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South Kent Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

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
9.8 out of 10, Exceptional, (26 reviews)
"Very private, rural spot. Immaculate, thoughtfully furnished, lacking nothing"
United States
benjamin
The price is NZ$377
includes taxes & fees
14 Oct - 15 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, (3 reviews)
"I really enjoyed my four night stay here."
United States
Jim B.
The price is NZ$237
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.
The price is NZ$985
includes taxes & fees
13 Oct - 14 Oct
Creek Side Cabin with Wood Fired Hot Tub and Fire Pit
A hot tub in a backyard with a house, trees, and a clear sky.

4. Las Flores Villa

Las Flores Villa
5.0 star property
New Preston
10.0 out of 10, Exceptional, (1 review)
The price is NZ$6,243
includes taxes & fees
13 Oct - 14 Oct
Las Flores Villa
A white house with a wooden staircase leading to a porch.

5. 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 NZ$216
includes taxes & fees
18 Oct - 19 Oct
Cozy One Bedroom Apartment Centrally Located in Southbury
A glass-top table with a woven placemat, a vase with white flowers, and a view of a balcony through a door with curtains.

6. 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, (19 reviews)
"Very clean & cozy with everything we needed!"
United States
Joe K.
The price is NZ$492
includes taxes & fees
13 Oct - 14 Oct
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.

7. 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 NZ$1,031
includes taxes & fees
11 Nov - 12 Nov
Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
A kitchen with wooden cabinets, a black countertop, a sink, and a window with a view of trees.

8. "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 NZ$1,019
includes taxes & fees
13 Oct - 14 Oct
"Country outside the city " 3 bedrooms 2 full bathrooms
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.

9. 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 NZ$580
includes taxes & fees
18 Oct - 19 Oct
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
A compact room with a kitchenette, a bed, a wall decorated with photos and a mirror, and a 'No Fishing From Bridge' sign.

10. 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 NZ$328
includes taxes & fees
13 Oct - 14 Oct
Welcome to Sweet Abby Rose!
A multi-story house with a dock and boats, surrounded by dense forest.

11. North Cliff House - Private Dock & Sauna

North Cliff House - Private Dock & Sauna
Danbury
10.0 out of 10, Exceptional, (9 reviews)
"Enjoyed the property. Beautiful house. Great location. Reserve, stay and enjoy!"
United States
Ron P.
The price is NZ$2,063
includes taxes & fees
14 Oct - 15 Oct
North Cliff House - Private Dock & Sauna
A modern kitchen with a dining area, large windows, and a TV displaying a streaming service.

12. 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 NZ$406
includes taxes & fees
25 Oct - 26 Oct
The Perch in the Purchase -- Cozy, unique, and private
A spacious living room with a large window overlooking a lake, wooden ceiling, and comfortable seating.

13. 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, (5 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 NZ$1,001
includes taxes & fees
2 Nov - 3 Nov
Escape to Bantam Lake- With Fireplace and Hot tub!
A white house with a steeply pitched roof and a small tower-like structure.

14. Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village

Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
Millbrook
9.8 out of 10, Exceptional, (8 reviews)
"We had a wonderful time at this property. It was quaint and clean and right in the middle of town near everything. Thank you, Tanya."
United States
Laurie F.
The price is NZ$852
includes taxes & fees
13 Oct - 14 Oct
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
A modern living room with a flat-screen TV mounted on a white wall, a clock, and a minimalist design.

15. 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 NZ$222
includes taxes & fees
10 Nov - 11 Nov
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
A room with a built-in bench along a wall with large windows, a door, and a tiled floor.

16. 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 NZ$1,427
includes taxes & fees
14 Oct - 15 Oct
The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
A spacious living room with large windows, a fireplace, and a view of the outdoors.

17. Watertown Home w/ Yard: 1 Mi to Echo Lake Park!

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
3.0 star property
Oakville
The price is NZ$960
includes taxes & fees
13 Oct - 14 Oct
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
A cozy cabin interior with a wooden ceiling, a sofa, a coffee table, and a sign reading "Our Happy Place".

18. The Little Lake Cabin with hot tub

The Little Lake Cabin with hot tub
New Fairfield
10.0 out of 10, Exceptional, (4 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 NZ$1,000
includes taxes & fees
26 Oct - 27 Oct
The Little Lake Cabin with hot tub
A two-story house with a front porch, a small balcony, and a white picket fence.

19. 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 NZ$600
includes taxes & fees
20 Oct - 21 Oct
Cozy Attic 10 min to Llitchfield
A spacious living room with a large wooden dining table, a comfortable sofa, and a bookshelf filled with books and decorative items.

20. Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway

Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
Millbrook
10.0 out of 10, Exceptional, (7 reviews)
"This is a charming, historic, well-maintained home on a beautifully landscaped lot. The updates in the home balance a respect for tradition while also providing modernization. The village of Millbrook is a quintessential twee New England village. The house felt very comfortable and homey and the caretaker was attentive and accommodating. We enjoyed our stay!"
United States
Beth E.
The price is NZ$1,453
includes taxes & fees
18 Oct - 19 Oct
Steps to the Delightful Village of Millbrook ☆ Fun Family 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 South Kent Hotel Reviews

The Abner Hotel

The Abner Hotel

10/10 Excellent
"The hotel is an old courthouse with an incredible charm. It is spacious and comfortable. It has the feel of old time charm yet it is brand new. The staff could not have been more helpful and pleasant. We really enjoyed our stay and will certainly go back!"
Roseann 1-night trip
Posted 1 hour ago
The Abner Hotel

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 favorite 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 depends 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 NZ$328 per night. Entering your travel dates in the search wizard you might find 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.