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House vacation rentals in Pawling

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Popular amenities for Pawling house rentals

House rentals with a hot tub

Top guest favorite
The guest house features a contemporary exterior with green paneling and wooden accents. An extensive patio surrounds the structure, furnished with lounge chairs and a dining set. Large glass doors and windows invite natural light, while views of the surrounding landscape are visible.
Home in High Falls
5 out of 5 average rating, 231 reviews

Our Place - A Big Little House

BrianRating, 5 stars3 weeks ago
Patti's home exceeded every expectation! From the moment we arrived, we were blown away by the thoughtful design and stunning architecture. The house is beautifully crafted with soaring high ceilings, an airy and light-filled interior, and countless thoughtful touches that made our stay feel truly special. The location couldn't be better - we were perfectly positioned for amazing hiking adventures and discovered some incredible restaurants nearby. Her local knowledge was invaluable and really enhanced our entire experience. Speaking of Patti, she is an absolutely wonderful host! Communication was seamless from booking through checkout - she was incredibly responsive, easy to reach, and genuinely helpful with every question we had. This home is a true gem, and Patti is the kind of host that makes Airbnb special. We can't wait to return! Highly recommend to anyone looking for a perfect getaway in Ulster County and the surrounding region.
Superhost
An outdoor hot tub is positioned on a wooden deck, with a view of the house and its large windows. Surrounding trees and a light covering of snow add to the serene winter setting.
Home in Wallkill
4.86 out of 5 average rating, 123 reviews

Modern Upstate Gem Surrounded by Trees | Hot Tub

DaynaRating, 5 stars3 weeks ago
Sahir’s place is exactly as described and matches the photos perfectly. Even though it rained during our stay, we still had a fun and relaxing weekend — including our 5-month-old baby and our dog! Everything was super clean, and I loved that it wasn’t too far from NYC or North Jersey.
Guest favorite
A sunlit seating area features light-colored, oversized chairs and a round coffee table. Large sliding glass doors open to a view of the forest, enhancing the connection to nature. A minimalistic pendant light hangs elegantly above, while a decorative plant adds a touch of greenery.
Home in Cold Spring
4.95 out of 5 average rating, 324 reviews

Hilltop Hideaway Forest Villa on 13 acres!

RebeccaRating, 5 stars2 weeks ago
My family of 8 adults needed a place to stay near a wedding at Glynwood. This wonderful spot was minutes away from the farm and town. The number of bedrooms and bathrooms gave everyone the privacy desired while the well equipped kitchen and living rooms had plenty of space for gathering. The house and land are beautiful, including the trail. Paula was easy to communicate with and my whole family felt comfortable and happy with the spot. Highly recommend!
Guest favorite
A serene lakeside view is captured at sunset, with vibrant pink and purple hues reflecting over the calm water. Silhouetted trees frame the scene, and distant hills provide a tranquil backdrop to the picturesque landscape.
Home in Pine Plains
4.98 out of 5 average rating, 123 reviews

Twin Island Lake House • Hot Tub

KaiRating, 5 stars3 weeks ago
We had a wonderful stay at this location during my daughter’s graduation from Bard College. The location has beautiful views of the lake and the layout of the property was perfect for the family to gather and celebrate, while also giving everyone the space for their own quiet time or rest. I would definitely recommend this location and hope to have the opportunity to stay again.
Superhost
A spacious backyard is highlighted by a shimmering in-ground pool surrounded by lounge chairs and cabana umbrellas. Lush greenery frames the area, creating a tranquil atmosphere. A slide is visible in the pool, and a vibrant blue sky with clouds adds to the inviting scene.
Home in Beacon
4.92 out of 5 average rating, 133 reviews

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

MarissaRating, 5 stars2 weeks ago
We had a great stay at Tiffany’s place! Everything was exactly as described and she was great at communicating throughout the stay.
Guest favorite
An outdoor hot tub is situated on a wooden deck, with a 55-inch TV mounted on the wall nearby. Soft lighting creates an inviting ambiance as the sun sets behind distant hills, offering a serene escape for relaxation and entertainment.
Home in Lanesville
4.95 out of 5 average rating, 118 reviews

Hunter Chalet | Hot Tub w Outdoor TV & Firepit!

