Holiday Rentals in South Kent

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Holiday Rentals in South Kent

Lake Cottage 3 Private Beaches w/ Kayaks, 1 hour & 15 Minutes from NYC
9.4 out of 10, Exceptional, 76 reviews
"Perfect weather for a getaway! Great location to get to get around. Cottage was perfect for us. Fire pit was great to hang out at. Went kayaking across the street. Beautiful lake. However, the access to the lake was a wee bit steep but we are in shape to handle it. All in all it was a great time!"
Lake Cottage 3 Private Beaches w/ Kayaks, 1 hour & 15 Minutes from NYC
Romantic Log Cabin on Privately-Owned Lake with Fireplace
9.8 out of 10, Exceptional, 71 reviews
"The cabin is really cute & has wind chimes & garden art all around it that integrates so perfectly with the natural oasis it is set in. This is a great place for a nature loving couple to enjoy. Singing birds, frogs, turtles chipmunks & fish in the lake, are the only neighbors you will notice o this beautiful property. Karen is a lovely gracious host and both she and the cabin are very welcoming & charming. Its a perfect spot go to with your soulmate & reconnect with nature."
Romantic Log Cabin on Privately-Owned Lake with Fireplace
Waterfront Luxury Lakehouse w/ Boat Dock & Kayaks. Priceless Views & Amenities.
10.0 out of 10, Exceptional, 6 reviews
"Great property, very clean and host was quick to reply. We were impressed with the amenities available (most places don’t have detergent, etc) and the view was amazing! We didn’t have time to go to the dock but it looked very nice! Wish we had time to stay longer. We will definitely try to stay there again for our next family event"
Waterfront Luxury Lakehouse w/ Boat Dock & Kayaks. Priceless Views & Amenities.
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Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
9.6 out of 10, Exceptional, 59 reviews
"We had a lovely weekend stay for a quick family get-away. The main kitchen and living area has spectacular views onto the lake as does the deck where we spent most of our time. The lake is just across the very quiet street. The kitchen is incredibly well stocked, the host super responsive and the rooms very comfortable. We did not use the well equipped basement work-out and additional TV space but it looked great. Easy to get to grocery store, hikes, local attractions but honestly we just loved...
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
9.0 out of 10, Wonderful, 30 reviews
"Very charming one room apartment with bathroom and kitchen area. Beautiful surrounding you with very pleasant hosts"
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
Spectacular Short Term Vacation Rental in Kent
9.6 out of 10, Exceptional, 75 reviews
"Very cool and fun farm/home feel location. Once we arrived it was just as relaxing as it looked before we booked. The pool is awesome, the grounds are open and if you have pets which we did are perfect for the pups to run around. There are Peacocks! I KNOW. So great to see the roosters just walking around. Easy access to the town for quick shopping but if your looking to relax this is the place."
Spectacular Short Term Vacation Rental in Kent
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...
10.0 out of 10, Exceptional, 11 reviews
"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...
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
9.0 out of 10, Wonderful, 22 reviews
"This house has an ideal location to see lots of local sites of interest in the Hyde Park and Poughkeepsie area. Easy trip from there to West Point, Hyde Park and the Culinary Institute from the location, and great restaurant, Tiramasu, is very close. The house is immaculate! The beds were very comfortable, linens were provided, the bathrooms were spacious and the five of us had plenty of room for our toiletries. The house has steps to its multiple levels for all essential rooms, not accessible....
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Candlewood Lake Retreat with year round views
10.0 out of 10, Exceptional, 8 reviews
"Pretty views over the lake in this tidy, charming cottage. We had everything we needed. Thanks!"
Candlewood Lake Retreat with year round views
Peaceful apartment on 3.5 acres w/ artist studio.
10.0 out of 10, Exceptional, 11 reviews
"Cute."
The price is €205
per night
10 Jul - 11 Jul
Peaceful apartment on 3.5 acres w/ artist studio.
Cozy & Chic Cabin by the Lake, with access to private Beach!
10.0 out of 10, Exceptional, 9 reviews
"The cabin was phenomenal! Would recommend it and am looking forward to a visit again."
The price is €468
per night
8 Jul - 9 Jul
Cozy & Chic Cabin by the Lake, with access to private Beach!
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
9.8 out of 10, Exceptional, 21 reviews
"The property was as described and the living space was perfect for our visit. The deck and views are amazing. If staying at this property, you just need to be aware that it is very difficult getting luggage and groceries into the property. You have to go down a long flight of stairs, walk down a very steep driveway and then go down another flight of stairs. Once you are in, bedroom access requires that you go up or down additional stairs."
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
Lakeview Estate - Chef's Kitchen - NYC Getaway
10.0 out of 10, Exceptional, 19 reviews
