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South Kent Holiday Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for South Kent holiday 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, (23 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.
The price is HK$1,530
HK$1,979 total
includes taxes & fees
23 Aug - 24 Aug
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.
The price is HK$863
HK$1,624 total
includes taxes & fees
16 Aug - 17 Aug
Hoppy Hill Farm House
Property grounds

3. Rare, peaceful glamping, hot shower, mini golf near appalachian trail

Rare, peaceful glamping, hot shower, mini golf near appalachian trail
Dover Plains
10.0 out of 10, Exceptional, (9 reviews)
"We thoroughly enjoyed our stay at this property, clean and spacious tents, impressive shower facility, and all the fun amenities you never thought you needed like an 18 hole putt putt course!"
United States
JoAnna S.
The price is HK$629
HK$1,048 total
includes taxes & fees
17 Aug - 18 Aug
Rare, peaceful glamping, hot shower, mini golf near appalachian trail
Cookware/dishes/utensils

4. Awesome Lake Home with tons of fun!

Awesome Lake Home with tons of fun!
New Fairfield
9.8 out of 10, Exceptional, (11 reviews)
"Nicole is a wonderful host. We had a fantastic stay at her house. The home was beautifully prepared, and we felt very comfortable throughout our visit. Even though it was a rainy weekend, we were still able to enjoy the huge hot tub and had a great time playing the card games and board games provided. Thank you!!"
United States
W Y.
The price is HK$3,178
HK$5,589 total
includes taxes & fees
17 Aug - 18 Aug
Awesome Lake Home with tons of fun!
Interior

5. 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, (13 reviews)
"The property was very clean and inviting and the owner was very welcoming and helpful!"
United States
Sarah
The price is HK$1,687
HK$2,183 total
includes taxes & fees
16 Aug - 17 Aug
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
1 bedroom, Internet, bed sheets

6. 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 HK$785
HK$1,463 total
includes taxes & fees
14 Aug - 15 Aug
Welcome to Sweet Abby Rose!
Exterior

7. 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
9.6 out of 10, Exceptional, (5 reviews)
"Tanya goes above and beyond for her guests. Thanks so much for the stay!"
United States
Lindsay S.
The price is HK$2,511
HK$3,906 total
includes taxes & fees
16 Aug - 17 Aug
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
Interior

8. 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.
The price is HK$3,139
HK$6,595 total
includes taxes & fees
23 Aug - 24 Aug
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
Coffee/tea maker, fridge, microwave, oven

9. "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 HK$1,709
HK$4,747 total
includes taxes & fees
24 Aug - 25 Aug
"Country outside the city " 3 bedrooms 2 full bathrooms
Coffee/tea maker, fridge, microwave, oven

10. The Jefferson Guest House, Spacious, Special Views

The Jefferson Guest House, Spacious, Special Views
Litchfield
10.0 out of 10, Exceptional, (8 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 HK$2,288
HK$2,979 total
includes taxes & fees
3 Sept - 4 Sept
The Jefferson Guest House, Spacious, Special Views
TV, fireplace

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
9.8 out of 10, Exceptional, (18 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is HK$2,236
HK$3,937 total
includes taxes & fees
10 Sept - 11 Sept
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Outdoor dining

12. Candlewood Lake Retreat with Private Dock

Candlewood Lake Retreat with Private Dock
New Milford
10.0 out of 10, Exceptional, (57 reviews)
"Great property for a family to enjoy the lake!"
United States
Jenny B.
The price is HK$11,602
HK$18,337 total
includes taxes & fees
25 Aug - 26 Aug
Candlewood Lake Retreat with Private Dock
Property grounds

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

Brand New Lakeview Suite: Hot Tub, Pet friendly & 4 Parking Spots
Danbury
10.0 out of 10, Exceptional, (1 review)
The price is HK$2,613
HK$4,394 total
includes taxes & fees
24 Aug - 25 Aug
Brand New Lakeview Suite: Hot Tub, Pet friendly & 4 Parking Spots
Dining

14. Classy Private Apt - 3 Beds 2nd Flr - Near Downtown

Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
Torrington
10.0 out of 10, Exceptional, (1 review)
"Good communication. Clean place in good location. Would stay again. "
United States
Jaimie S.
The price is HK$1,836
HK$4,088 total
includes taxes & fees
16 Aug - 17 Aug
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
Smart TV, fireplace

15. Pristine Cozy Walkable Downtown 2BR Getaway

Pristine Cozy Walkable Downtown 2BR Getaway
Torrington
10.0 out of 10, Exceptional, (19 reviews)
"Wow what an enjoyable stay! Clean, fresh, relaxing, and wonderful to meet owners Corin and Jen… gracious and hospitable hosts. Very comfortable, great location, well appointed… everything we were looking for!"
United States
James M.
The price is HK$1,224
HK$2,139 total
includes taxes & fees
2 Sept - 3 Sept
Pristine Cozy Walkable Downtown 2BR Getaway
Dining

16. 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 HK$1,120
HK$3,435 total
includes taxes & fees
1 Sept - 2 Sept
Art House 3 Beds Close to Warner Theater
Outdoor dining

17. 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 price is HK$1,144
HK$1,828 total
includes taxes & fees
25 Aug - 26 Aug
The Perch in the Purchase -- Cozy, unique, and private
Exterior

18. 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
The price is HK$727
HK$993 total
includes taxes & fees
8 Sept - 9 Sept
Cozy One Bedroom Apartment Centrally Located in Southbury
Living area

19. The Hideaway

The Hideaway
Brewster
10.0 out of 10, Exceptional, (8 reviews)
"Nice, clean, comfortable place to stay. Beautiful, convenient setting. Will look to come back again some day for sure. "
United States
Kenneth M.
The price is HK$1,216
HK$2,466 total
includes taxes & fees
1 Sept - 2 Sept
The Hideaway
Outdoor dining

20. Glamping, family fun, pet friendly

Glamping, family fun, pet friendly
Dover Plains
10.0 out of 10, Exceptional, (4 reviews)
"Great Glamping spot. The hosts were very responsive and the place provided many activities. "
United States
Gui
The price is HK$629
HK$1,048 total
includes taxes & fees
17 Aug - 18 Aug
Glamping, family fun, pet friendly
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
"Decent basic hotel, very clean room and bedding, slept well. Bathroom amenities were good. Staff was very helpful. Breakfast was OK but happy to have it available to get started in the AM. (*Please offer honey or another jam option for the continental breakfast- the dispenser was filled, but only with grape jam) I liked that they had good clementine oranges as a fresh fruit option. The hotel is near some food options for dinner or lunch, and a 10 min drive to Danbury Center. Would definitely stay here again if in the area."
Linda 1-night trip
Posted 2 hours ago
Microtel Inn & Suites by Wyndham Bethel/Danbury

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 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?

Lakefront Fall Foliage in New England Just 2 Hours From NYC: This holiday home rental outside of South Kent is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You can relax into your holiday with a private 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 White Memorial Conservation Center, or get outside and enjoy nature at Housatonic River. In the wider area, you’ll find Lake Waramaug State Park and Lake Waramaug.

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.