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Kent Holiday Rentals

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Check prices for these dates

In two weeks
23 Jan - 25 Jan
In two months
6 Mar - 8 Mar
In three months
3 Apr - 5 Apr
In four months
1 May - 3 May

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

Mid Century Modern Studio w/ Full Kitchen - Newly Built
Kent
9.8 out of 10, Exceptional, (10 reviews)
"We had a great stay, very cute town and close to our destination "
United States
Danielle F.
The price is HK$1,519
HK$1,942 total
includes taxes & fees
20 Jan - 21 Jan
Mid Century Modern Studio w/ Full Kitchen - Newly Built
1 bedroom, free WiFi, bed sheets
Creekside Retreat Tent

Creekside Retreat Tent

Creekside Retreat Tent
New Milford
10.0 out of 10, Exceptional, (4 reviews)
"Absolutely beautiful location and wonderful hosts very romantic spot lots of hiking trails near and on premises me and my husband loved the fact we slept by the water and can hear the water running all night very peaceful and beautiful site ."
United States
yarelis t.
The price is HK$1,169
HK$1,500 total
includes taxes & fees
14 Jan - 15 Jan
Creekside Retreat Tent
Exterior detail
Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake

Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake

Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake
New Fairfield
10.0 out of 10, Exceptional, (34 reviews)
"Stunning property!!"
United States
Samantha
The price is HK$2,143
HK$3,680 total
includes taxes & fees
12 Jan - 13 Jan
Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake
Exterior
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village

Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village

Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
Millbrook
10.0 out of 10, Exceptional, (2 reviews)
"Tanya goes above and beyond for her guests. Thanks so much for the stay!"
United States
Lindsay S.
The price is HK$2,493
HK$3,861 total
includes taxes & fees
11 Jan - 12 Jan
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
Exterior
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View

Cozy 3 Flr Private 1 Bdrm Apt Tree Line View

Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
Torrington
9.6 out of 10, Exceptional, (4 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$761
HK$2,743 total
includes taxes & fees
13 Jan - 14 Jan
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
Property grounds
Hoppy Hill Farm House

Hoppy Hill Farm House

Hoppy Hill Farm House
Dover Plains
9.6 out of 10, Exceptional, (4 reviews)
"The cabin was perfect. Had everything we needed and clear directions. "
United States
Jocelyn L.
The price is HK$779
HK$1,516 total
includes taxes & fees
11 Jan - 12 Jan
Hoppy Hill Farm House
Exterior
Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (21 reviews)
"Perfect sized apartment for a short stay - very convenient to my destination"
United States
S
The price is HK$717
HK$980 total
includes taxes & fees
15 Jan - 16 Jan
Cozy One Bedroom Apartment Centrally Located in Southbury
Fridge, microwave, oven, stovetop
The Jefferson Guest House, Spacious, Special Views

The Jefferson Guest House, Spacious, Special Views

The Jefferson Guest House, Spacious, Special Views
Litchfield
10.0 out of 10, Exceptional, (8 reviews)
"The place was absolutely spotless and magnificent in every way. Highly recommended."
United States
Robert A.
The price is HK$2,272
HK$2,880 total
includes taxes & fees
21 Jan - 22 Jan
The Jefferson Guest House, Spacious, Special Views
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.

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Carmel Hamlet
9.8 out of 10, Exceptional, (12 reviews)
"We loved the cleanliness, the location near the lake and the neighborhood restaurant, The Great Blue Heron."
United States
Hannah P.
The price is HK$1,298
HK$2,758 total
includes taxes & fees
11 Jan - 12 Jan
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Property grounds
Hudson Valley Farm Getaway- West/Llama Lover Lane

Hudson Valley Farm Getaway- West/Llama Lover Lane

Hudson Valley Farm Getaway- West/Llama Lover Lane
2.0 star property
Hyde Park
9.8 out of 10, Exceptional, (6 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$1,243
HK$1,622 total
includes taxes & fees
14 Jan - 15 Jan
Hudson Valley Farm Getaway- West/Llama Lover Lane
1 bedroom, iron/ironing board, free WiFi, bed sheets
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.

