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.

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Top guest favourite

Home in Greenwood Lake

5 out of 5 average rating, 121 reviews

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

Lakefront, fully renovated and ready for guests to experience lake living at its best from the inside out. The modern gas fireplace and cozy sectional sofa make the living room the perfect place to perch over crisp autumn evenings. Or take a steaming soak in the backyard hot tub after a day of hiking or exploring all of neighboring Warwick’s wineries, breweries and local farms.With direct access to the lake from the property our location is ideal for kayaking. All within a 1 hour drive from NYC!

Guest favourite

Home in Woodstock

4.92 out of 5 average rating, 470 reviews

Mountain View Cottage - Sauna, Jacuzzi, Fire Place

Completely Private w/ Exceptional, Expansive Mountain View, All-Seasons Hot Tub and Sauna. Billiards room, Fireplace, Woodstove, Screen Porch, 300 Vinyl records, Full Kitchen, bathtub and Bidet Surrounded by nature, but 2 miles from center of town. Hiking and creek swimming walking distance This property is for Love. La Dolce Vita. The Love of Friends and Family. The Love of Time. Fall in Love here, with the Land and with One-Another. *No checkins are avail Tgiving,Xmas Day, Easter Sunday

Superhost

Home in Roxbury

5 out of 5 average rating, 10 reviews

Zoom In Map To 5*Roxbury "Painter Hill" PoshPadsCT

PoshPadsCT - Private 4-5-Bedroom hilltop retreat on a serene brook - a perfect getaway. New Hot Tub, Terrace, Trampoline. Located on a 3 acre property near historic estates, Maple Bank farm stand and Toplands Farm and just 1.5 hours from NYC. The house features beautiful fields, views, a large terrace with a gas grill, a firepit. Nearby hiking trails & Washington restaurants, shopping, distilleries, vineyards, breweries, and more! Ski Mohawk Mountain or Swim Lake Waramaug State Beach.

Guest favourite

Chalet in Goshen

4.89 out of 5 average rating, 141 reviews

The Goshen Glass Chalet

A vacation house furnished decorated 1 large master bedroom down stairs and full bathroom.2 bedrooms 1 full size bed upstairs & 2 twin size beds upstairs with a full bathroom bathroom .1 well stocked & equipped kitchen 1 large spacious combined living and a dining room with fireplace and large screened TV.A beautiful outdoor deck that sits 6 people for dining outside 1 screened in porch with a beautiful large patio with a barbecue & stunning woods view, 10 minute drive to Woodridge Lake.

Guest favourite

Townhouse in Hunter

4.91 out of 5 average rating, 79 reviews

Mountain View Catskill Escape-2 Mins to Slopes!

Enjoy the BEST LOCATION IN THE CATSKILLS with Scribner's Lodge right next door, Hunter Mountain 1 mile away, Tannersville a town over, Windham mountain 7 miles away, hiking, lakes, restaurants and breweries all around! Amazing 4 bedroom, 3 bathroom townhome with unbeatable views of Hunter Mountain. Stocked with all the essentials, multiple fireplaces, outdoor grill and a new patio! Bring your skis and snowshoes or rent skates for the winter and enjoy the shared outdoor pool in the summer.

Guest favourite

Home in Sheffield

4.91 out of 5 average rating, 117 reviews

Wow! Best BERKSHIRE SnowHome #1 Private SuperClean

"238 Main" has two rentals. Only one rental is rented at a time. Rental #1 has 2 bedrooms, FULLY EQUIPPED KITCHEN and is SUPERCLEAN! (SEE THE 1 BEDROOM LISTING #2!) We are conveniently located between Butternut and Catamount ski stations. Fully renovated, large garden, private entrance, terrace and parking space. Queen size beds. High Speed WiFi. Bathroom has radiant floor heat, towel warmer, plush bathrobes, hairdryer and toiletries. We are in the heart of the Berkshires come visit!

Superhost

Home in Middletown

4.9 out of 5 average rating, 130 reviews

Riverfront! Swim, Fish, Hot Tub & Game Barn.

Fish, Tube, Hot tub and Game room! All in one property! This exquisite riverfront home has 3 bedrooms and a sleeping loft. This magical property is 7 acres on the River. Bellayre beach 15 mins and Windham mountain biking 30 mins. Hike, s’mores by the fire, hang out in the 3 season game barn equipped with a pool table and darts, have a drink in the riverside hot tub. 5 mins to retro bowling and restaurants. NO FIRST TIME RENTERS ID VERIFIED/REVIEWED RENTERS ONLY.

Top guest favourite

Apartment in Vernon Township

4.94 out of 5 average rating, 145 reviews

Ski-In/Ski-Out @ Mountain Creek-Pool/Hot Tub/Sauna

NEWLY Renovated! Top floor 1 bedroom Condo with Mountain/Pool View at Mountain Creek Resort. Steps away from ski mountain & gondola ! Swim in the outdoor heated saltwater pool, relax in the sauna or soak in the hot tub while taking in mountain views, Catch the sunset from your private top floor balcony or cozy up by your gas fireplace. Visit award-winning spas, golf, breweries, wineries, farms, and fine dining at Crystal Springs & Warwick, NY--only 10 min away.

Top guest favourite

Apartment in Vernon Township

4.92 out of 5 average rating, 356 reviews

Appalachian TOP 4TH FLOOR Studio+ w/amazing views!

Location, location, location! This is a very unique, open concept unit. In lieu of a balcony, it has a huge picture window that allows breathtaking center building panoramic views of the slopes! It's also a top floor unit so extra height ceilings. That open concept continues inside where the walls were minimized leading to the master bedroom having an archway in lieu of a door. The result is a very spacious main living area perfect to gather in front of the fire.

Guest favourite

Cottage in Greenwood Lake

4.92 out of 5 average rating, 88 reviews

Cottage with Picturesque Views

Quaint Cottage set high above Greenwood Lake with Private beach and lake front community access. Minutes away from Mountain Creek Ski Resort, Spa & Water park, Mt. Peter Ski & Tubing, Warwick creameries, breweries & vineyards & apple picking. 2 BR, 1 Bath private 2 car parking. Fenced in deck allows for scenic dining. Fire pit with Adirondack seating allows for around the fire gatherings. #CozzyCottage_GWL Town of Warwick Short Term Rental Permit # 34234

Superhost

Flat in Saugerties

5 out of 5 average rating, 3 reviews

Creekfront I Hot Tub I Sauna I Fire Pit I Kayaks

Welcome to Upstate Waterfronts! Looking for a restorative Upstate getaway? This Creekside gem has you covered. - HOT TUB - SAUNA - 3 bedrooms/ 1 full bathroom - Fully equipped kitchen & high-end amenities - Private creek access - including kayaks/vests/paddles - Stunning creek views - including a water facing balcony - 3,000 Arcade games, 75'' Smart TV, endless board games - High-speed WiFi - Prime location - walkable to town/restaurants/shops/beach

Top guest favourite

Chalet in Craryville

5 out of 5 average rating, 13 reviews

Lockwood Lodge Mountaintop

Welcome to our slice of paradise in the Hudson Valley! Enjoy a secluded hilltop home with beautiful mountain and valley views, surrounded by 18 acres of woods. The open floor plan is perfect for cooking or relaxing in front of the fire, and enjoy grilling and the pool when the weather is right. The location is minutes from Hillsdale, and a 15-20 minute drive from Hudson and Great Barrington, with amazing restaurants and activities for every season.