
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.
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.

Fully stocked creekside sauna retreat with privacy
Welcome to Bluskyz! (Blue Skies) Perfectly nestled between the charming village of New Paltz and the beauty of the Gunks and it’s surrounding countryside. Quiet culdesac road close to everything, ONE HOUR FROM THREE MOUNTAINS and within walking distance to a couple of real country gems. Top of a hill, this home has amazing privacy, and the quiet of being the last home on a dead end street. With a natural spring pool, pergoladining, sauna in the back yard, your private spa in the Gunks awaits

Serene Waterfront Mill House, Stroll to Village
Sweet 1840 mill house on the water, nature-filled back deck yet 5 mins walk to antiquing & excellent Millbrook restaurants. Make this your base as you explore the beautiful Hudson Valley. Or relax out back & enjoy the birds & stream. Farmhouse antique shabby chic decor with king tempurepedic bed in large second floor master BR, two BRs with twin trundle beds, 1 bathroom upstairs & 1 down, A/C, ceiling fan, cozy woodstove, wifi with smart tv, eat-in kitchen, coffee/tea, plenty of free parking.

Cottage on the Creek
Charming vintage cottage on the Esopus Creek. Craftsman style with original 1930's details and essential modern updates. A short drive to Saugerties, Kingston, Rhinebeck, and Woodstock. Peaceful setting with cool breezes, eagles, ducks, great fishing, swimming, and a boat launch/swim ramp - two kayaks are available for use if arranged prior to your stay. If you are participating in the HITS equestrian events - the location is very convenient and the driveway can accommodate horse trailers.

Waterfront Lake House
Welcome to your lakeside retreat! Escape to tranquility and breathtaking views with our unique lakefront Airbnb. Nestled right into the water of Lake Peekskill, our cozy lake house promises the ultimate getaway. Adventure awaits right outside your door! Take advantage of complimentary paddleboard or kayaks for a leisurely paddle on the lake. Located just minutes from renowned hiking trails and delicious dining options, our Airbnb offers the perfect balance of serenity and convenience.

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.

3Br Hilltop Ranch on 130acre farm w/ falls & creek
Newly renovated ranch house on a private hill top of an 130 acre magical property with stunning eastern views and overlooking a historic farm. Explore the hiking trails, dip in the wading pools of 90ft waterfall's upper cascades, bike to town or simply relax on the hammock while taking in views of the rolling hills. Escape to a beautifully designed private retreat, complete with a gourmet kitchen, cozy fireplaces, and comfortable bedrooms with quiet workspaces- learn more at cascadafarm

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!

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!

Spectacular Lake Views from Every Room & Garden
Our property boasts unparalleled views of Greenwood Lake and the mountains beyond. Our private garden features a seasonal waterfall cascading into a lily pond with fish and frogs. The shaded patio offers panoramic views and a gas grill. During the winter months, after skiing at nearby slopes, unwind in the claw foot tub or retreat to the cozy ambiance of our living room, with exposed wooden ceilings, a welcoming fireplace, a smart TV, a record player and board games.

Honeybug Snug near Omega Institute!
Welcome to the Honeybug Snug! Now with AIR CONDITIONING : ) The Snug is perfect for a family of 4 or 4 close friends. : ) We still have a little work to do on her and you get to watch her grow. Your comments will be taken to heart, as your comfort is our priority! We live right next door if you need anything : ) We are .9 miles for The World Renowned Omega Institute -Center for Holistic Studies. Less than 15 Minutes to Downtown Rhinebeck.

Farmhouse Oasis in the Hudson Valley, Stream Views
Plan your getaway to our farmhouse oasis at Wicked Finch Farm. Enjoy your Hudson Valley escape with expansive valley and stream views. Design meets rustic charm in the 4 bedrooms, 3 bathroom farmhouse. A huge updated kitchen, lots of gathering spaces, and loads of amenities make this the perfect choice for your family and friends. Recently featured on HGTV, InStyle Magazine, First for Women, AOL Living.
Popular amenities for house rentals in Pawling
House rentals with a pool

The Getaway-HOST & Co.

midcentury mod * HOT TUB * walk out trail 2 mohonk

Entire Home (private pool), Event Friendly

Bluestone Escape - Where everyone is at home.

Hudson River Sunset Getaway

BoHo Scandi Farm Retreat, Fire, Pool, Dog Paradise

Port Jefferson Convenient, Cozy and Chic!

Sunbeam Lodge: Pool+Sauna, 50 Acres, ‘70s Oasis
Weekly house rentals

Lakefront A-Frame Hudson Valley

Mohonk Abode | dog friendly + near hiking

Cabin with a View

Millstone Manor with East Mountain View

Modern Ski-Home With Views Near Hunter & Windham

Harlem Valley Hideout: Artsy ~ Pool ~ Tennis

Lakefront retreat

Private Lake House, Retreat
Private house rentals

Hillside Grove

Modern 3BD USMA Home near West Point with Hot Tub!

Unique Catskills Retreat: 3BR with deck & 3 acres

The Art House: 5-Acre Getaway w/ Fireplace

Private farm cottage +hiking

Beautiful Escape! Hudson Valley House

Designers Historic Connecticut Home

Lake house, ONE HOUR from NYC
Quick stats about house rentals in Pawling

Nightly prices starting at
Pawling holiday rentals start at £89 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
- Thunder Ridge Ski Area
- Catamount Mountain Ski Resort
- Minnewaska State Park Preserve
- Butternut Ski Area and Tubing Center
- Mount Peter Ski Area
- Sunken Meadow State Park
- Bash Bish Falls State Park
- Kent Falls State Park
- Brotherhood, America's Oldest Winery
- Mohawk Mountain Ski Area
- Powder Ridge Mountain Park & Resort
- Taconic State Park
- Bear Mountain State Park
- Mount Southington Ski Area
- Yale University Art Gallery
- Sherwood Island State Park
- Sleeping Giant State Park
- Ski Sundown
- Opus 40
- Compo Beach
- Warwick Valley Winery & Distillery
- Benmarl Winery




