South Kent Vacation Rentals

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Vacation Rentals in South Kent

Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

Brookfield
9.6 out of 10, Exceptional, (4)
"The host was very kind and welcoming. The home was spacious and the perfect setting for our celebration weekend. Everyone had their own space and we had multiple spaces for group activities. We enjoyed our time and appreciate the hospitality. "
United States
Valerie V.
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

New Fairfield
9.2 out of 10, Wonderful, (34)
"Amazing beautiful place!! Everything clean!! Definitely going to come back! "
United States
Andrew E.
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

Wappinger Cottage - Scandinavian retreat on a creek

Poughkeepsie
10.0 out of 10, Exceptional, (23)
"This was the perfect get away spot! Serene location, lovely amenities, and a gracious host."
United States
Laurie C.
Wappinger Cottage - Scandinavian retreat on a creek

Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.

Danbury
10.0 out of 10, Exceptional, (24)
"Gorgeous views and comfortable stay!"
United States
Sam C.
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.

Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

Northwest Harwinton
8.6 out of 10, Excellent, (27)
"Love the place.. very clean ..loved the neighbors.. got to catch up on well needed rest.. the neighbors on the right were wonderful than the owners came and they were also wonderful also"
United States
Andrea m.
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.

3.0 star property
Carmel
10.0 out of 10, Exceptional, (3)
"It was great! We loved staying in this cute house. Proximity to the lake is great, and the backyard is quite beautiful."
United States
Varuna S.
Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.

Cozy Lakefront Bungalow w firepit/dock/kayaks

Plymouth
9.8 out of 10, Exceptional, (39)
"Owners were there, helpful, all in all very good"
United States
Walter B.
Cozy Lakefront Bungalow w firepit/dock/kayaks

Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!

New Fairfield
10.0 out of 10, Exceptional, (80)
"Beautiful fun home, great owner!"
United States
Robin B.
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!

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

New Fairfield
9.8 out of 10, Exceptional, (35)
"Perfect location, well equipped from decks and dock, kayaks and fire pit. Beautiful well kept landscape. Nice open floor plan for family gatherings."
United States
Brian W.
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger

Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! No Pet Fees!

Holmes
10.0 out of 10, Exceptional, (196)
"Great place to get away. Absolutely recommend it. "
United States
Demian B.
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! No Pet Fees!

Awesome Lake Home with tons of fun!

2.0 star property
New Fairfield
9.8 out of 10, Exceptional, (6)
"Great spot "
United States
Mike P.
$686 nightly
The price is $776
Dec 5 - Dec 6
Total with taxes and fees
Awesome Lake Home with tons of fun!

The Goshen Glass Chalet

Goshen
9.6 out of 10, Exceptional, (41)
"The place was very nice met all of our expectations. "
United States
Marie G.
The Goshen Glass Chalet

Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust

Watertown
9.6 out of 10, Exceptional, (16)
"It was a great time. Loved it hear would come back again. Owner was very helpful."
United States
Nosa I.
Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust

Spacious New Luxurious holiday house in lovely Hudson Valley

Poughkeepsie
9.8 out of 10, Exceptional, (24)
"Amazing property and super helpful hosts. Can’t recommend enough! "
United States
Lou D.
$601 nightly
The price is $697
Dec 10 - Dec 11
Total with taxes and fees
Spacious New Luxurious holiday house in lovely Hudson Valley

Charming 1870 cape cottage in Litchfield

Litchfield
10.0 out of 10, Exceptional, (66)
"Beautiful home with everything you could possibly need for a vacation. Welcoming and very kind and helpful hosts. Lovely place for a family vacation. "
United States
Susanna Z.
Charming 1870 cape cottage in Litchfield

New One Bedroom Apartment Centrally Located in Southbury

Southbury
9.8 out of 10, Exceptional, (19)
"Perfect sized apartment for a short stay - very convenient to my destination"
United States
S
$115 nightly
The price is $129
Dec 4 - Dec 5
Total with taxes and fees
New One Bedroom Apartment Centrally Located in Southbury

Lakefront Fall Foliage in New England Just 2 Hours From NYC

Sharon
10.0 out of 10, Exceptional, (87)
"Great hosts and very charming cottage. All the amenities you could want. Beautiful kayaking and birdwatching. "
United States
Paula S.
Lakefront Fall Foliage in New England Just 2 Hours From NYC

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

Hopewell Junction
8.8 out of 10, Excellent, (45)
"The house is clean and nice. Location is really good, quiet and not to far from the city."
United States
Cecilia G.
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.

Carmel Hamlet
10.0 out of 10, Exceptional, (17)
"We had a great stay and had everything we needed!"
United States
Maueen Q.
$856 nightly
The price is $928
Dec 27 - Dec 28
Total with taxes and fees
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.

Summer Lake Cottage, private beach, Berkshire Hills, small village

Lakeville
9.4 out of 10, Exceptional, (84)
"The house is very comfortable and perfect for visiting with family and friends.We enjoyed the roomy kitchen space. The porch is great for relaxing and gazing at the tranquil lake. We appreciated the use of the canoe and the dock."
United States
Jenny P.
Summer Lake Cottage, private beach, Berkshire Hills, small village
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

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 $129 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?

Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit: Visitors like this South Kent vacation home rental. It is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, an arcade game room, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals will I find in South Kent?

Expedia has 10 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.