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Vacation rentals in Pawling

Vacation rentals in Pawling

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Pawling

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

  • Cozy room in safe neighborhood
    SUPERHOSTPrivate room · 2 guests · 1 bed · 1 private bath
    Cozy room in safe neighborhood

    Cozy room, within walking distance to Metro North.

    What guests are saying:

    “The one thing that my husband and I were looking for was a comfortable bed near Daryl's House (a small concert venue and club). Deborah's place fit the bill perfectly. The room was immaculately clean with the bathroom just next to it. We unfortunately didn't get to meet Deborah, but that's because our schedule was tight. But communication and location were perfect as well. If we need to be in Pawling again, we will definitely considering that comfy bed and great location and price.”

  • Hoppy Hill
    SUPERHOSTEntire guest suite · 4 guests · 2 beds · 1 bath
    Hoppy Hill

    Newly renovated, comfortable and neat. Private apartment in the Harlem Valley with one queen bedroom, full bathroom, kitchenette/living room combo with pull out queen sofa. Watch the sun rising over the mountains and enjoy the quiet life settings. Located only 10 minutes from the Appalachian Trail, 5 mins. from Old Dovers Inn and Harlem Valley Homestead, 15 mins. to Thunder Ridge Mt ski, 8 mins. from Metro North Train Station, 15 mins. from Kent. Close to all private schools and wedding venues.

    What guests are saying:

    “A great stay for a quick getaway! The picture's don't do this apartment justice. This is a beautiful, sparkling clean one bedroom apartment with a working electric fireplace! It's extremely spacious and private. The guesthouse has a large porch with amazing views of the mountains! Comfy and clean bed too. Would definitely stay again or recommend to a friend! The host gave easy instructions on check in/out and even left a guide for things to do in the area! We never met in person but she was extremely communicative. A must stay if you are looking in the area!”

  • Appalachian Trail House! Easy access to NYC trains
    SUPERHOSTEntire house · 6 guests · 6 beds · 1 bath
    Appalachian Trail House! Easy access to NYC trains

    Have you been wanting to hike the Appalachian Trail, but don't know where to start? Here you go! This is a cozy 3 bedroom, 1 bath, with full basement, and 3 acres of land. Located in quaint and historic town of Pawling, NY, about 90 minutes from NYC. Walking distance from the train! Enjoy mother nature at it's finest with a short hike up historic Quaker Hill section of the Appalachian Trail. Start from the steps out the back door! Pets and kids welcome!

    What guests are saying:

    “Irena and Jerzy’s home was really clean and we felt right at home. The pictures on the app do the home no justice, it is truly beautiful. My family and I made a camp fire and had s’mores in the beautiful fire pit and went on a hike right behind the house on the AT. Thank you for being a great host and making our family getaway a great time.”

Vacation rentals for every style

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  • Homes
  • Hotels
  • Unique stays

Popular amenities for Pawling vacation rentals

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

Other great vacation rentals in Pawling

Fun bedroom space in the countryside
SUPERHOSTPrivate room
Fun bedroom space in the countryside
Price:$65 / night
Blue Bird Inn
SUPERHOSTEntire apartment
Blue Bird Inn
Price:$96 / night
Master Suite with a Private Entrance
SUPERHOSTPrivate room
Master Suite with a Private Entrance
Price:$65 / night
Beautiful  Cozy Cottage
SUPERHOSTEntire cottage
Beautiful Cozy Cottage
Price:$135 / night
Cozy  apartment in quiet setting
SUPERHOSTEntire apartment
Cozy apartment in quiet setting
Price:$92 / night
Private Wing in a Modern Home
SUPERHOSTPrivate room
Private Wing in a Modern Home
Price:$55 / night
Gorgeous East Treehouse & Sunrise Bedroom.
SUPERHOSTPrivate room
Gorgeous East Treehouse & Sunrise Bedroom.
Price:$129 / night
Serene, Peaceful Cabin by the Lake
PlusEntire cabin
Serene, Peaceful Cabin by the Lake
Price:$195 / night
The Fabulous Retreat - Pet Friendly and Fenced
Entire house
The Fabulous Retreat - Pet Friendly and Fenced
Price:$149 / night
Renovated 1840 Collins Estate Private East Wing
SUPERHOSTEntire guest suite
Renovated 1840 Collins Estate Private East Wing
Price:$119 / night
Historic Private Log Cabin (room) in Forest Lodge
SUPERHOSTPrivate room
Historic Private Log Cabin (room) in Forest Lodge
Price:$135 / night
Getaway! Full Fl Apt in Carriage house w/Pool!
SUPERHOSTEntire guest suite
Getaway! Full Fl Apt in Carriage house w/Pool!
Price:$150 / night
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