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Harlem Valley Hideout - Artsy Home with Pool & Tennis

House in Pawling, NY

5 guests·3 bedrooms·3 bathrooms
4.8 · 12 reviews

Why you'll love this stay

Outdoor Living

Outdoor Living

Seasonal pool and private tennis court elevate summer and weekend escapes.

Entertainment & Amenities

Entertainment & Amenities

Chef's kitchen and color-rich decor inspire playful, memorable gatherings.

Location & Accessibility

Location & Accessibility

Easy day trips to Beacon, Millbrook, and quaint Pawling villages.

Property details

Marvel at the playful design of this 2-Bed, 3.5-Bath mid-century cottage with a nursery, just 1hr 40min from NYC. Perfect for art lovers & families alike, this one-of-a-kind renovated home is full of life, bursting with color & dynamic designs. Highlights include a chef's kitchen, pool, fireplace, firepit & a private tennis court—an ideal family getaway. Nearby towns: Wassaic, NY (25mins), Kent, CT (25mins), Millbrook (30mins), New Preston, CT (35mins), Beacon (35mins), Poughkeepsie (35mins) Pets: Not allowed. Smoking: Not allowed. Events: Not allowed. Suitable for: children and infants. Additional rules: AGE REQUIREMENT Primary guest booking must be 25 years or older. PETS Sorry, pets are not permitted at this property. SMOKING No smoking is permitted inside the house. If you must smoke, please do so outside and dispose of butts properly.. EXCESSIVE CLEANING FEES We kindly ask that guests treat the home with care and respect. Should the property require cleaning beyond the standard turnover—due to excessive mess or incidents involving bodily fluids such as blood, vomit, or waste—a $500 fee may apply. Any linens or furnishings damaged beyond repair will also be subject to replacement charges. These situations are considered outside the scope of routine housekeeping and require specialized attention to ensure the safety and well-being of our team. MID-STAY CLEANING REQUIREMENT For stays of 28 nights or longer, a guest-paid mid-stay cleaning is required. The cleaning will be scheduled at a mutually convenient time during your stay. The cost varies by property and will be confirmed before scheduling. ACCURATE GUEST COUNT The number of guests must be accurately disclosed at the time of booking. While we don’t charge extra for additional guests up to the home’s maximum occupancy, this information is essential so we can properly prepare and stock the home. Please note that penalties may apply if guest counts are inaccurate or intentionally misrepresented. OUTSIDE SERVICE PROVIDERS Outside staff such as private chefs, massage therapists, or other service providers are welcome, but prior approval is required before they come on-site. SUPPLEMENTAL AGREEMENTS Guests may be required to sign a rental agreement. If applicable, it will be sent after the booking is confirmed. SEPTIC Please be mindful of the septic system and do not flush anything down the toilets or drains other than toilet paper. This includes any and all personal hygiene products, baby wipes, bleaches and strong chemical cleaners. Harlem Valley Hideout is a tranquil mid century oasis that feels worlds away from the hustle and bustle. The circular driveway positions the home thoughtfully, offering a comfortable distance from the road and the captivating grounds have ample space for enjoying quality time with family and friends. The home is committed to sustainability, it is partially powered by the solar roof and uses plant-based and EWG-certified cleaning products for a healthier, eco-friendly living environment. The fully equipped kitchen, located on the main level, showcases sleek black cabinetry with brass hardware complemented by Italian spinning top-shaped pendant lights over the center island. The cooktop is framed by a striking Bianco Ondulare marble backsplash chosen to match the vintage dining table crafted from the same marble. The kitchen also contains a vintage, Danish mid-century secretary desk cabinet, which doubles as a laptop workspace next to a sliding glass door and just off the kitchen is a convenient powder room. The home boasts lots of natural light creating a bright and airy feel. Beyond the dining area lies the living room which blends modern and vintage furnishings, and is further accented by a curated gallery wall. To the right, a tranquil library with comfortable chairs offers the perfect spot for relaxation. Adjacent to the library is a cozy office and TV room containing a sleek modular sofa. Downstairs, the expansive family room exudes rustic charm with large windows and comfy, oversized furniture - the perfect setting to watch a movie by the fire.. This space includes a mini kitchen with a breakfast bar, fireplace, smart TV and full bathroom making it an ideal place to unwind or entertain. Upstairs, the primary bedroom offers a serene retreat complete with a renovated ensuite bathroom that retains its mid century charm. The queen bedroom, adorned with calming palm leaf wallpaper, evokes a vintage Polynesian vibe and shares a bathroom with the nursery. The nursery features a crib, rainbow hues and an assortment of books and toys. Each bathroom throughout the home embraces bold colors and playful patterns characteristic of 1950s bathroom design, adding a fun and vibrant touch. The blue sofa in the office converts to a double-size bed for extra sleeping. The fenced-in pool area is a peaceful hangout spot complete with sunbeds, side tables and umbrellas, a dining table with chairs, and additional seating options. Nearby, the newly resurfaced tennis courts offer a great way to stay active—white-soled tennis shoes only, please. The patio and BBQ area include another dining table and lounge furniture, while raised garden beds produce fresh vegetables and herbs throughout the summer. A cozy outdoor fire pit with seating invites you to unwind, with additional seating areas scattered throughout the grounds for plenty of outdoor relaxation. THE POOL IS NOT HEATED. Ideal for families, the home has an additional room with a crib, a highchair and Pack 'n Play. Other infant accessories are available on request. Duchess county is known for its small town charm, historical background and beautiful surroundings. With a wide range of outdoor activities, important landmarks and nearby towns worth visiting, Harlem Valley Hideout is a great base to explore all that Pawling and the surrounding Hudson Valley region has to offer. Check out these recommendations from the owners: Pawling, NY: Groceries: Hannaford just 3 mins away. DeCicco & Sons in Brewster or WholeFoods in Danbury for larger grocery orders both have delivery services. Coffee/Breakfast: The Dancing Bear Cafe, Sunflour Bakery Pawling, McKinney & Doyle Corner Bakery. Hiking/ Outdoor Activities: Nuclear Lake with more than 4 miles of trails loops & stunning views on the Appalachian Trail; Pawling Nature Preserve for hikes, nature walks & bird watching; Maybrook Trailway dedicated to bicyclists and hikers only; Dutcher golf course the oldest 9-hole municipal golf course in the US; Pawling Mountain Club a sports club and shooting range. Ski options: Thunder Ridge Ski (8mins); Mohawk Mountain (45 mins); Catamount Ski (1 hour). Horseback Riding Lessons with Kirby Hill Farm or Rounded Crest Farm. Seasonal Activities: Dykeman Farm for pumpkin picking, hayrides and fall activities. Pawling Farmers Market or Barton Orchards for locally produced goods. Wassaic, NY Vitsky Bakery; Wassaic Lantern Inn - a pizza restaurant; Wassaic Project - an artist-run nonprofit contemporary art gallery, artist residency & art education center; Tenmile Distillery Kent, CT Kent Barns - historic village with curated shops, modern art galleries & award winning restaurants; One Hill Swyft a modern tavern; Kent Falls Brewing. New Preston, CT Lake Waramaug State Park; The Smithy Cafe at 9 Main; The Privet House for home goods, antiques & curiosities; Plain Goods for shopping; Sweeets for worldwide chocolates & candies. *Please note that the pool is available during the summer season only. Please inquire regarding opening and closing dates.

