
House holiday rentals in Pawling
Find and book unique houses on Airbnb
Top-rated house rentals in Pawling
Guests agree: These houses are highly rated for location, cleanliness and more.

Private Hudson Valley Country Retreat
Beautiful 1930s house set on 18 private acres of land overlooking a private lake. Immaculately landscaped surrounding area with koi and gold fish pond with a waterfall, gazebo, hammock and most importantly untouched nature. Very private! Enjoy your morning coffee or tea in the outdoor covered patio overlooking the property, wine and dine under the pergola, enjoy the fire pit or wood burning fireplace on a chilly evening. Serenity and relaxation at its best! Pond dock coming up in Spring of 2021

Lux Bungalow on the Lake
Beautiful, light flooded, waterfront home 1 hour from New York City. The 2 bedroom home is on picturesque Lake Carmel. Wake up, eat, sleep and relax to the tranquil view of the glistening water - truly an oasis! Take in a sunset while eating a meal at home, explore the shops and restaurants in a cute nearby town, take a walk around the lake, read a book by the cozy fireplace, hike, cook, kayak, ski, or just sit and enjoy. Centrally located close to Hudson Valley, Westchester and Connecticut.
Woodstock Historic Artist Estate - The Pond House
Awaken to an idyllic lake view through a timber-framed glass facade. Acclaimed social realist painter Reginald Marsh's family estate is known to be unique for Woodstock with its ball shaped junipers, a pond that brackets the house, expansive lawns, a gathering of birches and 100 year old cone shaped cedar trees. In short walking distance to the center of Woodstock the secluded setting with a private waterfall bordering a public preserve as well as the attention to architectural detail is unique.

Mindful Escape: Theater, Trails, Wood Stove
Exhale and recharge in this luxurious space at the foot of the Shawangunk Mountains. This gem features an open-concept kitchen and living room, perfect for connecting with nature. Enjoy the high-end Foster Leather Sofa, cozy movie nights on a 120" projector screen, and a wood-burning stove for chilly evenings. Every detail, from fresh linens to a meaningful library, is thoughtfully curated. Discover hidden messages throughout the house, inviting you to explore and unwind in this serene retreat.

Boulder Tree House
Boulder Tree House 🌲🌲🌲 FRESH AIR • SMOKE FREE • ALLERGY FREE Early Check In & Late Check Out! Boulder Tree House is an Inhabitable Work of Art, created by owner architects. The design is based on organic and innovative blending of natural elements and environmentally conscious technology, creating a happy and healthy living space. Boulder Tree House is ideal for a couple looking for a exciting, romantic and unique experience. The space can also comfortably accommodate a 3rd person.

Renovated, one level home in an excellent location
Guests are sure to enjoy a memorable time in this beautiful fully furnished 3 bedrooms and 2 bathroom house. The house has been recently renovated to maximize comfort and overall experience. Excellent location close to major stores, restaurants and at walking distance to Candlewood Lake and Candlewood Lake Point private beach. Highlights: Free WIFI, Roku TV with Youtube TV, towels & beach towels, bed linens, and a beautiful deck with dining table, propane grill, and patio furniture.

Modern House with Mountain View @Getawind
Experience luxury and comfort in our newly built property. Marvel at the breathtaking panoramic views of Rusk mountain through floor-to-ceiling windows. Unwind in the sauna or hot tub, and gather around the fire pit for cozy evenings. Enjoy outdoor movie nights with our projector, or savor grilled delights in the patio area. Warm up by the fireplace, explore Ski resorts, Golf Clubs and more. It's the perfect retreat for families and friends. Book now and create unforgettable memories!

Waterfront, Dog & Family Friendly, Cozy Cottage
El Girasol, "The Sunflower," a sunny, family and pet friendly cottage on the Esopus Creek in the Catskill Mountains. Our home is fully furnished with global & vintage finds. This charming cottage has 2 beds, spacious living room with a big, comfy sleeper sofa and cozy electric fireplace & fully equipped kitchen combined with a dining room. Creek access, BBQ, fire pit, fenced in backyard, & 2 decks makes our home a great destination for a relaxing getaway with family, friends and pets.

