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Southfield Vacation Rentals

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Southfield vacation rentals

A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

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

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
9.4 out of 10, Exceptional, (3 reviews)
"Great location, great property, great host"
United States
Shelly B.
The price is ￥17,281
￥25,309 total
includes taxes & fees
Sep 27 - Sep 28
Cozy 1-bedroom studio in serene Great Barrington with AC
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

2. 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 ￥29,309
￥47,324 total
includes taxes & fees
Sep 15 - Sep 16
Home in Great Barrington
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

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

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
8.0 out of 10, Very Good, (1 review)
"Very good trip overall. Great location. Just a few things needed to make it over the top!"
United States
William C B.
The price is ￥7,988
￥44,612 total
includes taxes & fees
Sep 16 - Sep 17
Real Estate: Therapy - Lake, Laundry, Love it
A garden area with potted plants, a wooden fence, and outdoor furniture.

4. Cozy Camper tucked into the woods

Cozy Camper tucked into the woods
Sandisfield
The price is ￥26,682
￥34,094 total
includes taxes & fees
Sep 14 - Sep 15
Cozy Camper tucked into the woods
An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

5. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (44 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is ￥28,618
￥67,827 total
includes taxes & fees
Sep 27 - Sep 28
Cheerful 3-bedroom cottage with woodstove
A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

6. 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, (9 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is ￥22,396
￥57,445 total
includes taxes & fees
Sep 14 - Sep 15
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A sandy beach with a lake and forest in the background.

7. 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, (4 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 ￥33,641
￥53,533 total
includes taxes & fees
Sep 14 - Sep 15
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

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

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (10 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 ￥26,882
￥48,902 total
includes taxes & fees
Sep 25 - Sep 26
Sweet Cozy Victorian in Housatonic. Close to everything.
A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

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 ￥43,318
￥88,651 total
includes taxes & fees
Sep 21 - Sep 22
Treetop Hideaway in Tyringham
A staircase leading to a second floor, a living room with a sofa, and a kitchen area.

10. Riverside Retreat in the Berkshires

Riverside Retreat in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (25 reviews)
"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."
United States
Kelly B.
The price is ￥31,106
￥48,301 total
includes taxes & fees
Sep 21 - Sep 22
Riverside Retreat in the Berkshires
A hot tub with a string of lights above it, set against a dark night sky.

11. 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 ￥26,544
￥62,765 total
includes taxes & fees
Sep 15 - Sep 16
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
A two-story house with a front porch, a small balcony, and a white picket fence.

12. Cozy Attic 10 min to Llitchfield

Cozy Attic 10 min to Llitchfield
Torrington
9.4 out of 10, Exceptional, (6 reviews)
"The check-in process was easy and all instructions were clear. Jonathan, the owner, was very responsive and easy to get a hold of if I had any questions. The place was cute, clean, and perfect for what I needed (a place to stay during my medical school rotation). As the review says, it is not ideal for taller guests as the roof slopes down in certain areas, but I found the place cozy."
United States
Nicole N.
The price is ￥16,774
￥56,691 total
includes taxes & fees
Sep 14 - Sep 15
Cozy Attic 10 min to Llitchfield
A bedroom with a bed, a window, a shelf with books, and a mirror.

13. Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature

Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature
Otis
The price is ￥33,733
￥52,437 total
includes taxes & fees
Sep 14 - Sep 15
Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature
A wooden cabin interior with a bench, a rug, and a hanging plant.

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

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
The price is ￥20,046
￥35,419 total
includes taxes & fees
Sep 14 - Sep 15
Peaceful and cozy 1 bed 1 bath in quaint Winchester
A wooden cabin with a porch, a grill, and a flower planter.

15. Ideal location for summer and winter activities with plenty of outdoor space.

Ideal location for summer and winter activities with plenty of outdoor space.
Hillsdale
9.8 out of 10, Exceptional, (79 reviews)
"Excellent host!"
United States
Kenny
The price is ￥30,722
￥58,323 total
includes taxes & fees
Sep 15 - Sep 16
Ideal location for summer and winter activities with plenty of outdoor space.
A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

16. 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 ￥48,157
￥84,848 total
includes taxes & fees
Sep 14 - Sep 15
Cozy. Clean. Free bagel shop. 3 Fireplaces.
A square fire pit with flames, surrounded by a grassy field and a green chair.

17. 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 ￥15,975
￥29,354 total
includes taxes & fees
Oct 5 - Oct 6
Peaceful Meadow Retreat
A house with a porch, a garden with pink flowers, and a stone wall along the road.

18. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (150 reviews)
"Great location"
United States
Will G.
The price is ￥26,267
￥50,657 total
includes taxes & fees
Sep 27 - Sep 28
Big farmhouse in the foothills of the Berkshires
A modern kitchen with a wooden dining table, blue chairs, and a colorful bowl centerpiece.

19. 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 ￥21,599
￥65,925 total
includes taxes & fees
Sep 14 - Sep 15
Art House 3 Beds Close to Warner Theater
A living room with a sofa, coffee table, and chairs, a kitchen area with a bar, and a door.

20. Pristine Cozy Walkable Downtown 2BR Getaway

Pristine Cozy Walkable Downtown 2BR Getaway
Torrington
10.0 out of 10, Exceptional, (19 reviews)
"It was great!"
United States
Amanda T.
The price is ￥25,960
￥42,796 total
includes taxes & fees
Sep 15 - Sep 16
Pristine Cozy Walkable Downtown 2BR Getaway
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
"Outstanding customer service from Wylie, delicious food, coffee in lobby always available, superb housekeeping staff, quiet room, wide range of television channels including multiple HBO stations. We’re coming back!"
Ira 1-night trip
Posted 2 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:

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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?

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 Benton Hill 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.