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Southfield Holiday Rentals

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Check prices for these dates

In two weeks
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sept - 13 Sept
In four months
9 Oct - 11 Oct

Our top choices for Southfield holiday rentals

Hair dryer, towels

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 HK$1,495
HK$3,807 total
includes taxes & fees
8 Jul - 9 Jul
Art House 3 Beds Close to Warner Theater
Property grounds

Peaceful Meadow Retreat

Peaceful Meadow Retreat
Granby
10.0 out of 10, Exceptional, (23 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$945
HK$1,702 total
includes taxes & fees
26 Jun - 27 Jun
Peaceful Meadow Retreat
TV, fireplace

Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is HK$726
HK$2,632 total
includes taxes & fees
18 Jun - 19 Jun
Real Estate: Therapy - Lake, Laundry, Love it
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, (147 reviews)
"The house is absolutely charming and cozy. It was very clean as well. "
United States
Amanda C.
The price is HK$1,489
HK$2,783 total
includes taxes & fees
17 Jun - 18 Jun
Big farmhouse in the foothills of the Berkshires
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 HK$1,142
HK$2,913 total
includes taxes & fees
17 Jun - 18 Jun
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Exterior

Cozy Attic 10 min to Llitchfield

Cozy Attic 10 min to Llitchfield
Torrington
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$658
HK$2,096 total
includes taxes & fees
16 Jun - 17 Jun
Cozy Attic 10 min to Llitchfield
Terrace/patio

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
9.2 out of 10, Wonderful, (47 reviews)
"Fantastic hosts and great facilities would highly recommend"
United States
Steve
The price is HK$1,371
HK$2,118 total
includes taxes & fees
2 Jul - 3 Jul
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Smart TV, fireplace

Pristine Cozy Walkable Downtown 2BR Getaway

Pristine Cozy Walkable Downtown 2BR Getaway
Torrington
10.0 out of 10, Exceptional, (19 reviews)
"Wow what an enjoyable stay! Clean, fresh, relaxing, and wonderful to meet owners Corin and Jen… gracious and hospitable hosts. Very comfortable, great location, well appointed… everything we were looking for!"
United States
James M.
The price is HK$1,176
HK$2,044 total
includes taxes & fees
16 Jun - 17 Jun
Pristine Cozy Walkable Downtown 2BR Getaway
Smart TV

stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
10.0 out of 10, Exceptional, (1 review)
"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 HK$1,467
HK$3,450 total
includes taxes & fees
16 Jun - 17 Jun
stylish Berkshires Retreat
Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.4 out of 10, Exceptional, (16 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is HK$1,664
HK$2,533 total
includes taxes & fees
18 Jun - 19 Jun
Cozy Riverside Berkshires Retreat
Outdoor spa tub

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, (15 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is HK$1,276
HK$3,115 total
includes taxes & fees
23 Jun - 24 Jun
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Interior

Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County
Sheffield
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$3,134
HK$5,461 total
includes taxes & fees
17 Jun - 18 Jun
Guesthouse Cabin vacation rentals in Berkshire County
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (32 reviews)
"Perfect space for an overnight stay. Very clean and well appointed. Communication from host was great and check in was a breeze. 2 minute drive from downtown Great Barrington."
United States
Anonymous traveller
The price is HK$1,869
HK$2,875 total
includes taxes & fees
16 Jun - 17 Jun
Home in Great Barrington
1 bedroom, desk, iron/ironing board, WiFi

Cozy Cabin Style Apt Private 1st Flr 1 Bdrm

Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
Torrington
The price is HK$1,102
HK$3,229 total
includes taxes & fees
8 Jul - 9 Jul
Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
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 HK$2,500
HK$4,911 total
includes taxes & fees
22 Jun - 23 Jun
Treetop Hideaway in Tyringham
Desk, iron/ironing board, WiFi, bed sheets

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 HK$1,175
HK$1,492 total
includes taxes & fees
16 Jun - 17 Jun
The Brooks Motel: Exceptional Suite
Private kitchen

Litchfield Retreat, Wineries, Foliage & Skiing

Litchfield Retreat, Wineries, Foliage & Skiing
Torrington
The price is HK$2,045
HK$3,116 total
includes taxes & fees
16 Jun - 17 Jun
Litchfield Retreat, Wineries, Foliage & Skiing
Property grounds

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 HK$1,857
HK$3,956 total
includes taxes & fees
16 Jun - 17 Jun
Cheerful 3-bedroom cottage with woodstove
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 HK$2,184
HK$4,771 total
includes taxes & fees
7 Jul - 8 Jul
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
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 HK$3,722
HK$6,748 total
includes taxes & fees
7 Jul - 8 Jul
Spacious 5-bedroom house in charming Lee with WiFi
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

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

10/10 Excellent
"This was our forth stay and we will return next year for sure. Family friendly easy and clean. We love it!"
Melissa 3-night trip
Posted 1 hour ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

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
  • Use the map to find apartments and other holiday homes in the Southfield neighbourhood you prefer
  • 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!

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?

Cozy Riverside Berkshires Retreat: This holiday 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 an electric kettle, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 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.