Vacation rentals in New Preston Hill

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Top-rated vacation rentals in New Preston Hill

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite
Apartment in Kent
Loft 22
Apartment/loft located above the garage in a private home. Set in the rolling hills of Kent, this 2 bedroom loft is cozy enough for anyone looking to explore this quaint little town. Sleeps 3 comfortably. Centrally located to all three private schools. 11 minute drive to Harlem Valley/Wingdale (NY) train station. *Pool is not solely for the use of the Air BNB. *Dogs on property. All friendly. *IF STAYING IN WINTER MONTHS. You must have 4 Wheel drive vehicle. Driveway/Road is long dirt road.*
Nov 6 – 13
$130 per night
4.93 out of 5 average rating, 127 reviews
Guest favorite
Guesthouse in Washington
Private, cozy woodland getaway.
Perched atop a hill and surrounded by woodland, The Cabin is a secluded getaway that offers all the modern comforts required for a truly restorative stay. With its own yard, driveway, fireplace and private woodland trail, this cozy cottage for two is perfect for an escape in any season. Easy access to skiing, water sports on nearby lakes and miles upon miles of hiking trails. Expect to spot abundant wildlife! Bustling nearby villages offer plenty of cultural, dining and shopping opportunities.
Jun 26 – Jul 3
$195 per night
5.0 out of 5 average rating, 15 reviews
Guest favorite
Guest suite in Bethlehem
Breezy Crest private & restful w/antique charm
Escape to this charming and historic two-story 1841 suite, nestled in the quaint town of Bethlehem. The upstairs bedroom boasts original exposed beams and antique details, creating a cozy and inviting atmosphere. Wake up to the sunrise from the comfort of your bed and enjoy a warm fire in the backyard while listening to the peaceful sounds of nature. Conveniently located between Litchfield and Woodbury, and just 90 miles from NYC, you'll have easy access to shops, restaurants, and ski slopes.
Apr 18 – 25
$128 per night
4.99 out of 5 average rating, 194 reviews

Popular amenities for New Preston Hill vacation rentals

Other great vacation rentals in New Preston Hill

Guest favorite
Guesthouse in Sharon
Cottage with a Waterfall View
Jul 12 – 19
$94 per night
5.0 out of 5 average rating, 58 reviews
Guest favorite
Guest suite in Kent
Bright 1-bedroom in walking distance to town
Jun 28 – Jul 5
$109 per night
5.0 out of 5 average rating, 52 reviews
Guest favorite
Cottage in Washington
Litchfield Hills Country Hideaway
Apr 7 – 14
$166 per night
4.93 out of 5 average rating, 41 reviews
Guest favorite
Guest suite in Washington
Custom industrial farmhouse Apt in Washington Dpt
Jan 19 – 26
$126 per night
5.0 out of 5 average rating, 36 reviews
Guest favorite
Guesthouse in New Milford
Luxury in the Litchfield Hills
Sep 19 – 26
$184 per night
5.0 out of 5 average rating, 40 reviews
Guest favorite
Home in Warren
Moody Pond House: Brand New Spring Country Escape
Jun 8 – 15
$800 per night
5.0 out of 5 average rating, 27 reviews
Guest favorite
Cabin in New Milford
Stylish Cabin Escape with Chef's Kitchen & Firepit
Oct 13 – 20
$400 per night
5.0 out of 5 average rating, 48 reviews
Guest favorite
Cabin in New Milford
Creek Side Cabin w/ Wood Fired Hot Tub & Fire Pit
Jan 10 – 17
$217 per night
4.99 out of 5 average rating, 82 reviews
Guest favorite
Cottage in Washington
The Cottage at Madison & Meadow Farm Washington CT
Feb 7 – 14
$246 per night
5.0 out of 5 average rating, 91 reviews
Guest favorite
Cottage in Bethlehem
Wood Burning Fireplace |Soaking Tub |Pet Friendly
Jul 19 – 26
$160 per night
5.0 out of 5 average rating, 25 reviews
Guest favorite
Cottage in Pawling
Twin Lakes Designer A-frame Stone Cottage
Jan 6 – 13
$315 per night
5.0 out of 5 average rating, 59 reviews
Guest favorite
Home in Cornwall
The Brookside Barn
Oct 28 – Nov 4
$140 per night
4.98 out of 5 average rating, 47 reviews

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