A waterfall cascading over rocks in a forest with autumn-colored trees.

Kent Holiday Rentals

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sept - 20 Sept
In four months
16 Oct - 18 Oct

Our top choices for Kent holiday rentals

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, (16 reviews)
"We had a great stay, very cute town and close to our destination "
United States
Danielle F.
The price is HK$1,106
HK$1,429 total
includes taxes & fees
1 Jul - 2 Jul
Mid Century Modern Studio w/ Full Kitchen - Newly Built
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 HK$628
HK$1,048 total
includes taxes & fees
29 Jun - 30 Jun
Rare, peaceful glamping, hot shower, mini golf near appalachian trail
Exterior

Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (33 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 HK$741
HK$1,009 total
includes taxes & fees
29 Jun - 30 Jun
Cozy One Bedroom Apartment Centrally Located in Southbury
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 HK$863
HK$1,606 total
includes taxes & fees
9 Jul - 10 Jul
Hoppy Hill Farm House
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 HK$1,103
HK$3,278 total
includes taxes & fees
29 Jun - 30 Jun
Art House 3 Beds Close to Warner Theater
Exterior

Peaceful and cozy 1 bed 1 bath in quaint Winchester

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
The price is HK$847
HK$1,590 total
includes taxes & fees
9 Jul - 10 Jul
Peaceful and cozy 1 bed 1 bath in quaint Winchester
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, (14 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is HK$1,764
HK$3,306 total
includes taxes & fees
2 Jul - 3 Jul
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
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 HK$863
HK$1,149 total
includes taxes & fees
2 Jul - 3 Jul
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
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 HK$659
HK$2,113 total
includes taxes & fees
29 Jun - 30 Jun
Cozy Attic 10 min to Llitchfield
Exterior

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.2 out of 10, Wonderful, (12 reviews)
"The chapel was just as it was pictured. It has been beautifully restored. It was a very unique experience."
United States
Stella
The price is HK$823
HK$1,552 total
includes taxes & fees
29 Jun - 30 Jun
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Terrace/patio

Enjoy a restful stay with fast internet, smart TV and the company of your pet.

Enjoy a restful stay with fast internet, smart TV and the company of your pet.
winsted
9.2 out of 10, Wonderful, (47 reviews)
"Fantastic hosts and great facilities would highly recommend"
United States
Steve
The price is HK$1,235
HK$1,962 total
includes taxes & fees
2 Jul - 3 Jul
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
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 HK$1,013
HK$3,169 total
includes taxes & fees
29 Jun - 30 Jun
Cozy Modern Farmhouse Private Apt - 3 Beds
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 HK$1,764
HK$3,162 total
includes taxes & fees
5 Jul - 6 Jul
Enchanting Lake front chalet with backyard and fire pit. Dog friendly.
Interior

The Tipsy Gypsy - Studio Apartment

The Tipsy Gypsy - Studio Apartment
Brewster
The price is HK$1,176
HK$2,159 total
includes taxes & fees
29 Jun - 30 Jun
The Tipsy Gypsy - Studio Apartment
Property grounds

Hudson Valley Farm Getaway- West/Llama Lover Lane

Hudson Valley Farm Getaway- West/Llama Lover Lane
Hyde Park
9.8 out of 10, Exceptional, (8 reviews)
"Perfect little apartment on an amazing farm property...thanks for having us and look forward to returning! "
United States
ADRIENNE
The price is HK$1,351
HK$1,767 total
includes taxes & fees
29 Jun - 30 Jun
Hudson Valley Farm Getaway- West/Llama Lover Lane
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 HK$1,143
HK$1,811 total
includes taxes & fees
1 Jul - 2 Jul
The Perch in the Purchase -- Cozy, unique, and private
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 HK$1,874
HK$2,516 total
includes taxes & fees
30 Jun - 1 Jul
Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
TV, fireplace, books

NEW: Chic Modern Barn Style Home in Fun Area

NEW: Chic Modern Barn Style Home in Fun Area
Pine Plains
The price is HK$1,691
HK$5,371 total
includes taxes & fees
30 Jun - 1 Jul
NEW: Chic Modern Barn Style Home in Fun Area
Fridge, microwave, oven, stovetop

"Country outside the city " 3 bedrooms 2 full bathrooms

"Country outside the city " 3 bedrooms 2 full bathrooms
Holmes
9.6 out of 10, Exceptional, (4 reviews)
"Great house! We had a fantastic weekend!! Thank you so much "
United States
pamela w.
The price is HK$1,877
HK$4,927 total
includes taxes & fees
6 Jul - 7 Jul
"Country outside the city " 3 bedrooms 2 full bathrooms
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 HK$2,287
HK$2,953 total
includes taxes & fees
29 Jun - 30 Jun
The Jefferson Guest House, Spacious, Special Views
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 Kent Hotel Reviews

Heidi's Inn

Heidi's Inn

10/10 Excellent
"Heidi’s was a great find. This place was very nice, the room s were nice, spacious and immaculately clean. The staff was very welcoming, helpful and friendly. The grounds were so nice and rustic looking with the buildings spread out on the property. The main building / lobby area was very cozy with an atrium and a fireplace. If in the area, I would highly recommend staying at Heidi’s , you won’t be disappointed!"
Roy 1-night trip
Posted 2 hours ago
Heidi's Inn

Find out more about Kent

Search for holiday rentals in Kent on Expedia! You can easily find your home rentals, villas, holiday apartments in Kent using one of the methods below:

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  • Enter your travel dates to view the best deals on holiday rentals in Kent while they last

Look no further and take a look at our great range of rental properties in Kent!

Frequently asked questions

Are there holiday rentals in Kent?

Yes, there are holiday rentals close to the most popular sights in Kent, or you can select a more secluded option if you're looking for a relaxing stay. Kent is known for its waterfalls and art. Make sure you have time to check out the museums and beaches during your trip.

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

Artistic barn: wood burning hottub, sauna and pizza oven : This highly rated holiday home rental in Kent is located on a lake, and has a fireplace, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

How many holiday rentals are there in Kent?

Expedia has 8 holiday rentals for your stay in Kent.

What’s there to see and do in Kent?

Cultural attractions include Morrison Gallery and Sloane-Stanley Museum, whereas Kent Falls State Park and Lake Waramaug State Park are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Macedonia Brook State Park and Bull's Bridge.

What’s a holiday rental in Kent like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Kent. Holiday rentals feature amenities like laundry facilities and kitchens so you'll have everything you need. If you're concerned about a clean environment, holiday rentals can provide a sense of security away from public hotel lifts and bustling concierge 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 popular choice for families.