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South Kent Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for South Kent vacation rentals

A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

1. Cozy private room in a shared home with a Full-size bed and private bathroom.

Cozy private room in a shared home with a Full-size bed and private bathroom.
New Milford
10.0 out of 10, Exceptional, (3 reviews)
"I really enjoyed my four night stay here."
United States
Jim B.
The price is ￥9,883
￥21,719 total
includes taxes & fees
Nov 9 - Nov 10
Cozy private room in a shared home with a Full-size bed and private bathroom.
A living room with a fireplace, two armchairs, a sofa, and a TV.

2. Mid Century Modern Studio w/ Full Kitchen - Newly Built

Mid Century Modern Studio w/ Full Kitchen - Newly Built
Kent
9.8 out of 10, Exceptional, (26 reviews)
"Very private, rural spot. Immaculate, thoughtfully furnished, lacking nothing"
United States
benjamin
The price is ￥26,001
￥33,509 total
includes taxes & fees
Oct 29 - Oct 30
Mid Century Modern Studio w/ Full Kitchen - Newly Built
A compact room with a kitchenette, a bed, a wall decorated with photos and a mirror, and a 'No Fishing From Bridge' sign.

3. Welcome to Sweet Abby Rose!

Welcome to Sweet Abby Rose!
Brewster
10.0 out of 10, Exceptional, (2 reviews)
"We had a wonderful experience! The RV was very nice and cozy. Everything was clean and well maintained. The property was beautiful. The host was very helpful and accommodating. Definitely plan on coming back!"
United States
Fernanda
The price is ￥15,687
￥29,071 total
includes taxes & fees
Oct 26 - Oct 27
Welcome to Sweet Abby Rose!
A white house with a wooden staircase leading to a porch.

4. Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (38 reviews)
"Great place. Had everything we needed and was very clean."
United States
Niki B.
The price is ￥16,236
￥21,810 total
includes taxes & fees
Nov 3 - Nov 4
Cozy One Bedroom Apartment Centrally Located in Southbury
A two-story house with a front porch, a small balcony, and a white picket fence.

5. Cozy Attic 10 min to Llitchfield

Cozy Attic 10 min to Llitchfield
Torrington
9.6 out of 10, Exceptional, (7 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 ￥16,471
￥58,172 total
includes taxes & fees
Oct 26 - Oct 27
Cozy Attic 10 min to Llitchfield
A modern kitchen with a dining area, large windows, and a TV displaying a streaming service.

6. The Perch in the Purchase -- Cozy, unique, and private

The Perch in the Purchase -- Cozy, unique, and private
Southbury
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful place. Very clean & welcoming "
United States
Chris
The price is ￥23,719
￥37,356 total
includes taxes & fees
Oct 28 - Oct 29
The Perch in the Purchase -- Cozy, unique, and private
A rustic cabin surrounded by a forest with a stream in the foreground.

7. Creek Side Cabin with Wood Fired Hot Tub and Fire Pit

Creek Side Cabin with Wood Fired Hot Tub and Fire Pit
New Milford
10.0 out of 10, Exceptional, (3 reviews)
"Great little house, our favorite part was the gorgeous creek. Absolutely would recommend to pet lovers and those looking for peaceful nature :)"
United States
Kristine W.
The price is ￥48,925
￥87,598 total
includes taxes & fees
Oct 29 - Oct 30
Creek Side Cabin with Wood Fired Hot Tub and Fire Pit
A residential property with a well-maintained lawn, a small house with a front porch, and a garage.

8. Sharon Retreat w/ Private Yard

Sharon Retreat w/ Private Yard
Sharon
9.2 out of 10, Wonderful, (37 reviews)
"Cagney’s home was so comfy! We loved the spacious family room. The beds were comfortable and the fully stocked kitchen made cooking much easier. Absolutely would love to stay at your cottage again!"
United States
Heidi F.
The price is ￥31,374
￥70,670 total
includes taxes & fees
Oct 28 - Oct 29
Sharon Retreat w/ Private Yard
A two-story house with a front porch, a small balcony, and a white picket fence.

9. 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 ￥22,072
￥66,703 total
includes taxes & fees
Oct 27 - Oct 28
Cozy Modern Farmhouse Private Apt - 3 Beds
A living room with a flat-screen TV displaying a streaming service interface, a white sofa, a small side table, and a patterned rug.

10. Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.

Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Watertown
8.4 out of 10, Very good, (12 reviews)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
The price is ￥16,628
￥22,260 total
includes taxes & fees
Nov 4 - Nov 5
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
A spacious living room with a fireplace, a dining area with a view of a lake, and a cozy seating arrangement.

11. Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Carmel Hamlet
10.0 out of 10, Exceptional, (21 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is ￥26,119
￥54,997 total
includes taxes & fees
Nov 3 - Nov 4
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
A hotel room with two beds, a desk, a chair, and a large window with curtains.

12. 2 Queen Beds | Non-Smoking

2 Queen Beds | Non-Smoking
Bethel
The price is ￥18,667
￥21,466 total
includes taxes & fees
Oct 28 - Oct 29
2 Queen Beds | Non-Smoking
A wooden cabin interior with a bench, a rug, and a hanging plant.

