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South Kent Vacation Rentals

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Check prices for these dates

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

Our top choices for South Kent vacation rentals

A living room with two grey armchairs, a round coffee table, a fireplace with a black and white patterned surround, and a TV mounted above the fireplace.

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
$220 nightly
The price is $249
Oct 29 - Oct 30
Total with taxes and fees
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.
$128 nightly
The price is $144
Nov 3 - Nov 4
Total with taxes and fees
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.
$527 nightly
The price is $597
Oct 20 - Oct 21
Total with taxes and fees
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)
$3,348 nightly
The price is $3,850
Oct 17 - Oct 18
Total with taxes and fees
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.
$108 nightly
The price is $121
Oct 18 - Oct 19
Total with taxes and fees
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.
$243 nightly
The price is $275
Oct 18 - Oct 19
Total with taxes and fees
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.
$545 nightly
The price is $618
Nov 10 - Nov 11
Total with taxes and fees
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.
$508 nightly
The price is $574
Oct 21 - Oct 22
Total with taxes and fees
"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.
$281 nightly
The price is $320
Oct 18 - Oct 19
Total with taxes and fees
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
$171 nightly
The price is $185
Oct 18 - Oct 19
Total with taxes and fees
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.
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, (6 reviews)
"Beautiful place. Very clean & welcoming "
United States
Chris
$210 nightly
The price is $238
Oct 28 - Oct 29
Total with taxes and fees
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.
$474 nightly
The price is $537
Nov 2 - Nov 3
Total with taxes and fees
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.
$434 nightly
The price is $491
Oct 18 - Oct 19
Total with taxes and fees
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.
$123 nightly
The price is $138
Nov 16 - Nov 17
Total with taxes and fees
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
10.0 out of 10, Exceptional, (1 review)
"Perfect!!"
United States
Jeni O.
$767 nightly
The price is $871
Oct 26 - Oct 27
Total with taxes and fees
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
$469 nightly
The price is $539
Oct 17 - Oct 18
Total with taxes and fees
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, (5 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.
$501 nightly
The price is $568
Oct 26 - Oct 27
Total with taxes and fees
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.
$307 nightly
The price is $353
Oct 18 - Oct 19
Total with taxes and fees
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.
$743 nightly
The price is $841
Oct 20 - Oct 21
Total with taxes and fees
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

Belden House & Mews

Belden House & Mews

10/10 Excellent
"The staff the rooms the atmosphere location the FOOD. Well deserved best hotel in the state by far."
Anthony 4-night trip
Posted 3 hours ago
Belden House & Mews

Find out more about South Kent

Everything you need to know about South Kent vacation rentals

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

South Kent vacation 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 low season months. For more hustle and bustle, you may prefer to visit South Kent in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $185 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on South Kent rentals

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

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 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.

What's the top vacation rental that South Kent has to offer?

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed: Visitors like this South Kent vacation home rental. It offers a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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 The Christmas Shop, 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.