in Sherwood Forest

Berkshires Cottage! Dog friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
9.8 out of 10, Exceptional, (14 reviews)
"Nicole was very attentive and very quick to respond to any question we had. Her cottage was perfect for a quiet getaway, just what everybody needs!"
United States
Matthew F.
The price is HK$1,253
HK$2,998 total
includes taxes & fees
13 Mar - 14 Mar
Berkshires Cottage! Dog friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Interior

Cabin in Sheffield

Guesthouse Cabin vacation rentals in Berkshire County
10.0 out of 10, Exceptional, (10 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.
The price is HK$3,128
HK$5,320 total
includes taxes & fees
12 Mar - 13 Mar
Guesthouse Cabin vacation rentals in Berkshire County
Desk, iron/ironing board, WiFi, bed sheets

Apartment in Hillsdale

The Brooks Motel: Exceptional Suite
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 HK$1,173
HK$1,489 total
includes taxes & fees
12 Mar - 13 Mar
The Brooks Motel: Exceptional Suite
Fridge, microwave, oven, stovetop

Holiday Home in Great Barrington

Home in Great Barrington
9.8 out of 10, Exceptional, (27 reviews)
"The house was pristine, bright, with everything we needed. We hope to come back again to enjoy the area. "
United States
maureen k.
The price is HK$1,295
HK$2,154 total
includes taxes & fees
15 Mar - 16 Mar
Home in Great Barrington
Exterior

Apartment in Salisbury

Dugway Hideaway Walking Distance to Lime Rock Park
9.2 out of 10, Wonderful, (15 reviews)
"Super clean, great communication and Super location if you are going to the track. Love my stay there, will definitely do it again and definitely recommend."
United States
Brig
The price is HK$1,564
HK$2,440 total
includes taxes & fees
14 Mar - 15 Mar
Dugway Hideaway Walking Distance to Lime Rock Park
Exterior detail

Holiday Home in Goshen

CT Gate House Goshen CT, Gate House Goshen CT
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.
The price is HK$830
HK$5,029 total
includes taxes & fees
12 Mar - 13 Mar
CT Gate House Goshen CT, Gate House Goshen CT
Interior

Holiday Home in Great Barrington

Family Ski Getaway in the Berkshires
9.0 out of 10, Wonderful, (12 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is HK$1,584
HK$2,476 total
includes taxes & fees
15 Mar - 16 Mar
Family Ski Getaway in the Berkshires
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.
The price is HK$706
HK$2,683 total
includes taxes & fees
15 Mar - 16 Mar
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
Exterior

Holiday Home in Stockbridge

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
10.0 out of 10, Exceptional, (34 reviews)
"A college friends' retreat was fantastic, in part due to the location, cleanliness and amenities in this 3 bedroom house. Furniture was comfortable and kitchen was stocked with everything we needed. "
United States
cathy c.
The price is HK$1,754
HK$4,319 total
includes taxes & fees
15 Mar - 16 Mar
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Interior

Holiday Home in Sherwood Forest

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
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.
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
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.
The price is HK$1,010
HK$3,121 total
includes taxes & fees
12 Mar - 13 Mar
Cozy Modern Farmhouse Private Apt - 3 Beds
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.
The price is HK$1,065
HK$3,196 total
includes taxes & fees
12 Mar - 13 Mar
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
Property grounds

Holiday Home in Sheffield

Cheerful 3-bedroom cottage with woodstove
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 HK$1,853
HK$3,948 total
includes taxes & fees
23 Mar - 24 Mar
Cheerful 3-bedroom cottage with woodstove
TV, fireplace, printers

Holiday Home in Great Barrington

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
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 HK$4,448
HK$10,419 total
includes taxes & fees
12 Mar - 13 Mar
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Exterior

Holiday Home in Goshen

Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills
10.0 out of 10, Exceptional, (1 review)
"Without a doubt, we will be back! Your home was so beautiful, warm and comfortable. Our host was so helpful and friendly. We can't thank you enough for providing such a wonderful experience to our trip. "
United States
Linda D.
The price is HK$2,072
HK$4,643 total
includes taxes & fees
13 Mar - 14 Mar
Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills
TV

Holiday Home in Monterey

Treetop Hideaway in Tyringham
9.0 out of 10, Wonderful, (10 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 HK$2,065
HK$4,364 total
includes taxes & fees
18 Mar - 19 Mar
Treetop Hideaway in Tyringham
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

Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"Clean room, recently renovated"
Adrian 1-night trip
Posted 16 hours ago
Quality Inn Great Barrington

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:

  • View our selection of featured holiday rentals in Southfield
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  • Enter your travel dates to view the best deals on holiday rentals in Southfield while they last

Look no further and take a look at our great range of rental properties in Southfield!

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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 9 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.