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South Kent Vacation Rentals

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 South Kent vacation rentals

Smart TV, fireplace, books

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)
"Clean, quiet, well stocked studio with everything we needed for our weekend in Kent. Very convenient to town. Highly recommend!"
United States
Joy P.
Mid Century Modern Studio w/ Full Kitchen - Newly Built
Property grounds

2. Hoppy Hill Farm House

Hoppy Hill Farm House
Dover Plains
9.8 out of 10, Exceptional, (6 reviews)
"The accommodations were wonderful and comfortable."
United States
Chuck S.
Hoppy Hill Farm House
Exterior

3. Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (36 reviews)
"Everything was perfect and it's a great place to stay. Highly recommended and the folks there are A+."
United States
Bob
Cozy One Bedroom Apartment Centrally Located in Southbury
Interior

4. 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.
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Exterior

5. Las Flores Villa

Las Flores Villa
5.0 star property
New Preston
10.0 out of 10, Exceptional, (1 review)
Las Flores Villa
Interior

6. 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 Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
Outdoor dining

7. Candlewood Lake Retreat with Private Dock

Candlewood Lake Retreat with Private Dock
New Milford
10.0 out of 10, Exceptional, (59 reviews)
"Great property for a family to enjoy the lake!"
United States
Jenny B.
Candlewood Lake Retreat with Private Dock
House (3 Bedrooms) | Interior

8. 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
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
Private kitchen

9. 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
Cozy private room in a shared home with a Full-size bed and private bathroom.
Marina

10. North Cliff House - Private Dock & Sauna

North Cliff House - Private Dock & Sauna
Danbury
10.0 out of 10, Exceptional, (8 reviews)
"Enjoyed the property. Beautiful house. Great location. Reserve, stay and enjoy!"
United States
Ron P.
North Cliff House - Private Dock & Sauna
Interior

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, (16 reviews)
"Very clean & cozy with everything we needed!"
United States
Joe K.
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
Property grounds

12. Brand New Lakeview Suite: Hot Tub, Pet friendly & 4 Parking Spots

Brand New Lakeview Suite: Hot Tub, Pet friendly & 4 Parking Spots
Danbury
9.6 out of 10, Exceptional, (4 reviews)
"Paula was an amazing host that helped us with our luggage as soon as we arrived in the wee hours of the night. The amount of love she has for her property shows, as everything you could need and more is there. A lovely stay, thank you so much!"
United States
Angelina L.
Brand New Lakeview Suite: Hot Tub, Pet friendly & 4 Parking Spots
Exterior

13. 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.
Cozy Attic 10 min to Llitchfield
TV, fireplace

14. 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
9.8 out of 10, Exceptional, (20 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
1 bedroom, desk, iron/ironing board, WiFi

15. Cozy Cabin Style Apt Private 1st Flr 1 Bdrm

Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
Torrington
Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
Outdoor dining

16. 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, (3 reviews)
"Beautiful place. Very clean & welcoming "
United States
Chris
The Perch in the Purchase -- Cozy, unique, and private
Coffee/tea maker, fridge, microwave, oven

17. "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.
"Country outside the city " 3 bedrooms 2 full bathrooms
Interior

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

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
Peaceful and cozy 1 bed 1 bath in quaint Winchester
Interior

19. 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, (6 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.
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
Exterior

20. 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, (6 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.
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
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

Best Western Danbury/Bethel

Best Western Danbury/Bethel

10/10 Excellent
"Well maintained. Clean"
Beverley 3-night trip
Posted 2 hours ago
Best Western Danbury/Bethel

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!

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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.

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 White Memorial Conservation Center, 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.