Places to stay in Pawling

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Popular amenities for Pawling places to stay

Stay near Pawling's top sights

McKinney & Doyle Fine Foods Cafe44 locals recommend
O'Connor's Public House14 locals recommend
Pawling Bread Co.10 locals recommend
Dutcher Golf Course9 locals recommend
Pawling Farmers Market9 locals recommend
Vinny's Deli & Pasta7 locals recommend

Other great vacation rentals in Pawling

Top guest favorite
Home in Millerton
4.97 out of 5 average rating, 181 reviews

Vacation Home In Millerton

SarahRating, 5 stars1 week ago
We had a wonderful week at Corina's house while out for a family event! The house was spotless and the kitchen was stocked with everything we could need. The outside space was just as amazing. We had a great campfire one night, enjoyed using the grill, and our dog loved being able to run around the large yard. I'm sure we'll be back next year!
Guest favorite
Chalet in Hunter
4.98 out of 5 average rating, 152 reviews

THE LAKEFRONT CHALET - SKI, RIDE, GOLF, BIKE, HIKE

ChristinaRating, 5 stars2 weeks ago
This place was perfect for our Mom’s Book Club Retreat. The living room was spacious enough for all 7 of us but still so cozy for chatting and reading (we were looking at tags to buy the same couches). The weather was terrible so we didn’t get to enjoy the outdoor spaces as much as we’d like but the hot tub and fire pit were great. The kitchen had everything we needed to cook all our meals . Communication and check in were a breeze. Would definitely recommend this place!
Guest favorite
Home in Hunter Mountain, Hunter
4.96 out of 5 average rating, 104 reviews

Private Mountain Lodge, 10mins to Hunter & Windham

PaulRating, 5 stars2 months ago
My family's second visit to this beautiful gem overlooking the mountains and frozen pond. Our hosts are highly communicative and helpful. The description is accurate. Considering our 2nd visit and rebooked for 3rd in 2026 - this speaks volumes -- more than meets our needs, well stocked. We're looking forward to visiting during the summer months to further appreciate the views. Grateful to them for sharing their home with us.
Superhost
Condo in Vernon Township
4.73 out of 5 average rating, 111 reviews

200 yds Minerals - great for hotel weddings

SaraRating, 5 stars5 months ago
We had a great time! The unit is an easy walk to Minerals, and the layout was perfect for our needs. Joann was a fantastic host and we can’t wait to stay again!
Guest favorite
Cottage in Greenwood Lake
4.96 out of 5 average rating, 48 reviews

5 bedroom 7 beds Cottage Sauna, Hike, Winery & Ski

JasonRating, 5 stars1 week ago
We had a great time at Carmine's place, highly recommend.
Guest favorite
Home in Woodstock
4.92 out of 5 average rating, 468 reviews

Mountain View Cottage - Sauna, Jacuzzi, Fire Place

SeanRating, 5 stars2 weeks ago
Unique space minutes form downtown Woodstock. The home offers peace and quiet to unwind from modern hectic life. Tune into focused intentional living. Records, wood fires, and sauna all help to create a retreat that’s sure to recharge and inspire. Lovely hosts!
Top guest favorite
Home in Greenwood Lake
5 out of 5 average rating, 119 reviews

Escape to the lake!LAKEFRONT/Hot-tub/1 hour to NYC

TatyanaRating, 5 stars1 month ago
We had a staycation here and it was absolutely lovely. We enjoyed the space, especially the view. The hot tub was great in the chilly nights, played in the game room a bit, cooked in the kitchen and enjoyed some meals in the dining room. Easy to find, but felt very private. Thank you for sharing the lovely place.
Guest favorite
Cabin in Shandaken
4.99 out of 5 average rating, 104 reviews

A Place Called Home in The Catskill

KateRating, 5 stars1 month ago
We just finished a two month rental of John’s wonderful home. Our family of 5 used the home primarily on the weekends when we were enjoying ski season at Belleayre Mountain. I can’t say enough great things about this home. Our family felt totally at home - every aspect was perfectly maintained and the home maximized comfort. Our favorite part of the home was the great room where we would watch movies on the huge family sofa in front of a crackling fire. It was the perfect way to end a day of skiing. Our kids loved the downstairs family room with the foosball table and there were lots of games to play and keep everyone busy and entertained. And the kitchen is huge and very well stocked with all the appliances you will ever need. So it was a fantastic 2 months and we look forward to renting this property again!

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