Kent Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Kent vacation rentals

A living room with a fireplace, two armchairs, a sofa, and a TV.

1. 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, (26 reviews)
"Very nice, great location in town"
United States
Lisa F.
The price is CA $212
CA $263 total
includes taxes & fees
Nov 17 - Nov 18
Mid Century Modern Studio w/ Full Kitchen - Newly Built
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

2. Cozy private room in a shared home with a Full-size bed and private bathroom.

Cozy private room in a shared home with a Full-size bed and private bathroom.
New Milford
10.0 out of 10, Exceptional, (3 reviews)
"I really enjoyed my four night stay here."
United States
Jim B.
The price is CA $90
CA $186 total
includes taxes & fees
Nov 17 - Nov 18
Cozy private room in a shared home with a Full-size bed and private bathroom.
A rustic cabin surrounded by a forest with a stream in the foreground.

3. Creek Side Cabin w/ Wood Fired Hot Tub & Fire Pit

Creek Side Cabin w/ Wood Fired Hot Tub & Fire Pit
New Milford
10.0 out of 10, Exceptional, (3 reviews)
"Great little house, our favorite part was the gorgeous creek. Absolutely would recommend to pet lovers and those looking for peaceful nature :)"
United States
Kristine W.
The price is CA $413
CA $739 total
includes taxes & fees
Dec 1 - Dec 2
Creek Side Cabin w/ Wood Fired Hot Tub & Fire Pit
A residential property with a well-maintained lawn, a small house with a front porch, and a garage.

4. Sharon Retreat w/ Private Yard

Sharon Retreat w/ Private Yard
Sharon
9.2 out of 10, Wonderful, (37 reviews)
"Cagney’s home was so comfy! We loved the spacious family room. The beds were comfortable and the fully stocked kitchen made cooking much easier. Absolutely would love to stay at your cottage again!"
United States
Heidi F.
The price is CA $308
CA $667 total
includes taxes & fees
Nov 16 - Nov 17
Sharon Retreat w/ Private Yard
A wooden barrel structure with a door, two wooden lounge chairs, and a small table.

5. Spa Cabin with Sauna, Hot Tub and Cold Plunge

Spa Cabin with Sauna, Hot Tub and Cold Plunge
Cornwall
10.0 out of 10, Exceptional, (7 reviews)
"This cabin is so cute we had a relaxing time , will return"
United States
Candice S.
The price is CA $492
CA $873 total
includes taxes & fees
Nov 29 - Nov 30
Spa Cabin with Sauna, Hot Tub and Cold Plunge
A white house with a wooden staircase leading to a porch.

6. Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (39 reviews)
"Charles was super responsive and the bed was amazingly comfortable. Also the shower head great water pressure :-)"
United States
Lisbeth
The price is CA $148
CA $187 total
includes taxes & fees
Dec 1 - Dec 2
Cozy One Bedroom Apartment Centrally Located in Southbury
A compact room with a kitchenette, a bed, a wall decorated with photos and a mirror, and a 'No Fishing From Bridge' sign.

7. Welcome to Sweet Abby Rose!

Welcome to Sweet Abby Rose!
Brewster
7.4 out of 10, Good, (3 reviews)
"We had a wonderful experience! The RV was very nice and cozy. Everything was clean and well maintained. The property was beautiful. The host was very helpful and accommodating. Definitely plan on coming back!"
United States
Fernanda
The price is CA $150
CA $258 total
includes taxes & fees
Nov 16 - Nov 17
Welcome to Sweet Abby Rose!
A two-story house with a front porch, a small balcony, and a white picket fence.

8. Cozy Attic 10 min to Llitchfield

Cozy Attic 10 min to Llitchfield
Torrington
9.6 out of 10, Exceptional, (7 reviews)
"The check-in process was easy and all instructions were clear. Jonathan, the owner, was very responsive and easy to get a hold of if I had any questions. The place was cute, clean, and perfect for what I needed (a place to stay during my medical school rotation). As the review says, it is not ideal for taller guests as the roof slopes down in certain areas, but I found the place cozy."
United States
Nicole N.
The price is CA $150
CA $509 total
includes taxes & fees
Nov 16 - Nov 17
Cozy Attic 10 min to Llitchfield
A hot tub in a backyard with a house, trees, and a clear sky.

9. Las Flores Villa

Las Flores Villa
5.0 star property
New Preston
10.0 out of 10, Exceptional, (1 review)
The price is CA $1,278
CA $2,040 total
includes taxes & fees
Nov 16 - Nov 17
Las Flores Villa
A spacious living room with a large window overlooking a lake, wooden ceiling, and comfortable seating.

10. Escape to Bantam Lake- With Fireplace and Hot tub!

Escape to Bantam Lake- With Fireplace and Hot tub!
Morris
10.0 out of 10, Exceptional, (6 reviews)
"This house is a dream. First, the views are incredible. Second, it’s beautifully decorated and very cozy. Lastly, the property location is perfect. I can’t wait to stay again!"
United States
Shannon M.
The price is CA $321
CA $661 total
includes taxes & fees
Nov 18 - Nov 19
Escape to Bantam Lake- With Fireplace and Hot tub!
A wooden cabin interior with a bench, a rug, and a hanging plant.

