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Our top choices for Kent vacation homes
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, (3 reviews)
"I really enjoyed my four night stay here."
Jim B.
The price is CA $90
CA $186 total
includes taxes & fees
Nov 17 - Nov 18
2. Las Flores Villa
Las Flores VillaNew 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
3. Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
Steps to the Delightful Village of Millbrook ☆ Fun Family GetawayMillbrook
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!"
Beth E.
The price is CA $571
CA $1,140 total
includes taxes & fees
Nov 19 - Nov 20
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 & DiningNew Milford
10.0 out of 10, Exceptional, (2 reviews)
"The house was perfect for our girls weekend. It was even nicer in person."
Lauren B.
The price is CA $685
CA $1,144 total
includes taxes & fees
Nov 16 - Nov 17
5. Peaceful and cozy 1 bed 1 bath in quaint Winchester
Peaceful and cozy 1 bed 1 bath in quaint WinchesterWinchester
10.0 out of 10, Exceptional, (6 reviews)
The price is CA $141
CA $263 total
includes taxes & fees
Nov 22 - Nov 23
6. "Country outside the city " 3 bedrooms 2 full bathrooms
"Country outside the city " 3 bedrooms 2 full bathroomsHolmes
9.6 out of 10, Exceptional, (5 reviews)
"Great house! We had a fantastic weekend!! Thank you so much "
pamela w.
The price is CA $294
CA $799 total
includes taxes & fees
Nov 17 - Nov 18
7. Bear Retreat - 2-bedroom house in Waterbury
Bear Retreat - 2-bedroom house in WaterburyWaterbury
10.0 out of 10, Exceptional, (13 reviews)
"Very clean, all you need away from home, super !!!"
Igor L.
The price is CA $166
CA $470 total
includes taxes & fees
Nov 22 - Nov 23
8. Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Chic Lakeside Oasis|Near Rhinebeck & MillbrookStanfordville
The price is CA $642
CA $938 total
includes taxes & fees
Nov 16 - Nov 17
9. Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock ParkHopewell Junction
9.4 out of 10, Exceptional, (13 reviews)
"Lovely space and situation, unique. Close to the AT, as well."
Peter W.
The price is CA $241
CA $384 total
includes taxes & fees
Nov 16 - Nov 17
10. 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!"
Robert T.
The price is CA $268
CA $518 total
includes taxes & fees
Nov 18 - Nov 19
11. The George is an elegant restored home in the Hudson Valley
The George is an elegant restored home in the Hudson ValleyStanfordville
9.8 out of 10, Exceptional, (15 reviews)
"Clean, comfortable, private, and plenty of room. Hosts went above and beyond to make our stay easy and memorable."
Polly J.
The price is CA $1,231
CA $1,692 total
includes taxes & fees
Nov 16 - Nov 17
12. Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
Spacious 4-bedroom estate in adorable Carmel Hamlet with ACCarmel Hamlet
The price is CA $257
CA $337 total
includes taxes & fees
Nov 17 - Nov 18
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."
Elizabeth H.
The price is CA $313
CA $741 total
includes taxes & fees
Nov 16 - Nov 17
14. 3-bedroom house in terrific Newtown
3-bedroom house in terrific NewtownNewtown
The price is CA $406
CA $917 total
includes taxes & fees
Nov 19 - Nov 20
15. A Country Lodge Straight Out of the Pages of a Great Novel
A Country Lodge Straight Out of the Pages of a Great NovelPine Plains
10.0 out of 10, Exceptional, (15 reviews)
"Stayed with a group for Millbrook Horse Trials, we had an amazing weekend at this calm and relaxing home with plenty of beds and amenities! What a treat!"
Marianne R.
The price is CA $1,118
CA $1,812 total
includes taxes & fees
Nov 16 - Nov 17
16. NEW: Chic Modern Barn Style Home in Fun Area
NEW: Chic Modern Barn Style Home in Fun AreaPine 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!"
Estefany G.
The price is CA $258
CA $1,015 total
includes taxes & fees
Dec 15 - Dec 16
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.
Learn more about Kent
Nestled in the Litchfield Hills, this charming town invites you to explore its scenic beauty and artistic spirit. Hike through Macedonia Brook State Park, then browse the Morrison Gallery for a perfect blend of nature and culture.