DianaRating, 5 stars6 days ago
We had a fantastic stay while celebrating my husband’s 40th birthday! Michael’s house was clean, comfortable, and exactly what we were hoping for. The location was perfect — peaceful and quiet. It was conveniently located between Phoenicia and Hunter/Tannersville, which made it easy to get out for hikes and explore the area with our kids. The hot tub was a huge highlight and got lots of use. And we loved the views from the second floor deck! It was also such a bonus that the house was dog-friendly — we loved being able to bring our pup along for the trip! The only thing we missed was a high chair, which would’ve been helpful with our toddler — but otherwise, the house was really well-stocked and family-friendly! Michael was a great host — responsive, helpful, and made the whole process really smooth. We’d definitely love to come back again!
Top guest favorite
An aerial view showcases a three-story chalet-style home surrounded by lush greenery. The extensive decks feature ample seating, while the structured landscaping blends seamlessly into the natural surroundings. The driveway leads to the main entrance, providing a welcoming approach.
Home in Port Ewen
4.99 out of 5 average rating, 120 reviews

River View outside Kingston w/ Hot Tub & Sauna

ShoshanaRating, 5 stars1 week ago
We had a wonderful stay at Jan's place. It was exactly what we were hoping for: The place itself was a great location, the aesthetics were very pleasing, the beds were comfortable, and it felt very relaxing to be there. And for anything that we needed, Jan responded very quickly and with care.
Guest favorite
A wooden lounge chair is positioned near a serene saltwater pool, surrounded by lush greenery. The pool's clear water reflects the inviting outdoor space, which is complemented by concrete paving and a manicured lawn.
Home in Cottekill
4.95 out of 5 average rating, 275 reviews

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

TylerRating, 5 stars4 weeks ago
Amy & Sean's place was perfect. We choose it for its proximity to our wedding venue and couldn't be happier. The HOT Tub was just what we needed after a long day of preparing for our wedding. 100% recommend and will definitely consider staying again.

House rentals with a pool

Superhost
The outdoor area is highlighted by a heated pool surrounded by lounge chairs and a well-maintained garden featuring a mix of hedges and trees. A spa is situated near the pool, with a stone patio providing additional seating under a blue sky dotted with clouds.
Home in Litchfield
4.82 out of 5 average rating, 105 reviews

The Getaway-HOST & Co.

CrystalRating, 5 stars9 months ago
I absolutely enjoyed my weekend here. The home is beautiful. Everything you could possibly need was provided In the home. Everything was clean, and neat. House is filled with light. The pool and hot tub were enjoyable. The host were amazing and had great communication, assisted us when needed right away. I would highly recommend staying here, and they are pet friendly which is always a plus for me. The yard is fenced in. Which made it easy to let the dog out, and great for the dog to explore. A++++ Will probably be back sometime In the future.
Top guest favorite
A serene pool area features a clear blue in-ground pool surrounded by lounge chairs with red cushions. A vibrant hibiscus flower adds a splash of color, and a slide is visible for added fun. The area is enclosed for safety.
Home in Monroe
4.97 out of 5 average rating, 201 reviews

Garden Level Suite with Beautiful Pool

GraceRating, 5 stars3 months ago
We had an amazing time at Marybeth’s suite—it truly felt like a winter wonderland. Our kids had a blast "swimming" in the snow and "rolling" over the gentle hills. Every moment was filled with joy, whether we were relaxing in the sunroom, playing in the snow, or swinging outside. The time spent together as a family, along with our conversations with Marybeth and her family, was truly precious. We can’t wait to return in the summer!
Superhost
An open living space is visible, featuring wooden beams that create a warm atmosphere. The dining area is filled with natural light, showcasing a wooden table surrounded by chairs, with modern light fixtures above. A staircase leads to the upper floor, enhancing the spacious design.
Home in New Paltz
4.86 out of 5 average rating, 159 reviews

Scenic River View Escape | New Paltz

TatiaRating, 5 stars2 weeks ago
I spent my birthday at this beautiful house and couldn’t have asked for a better experience. The place was spotless and full of natural light, with lovely views that made the stay even more special. The atmosphere was peaceful and clean, and the house had everything we needed for cooking and relaxing. I truly felt at home and appreciated all the thoughtful touches. Highly recommend for anyone looking for a cozy, well-equipped getaway!
Guest favorite
A serene heated saltwater pool is framed by lush greenery, reflecting the sky above. A rustic wooden edge provides a natural transition between the pool and the surrounding landscape, which includes a prominent tree adding to the tranquil ambiance.
Home in Woodstock
4.92 out of 5 average rating, 244 reviews

Little owl Japanese teahouse: pool is OPEN

JaneRating, 5 stars2 weeks ago
My husband and I had a wonderfully relaxing time at the Little Owl Teahouse. It’s a cozy and well-outfitted cabin with a super comfy bed and a great leather reading chair. Drank lots of the delicious mountain well water. Made breakfast in kitchen — love the pans and electric cooktop. Short drive to Woodstock for dinner. And oh the beauty of the surroundings - scenic views everywhere. Our two little doggies were happy to romp in the fenced in yard. Little too chilly when we were there but pool looks so appealing. Lisa is a proactive and super responsive host.
Guest favorite
A spacious outdoor pool is surrounded by a stone patio, nestled within a serene environment of tall trees. The pool features a diving board and is complemented by nearby planters. A main house can be seen in the background, enhancing the tranquil setting.
Home in Stamford
4.96 out of 5 average rating, 251 reviews