"This place was amazing! The only reason why I’m giving it 4 stars is because check in is way too late. It would have been nice if it was earlier 4pm? Every other place that we have ever stayed whether it’s in US or abroad has always been 3 the latest."
The price is €971
per night
2 Jul - 3 Jul
Lakeview Estate - Chef's Kitchen - NYC Getaway
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC!
10.0 out of 10, Exceptional, 172 reviews
"This property is exactly what we were looking for… quiet, cozy, and clean with a full complement of water toys and easy access to the dock. Love it!"
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC!
Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake
10.0 out of 10, Exceptional, 99 reviews
"This house and property are well appointed and very nice in all respects! The family room with the large, glazed overhead door is a great space (we had the door open during the day, and then closed it in the evening for dinner.) The deck overlooking Candlewood Lake has several nice seating areas, hot tub and fire pit. Down at the lake, there is another nice seating area (along with the dock and boat shed.) Everything was labeled with clear instructions for use (fireplace dampers, hot tub,...
Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake
Beautiful Escape! 'Parole LakeHouse' located 90min from NYC & 30min from Beacon
10.0 out of 10, Exceptional, 1 review
"We went to the area to celebrate my husbands 30th birthday with some friends and absolutely loved the home. It was brand new and decorated immaculately. It comfortably fit our group and we thoroughly enjoyed our time there. The hosts were super accommodating and quick to respond. Would absolutely reccomend and go again!"
The price is €878
per night
30 Jun - 1 Jul
Beautiful Escape! 'Parole LakeHouse' located 90min from NYC & 30min from Beacon
Tidal Time Estate with Heated Pool, Game Room, and Golf Cart
9.4 out of 10, Exceptional, 8 reviews
"The check in process was very easy. Four hours after arrival, our refrigerator went out. We couldn't get in contact with maintenance until the next day. So we lost some of our food that was in the refrigerator. The house is beautiful and was very clean. The golf cart was so much fun and very convenient. It was a blast and I will definitely recommend staying here again."
Tidal Time Estate with Heated Pool, Game Room, and Golf Cart
Stunning Pawling Retreat w/ Ponds & Waterfall
10.0 out of 10, Exceptional, 2 reviews
"This property is even better than the pictures. The fall colors and temperature was a perfect complement to an amazing house"
Stunning Pawling Retreat w/ Ponds & Waterfall
Beautiful Renovated 2BR 2B Direct Waterfront Candlewood Lake Home~Sunset Views!
10.0 out of 10, Exceptional, 17 reviews
"Gorgeous, as advertised!"
Beautiful Renovated 2BR 2B Direct Waterfront Candlewood Lake Home~Sunset Views!
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!
10.0 out of 10, Exceptional, 72 reviews
"We stayed here for my friend's low-key bachelorette party. Peter was a great and responsive host, and the property was wonderful. We sang lots of karaoke and enjoyed cocktails on the large deck with beautiful views. Access to the community beach club was a big plus. Everyone had a great time and was really impressed with this property. Highly recommend it!"
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!
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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.

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

Comfort Inn & Suites Danbury-Bethel
2.5 star property
8.8 out of 10, Excellent, 154 reviews
"Special thanks to the Manager Steven, he was great"
The price is €124
per night
3 Jul - 4 Jul
Comfort Inn & Suites Danbury-Bethel
Wyndham Southbury
3.0 star property
8.0 out of 10, Very good, 1,002 reviews
"This hotel offered a spacious room, comfy bed and convenience to town. No bells and whistles but it fit the bill for a night stay. No complaints. "
The price is €118
per night
8 Jul - 9 Jul
Wyndham Southbury
Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection
3.5 star property
8.2 out of 10, Very good, 1,004 reviews
"Perfect stay"
The price is €146
per night
28 Jul - 29 Jul
Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection
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.

Everything you need to know about South Kent holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the South Kent holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

South Kent holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A South Kent holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of South Kent holiday rentals we have selected for you start as low as €205 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on South Kent rentals

At Expedia, we put the best South Kent holiday 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 holiday.

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 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.

What are some of the best holiday rentals that South Kent has to offer?

Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond: This holiday home rental outside of South Kent is located on the beach, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

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.

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