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

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Check prices for these dates

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

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 AED 215
AED 490 total
includes taxes & fees
14 Oct - 15 Oct
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 AED 430
AED 1,253 total
includes taxes & fees
18 Oct - 19 Oct
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 AED 1,469
AED 3,087 total
includes taxes & fees
13 Oct - 14 Oct
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 AED 1,735
AED 2,956 total
includes taxes & fees
15 Oct - 16 Oct
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 AED 734
AED 2,110 total
includes taxes & fees
21 Oct - 22 Oct
"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 AED 9,917
AED 12,874 total
includes taxes & fees
9 Oct - 10 Oct
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 AED 422
AED 774 total
includes taxes & fees
1 Nov - 2 Nov
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 AED 426
AED 1,249 total
includes taxes & fees
12 Oct - 13 Oct
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 AED 1,178
AED 4,466 total
includes taxes & fees
14 Oct - 15 Oct
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 AED 621
AED 1,026 total
includes taxes & fees
13 Oct - 14 Oct
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 AED 1,653
AED 2,530 total
includes taxes & fees
21 Oct - 22 Oct
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 AED 850
AED 1,578 total
includes taxes & fees
12 Oct - 13 Oct
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 AED 804
AED 1,972 total
includes taxes & fees
11 Oct - 12 Oct
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 AED 2,645
AED 4,105 total
includes taxes & fees
11 Oct - 12 Oct
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 AED 824
AED 2,694 total
includes taxes & fees
28 Oct - 29 Oct
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 AED 2,920
AED 4,961 total
includes taxes & fees
16 Oct - 17 Oct
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.
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Top Kent Hotel Reviews

Heritage Hotel, Golf & Conference Center

Heritage Hotel, Golf & Conference Center

8/10 Good
"Beds were great. Bathroom clean, but shower was slippery. TV remote was almost useless. Support staff were helpful. Location was excellent. Parking was great for early arrivals, but an extended wait for late arrivals. I did not eat breakfast on the premises. Small shopping plaza a mile away with TJMaxx. Other restaurants nearby. One mile from I-84."
Robert 3-night trip
Posted 19 hours ago
Heritage Hotel, Golf & Conference Center