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South Kent Vacation Rentals

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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

Property grounds

1. 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 ￥16,909
￥31,649 total
includes taxes & fees
Sep 13 - Sep 14
Hoppy Hill Farm House
Living area

2. 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.
The price is ￥29,975
￥38,314 total
includes taxes & fees
Sep 27 - Sep 28
Mid Century Modern Studio w/ Full Kitchen - Newly Built
Private kitchen

3. 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
The price is ￥11,760
￥23,670 total
includes taxes & fees
Oct 4 - Oct 5
Cozy private room in a shared home with a Full-size bed and private bathroom.
Exterior

4. 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 ￥13,558
￥18,666 total
includes taxes & fees
Sep 18 - Sep 19
Cozy One Bedroom Apartment Centrally Located in Southbury
Interior

5. 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 ￥13,681
￥18,808 total
includes taxes & fees
Sep 15 - Sep 16
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Room

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 ￥15,372
￥28,321 total
includes taxes & fees
Sep 10 - Sep 11
Welcome to Sweet Abby Rose!
Outdoor dining

7. 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 ￥22,412
￥35,497 total
includes taxes & fees
Sep 15 - Sep 16
The Perch in the Purchase -- Cozy, unique, and private
Exterior

8. 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.
The price is ￥12,912
￥51,416 total
includes taxes & fees
Sep 10 - Sep 11
Cozy Attic 10 min to Llitchfield
Interior

9. 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 price is ￥33,050
￥42,158 total
includes taxes & fees
Sep 10 - Sep 11
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
Private kitchen

10. "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 ￥30,522
￥88,063 total
includes taxes & fees
Sep 15 - Sep 16
"Country outside the city " 3 bedrooms 2 full bathrooms
Interior

11. 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 ￥62,257
￥110,717 total
includes taxes & fees
Sep 10 - Sep 11
The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
Property grounds

12. 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 ￥58,537
￥96,486 total
includes taxes & fees
Sep 10 - Sep 11
Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
Room

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

Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
Torrington
The price is ￥19,853
￥61,508 total
includes taxes & fees
Sep 13 - Sep 14
Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
Living area

14. 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 ￥24,595
￥42,158 total
includes taxes & fees
Sep 16 - Sep 17
Pristine Cozy Walkable Downtown 2BR Getaway
Dining

15. 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 ￥21,615
￥65,972 total
includes taxes & fees
Sep 10 - Sep 11
Art House 3 Beds Close to Warner Theater
Exterior

16. 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.
The price is ￥49,190
￥75,470 total
includes taxes & fees
Sep 10 - Sep 11
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
Exterior

17. Las Flores Villa

Las Flores Villa
5.0 star property
New Preston
10.0 out of 10, Exceptional, (1 review)
The price is ￥415,044
￥538,789 total
includes taxes & fees
Oct 1 - Oct 2
Las Flores Villa
Living area

18. 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.
The price is ￥34,587
￥64,805 total
includes taxes & fees
Sep 21 - Sep 22
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
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.
The price is ￥61,488
￥123,293 total
includes taxes & fees
Sep 14 - Sep 15
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
Interior

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

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
The price is ￥19,092
￥34,330 total
includes taxes & fees
Sep 13 - Sep 14
Peaceful and cozy 1 bed 1 bath in quaint Winchester
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

Americas Best Value Inn Torrington CT

Americas Best Value Inn Torrington CT

8/10 Good
".."
Teresa 2-night trip
Posted 1 hour ago
Americas Best Value Inn Torrington CT

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 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 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.