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$877
HK$1,523 total
includes taxes & fees
16 Jan - 17 Jan
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Smart TV, fireplace, video games, DVD player
Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.

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

Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.
Carmel Hamlet
10.0 out of 10, Exceptional, (19 reviews)
"Lovely house with all the amenities. We had a wonderful time."
United States
Diana P.
The price is HK$4,202
HK$7,620 total
includes taxes & fees
12 Jan - 13 Jan
Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.
Exterior
Cozy Modern Farmhouse Private Apt - 3 Beds

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$1,096
HK$3,235 total
includes taxes & fees
11 Jan - 12 Jan
Cozy Modern Farmhouse Private Apt - 3 Beds
Dining
The George is an elegant restored home in the Hudson Valley

The George is an elegant restored home in the Hudson Valley

The George is an elegant restored home in the Hudson Valley
Stanfordville
9.4 out of 10, Exceptional, (6 reviews)
"Clean, comfortable, private, and plenty of room. Hosts went above and beyond to make our stay easy and memorable."
United States
Polly J.
The price is HK$5,610
HK$8,612 total
includes taxes & fees
11 Jan - 12 Jan
The George is an elegant restored home in the Hudson Valley
Dining
Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake

Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake

Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake
New Fairfield
10.0 out of 10, Exceptional, (17 reviews)
"Great location and condition. Roome enough for everyone."
United States
Christopher H.
The price is HK$1,372
HK$3,689 total
includes taxes & fees
14 Jan - 15 Jan
Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake
Outdoor dining
Entire guesthouse in Southbury, Connecticut 3 guests1 bedroom2 beds1 bath.

Entire guesthouse in Southbury, Connecticut 3 guests1 bedroom2 beds1 bath.

Entire guesthouse in Southbury, Connecticut 3 guests1 bedroom2 beds1 bath.
2.0 star property
Southbury
10.0 out of 10, Exceptional, (1 review)
"Beautiful place. Very clean & welcoming "
United States
Chris
The price is HK$886
HK$1,496 total
includes taxes & fees
20 Jan - 21 Jan
Entire guesthouse in Southbury, Connecticut 3 guests1 bedroom2 beds1 bath.
Exterior
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.0 out of 10, Wonderful, (10 reviews)
"We had a great last minute visit to Hopewell Junction and enjoyed a lovely stay at the chapel! It’s a very unique experience and quiet and peaceful. We enjoyed the bbq and an evening fire with smores! "
United States
Esther P.
The price is HK$1,185
HK$1,993 total
includes taxes & fees
14 Jan - 15 Jan
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
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.

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$693
HK$953 total
includes taxes & fees
18 Jan - 19 Jan
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Fridge, microwave, oven, stovetop
"Country outside the city " 3 bedrooms 2 full bathrooms

"Country outside the city " 3 bedrooms 2 full bathrooms

"Country outside the city " 3 bedrooms 2 full bathrooms
2.0 star property
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$1,515
HK$4,420 total
includes taxes & fees
12 Jan - 13 Jan
"Country outside the city " 3 bedrooms 2 full bathrooms
2 bedrooms, desk, free WiFi, bed sheets
Charming apartment 7 minute walk to downtown

Charming apartment 7 minute walk to downtown

Charming apartment 7 minute walk to downtown
Torrington
10.0 out of 10, Exceptional, (16 reviews)
"Everything about our stay was great - Corin and Jen were wonderful hosts. The place is spotless, cozy, comfy. Love that they were right next to the Green Way Trail along the river. Will absolutely stay there again! "
United States
Kate B.
The price is HK$1,255
HK$2,144 total
includes taxes & fees
4 Feb - 5 Feb
Charming apartment 7 minute walk to downtown
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

The Litchfield Inn

The Litchfield Inn

10/10 Excellent
"Very good. Nice selection "
Debbie 2-night trip
Posted 2 days ago
The Litchfield 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:

  • View our selection of featured holiday rentals in Kent
  • Use the map to find apartments and other holiday homes in the Kent neighbourhood you prefer
  • 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!

Explore a world of travel with Expedia

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?

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed: This holiday home rental outside of Kent offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable 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. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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 Bull's Bridge and Lake Waramaug.

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.