Search Holiday Rentals in South Kent

Top Holiday Rentals in South Kent

On the beach, sun-loungers
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
9.6 out of 10, Exceptional, (58)
"Property manager was very kind and responsive. Greatly enjoyed the views of the pond and the basement pool and ping pong tables. Great time playing these games with mybson as the weather wasn't conducive for water activities."
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
Property grounds
Guest Cottage on Country Estate
9.2 out of 10, Wonderful, (33)
"My husband and son stayed here for 5 days. They had a fabulous time hiking in the state park nearby. Thanks for a great stay!"
Guest Cottage on Country Estate
Property grounds
Lake Luxury
10.0 out of 10, Exceptional, (8)
"We loved our stay at this home. Plenty of space so we didn’t feel like we were on top of each other, gorgeous kitchen (plus a separate butler’s kitchen!), and lux bathrooms made this rental exactly what we needed. Thanks Gianna!"
Lake Luxury
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Games room
Peaceful apartment on 3.5 acres w/ artist studio.
10.0 out of 10, Exceptional, (11)
"Cute."
The price is €201
per night
19 May - 20 May
Peaceful apartment on 3.5 acres w/ artist studio.
Property grounds
Beautiful Renovated 2BR 2B Direct Waterfront Candlewood Lake Home~Sunset Views!
10.0 out of 10, Exceptional, (15)
"The house was very clean and comfortable with really nice seating inside and out with great views of the lake. Our family really enjoyed"
Beautiful Renovated 2BR 2B Direct Waterfront Candlewood Lake Home~Sunset Views!
Smart TV, fireplace
The Long View of Candlewood Lake
10.0 out of 10, Exceptional, (6)
"It was such a nice property and the host was amazing"
The Long View of Candlewood Lake
Exterior
The Lucky Goat, a quiet country cottage about an hour from NYC, just off the TSP
9.6 out of 10, Exceptional, (55)
"My husband and I are older. 60s and 70s. The stairs going up to the bedroom were a little steep. Was a little scary in the middle of the night since the bathroom is on the first floor… other than that very nice stay."
The Lucky Goat, a quiet country cottage about an hour from NYC, just off the TSP
Beach nearby, beach towels
Lake Cottage 3 Private Beaches w/ Kayaks, 1 hour & 15 Minutes from NYC
9.4 out of 10, Exceptional, (74)
"Thoroughly enjoyed our stay at Squantz Cottage. Property was well maintained, clean, and convenient. Parking at the cottage can be a little tricky backing out and getting on to the road. An option to park at the main house could be helpful. I would definitely rent again!"
Lake Cottage 3 Private Beaches w/ Kayaks, 1 hour & 15 Minutes from NYC
Bar (on property)
Romantic Log Cabin on Privately-Owned Lake with Fireplace
9.8 out of 10, Exceptional, (68)
"The cabin was wonderful and was stocked will everything we needed and more. The lake was both beautiful and private to just this cabin. The grounds had several trails that we enjoyed."
Romantic Log Cabin on Privately-Owned Lake with Fireplace
Exterior
Spectacular Short Term Vacation Rental in Kent
9.6 out of 10, Exceptional, (74)
"For the groomsman it was perfect crazy fun."
Spectacular Short Term Vacation Rental in Kent
Property grounds
Candlewood Lake Retreat with year round views
10.0 out of 10, Exceptional, (6)
"This house was exactly as advertised and very charming. The owners were very easy to work with. We had a beautiful view of the lake from the porch. We would stay here again."
Candlewood Lake Retreat with year round views
Exterior
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
9.2 out of 10, Wonderful, (27)
"For a woodsy getaway close to real highways, here’s your spot. A good home base for local activities. Cute not chic, clean and functional. Chickens and goats on the property added a great farm with no work charm."
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
Exterior
Remodeled 1795 Carriage House with two acres of gardens rimmed by forests
9.0 out of 10, Wonderful, (37)
"Charming and comfortable, lots of living space on beautiful grounds in picturesque small village. Collected objects of international art and crafts added to the enjoyment. Quiet and private with good internet connection and great suggestions for local food and necessities. Interesting and gracious host Jay was a trove of stories and information- but never intrusive."
Remodeled 1795 Carriage House with two acres of gardens rimmed by forests
Living area
Spacious New 5-bedroom holiday house in lovely Hudson Valley
Spacious New 5-bedroom holiday house in lovely Hudson Valley
Exterior
Cozy & Chic Cabin by the Lake, with access to private Beach!
10.0 out of 10, Exceptional, (7)
"Absolutely loved my stay. The host was incredibly accommodating and went above and beyond to make sure we had everything we needed. The space was stylish, clean, and cozy, with thoughtful touches throughout. The location was perfect, close to all the attractions yet tucked away in a quiet neighborhood. Would highly recommend to anyone looking for a comfortable and enjoyable stay!"
The price is €400
per night
20 May - 21 May
Cozy & Chic Cabin by the Lake, with access to private Beach!
Property grounds
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
9.6 out of 10, Exceptional, (20)
"We came for a girls weekend. The house is beautiful with plenty of comfy seating. Super clean. The view is beautiful and fun to watch all the boaters. We could not get fire pit to work, but this could have been user error. I would caution others that the stairs are a lot! Definitely not for elders and a real workout, but this was clearly stated in description. Otherwise an absolute dream house with plenty of space. The attention to detail and decor (especially in the bathrooms) was appreciated!...
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
Outdoor dining
Lakeview Estate - Chef's Kitchen - NYC Getaway
10.0 out of 10, Exceptional, (17)
"We had a wonderful stay in the house. It has incredible views and the lake is beautiful."
The price is €886
per night
23 May - 24 May
Lakeview Estate - Chef's Kitchen - NYC Getaway
Smart TV
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
9.0 out of 10, Wonderful, (20)
"Overall we had a nice stay but there are a few things that future guests should be aware of and some improvements I feel are needed to make the stay more comfortable. Pros: The house was very clean. Beds are very comfortable!! Rooms are a good size and the living room had a cozy fireplace with blankets for many to enjoy. Updates to the kitchen and bathrooms were modern and nice. Kitchen has many pots and pans and cooking utensils stocked and there is a K cup coffee maker and a regular one...
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Smart TV, fireplace, ping pong, stereo
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...
10.0 out of 10, Exceptional, (11)
"We absolutely loved the house! This was the perfect place to bring my adult children together for a weekend away. The rooms were beautiful, beds were super comfortable, and house nicely decorated. There were spots for smaller groups to sit together and hang out or to come together and chat. The hot tub was appealing to my 20somethings but it was rainy- next time!"
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...
Property grounds
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC!
10.0 out of 10, Exceptional, (168)
"If you need a relaxing few days in the winter, very good place. Great views and quiet is the key."
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC!
Don't see what you're looking for?
See all available properties in South Kent
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.