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

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
10.0 out of 10, Exceptional, (4 reviews)
"Great place and wonderful host."
United States
Thomas C.
The price is ￥16,236
￥30,830 total
includes taxes & fees
Nov 8 - Nov 9
Peaceful and cozy 1 bed 1 bath in quaint Winchester
A glass-top table with a woven placemat, a vase with white flowers, and a view of a balcony through a door with curtains.

14. The Overlook near South Farms in Litchfield County is Hospitality, integrated.

The Overlook near South Farms in Litchfield County is Hospitality, integrated.
Morris
9.8 out of 10, Exceptional, (21 reviews)
"Very clean & cozy with everything we needed!"
United States
Joe K.
The price is ￥33,727
￥43,335 total
includes taxes & fees
Oct 26 - Oct 27
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
A wooden barrel structure with a door, two wooden lounge chairs, and a small table.

15. Peaceful Cabin with Sauna, Hot Tub & Cold Plunge

Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
Cornwall
10.0 out of 10, Exceptional, (6 reviews)
"This cabin is so cute we had a relaxing time , will return"
United States
Candice S.
The price is ￥55,661
￥96,756 total
includes taxes & fees
Nov 10 - Nov 11
Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
A spacious living room with a large window overlooking a lake, wooden ceiling, and comfortable seating.

16. Escape to Bantam Lake- With Fireplace and Hot tub!

Escape to Bantam Lake- With Fireplace and Hot tub!
Morris
10.0 out of 10, Exceptional, (6 reviews)
"This house is a dream. First, the views are incredible. Second, it’s beautifully decorated and very cozy. Lastly, the property location is perfect. I can’t wait to stay again!"
United States
Shannon M.
The price is ￥42,355
￥84,710 total
includes taxes & fees
Nov 16 - Nov 17
Escape to Bantam Lake- With Fireplace and Hot tub!
A cozy cabin interior with a wooden ceiling, a sofa, a coffee table, and a sign reading "Our Happy Place".

17. The Little Lake Cabin with hot tub

The Little Lake Cabin with hot tub
New Fairfield
10.0 out of 10, Exceptional, (6 reviews)
"Great location and lots to do despite it raining for half our stay! My dog enjoyed the yard and walks around the neighborhood. My son loved kayaking and having his first ever s’more. Honestly I wished we had booked a longer trip! "
United States
Lyndsey F.
The price is ￥46,975
￥86,102 total
includes taxes & fees
Nov 9 - Nov 10
The Little Lake Cabin with hot tub
A kitchen with wooden cabinets, a black countertop, a sink, and a window with a view of trees.

18. "Country outside the city " 3 bedrooms 2 full bathrooms

"Country outside the city " 3 bedrooms 2 full bathrooms
Holmes
9.6 out of 10, Exceptional, (4 reviews)
"Great house! We had a fantastic weekend!! Thank you so much "
United States
pamela w.
The price is ￥31,201
￥90,487 total
includes taxes & fees
Nov 2 - Nov 3
"Country outside the city " 3 bedrooms 2 full bathrooms
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 ￥23,719
￥70,159 total
includes taxes & fees
Oct 26 - Oct 27
Art House 3 Beds Close to Warner Theater
A spacious kitchen with wooden cabinets, a large island with stools, and a clock on the wall.

20. The Jefferson Guest House, Spacious, Special Views

The Jefferson Guest House, Spacious, Special Views
Litchfield
10.0 out of 10, Exceptional, (9 reviews)
"I stayed here for four nights, including one with my son, and it was fantastic.Everything is brand new, clean, and beautifully appointed, with every amenity you could want."
United States
Jennifer A.
The price is ￥48,285
￥61,933 total
includes taxes & fees
Oct 27 - Oct 28
The Jefferson Guest House, Spacious, Special Views
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 South Kent Hotel Reviews

Wyndham Southbury

Wyndham Southbury

10/10 Excellent
"Clean spacious room. Staff was very helpful. My only issue is that the sheets were too big for the bed and did not stay on. Otherwise, great stay!"
Doris 2-night trip
Posted 6 hours ago
Wyndham Southbury

Find out more about South Kent

Search for holiday rentals in South Kent on Expedia! You can easily find your home rentals, villas, holiday apartments in South Kent using one of the methods below:

  • View our selection of featured holiday rentals in South Kent
  • Use the map to find apartments and other holiday homes in the South Kent neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in South Kent while they last

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

Frequently asked questions

Can I find a vacation rental in South Kent?

Yes, there are vacation rentals close to well known attractions in South Kent, or you can select a more remote option if you'd like a relaxing place to stay.

What's the top vacation rental that South Kent has to offer?

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed: Visitors like this South Kent vacation home rental. It offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals will I find in South Kent?

Expedia has 11 vacation rentals for your stay in South Kent.

What can I see and do in South Kent?

While exploring the area, visit family-friendly sights like The Christmas Shop, or get outside and enjoy nature at Housatonic River. In the larger area, you’ll find Bull's Bridge and Lake Waramaug State Park.

What are vacation rentals like in South Kent?

Vacation rentals are privately owned properties you can stay in for a few days or a quick weekend in South Kent. Vacation rentals feature extras like kitchens and laundry facilities so you'll have everything you need. If you're concerned about cleanliness, vacation rentals can offer a sense of security away from public hotel elevators and bustling concierge desks while still allowing you to travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for a family getaway.