Default HTG hotel image

South Kent Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for South Kent vacation rentals

Private kitchen

Cozy private room with a comfortable Full-size bed and private bathroom.

Cozy private room with a comfortable Full-size bed and private bathroom.
New Milford
The price is ￥13,096
￥25,731 total
includes taxes & fees
Jul 20 - Jul 21
Cozy private room with a comfortable Full-size bed and private bathroom.
Internet, bed sheets

Welcome to Sweet Abby Rose!

Welcome to Sweet Abby Rose!
Brewster
The price is ￥16,168
￥29,963 total
includes taxes & fees
Jul 16 - Jul 17
Welcome to Sweet Abby Rose!
Dining

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 ￥28,685
￥78,271 total
includes taxes & fees
Jul 29 - Jul 30
Art House 3 Beds Close to Warner Theater
Exterior

Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (34 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 ￥15,352
￥20,905 total
includes taxes & fees
Aug 8 - Aug 9
Cozy One Bedroom Apartment Centrally Located in Southbury
Property grounds

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, (8 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 ￥12,951
￥21,602 total
includes taxes & fees
Jul 20 - Jul 21
Rare, peaceful glamping, hot shower, mini golf near appalachian trail
Property grounds

Hoppy Hill Farm House

Hoppy Hill Farm House
Dover Plains
9.8 out of 10, Exceptional, (6 reviews)
"Location was great. Accommodations were clean and comfortable. Host was accessible and responsive. Will stay here again if in the area again."
United States
Ken K.
The price is ￥17,785
￥33,106 total
includes taxes & fees
Jul 15 - Jul 16
Hoppy Hill Farm House
Exterior

Cozy Attic 10 min to Llitchfield

Cozy Attic 10 min to Llitchfield
Torrington
9.2 out of 10, Wonderful, (5 reviews)
"A couple of the surfaces were not clean but mostly a clean comfy space. The bed was very comfortable and the bathroom was spacious and clean.The stairs are not for the faint of heart. A nice cozy place to stay once the luggage and groceries are up there."
United States
Rhonda H.
The price is ￥15,693
￥45,936 total
includes taxes & fees
Jul 27 - Jul 28
Cozy Attic 10 min to Llitchfield
Property grounds

Enchanting Lake front chalet with backyard and fire pit. Dog friendly.

Enchanting Lake front chalet with backyard and fire pit. Dog friendly.
Carmel Hamlet
10.0 out of 10, Exceptional, (3 reviews)
"Great place, responsive host. Would return!"
United States
Brian S.
The price is ￥19,494
￥44,718 total
includes taxes & fees
Jul 15 - Jul 16
Enchanting Lake front chalet with backyard and fire pit. Dog friendly.
Interior

Architect-Designed Dome on Private 7-Acre Retreat

Architect-Designed Dome on Private 7-Acre Retreat
Dover Plains
The price is ￥40,016
￥79,653 total
includes taxes & fees
Jul 15 - Jul 16
Architect-Designed Dome on Private 7-Acre Retreat
Exterior

Cozy Modern Farmhouse Private Apt - 3 Beds

Cozy Modern Farmhouse Private Apt - 3 Beds
Torrington
10.0 out of 10, Exceptional, (4 reviews)
"My husband and I came down from Boston for Christmas to see family and couldn’t find one decent hotel in the area. We were relieved to find this place. Cute, comfortable, clean environment and just what we needed. "
United Kingdom
Louisa A.
The price is ￥20,980
￥54,117 total
includes taxes & fees
Jul 16 - Jul 17
Cozy Modern Farmhouse Private Apt - 3 Beds
2 bedrooms, free WiFi, bed sheets

Peaceful and cozy 1 bed 1 bath in quaint Winchester

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
The price is ￥17,461
￥32,610 total
includes taxes & fees
Jul 20 - Jul 21
Peaceful and cozy 1 bed 1 bath in quaint Winchester
Interior

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
8.6 out of 10, Excellent, (10 reviews)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
The price is ￥17,785
￥23,686 total
includes taxes & fees
Jul 21 - Jul 22
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Interior

The Tipsy Gypsy - Studio Apartment

The Tipsy Gypsy - Studio Apartment
Brewster
The price is ￥24,252
￥44,506 total
includes taxes & fees
Jul 15 - Jul 16
The Tipsy Gypsy - Studio Apartment
TV, fireplace

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, (17 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is ￥36,551
￥69,189 total
includes taxes & fees
Jul 22 - Jul 23
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Smart TV, fireplace, books

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, (19 reviews)
"We had a great stay, very cute town and close to our destination "
United States
Danielle F.
The price is ￥26,798
￥34,374 total
includes taxes & fees
Jul 15 - Jul 16
Mid Century Modern Studio w/ Full Kitchen - Newly Built
Outdoor dining

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 ￥23,573
￥37,335 total
includes taxes & fees
Jul 15 - Jul 16
The Perch in the Purchase -- Cozy, unique, and private
House (3 Bedrooms) | Interior

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
The price is ￥44,139
￥87,152 total
includes taxes & fees
Aug 3 - Aug 4
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
Interior

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, (11 reviews)
"The property was very clean and inviting and the owner was very welcoming and helpful!"
United States
Sarah
The price is ￥34,761
￥44,502 total
includes taxes & fees
Jul 15 - Jul 16
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
Fridge, microwave, oven, stovetop

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 ￥47,146
￥60,565 total
includes taxes & fees
Jul 15 - Jul 16
The Jefferson Guest House, Spacious, Special Views
Interior

Spacious 4-bedroom estate in adorable Carmel Hamlet with AC

Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
Carmel Hamlet
The price is ￥39,288
￥52,392 total
includes taxes & fees
Jul 25 - Jul 26
Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top South Kent Hotel Reviews

Wyndham Southbury

Wyndham Southbury

8/10 Good
"Hotel was clean and comfortable for a one-night stay. The restaurant was inexplicably closed for breakfast when we woke up."
Jessica 1-night trip
Posted 10 hours ago
Wyndham Southbury

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, King Bed, 1 Hour & 15 Min from NYC etc!: Visitors like this South Kent vacation home rental. It is located in the mountains and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Make the most of the selection of games in this rental home to help you unwind.

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 Lake Waramaug State Park and Lake Waramaug.

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.