Midcentury Modern ZenHouse Sculptor Studio

EamonRating, 5 stars6 days ago
Truly one of a kind property. Relaxing, calm, extremely responsive and helpful host. If you are looking to get out of the city or just need some time away to think, look no further. 10/10.
Guest favorite
Home in New Paltz
4.93 out of 5 average rating, 135 reviews

Harrison Field Pool SummerUpstate GetAway Hiking

EmmaRating, 5 stars3 weeks ago
We had a great stay at Nathan’s place. The playroom was great for our kids and we all enjoyed the pool. The view was also beautiful. We will definitely be back!
Guest favorite
An open living space features a grand piano positioned near large windows that offer views of the surrounding mountains. A light-colored sectional sofa and a round coffee table create a comfortable seating area, accented by a dining table beside it. Natural wood beams add architectural interest.
Home in Saugerties
5 out of 5 average rating, 152 reviews

Upstate Modern Scandinavian Barn in the Catskills

Zoe StarRating, 5 stars3 weeks ago
We truly enjoyed our stay at Wilderkill Barn. Maria Cristina and William were exceptional hosts—warm, attentive, and genuinely committed to making our visit special. They went above and beyond to make us feel welcome. The home was a haven, with a hot tub, sauna, pool, fire pit, pool table, and immersive sound and movie systems—all of which made our stay delightful despite the cold, dreary May weather. We can't thank them enough. ***That said, we feel it's necessary to address a serious issue with Airbnb itself that arose while booking this property, unrelated to the property itself. An unexpected tax was added after booking, and Airbnb has yet to provide a clear explanation. After years of loyalty, we were disappointed by their evasive and unhelpful customer support. This experience has made us reconsider using the platform in the future. We urge potential users to scrutinize all fees carefully and be aware that Airbnb’s support may be difficult to navigate if problems arise.***
Top guest favorite
A serene outdoor space features a heated saltwater pool surrounded by well-maintained grass. Lounge chairs are positioned along the pool's edge under the shade of a large tree, creating a peaceful area for relaxation. The property is bordered by a wooden fence and offers expansive views of the surrounding landscape.
Home in Pound Ridge
5 out of 5 average rating, 163 reviews

Peaceful Light-Filled Guesthouse 1 Hour From NYC

MollieRating, 5 stars3 weeks ago
Obsessed with this Airbnb! My husband, dog and I typically go to upstate NY or the Berkshires for long weekends but I came across this Airbnb as I had an event in westchester over the long weekend. Highly recommend! So much hiking, wonderful restaurants and so close to the city. My dog loved this property as well! Will be back.

Weekly house rentals

Guest favorite
The image displays a serene waterfront view, showcasing a private home nestled among lush greenery. The water reflects the building and surrounding trees, creating a peaceful atmosphere. A small dock with a boat is visible, enhancing the outdoor recreational appeal.
Home in New Milford
4.91 out of 5 average rating, 93 reviews

The Getaway: Beautiful Waterfront - New Milford CT

RosemarieRating, 5 stars2 weeks ago
Enjoyed our stay in the woods with a beautiful view of the river. Easy to get to and very close to the charming town of New Milford and many good restaurants. Although right off a busy road it was quiet inside the house. The great room, which is on the top floor, is wonderful and perfect for both working and entertaining and has a full bath. It looks like the photos with an amazing view. The bedrooms and another bath are underneath. The master bedroom is the best. Just be aware you can hear the footsteps from above and not all of the bedroom windows have bug screens. The entertainment room on the lower level which opens into the yard is filled with games and a large tv and was lots of fun. The weather was cool & rainy so we didn’t use the outdoor space as much as we thought we would but there was a kayak. The house was private and although there is no interior deadbolt we felt safe. The house was clean with good heat/ac and wi fi. Hosts were responsive.
Top guest favorite
Home in New Milford
4.97 out of 5 average rating, 31 reviews

OWL's PERCH Candlewood Lakefront Rustic Cottage!

