Holiday rentals in Pound Ridge

1840Farmhouse, 65"OLED4k, firepit, 3x4ktvs, 3acres

Relax in this calm, stylish country estate. 65" LG OLED surround sound home theater! Gorgeous renovated 1840 farmhouse and barn on 3 acres in Pound Ridge NY. 55" 4k TVs with bluetooth soundbars in each bedroom. Enjoy grilling on the gas range and cooking smores in the firepit on 3 private acres. escape the city but with easy commute to NYC via the Stamford Express train to Grand Central. Full Solar with Battery backup so no power outages. listed Streaming services require your own account.

Ranch in the Woods | A Peaceful Designer Retreat

Welcome to @ranch_inthewoods No cleaning fee STR permit #34035 This newly built ranch-style home with thoughtfully designed wabi-sabi interiors sits in the woods of the Warwick Valley. It's located a short drive away from several lakes, hiking trails, breweries, and dining experiences. It features forest/creek views, designer furniture, modern appliances (dishwasher, washer/dryer, gas cooktop), smart 4k TV, gym & yoga studio, gas firepit, and ample deck with an outdoor kitchen & dining area.

Serene Pond Views Charming private patio…

Country Charm Awaits. 45 miles north of George Washington Bridge. Our 2 room efficacy apartment w. microwave, mini fridge & private entrance + parking space. Great WiFi, Apple TV. Enjoy views overlooking Henderson Pond. 1/4 walk to Query State Park, 36 acres w. trails. Our apartment is 4 miles from town of Ridgefield, 3 miles from Wilton town center, 6 miles from New Caanan & 8 miles from Westport Town Center. We have a couple of small puppies who will welcome you too. So we don’t allow pets…

Sunny French Cottage

This unique, sunny cottage has it's own style. Private and peaceful, completely renovated cottage with French vibes. Originally used as a painting/design studio. It is an ideal place to relax and enjoy the surrounding nature. The upstairs bedroom is loft style and has a luxurious queen size bed. It's ideal for short and long stays. It is a perfect place for cozy evenings and lazy mornings, it can also serve as a temporary workplace. High tea style, organic breakfast available (20$ per person)

1795 colonial w private 2 bd rm, 1 bth,LR,Kit apt

A unique private and quiet 2 bedroom (1 double bed, two single full beds, 1 sofa bed ) totally self contained apt over 2 floors ,with its own seperate entrance.The ground floor has a mud room and full eat in kitchen.The 1 st floor has a sitting room,bathroom and 2 bedrooms. The space is the end wing of and attached to Shaker Hollow, a classic 1795 colonial.A Stone patio with outdoor furniture overlooks 3 1/2 acres of garden and a meadow .There is the use of a large fire pit and gas BBQ.

Oscaleta Guest House: Lakefront Cabin

Escapology-A spectacular lakeside destination, designed as a luxury suite with its own dock. Close to NYC and ideal for a quick trip, remote work or an extended retreat. Glamping-A cabin in the woods on a lake surrounded by nature, but tech-enabled with all the modern perks. Artfully Designed Space-Modern retrofit thoughtfully curated with custom artwork throughout this historic 1920's cottage. Purpose built for your outdoor routine- from grill to canoe…. We recommend 3+nights if you can.

French Estate Guest House on Private Lake

A private, European-inspired guest house set on an eight-acre gated French estate, just 60 minutes from NYC. Surrounded by manicured gardens, 18th-century statuary, and a private lake, the setting feels transportive—a French countryside retreat. Designed by architect David Easton, the space blends classic elegance with modern comfort: heated stone floors, a heated towel rack, fine linens, curated finishes, and a private entrance. Perfect for a refined weekend escape or a quiet reset.

Private farm cottage +hiking

Private home with large stone patio with access to over 4,000 acres of trails in Ward Pound Ridge. Owner lives on the property and is happy to introduce you to the horses Lincoln, Domino, and Forceti. The house has its own driveway and sits on two acres and is quiet and private. We have a great internet connection, with two working spaces set up in the house (1 in the bedroom and another in the kitchen) for remote work. Enjoy the scenery and tranquility of northern Westchester.

The Perch: Saltwater Pool Woodland Cottage Retreat

The Perch, a design-forward woodland cottage surrounded by nature just one hour from NYC perfect for couples escaping the city for a quiet Hudson Valley weekend. Spend slow mornings overlooking the woods, afternoons by the saltwater pool, and evenings exploring Bedford’s historic village restaurants and trails. "The Perch is a peaceful, thoughtfully appointed woodland haven." - Elyssa *Pool re-opens late May through mid-Sept* inquire for details

Private cottage in horse country &1 hour from NYC!

Private cozy cottage located in horse country on the the NY/CT borders ( New Canaan, Ridgfield, Wilton ) It is a perfect quiet getaway for couples or a friends night out , a great pit stop for travelers /skiers , fine dining , shopping /antiquing , Ridgefield Playhouse , hiking ,and a short ride to Grace Farms . 1 hour train ride to NYC . We provide organic fruit,breakfast snacks, coffee and tea . It is your home away from home and more :)

Peaceful Light-Filled Guesthouse salt pool/sauna

Step into a peaceful, well-appointed home nestled on 14 acres of ancient trees, stone walls, and meadows in Pound Ridge, NY. This light-filled guesthouse is designed for relaxation, with a heated saltwater pool available in summer, sunbathing under a majestic maple tree, and evening stargazing by the outdoor fire pit, or unwind in the pool side sauna.. Perfect for families, small groups, or couples seeking a peaceful nature retreat.

Charming Cottage in historic Bedford Village

“This place emanates why I would live here!” - Robert 7/24 Welcome to your cozy retreat just a 5-minute walk from the heart of historic Bedford Village. This private petite but cozy one-bedroom cottage sits among 200-year-old maple trees on the grounds of an original 1840s farmhouse, offering charm, comfort, and convenience—just 39 miles from Manhattan and under 10 minutes to the Bedford Hills (Harlem Line) train station.