Sleeping arrangements

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 King Bed

What’s included

  • Parking

    Parking

  • EV charger

    EV charger

  • Pool

    Pool

  • Washer

    Washer

  • Dryer

    Dryer

  • Air conditioning

    Air conditioning

  • Heating

    Heating

  • Fireplace

    Fireplace

Guest reviews

Star icon 4.8 | 12 reviews
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Colleen

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October 2026

We thoroughly enjoyed our stay here in Pawling — the house had plenty of space for board games, movie night, cooking family meals, s’more’s by the fire pit and of course playing tennis!! Court was in great condition with fresh coat of paint and no cracks too. House has a lot of character and whimsical decor which we all appreciated. Very close drive to downtown Pawling and parks with hiking.

J

Jill

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October 2026

Hard to put into words what a wonderful stay we enjoyed at the Harlem Valley Hideout! It absolutely exceeded all our expectations! It was the most comfortable, stylish, well appointed rental we’ve ever stayed in over the years of visiting family in the area. The second we walked in we felt like it was a home away from home. The floor plan flows so nicely and it has abundant living spaces without feeling too huge. The home has been immaculately restored by the owners, who clearly have passion and skill when it comes to design, art and architecture! It has tons of funky mid century charm that fits perfectly with the architecture and history of the rehabbed home. Thank you so much and we’ll hope to return on our next trip.

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Emma

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September 2026

We had a wonderful weekend stay with our three children , playing tennis and enjoying the lovely garden and surroundings! The house is beautiful and the interior decor is so much fun!

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Nichol

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September 2026

A beautiful house with great design, close to NYC, very responsive management, and very well appointed. And a beautiful pool to sit next to!

Know before you go

House rules

Check-in: 4:00pm

Checkout: 11:00am

No pets allowed

Min. age to rent: 25

No smoking

No parties

Have a question about this property?

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