Vacation rentals in Pawling

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Top-rated holiday rentals in Pawling

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

Superhost
Cabin in Pawling
Serene, Peaceful Cabin by the Lake
Take a stroll down to the lake in the crisp morning air, then light the fire and sink into the cherry leather armchair at this rustic log cabin. Touches of soft sage add a soothing side, while patterned rugs and chunky beams keep things homey. Authentic Log cabin, private lake with swimming, kayaking --1000's acres adjacent private land, fishing, hunting-- Enjoy the harvest of the Hudson Valley-- minutes to wineries, Pawling train to NYC, Appalachian trail and hiking, Child safe. Minutes walk to Lake! Private Lake-- We are here to check you in and only if you need us. We respect your privacy and "time-away". The property sits in a private, sprawling lake community minutes from wineries for tastings, Pawling station for trains to New York City, and the Appalachian trail for scenic hiking. Explore Wallkill and Warwick within around an hour's drive. Car, Metro North (train to NYC), Uber, Lyft...
23 Feb – 2 Mar
4.95 out of 5 average rating, 110 reviews
Guest favourite
Home in Stormville
Private Hudson Valley Country Retreat
Beautiful 1930s house set on 18 private acres of land overlooking a private lake. Immaculately landscaped surrounding area with koi and gold fish pond with a waterfall, gazebo, hammock and most importantly untouched nature. Very private! Enjoy your morning coffee or tea in the outdoor covered patio overlooking the property, wine and dine under the pergola, enjoy the fire pit or wood burning fireplace on a chilly evening. Serenity and relaxation at its best! Pond dock coming up in Spring of 2021
15 – 22 May
4.94 out of 5 average rating, 156 reviews
Guest favourite
Home in Carmel Hamlet
Lux Bungalow on Lake. Hike Kayak Great Restaurants
Beautiful, light flooded, waterfront, newly renovated 2 bedroom home on picturesque Lake Carmel. Wake up, eat, sleep and relax to the tranquil view of the glistening water - truly an oasis! (1 hour north of nyc) Take in a sunset while eating a meal at home, explore the shops and restaurants in a cute nearby town, take a walk around the lake, read a book by the cozy fireplace, hike, cook, kayak, ski, or just sit and enjoy. Centrally located close to Hudson Valley, Westchester and Connecticut.
30 May – 6 June
4.92 out of 5 average rating, 121 reviews

Popular amenities for Pawling holiday rentals

Stay near Pawling's top sights

McKinney & Doyle Fine Foods Cafe44 locals recommend
O'Connor's Public House14 locals recommend
Vinny's Deli & Pasta7 locals recommend
CVS4 locals recommend
Lakeside Park3 locals recommend
Sunflour Bakery4 locals recommend

Other great holiday rentals in Pawling

Guest favourite
Home in Rhinebeck
Architectural wonder in the woods
6 – 13 July
4.91 out of 5 average rating, 253 reviews
Guest favourite
Cottage in Pawling
Twin Lakes Designer A-frame Stone Cottage
6 – 13 Jan
5.0 out of 5 average rating, 59 reviews
Guest favourite
Guest suite in Pawling
Cozy retreat just a short stroll from the village
2 – 9 Sept
4.92 out of 5 average rating, 62 reviews
Guest favourite
Home in Pawling
Country Village Getaway
20 – 27 Nov
4.95 out of 5 average rating, 21 reviews
Guest favourite
Guest suite in Pawling
Charming Private Studio Apartment Retreat
4 – 11 June
4.98 out of 5 average rating, 46 reviews
Guest favourite
Cottage in Pawling
Forest Acres Cottage: Ski, hike, bike, 10 min away
9 – 16 May
4.98 out of 5 average rating, 82 reviews
Guest favourite
Home in Pawling
Farmhouse Oasis in the Hudson Valley, Stream Views
12 – 19 June
4.97 out of 5 average rating, 76 reviews
Guest favourite
Cottage in Pawling
Cozy Cottage Getaway with Wood Burning Stove
1 – 8 Oct
5.0 out of 5 average rating, 33 reviews
Guest favourite
Home in Patterson
Cozy Lakehouse
1 – 8 July
5.0 out of 5 average rating, 19 reviews
Guest favourite
Guesthouse in Dover Plains
Spilt Milk Cottage - Hudson Valley, NY
14 – 21 Nov
4.88 out of 5 average rating, 82 reviews
Superhost
Farm stay in Brewster
Crooked Cottage at Lobster Hill Farm
28 Oct – 4 Nov
4.8 out of 5 average rating, 25 reviews
Guest favourite
Cabin in Holmes
Cabin Charadora
27 Feb – 6 Mar
5.0 out of 5 average rating, 33 reviews

Destinations to explore

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