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South Kent Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for South Kent holiday rentals

A living room with a fireplace, two armchairs, a sofa, and a TV.

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

Mid Century Modern Studio w/ Full Kitchen - Newly Built
Kent
10.0 out of 10, Exceptional, (24 reviews)
"Very nice, great location in town"
United States
Lisa F.
The price is AU$303
includes taxes & fees
1 Oct - 2 Oct
Mid Century Modern Studio w/ Full Kitchen - Newly Built
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

2. 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, (1 review)
"Clean and close to activitys"
United States
randall
The price is AU$228
includes taxes & fees
13 Oct - 14 Oct
Cozy private room in a shared home with a Full-size bed and private bathroom.
A rustic cabin surrounded by a forest with a stream in the foreground.

3. 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.
Creek Side Cabin with Wood Fired Hot Tub and Fire Pit
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, (37 reviews)
"Great place. Had everything we needed and was very clean."
United States
Niki B.
The price is AU$171
includes taxes & fees
13 Oct - 14 Oct
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
9.4 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 AU$493
includes taxes & fees
6 Oct - 7 Oct
Cozy Attic 10 min to Llitchfield
A picnic setup with a checkered blanket, a basket, and two wine glasses on a grassy area with a lake and trees in the background.

6. Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
New Fairfield
8.6 out of 10, Excellent, (36 reviews)
"Very serene location, the host was very responsive and helpful."
United States
Stephen L.
The price is AU$496
includes taxes & fees
18 Oct - 19 Oct
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
A modern living room with a flat-screen TV mounted on a white wall, a clock, and a minimalist design.

7. 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 AU$193
includes taxes & fees
18 Oct - 19 Oct
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
A compact room with a kitchenette, a bed, a wall decorated with photos and a mirror, and a 'No Fishing From Bridge' sign.

8. Welcome to Sweet Abby Rose!

Welcome to Sweet Abby Rose!
Brewster
10.0 out of 10, Exceptional, (1 review)
"The place is super comfortable and has a great outdoor area for chatting; I would definitely like to come back and stay longer."
United States
Yasmin G.
The price is AU$265
includes taxes & fees
30 Sept - 1 Oct
Welcome to Sweet Abby Rose!
A modern kitchen with a dining area, large windows, and a TV displaying a streaming service.

9. 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, (5 reviews)
"Beautiful place. Very clean & welcoming "
United States
Chris
The price is AU$331
includes taxes & fees
18 Oct - 19 Oct
The Perch in the Purchase -- Cozy, unique, and private
A two-story house with a front porch, a small balcony, and a white picket fence.

10. 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 AU$573
includes taxes & fees
1 Oct - 2 Oct
Cozy Modern Farmhouse Private Apt - 3 Beds
A glass-top table with a woven placemat, a vase with white flowers, and a view of a balcony through a door with curtains.

11. 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, (18 reviews)
"Very clean & cozy with everything we needed!"
United States
Joe K.
The price is AU$394
includes taxes & fees
12 Oct - 13 Oct
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
A living room with a sofa, coffee table, and chairs, a kitchen area with a bar, and a door.

12. Pristine Cozy Walkable Downtown 2BR Getaway

Pristine Cozy Walkable Downtown 2BR Getaway
Torrington
10.0 out of 10, Exceptional, (21 reviews)
"It was great!"
United States
Amanda T.
The price is AU$394
includes taxes & fees
30 Sept - 1 Oct
Pristine Cozy Walkable Downtown 2BR Getaway
A kitchen with wooden cabinets, a black countertop, a sink, and a window with a view of trees.

13. "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 AU$818
includes taxes & fees
30 Sept - 1 Oct
"Country outside the city " 3 bedrooms 2 full bathrooms
A room with a built-in bench along a wall with large windows, a door, and a tiled floor.

14. The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining

The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
New Milford
The price is AU$1,098
includes taxes & fees
30 Sept - 1 Oct
The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
A house surrounded by a dense forest with a hammock and a small shed.

15. Enchanting Lake front chalet with backyard and fire pit. Dog friendly.

Enchanting Lake front chalet with backyard and fire pit. Dog friendly.
Carmel Hamlet
10.0 out of 10, Exceptional, (3 reviews)
"Great place, responsive host. Would return!"
United States
Brian S.
Enchanting Lake front chalet with backyard and fire pit. Dog friendly.
A room with a bed, a couch, a desk with a computer, and various wall decorations.

16. Spacious 4-bedroom estate in adorable Carmel Hamlet with AC

Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
Carmel Hamlet
The price is AU$407
includes taxes & fees
6 Oct - 7 Oct
Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
A two-story house with a balcony, surrounded by lush greenery.

17. Quiet Solitude with Firepit, Electric Stove & Private Deck

Quiet Solitude with Firepit, Electric Stove & Private Deck
Hopewell Junction
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our stay at Sara's place. Unfortunately due to all the rain we couldn't enjoy the outside facilities. The bedroom loft is charming and everything you need is there. Thanks for a great stay!"
United States
stephanie a.
The price is AU$801
includes taxes & fees
1 Oct - 2 Oct
Quiet Solitude with Firepit, Electric Stove & Private Deck
A modern kitchen with a wooden dining table, blue chairs, and a colorful bowl centerpiece.

18. 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 AU$598
includes taxes & fees
1 Oct - 2 Oct
Art House 3 Beds Close to Warner Theater
A spacious living room with a large window overlooking a lake, wooden ceiling, and comfortable seating.

19. 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, (4 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 AU$814
includes taxes & fees
5 Oct - 6 Oct
Escape to Bantam Lake- With Fireplace and Hot tub!
A hot tub in a backyard with a house, trees, and a clear sky.

20. Las Flores Villa

Las Flores Villa
5.0 star property
New Preston
10.0 out of 10, Exceptional, (1 review)
The price is AU$4,991
includes taxes & fees
2 Oct - 3 Oct
Las Flores Villa
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

Microtel Inn & Suites by Wyndham Bethel/Danbury

Microtel Inn & Suites by Wyndham Bethel/Danbury

10/10 Excellent
"Staff was friendly, property was pretty clean and the rooms were very comfy and"
Loze 1-night trip
Posted 8 hours ago
Microtel Inn & Suites by Wyndham Bethel/Danbury

Find out more about South Kent

Everything you need to know about South Kent holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the South Kent holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 South Kent holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

South Kent holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in South Kent. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A South Kent holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of South Kent holiday rentals we have selected for you start as low as AU$265 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on South Kent rentals

At Expedia, we put the best South Kent holiday 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 South Kent 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 South Kent holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around South Kent. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in South Kent?

Yes, there are holiday rentals close to the most popular sights in South Kent, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that South Kent has to offer?

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed: This holiday home rental outside of South Kent offers a fireplace, a patio and a BBQ 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 that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals will I find in South Kent?

Expedia has 11 holiday 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 wider area, you’ll find Bull's Bridge and Lake Waramaug State Park.

What are holiday rentals like in South Kent?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in South Kent. Holiday rentals feature amenities like kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from public hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great choice for families.