South Kent Holiday Rentals from NZ$269: Search Short-Term Rentals

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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

Kent

Joy P.

includes taxes & fees

31 Aug - 1 Sept

A covered outdoor area with a wooden deck and a view of a grassy landscape with trees and a distant white building.

2. Hoppy Hill Farm House

Dover Plains

includes taxes & fees

7 Sept - 8 Sept

Two camping tents set up in a forest with chairs and a wooden platform nearby.

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

Dover Plains

JoAnna S.

includes taxes & fees

7 Sept - 8 Sept

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

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

New Milford

includes taxes & fees

1 Sept - 2 Sept

A covered outdoor kitchen with a grill, bar stools, and a refrigerator stocked with snacks.

5. Glamping, family fun, pet friendly

Dover Plains

Gui

includes taxes & fees

31 Aug - 1 Sept

Two tents set up in a forest with a table and chairs in front.

6. Campers Paradise, cozy tents, hot tub, free EV charger. Pet friendly

Dover Plains

Tania

includes taxes & fees

31 Aug - 1 Sept

A compact room with a kitchenette, a bed, a wall decorated with photos and a mirror, and a 'No Fishing From Bridge' sign.

7. Welcome to Sweet Abby Rose!

Brewster

Yasmin G.

includes taxes & fees

30 Aug - 31 Aug

A white house with a wooden staircase leading to a porch.

8. Cozy One Bedroom Apartment Centrally Located in Southbury

Southbury

Bob

includes taxes & fees

7 Sept - 8 Sept

A white house with a grey roof, a balcony with a blue umbrella, and a visible chimney.

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

Southbury

Chris

includes taxes & fees

7 Sept - 8 Sept

A glass-top table with a woven placemat, a vase with white flowers, and a view of a balcony through a door with curtains.

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

Morris

Joe K.

includes taxes & fees

31 Aug - 1 Sept

A modern living room with a flat-screen TV mounted on a white wall, a clock, and a minimalist design.

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

Watertown

Laurie P.

includes taxes & fees

15 Sept - 16 Sept

A kitchen with wooden cabinets, a black countertop, a sink, and a window with a view of trees.

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

Holmes

pamela w.

includes taxes & fees

8 Sept - 9 Sept

A two-story house with a front porch, a small balcony, and a white picket fence.

13. Cozy Modern Farmhouse Private Apt - 3 Beds

Torrington

Louisa A.

includes taxes & fees

30 Aug - 31 Aug

14. Cozy Attic 10 min to Llitchfield

Torrington

Nicole N.

includes taxes & fees

30 Aug - 31 Aug

A spacious living room with a fireplace, a dining area with a view of a lake, and a cozy seating arrangement.

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

Carmel Hamlet

Robert T.

includes taxes & fees

8 Sept - 9 Sept

A living room with a sofa, coffee table, and chairs, a kitchen area with a bar, and a door.

16. Pristine Cozy Walkable Downtown 2BR Getaway

Torrington

James M.

includes taxes & fees

16 Sept - 17 Sept

A modern kitchen with a wooden dining table, blue chairs, and a colorful bowl centerpiece.

17. Art House 3 Beds Close to Warner Theater

Torrington

Brittany M.

includes taxes & fees

1 Sept - 2 Sept

A white house with a steeply pitched roof and a small tower-like structure.

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

Millbrook

Laurie F.

includes taxes & fees

9 Sept - 10 Sept

A room with a bed, a couch, a desk with a computer, and various wall decorations.

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

Carmel Hamlet

includes taxes & fees

14 Sept - 15 Sept

A kitchen with a marble island, wooden cabinets, a clock, and a window with a view of trees.

20. The Jefferson Guest House, Spacious, Special Views

Litchfield

"Everything about Jefferson House was perfect. It was located in a beautiful part of Connecticut adjoining a state park. The house was beautifully decorated. The kitchen was fully equipped and had a large island for dining. The bed, pillows and living room furnishings were very comfortable. The house was well up-to-date with two TVs, a charging device with multiple cords, a double oven (!), and countless thoughtful touches. I cannot recommend it highly enough!"

genevieve

includes taxes & fees

31 Aug - 1 Sept

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Top South Kent Hotel Reviews

Best Western Danbury/Bethel

8/10 Good

"The room was clean, had a slight smell, not sure what it was, but had to get an air freshener. The staff is very accommodating and the breakfast was decent."

The Abner Hotel

10/10 Excellent

"I think this hotel would be wonderful in any season...beautiful area to walk on the wide, stately streets with beautiful 1800's home in the summer, spring or fall; lots of beautiful autumn leaves in the fall, perfect New England town with center green in winter, summer, spring and fall, to beautiful spring with flowers all over the town too. At Abner Hotel you can enjoy any season with the great rooftop bar, the cozy fireplace in the lounge outside the restaurant in the winter.... A special attraction for attorneys or anyone interested in the law is the unique nature of this property which was a renovated and preserved old courthouse.... Don't forget the fascinating attraction of country's very first Law School, walking distance from the hotel! Lourdes of Litchfield Grotto, lovely with outdoor masses, stations of the cross, gift shop and Cafe, open to all, just down the road."

Mayflower Inn & Spa, Auberge Collection

10/10 Excellent

"Beautiful property with lovely pool and spa area. The rooms are beautifully decorated. The staff are all friendly, welcoming, and very helpful. The grounds and gardens are well maintained. The hiking trail is highly recommended. My room in the main house was a bit noisy; the room above mine appeared to be a utility room that was active early in the morning. I could hear footsteps throughout the day. The dinner was overrated, but the breakfast and lunch were delicious."

Find out more about South Kent

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our South Kent holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up South Kent. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in South Kent. Seeing all the best attractions is bound to make you fall in love with South Kent. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in South Kent short-term rentals, that won’t be hard to do.

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 White Memorial Conservation Center, 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.

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Check prices for these dates

Our top choices for South Kent holiday rentals

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

2. Hoppy Hill Farm House

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

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

5. Glamping, family fun, pet friendly

6. Campers Paradise, cozy tents, hot tub, free EV charger. Pet friendly

7. Welcome to Sweet Abby Rose!

8. Cozy One Bedroom Apartment Centrally Located in Southbury

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

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

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

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

13. Cozy Modern Farmhouse Private Apt - 3 Beds

14. Cozy Attic 10 min to Llitchfield

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

16. Pristine Cozy Walkable Downtown 2BR Getaway

17. Art House 3 Beds Close to Warner Theater

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

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

20. The Jefferson Guest House, Spacious, Special Views

Find holiday rentals that suit your style

Top South Kent Hotel Reviews

Best Western Danbury/Bethel

The Abner Hotel

Heritage Hotel, Golf & Conference Center

Courtyard By Marriott Danbury

Econo Lodge Bethel - Danbury

Hampton Inn Danbury

Rocky River Inn

Mayflower Inn & Spa, Auberge Collection

Americas Best Value Inn Torrington CT

Find out more about South Kent

Frequently asked questions

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