
House vacation rentals in Pawling
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Top-rated house rentals in Pawling
Guests agree: these houses are highly rated for location, cleanliness, and more.

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.

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.

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!

Lakeview Estate - Chef's Kitchen - NYC Getaway
Stunning lake views from every angle! Gorgeous 3,200 square foot custom home with an open floor plan. Highlights include: * Chef's kitchen with Viking Range, Sub Zero Refrigerator, granite countertops & custom cabinets * Expansive 20x30 stone patio overlooking the lake with a fire-pit, speakers & outdoor lighting * 3 spacious bedrooms and 3 full bathrooms with double vanities, showers & separate bathtubs. * 5 SmartTVs including a 65" TV in the main living area

Tranquil Tree-House on the beautiful Hudson River
Take it easy at this unique and tranquil getaway. I look forward to hosting you. Enjoy a private room with a queen size bed and a large screen smart tv. The full bathroom is located across the hallway. Enjoy a warm fire in the sitting area. There is a work area and a high table to enjoy some tea/coffee or wine with dinner while enjoying the view of the Hudson through the large windows and sliding door.

Architectural wonder in the woods
Unique experience, secluded. Enjoy a weekend or a few days eco-friendly retreat in an architectural, geometric masterpiece on 30 preserved acres just minutes from all that Rhinebeck and the Hudson Valley have to offer. The house is an open plan, and though it has zero bedrooms, it can sleep 4! Feel free to send us a message for any requests, we love hearing from people.
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

Upstate Modern Scandinavian Barn in the Catskills

Peaceful Light-Filled Guesthouse 1 Hour From NYC

Cozy & Spacious Country Home - All Seasons

Stunning Views, Bucolic Bliss in 1790s Farmhouse

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

Peace & Privacy - High Falls (hot tub & salt pool)
Weekly house rentals

Farmhouse Oasis in the Hudson Valley, Stream Views

Farmhouse & private yard

Cozy cottage

Slice of Paradise in the Country

Hilltop Retreat- Lakefront with Dock

Harlem Valley Hideout: Artsy ~ Pool ~ Tennis

Private Lake House, Retreat

Designers Historic Connecticut Home
Private house rentals

Dog & Family Friendly A-Frame - Private and Cozy

Private Dock & Pool - Candlewood Lake

Candlewood Isle Cabin ~ Dog Friendly~ Lake ~ Dock

Dutchess Chalet - Hudson Valley Home w/ Hot Tub!

Country Retreat | Fire Pit | BBQ

The Art House: 5-Acre Getaway w/ Fireplace

Millstone Manor with East Mountain View

Luxe Historical Style - 2 FP’s & Soaking Tub
Quick stats about house rentals in Pawling

Nightly prices starting at
Pawling vacation rentals start at G$25,096 GYD per night before taxes and fees

Verified guest reviews
Over 60 verified reviews to help you choose

Popular amenities for guests
Guests love Kitchen, Wifi, 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
- Wildemere Beach
- Kent Falls State Park
- Hudson Highlands State Park
- Brotherhood, America's Oldest Winery
- Seaside Beach
- Walkway Over the Hudson State Historic Park
- Ringwood State Park
- Catamount Mountain Ski Resort
- Pelham Bay and Split Rock Golf Courses
- Bayview Beach