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Holiday 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.

Hobbit House of Pawling
SUPERHOST
Entire house · 6 guests · 3 beds · 2 bathrooms

Hobbit House of PawlingOne of a kind, cozy hobbit house with hot tub. Beautiful, private setting offering you the ultimate getaway. 5 minutes from the quaint village of Pawling with Metro North railway access. 2 bedrooms w/ king size beds, 2 bathrooms each with walk in shower. A queen size pull out couch in living room and a queen size inflatable air mattress. Electric fireplace in living room. Perennial gardens, 3 patios, babbling brook, bbq grill, hammock, and 2 outdoor fire pits. Ring Quests upon request!

Bushwhack Farm | Stay
Entire loft · 2 guests · 1 bed · 1 bathroom

Bushwhack Farm | StayThe Bushwhack Farm Stay, located in beautiful Pawling, NY. Just 65 miles from NYC and minutes to popular cities in the Hudson Valley/Catskills. The barn loft is situated next to the original historical farmhouse right off the Appalachian Trail with views of Cat Rock Mountain. Originally c. 1800’s, the farm barn, has been lovingly restored/converted into a private 1 bed / 1 bath barn loft with original barn beam detail, outfitted with vintage furniture & antiques with modern amenities.

Lakeside 4BR chalet: deck, fireplace, & lake views
Entire chalet · 8 guests · 4 beds · 3 bathrooms

Lakeside 4BR chalet: deck, fireplace, & lake viewsRelax and enjoy nature in this lakeside retreat! Only 75 minutes from Manhattan, with Metro North access nearby. Wake up to the sunrise over the lake with stunning views from the master bedroom; enjoy the private lake or one of many nearby hiking & biking trails; cook in the fully equipped kitchen or outdoor grill; and wind down with a bath in the jetted tub and a fire in the indoor woodstove or outdoor firepit. Everything you need for a weekend getaway or week by the lake!

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Popular amenities for Pawling holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Pawling

PLUS
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Serene, Peaceful Cabin by the Lake
₹15,721 per night
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Forest Acres Cottage: Tranquil. Ideal location.
₹11,751 per night
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Secluded country upstate near train 1 1/2 hrs nyc
₹13,893 per night
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Appalachian Trail House! Easy access to NYC trains
₹10,630 per night
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Lakefront Escape with Gorgeous Views
₹22,982 per night
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  2. Patterson
Country Retreat and Near Everything
₹6,748 per night
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Cozy apartment in quiet setting
₹6,957 per night
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Cozy retreat just a short stroll from the village
₹14,551 per night
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Cozy room in safe neighborhood
₹6,947 per night
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  2. Sherman
NEW! Historic Sherman Home on Valley Pond w/ Pool!
₹80,340 per night
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Beautiful Lakefront House
₹28,883 per night
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Country Village Getaway
₹10,968 per night

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