11. Peaceful and cozy 1 bed 1 bath in quaint Winchester

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
10.0 out of 10, Exceptional, (6 reviews)
The price is CA $141
CA $263 total
includes taxes & fees
Nov 22 - Nov 23
Peaceful and cozy 1 bed 1 bath in quaint Winchester
A glass-top table with a woven placemat, a vase with white flowers, and a view of a balcony through a door with curtains.

12. The Overlook near South Farms in Litchfield County is Hospitality, integrated.

The Overlook near South Farms in Litchfield County is Hospitality, integrated.
Morris
9.8 out of 10, Exceptional, (21 reviews)
"Very clean & cozy with everything we needed!"
United States
Joe K.
The price is CA $307
CA $380 total
includes taxes & fees
Nov 16 - Nov 17
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
A two-story house with a front porch, a small balcony, and a white picket fence.

13. 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 CA $201
CA $584 total
includes taxes & fees
Nov 16 - Nov 17
Cozy Modern Farmhouse Private Apt - 3 Beds
A hot tub under a pergola with string lights, surrounded by a patio area with chairs and an umbrella.

14. 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
9.4 out of 10, Exceptional, (55 reviews)
"It was a nice stay…worked well for the event we attended in town. The host was very nice to work with"
United States
Roberta S.
The price is CA $159
CA $303 total
includes taxes & fees
Nov 29 - Nov 30
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
A cozy cabin interior with a wooden ceiling, a sofa, a coffee table, and a sign reading "Our Happy Place".

15. Little Lake Cabin with Hot Tub and Fire Pit

Little Lake Cabin with Hot Tub and Fire Pit
New Fairfield
10.0 out of 10, Exceptional, (7 reviews)
"Great location and lots to do despite it raining for half our stay! My dog enjoyed the yard and walks around the neighborhood. My son loved kayaking and having his first ever s’more. Honestly I wished we had booked a longer trip! "
United States
Lyndsey F.
The price is CA $342
CA $648 total
includes taxes & fees
Nov 17 - Nov 18
Little Lake Cabin with Hot Tub and Fire Pit
A modern hotel room with a bed, bedside table, lamp, desk, and window.

16. 1 Queen Bed | Non-Smoking

1 Queen Bed | Non-Smoking
Bethel
10.0 out of 10, Exceptional, (4 reviews)
"Quick check-in and a quiet room made sleeping easy here. Everything felt straightforward without hassle."
United States
Anonymous traveller
The price is CA $153
CA $176 total
includes taxes & fees
Nov 16 - Nov 17
1 Queen Bed | Non-Smoking
A modern kitchen with a wooden dining table, blue chairs, and a colorful bowl centerpiece.

17. 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 CA $216
CA $615 total
includes taxes & fees
Nov 16 - Nov 17
Art House 3 Beds Close to Warner Theater
A two-story house with a porch, a front door with a wreath, and a small garden area.

18. Bear Retreat - 2-bedroom house in Waterbury

Bear Retreat - 2-bedroom house in Waterbury
Waterbury
10.0 out of 10, Exceptional, (13 reviews)
"Very clean, all you need away from home, super !!!"
United States
Igor L.
The price is CA $166
CA $470 total
includes taxes & fees
Nov 22 - Nov 23
Bear Retreat - 2-bedroom house in Waterbury
A spacious living room with a large wooden dining table, a comfortable sofa, and a bookshelf filled with books and decorative items.

19. Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway

Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
Millbrook
10.0 out of 10, Exceptional, (8 reviews)
"This is a charming, historic, well-maintained home on a beautifully landscaped lot. The updates in the home balance a respect for tradition while also providing modernization. The village of Millbrook is a quintessential twee New England village. The house felt very comfortable and homey and the caretaker was attentive and accommodating. We enjoyed our stay!"
United States
Beth E.
The price is CA $571
CA $1,140 total
includes taxes & fees
Nov 20 - Nov 21
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

20. Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.4 out of 10, Exceptional, (13 reviews)
"Lovely space and situation, unique. Close to the AT, as well."
United States
Peter W.
The price is CA $241
CA $384 total
includes taxes & fees
Nov 16 - Nov 17
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
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

A spacious living room with hardwood floors, a large dining area, and a cozy seating area with a red sofa and matching cushions.
Homestead Inn

Homestead Inn

Homestead Inn
New Milford

10/10 Excellent

Staying in the Annex is a pleasure, particularly with easy access to the original building, where a comfortable sitting room awaits guests. This was not my first visit. I’ll be back.
Canada
DOUGLAS
Reviewed May 6, 2023
Homestead Inn

Find out more about Kent

Everything you need to know about 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 Kent vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, 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 Kent vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Kent vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in 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 Kent vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Kent vacation rentals we have selected for you start as low as CA $89 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Kent rentals

At Expedia, we put the best 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 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 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 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

Are there vacation rentals in Kent?

Yes, we give you a choice of vacation rentals near well known attractions in Kent, or you can select a more secluded option if you're looking for relaxation. 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 vacation rentals that Kent has to offer?

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed: You might want to consider this vacation home rental near Kent, which offers a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals are there in Kent?

Expedia has 8 vacation 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 vacation rental in Kent like?

A vacation rental is a private property you can book for a few weeks or just a few days in Kent. Vacation rentals feature amenities like laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a clean environment, a vacation rental can offer a sense of privacy away from public hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for small groups.