Hillside Views in Hudson Valley
Escape to this modern, cozy retreat where nature surrounds you. Fall asleep to owls, crickets, and frogs. Just 2 mins from Rosendale and a short drive to Kingston, New Paltz, and Stone Ridge, with restaurants and trails nearby. Enjoy a gas fireplace, a reading nook with treetop views, and a large deck that feels like you’re in the trees. The private outdoor space includes a fire pit, all on a serene 3-acre lot offering total peace and quiet. Your perfect Hudson Valley escape awaits!

The Farmhouse
Enjoy staying at our charming Farmhouse in the heart of our working dairy farm. Our farm sits on some of the most beautiful hills in Cornwall with the famous Gateway to Cornwall view where you can see our dairy cows grazing in the grandeur of nature. Come say hello to the cows in the barn during milking or watch the herd cross the road evoking sites you might expect to see in small European farming villages. You'll likely see us on our tractors bringing hay and water to our cows!

Comfortable home away from home- near everything
Price includes Airbnb fees. Cozy, pet-friendly cottage in a peaceful setting just 70 miles from NYC and minutes from I-84 (Exit 8 or 9). This clean & comfortable retreat features 3 bedrooms (2 queens, 1 full), and pull-out couch. Portable A/C's in summer, and fireplace for cozy nights. The greenhouse adds plenty of natural light, the yard is perfect for kids, the front deck is great for morning coffee, and the gas grill great for cooking out. High-speed WiFi and 3 smart TVs.

Beautiful Lakefront Retreat with Private Dock
Relax on the lake at this beautiful, one of a kind 3 bedroom, 2.5 bath DIRECT waterfront home in a private community on peaceful Squantz Pond, adjacent to Candlewood Lake. Enjoy spectacular views across the lake of unspoiled Pootatuck State Forest from the deck or screened in porch. Swim, fish, or just relax on the private dock. Kayak and paddleboard rental nearby. The home is central air-conditioned with a fully equipped kitchen. Our special place is waiting for you!
Popular amenities for Pawling house rentals
House rentals with a pool

midcentury mod * HOT TUB * walk out trail 2 mohonk

Entire Home (private pool), Event Friendly

Bluestone Escape - Where everyone is at home.

4Br Mountain Brook House on 130 acres w/ trails

Upstate Modern Scandinavian Barn in the Catskills

Peaceful Light-Filled Guesthouse 1 Hour From NYC

Beacon Beauty 4/2, Hot Tub,Pool,Wifi,1.5m to Town

Luxury modern farmhouse with heated pool & hot tub
Weekly house rentals

Farmhouse & private yard

Sleeps 10 - Private Dock, Sauna, Outdoor Dining

Escape to a Celebrity Chef's Waterfront Sanctuary

Cozy cottage

Millstone Manor with East Mountain View

Hilltop Retreat- Lakefront with Dock

Harlem Valley Hideout: Artsy ~ Pool ~ Tennis

Private Lake House, Retreat
Private house rentals

OWL's PERCH Candlewood Lakefront Rustic Cottage!

Dog & Family Friendly A-Frame - Private and Cozy

Candlewood Isle Cabin ~ Dog Friendly~ Lake ~ Dock

Country Retreat | Fire Pit | BBQ

Dutchess Chalet - Hudson Valley Home w/ Hot Tub!

The Art House: 5-Acre Getaway w/ Fireplace

Creekside Couple's Retreat w/Hot tub, Sauna & More

Country outside the city
Quick stats about house rentals in Pawling

Nightly prices starting at
Pawling holiday rentals start at $213 NZD per night before taxes and fees

Verified guest reviews
Over 60 verified reviews to help you choose

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Pawling rentals

4.9 Average rating
Pawling stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
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- Yale University
- Fairfield Beach
- Rye Beach
- Minnewaska State Park Preserve
- Thunder Ridge Ski Area
- Walnut Public Beach
- Rowayton Community Beach
- Rye Playland Beach
- Brownstone Adventure Sports Park
- Woodmont Beach
- Silver Sands Beach
- Bash Bish Falls State Park
- Sunken Meadow State Park
- Jennings Beach
- Hudson Highlands State Park
- Wildemere Beach
- Kent Falls State Park
- Brotherhood, America's Oldest Winery
- Seaside Beach
- Walkway Over the Hudson State Historic Park
- Catamount Mountain Ski Resort
- Ringwood State Park
- Sherwood Island State Park
- Pelham Bay and Split Rock Golf Courses