Other types of properties in South Kent you may be interested in

Lobby
Wyndham Southbury
3.0 star property
8.0 out of 10, Very good, (1003)
"👍"
The price is €101
per night
26 May - 27 May
Wyndham Southbury
Standard Room, 2 Queen Beds, Non Smoking | Bathroom | Combined shower/bathtub, free toiletries, hair dryer, towels
Comfort Inn & Suites Danbury-Bethel
2.5 star property
9.0 out of 10, Wonderful, (95)
"Front desk folks were great. It was a bit noisy at night, routy guests. "
The price is €112
per night
26 May - 27 May
Comfort Inn & Suites Danbury-Bethel
Seasonal outdoor pool
La Quinta Inn & Suites by Wyndham Danbury
2.5 star property
8.2 out of 10, Very good, (1004)
"Will come back in the future. Thank you "
The price is €135
per night
27 May - 28 May
La Quinta Inn & Suites by Wyndham Danbury
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.

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.

How many holiday rentals will I find in South Kent?

Expedia has 10 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.

Recent reviews of South Kent properties
Expedia verified reviews

La Quinta Inn & Suites by Wyndham Danbury

La Quinta Inn & Suites by Wyndham Danbury

5/5 Excellent
Nice Environment
"Will come back in the future. Thank you "
A verified traveller stayed at La Quinta Inn & Suites by Wyndham Danbury
Posted 2 days ago
La Quinta Inn & Suites by Wyndham Danbury