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

Search Vacation Homes in Kent

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Kent vacation homes

A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

1. 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, (2 reviews)
"Clean and close to activitys"
United States
randall
The price is ￥9,243
￥21,058 total
includes taxes & fees
Oct 13 - Oct 14
Cozy private room in a shared home with a Full-size bed and private bathroom.
A picnic setup with a checkered blanket, a basket, and two wine glasses on a grassy area with a lake and trees in the background.

2. Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
New Fairfield
8.6 out of 10, Excellent, (36 reviews)
"Very serene location, the host was very responsive and helpful."
United States
Stephen L.
The price is ￥16,627
￥51,570 total
includes taxes & fees
Oct 18 - Oct 19
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
A spacious living room with a large wooden dining table, a comfortable sofa, and a bookshelf filled with books and decorative items.

3. 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, (6 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 ￥63,160
￥132,720 total
includes taxes & fees
Oct 18 - Oct 19
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
A room with a built-in bench along a wall with large windows, a door, and a tiled floor.

4. The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining

The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
New Milford
The price is ￥74,608
￥127,407 total
includes taxes & fees
Nov 3 - Nov 4
The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
A kitchen with wooden cabinets, a black countertop, a sink, and a window with a view of trees.

5. "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 ￥31,548
￥90,707 total
includes taxes & fees
Oct 21 - Oct 22
"Country outside the city " 3 bedrooms 2 full bathrooms
A hot tub in a backyard with a house, trees, and a clear sky.

6. Las Flores Villa

Las Flores Villa
5.0 star property
New Preston
10.0 out of 10, Exceptional, (1 review)
The price is ￥426,330
￥553,438 total
includes taxes & fees
Oct 11 - Oct 12
Las Flores Villa
A wooden cabin interior with a bench, a rug, and a hanging plant.

7. 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, (2 reviews)
"Great place and wonderful host."
United States
Thomas C.
The price is ￥18,159
￥33,278 total
includes taxes & fees
Nov 1 - Nov 2
Peaceful and cozy 1 bed 1 bath in quaint Winchester
A two-story house with a porch, a front door with a wreath, and a small garden area.

8. Bear Retreat - 2-bedroom house in Waterbury

Bear Retreat - 2-bedroom house in Waterbury
Waterbury
10.0 out of 10, Exceptional, (9 reviews)
"Perfect, spacious area. Super clean. Communication was great. Would definitely book here again."
United States
Radha
The price is ￥18,332
￥54,163 total
includes taxes & fees
Oct 18 - Oct 19
Bear Retreat - 2-bedroom house in Waterbury
A multi-story house with a dock and boats, surrounded by dense forest.

9. North Cliff House - Private Dock & Sauna

North Cliff House - Private Dock & Sauna
Danbury
10.0 out of 10, Exceptional, (9 reviews)
"Enjoyed the property. Beautiful house. Great location. Reserve, stay and enjoy!"
United States
Ron P.
The price is ￥48,070
￥188,775 total
includes taxes & fees
Oct 14 - Oct 15
North Cliff House - Private Dock & Sauna
A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

10. 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 ￥26,685
￥44,120 total
includes taxes & fees
Oct 12 - Oct 13
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
A living room with a television, a cabinet, a glass coffee table, and a framed picture on the wall.

11. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Stanfordville
The price is ￥71,055
￥108,247 total
includes taxes & fees
Oct 13 - Oct 14
Chic Lakeside Oasis|Near Rhinebeck & Millbrook
A spacious living room with a fireplace, a dining area with a view of a lake, and a cozy seating arrangement.

12. 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
10.0 out of 10, Exceptional, (21 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is ￥29,230
￥58,904 total
includes taxes & fees
Nov 3 - Nov 4
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
A spacious living room with large windows, a fireplace, and a view of the outdoors.

13. Watertown Home w/ Yard: 1 Mi to Echo Lake Park!

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
Watertown
9.0 out of 10, Wonderful, (6 reviews)
"In town to visit our new grandchild. It was just my husband and me. It had more then enough room and was very comfortable."
United States
Elizabeth H.
The price is ￥34,580
￥84,792 total
includes taxes & fees
Oct 20 - Oct 21
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
A large wooden dining table surrounded by chairs, with a stone fireplace and large windows in the background.

14. The George is an elegant restored home in the Hudson Valley

The George is an elegant restored home in the Hudson Valley
Stanfordville
9.8 out of 10, Exceptional, (11 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 ￥113,688
￥176,482 total
includes taxes & fees
Oct 11 - Oct 12
The George is an elegant restored home in the Hudson Valley
A modern living room with a grey sofa, a wooden coffee table, and a staircase leading to an upper floor.

15. Chic Barn Style * Fireplace * Near Stissing House

Chic Barn Style * Fireplace * Near Stissing House
Pine Plains
10.0 out of 10, Exceptional, (3 reviews)
"We loved the property and everything was so welcoming! Having a pool there would be the best addition for this place!"
United States
Estefany G.
The price is ￥35,803
￥116,336 total
includes taxes & fees
Oct 28 - Oct 29
Chic Barn Style * Fireplace * Near Stissing House
A modern kitchen with white cabinets, a large island, and a skylight.

16. A Country Lodge Straight Out of the Pages of a Great Novel

A Country Lodge Straight Out of the Pages of a Great Novel
Pine Plains
10.0 out of 10, Exceptional, (15 reviews)
"We loved the house and it really added to our upstate experience!!"
United States
stephen r.
The price is ￥125,610
￥213,414 total
includes taxes & fees
Oct 16 - Oct 17
A Country Lodge Straight Out of the Pages of a Great Novel
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Kent Hotel Reviews

Heidi's Inn

Heidi's Inn

8/10 Good
"Very clean. Very basic. Fair price. Beautiful breakfast room. Very nice continental breakfast."
Christine 2-night trip
Posted 6 hours ago
Heidi's Inn

Find out more about Kent

Kent Vacation Homes information

Number of reviews
134
Accommodation
244 Vacation Homes
Lowest Price
￥21,058
Highest Price
￥553,438