JackieRating, 5 stars1 week ago
If you're looking for a cute little cottage in the woods near the lake to recharge and relax - this is it! KC provided an extensive list of instructions and to know's, which made check in/check out and all the in-between fool proof. KC was super friendly and responsive as well!
Guest favorite
An inviting inground pool is surrounded by a wooden fence and shaded by lush trees. Several lounge chairs are positioned on the deck, and a colorful inflatable ring floats in the water, offering a serene outdoor space for relaxation.
Home in Hopewell Junction
5 out of 5 average rating, 20 reviews

MCM in the Hudson Valley

LesleyRating, 5 stars3 weeks ago
We had a fantastic stay at this Airbnb! The place was impeccably clean and incredibly comfortable, making it a perfect retreat. The host was very responsive and helpful, addressing all our needs promptly. Highly recommend!
Guest favorite
A modern cabin features a dark wooden exterior and large glass windows allowing natural light to fill the interior. A welcoming deck is furnished with chairs, surrounded by lush greenery and mature trees, creating a peaceful and inviting outdoor space.
Home in Pleasant Valley
5 out of 5 average rating, 27 reviews

The Wildflower House

MatthewRating, 5 stars1 month ago
Loved every part of our stay with Kristine. Perfect for a romantic weekend away - gorgeous cabin, well appointed, and great kitchen for cooking-in. Her recommendations for local spots were also so thoughtful. Thank you again!
Top guest favorite
A cozy living room is furnished with two gray sofas and a patterned armchair. A wooden coffee table sits in the center, complemented by a decorative plant. Natural light enters through large bay windows, highlighting the space's warm, neutral tones.
Home in Sherman
5 out of 5 average rating, 88 reviews

Slice of Paradise in the Country

AmoryRating, 5 stars1 month ago
This place is even better than the photos! Wow. It felt luxurious. Such a beautiful home. I loved all the snacks Deborah left us and the thoughtful touches (chocolates and water bottles next to the bed). So incredibly kind and very appreciated. This is definitely the best AirBnB I have ever stayed in. One “tip,” if you are someone who is used to sleeping in a dark room, then bring an eye mask because the primary bedroom has the most gorgeous window behind the bed and two magnificent skylights above the bed, but there aren’t blinds/shades. So the room is very bright. I would definitely love to go back (and bring my eye mask). Haha. Everything is so nice, the place is SPOTLESS, and the home feels very “new.” I just loved it. Also, Deborah has the NBA channel, which my son is obsessed with watching. This is just the best house - beautiful and pristine, yet cozy. Way nicer than most hotels. I loved the house so much! I loved the shampoo, the fluffy robes, the kids toys, everything!
Top guest favorite
The exterior of Millstone Manor is framed by lush greenery and mature trees. The home is characterized by a blend of siding and stone accents, featuring multiple windows and a welcoming entryway. A decorative gazebo with floral arrangements complements the inviting landscape.
Home in Dover Plains
5 out of 5 average rating, 69 reviews

Millstone Manor with East Mountain View

JamesjRating, 5 stars6 days ago
I've stayed at Richards' place before. Each time it is the same. The home is very neat and clean, all the room are very comfortable. The view is truly awesome. If the host is ever needed, he is always very responsive. Self-sufficient home, we never needed anything. Would stay there again for sure!
Top guest favorite
A spacious wooden deck is visible, overlooking a vast landscape of rolling green hills. Fresh foliage is seen on scattered trees, and the clear blue sky enhances the tranquil outdoor setting.
Home in Sharon
5 out of 5 average rating, 28 reviews

Nature lover’s retreat in NWCT, breathtaking views

ScottRating, 5 stars5 months ago
Kellen and Samantha's home and property are very special--a wonderful location for a restful retreat in nature that is also a short drive to several charming towns in northwest Connecticut. The hilltop site offers breathtaking views of surrounding mountains, valleys, and forest. The residence sits atop a long driveway off a gravel road so is serenely quiet and private. Inside, the space was immaculate, thoughtfully designed, and very comfortably furnished. The shower, bed, towels, and linens were all particularly fantastic, as was the full kitchen which allowed us to cook nightly. The area is exceptional for hiking, culinary delights, and all sorts of shops. And our hosts were proactive, helpful, and clear in all of their communications. We really loved staying here, as did our dog, and we hope to return. Highly recommended!
Guest favorite
The exterior of a large three-bedroom home is captured, showcasing a light-colored facade with multiple windows. A welcoming front porch with a double door entry is visible. The surrounding lush green lawn is accented by neatly trimmed shrubs and trees, contributing to a serene outdoor setting.
Home in Dover Plains
5 out of 5 average rating, 34 reviews

Somewhere That’s Green, Gameroom/Bar, Fenced yard

DinaRating, 5 stars6 months ago
This was an amazing place! The host was incredibly kind, providing beds, treats, and toys for my dogs. The atmosphere was cozy and felt like home, making it perfect for spending Thanksgiving with my family. I highly recommend this place and would definitely love to come back again!

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