Book Holiday Homes in South Kent

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Featured Holiday Homes in South Kent

Spacious New Luxurious holiday house in lovely Hudson Valley

Spacious New Luxurious holiday house in lovely Hudson Valley

Poughkeepsie
The price is AU$1,483 per night from 1 May to 2 May
AU$1,483
includes taxes & fees
1 May - 2 May
With a stay at this vacation home in Poughkeepsie, you'll be within a 15-minute drive of Vassar College and Marist College.
Spacious New Luxurious holiday house in lovely Hudson Valley
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

Hopewell Junction
Located in Hopewell Junction, this vacation home is in the mountains, within a 10-minute drive of Clarence Fahnestock State Park and Hudson Valley Research ...
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake

Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake

Danbury
Located in Danbury, this vacation home is on the waterfront, a 1-minute drive from Candlewood Lake and 7 minutes from Candlewood Plaza Shopping Center.
Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake
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Hidden Charm in Hudson Valley In Dutchess County

Hidden Charm in Hudson Valley In Dutchess County

2 out of 5
Salt Point
Located in Salt Point, this vacation home is in the mountains, within a 15-minute drive of Clinton Vineyards and Institute of Ecosystem Studies.
Hidden Charm in Hudson Valley In Dutchess County
Mountain View Getaway

Mountain View Getaway

West Cornwall
Located in Cornwall, this vacation home is on a lake, within a 15-minute drive of Music Mountain and West Cornwall Covered Bridge.
Mountain View Getaway
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger

Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger

New Fairfield
Located in New Fairfield, this vacation home is on the waterfront, a 1-minute drive from Candlewood Lake and 7 minutes from Squantz Pond State Park.
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
Tranquil Litchfield Connecticut Retreat".

Tranquil Litchfield Connecticut Retreat".

Litchfield
The price is AU$503 per night from 9 Apr to 10 Apr
AU$503
includes taxes & fees
9 Apr - 10 Apr
This vacation home is 4.1 mi (6.6 km) from Black Rock State Park and 6.3 mi (10.1 km) from Haight-Brown Vineyard.
Tranquil Litchfield Connecticut Retreat".
Pet-Friendly Beacon Area Vacation Rental: 6 Acres

Pet-Friendly Beacon Area Vacation Rental: 6 Acres

Lagrangeville
With a stay at this vacation home in Lagrangeville, you'll be within a 10-minute drive of Beekman Golf Course and East Fishkill Community Library.
Pet-Friendly Beacon Area Vacation Rental: 6 Acres
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
Located in New Fairfield, this vacation home is in the mountains, within a 5-minute drive of Candlewood Lake and Squantz Pond State Park.
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
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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.

South Kent Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our South Kent vacation homes are the perfect way for you to wing it.

Holiday houses in South Kent let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of South Kent in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local South Kent adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in South Kent with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of South Kent vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

South Kent Holiday Homes essential information

Accommodation
256 Holiday Homes
Lowest Price
AU$155
Highest Price
AU$1,483
Popular accommodation
Spacious New Luxurious holiday house in lovely Hudson Valley, 1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views, Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake, Hidden Charm in Hudson Valley In Dutchess County, Mountain View Getaway, Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger, Tranquil Litchfield Connecticut Retreat"., Pet-Friendly Beacon Area Vacation Rental: 6 Acres, Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

Top trending hotels in South Kent

Wyndham Southbury

Wyndham Southbury

3 out of 5
1284 Strongtown Road, Southbury, CT
Fully refundableReserve now, pay when you stay
The price is AU$155 per night from 20 Apr to 21 Apr
AU$155
includes taxes & fees
20 Apr - 21 Apr
Located in Southbury, Wyndham Southbury is a 4-minute drive from Lake Quassapaug and 5 minutes from Southford Falls State Park.
Wyndham Southbury
Microtel Inn & Suites by Wyndham Bethel/Danbury

Microtel Inn & Suites by Wyndham Bethel/Danbury

2 out of 5
80 Benedict Rd, Bethel, CT
Fully refundableReserve now, pay when you stay
The price is AU$160 per night from 8 Apr to 9 Apr
AU$160
includes taxes & fees
8 Apr - 9 Apr
When you stay at Microtel Inn & Suites by Wyndham Bethel/Danbury in Bethel, you'll be in the business district, within a 5-minute drive of The Cave and Still ...
Microtel Inn & Suites by Wyndham Bethel/Danbury
Best Western Danbury/Bethel

Best Western Danbury/Bethel

2.5 out of 5
11 Stony Hill Road, Bethel, CT
Fully refundableReserve now, pay when you stay
The price is AU$170 per night from 20 Apr to 21 Apr
AU$170
includes taxes & fees
20 Apr - 21 Apr
With a stay at Best Western Danbury/Bethel in Bethel, you'll be near the airport, just steps from The Cave and a 2-minute drive from Still River Greenway.
Best Western Danbury/Bethel
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La Quinta Inn & Suites by Wyndham Danbury

La Quinta Inn & Suites by Wyndham Danbury

2.5 out of 5
116 Newtown Road, Danbury, CT
Fully refundableReserve now, pay when you stay
The price is AU$203 per night from 8 Apr to 9 Apr
AU$203
includes taxes & fees
8 Apr - 9 Apr
Located in Danbury, La Quinta Inn & Suites by Wyndham Danbury is in the business district, a 5-minute drive from Western Connecticut State University and 5 minutes ...
La Quinta Inn & Suites by Wyndham Danbury
Don't see what you're looking for?
See all available properties in South Kent
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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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^Subject to availability and chosen travel dates.