Places to stay in Pawling

Book unique places to stay, houses, and more on Airbnb

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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, 183 reviews

Vacation Home In Millerton

BettyRating, 5 stars1 week ago
We wanted to get away from the city for some peace and quiet and Corina’s place was exactly what we were looking for. It felt very tucked away. The home was stocked with pretty much anything I think one would need. The outdoor space is huge, nice and safe for our dog to frolic. Loved the large firepit - wish we had more time to sit outside. Corina was super friendly, accommodating, and extremely quick to respond to any inquiries, so you should be in good hands if you need any help. I like to try a new airbnb whenever I can, but when we return to Millerton, we’ll be going back to Corina’s!
Guest favorite
Chalet in Hunter
4.98 out of 5 average rating, 153 reviews

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

CarmenRating, 5 stars2 weeks ago
The house was well stocked, neat and clean. The property has lots of great outdoor space to relax in. Nataliya was very responsive. Thank you.
Top guest favorite
Home in Great Barrington
5 out of 5 average rating, 6 reviews

Summer & Leaf Season Rental!

AnnieRating, 5 stars4 months ago
What a lovely home! It’s in the residential neighborhood above Great Barrington, which means it’s walkable to Lake Mansfield and the trails there and also either a short drive or a nice walk to everything downtown GB has to offer. The house is squeaky clean with nice kitchen amenities, a yard, and a beautiful detached screen porch for warmer months. Perfect size for a small family and very cozy. We will be back!
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, 112 reviews

200 yds Minerals - great for hotel weddings

CindyRating, 5 stars3 days ago
The place was great and just as pictured/described. Joann gave great instructions and was very responsive. We were only there for a short stay for a race, but it looked like a great area I would’ve loved to explore if we had more time. The only thing I didn’t care for was the requirement for to wash and dry all towels before leaving. Since I already paid a hefty cleaning fee that seemed like a bit much. And the washer/dryer is small so this took a couple of loads to get done.
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, 470 reviews

Mountain View Cottage - Sauna, Jacuzzi, Fire Place

NiharRating, 5 stars2 weeks ago
fantastic host and super helpful whenever we had questions. my wife left her iPad there and they mailed it back. verry appreciative of that. first time using a wood fired sauna- I was skittish at first, but it was a great amenity. hot tub was clean and worked well as well. would definitely recommend if you're eyeing a rustic retreat.
Top guest favorite
Home in Greenwood Lake
5 out of 5 average rating, 121 reviews

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

LauraRating, 5 stars1 week ago
Our stay at Starlight Serene was everything we hoped it would be! John was very responsive and helpful, especially as this was our first time using AirBnB. The pictures are very accurate, there were plenty of towels, linens, and a VERY well equipped kitchen - much more than we expected (or I have in my own house, I think!). Lots of nice bonuses to this place - my kids loved the firepit and there was wood on hand as well as a s'mores kit; the hot tub was warm and ready when we arrived. You are at the narrower end of the lake, but still a beautiful view with plenty of wildlife. The location is great - roughly 30ish minutes to Bear Mountain, Legoland, and the Palisades Center (which had tons of rainy-day fun for kids). We even rented a pontoon boat from Murphy's Cove Marina - Richie was really wonderful to us and our kids and they loved their first time boating and fishing on the lake. Thanks for a great experience John!

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