Vacation rentals in Town of Pound Ridge

Spacious, private retreat 45 mins to NYC

Private, spacious, woodland views, perfect writer's retreat, romantic getaway, or space to chill! Ground-floor apartment in single-family home on 5 acres, 45 mins from NYC. 900 sq. feet of space. Full kitchen, 1 large bedroom, king-size bed & fun bunkbed. Premium bedding, fresh towels, toiletries. Simple, healthy breakfast, coffee, tea, fruit, drinks and snacks provided. 2 miles to Mt Kisco Metro North Station. EV charger. Walk to local nature reserves. 5 mins drive to restaurants and shops.

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…

Beautifully Renovated Studio - 1 hr from NYC

Completely new beautifully decorated apartment with easy access to many nearby towns (Ridgefield, Pound Ridge, New Canaan, Katonah, Bedford, etc.) We are near many hiking trails and parks such as Sal J. Prezioso Mountain Lakes Park. If you are planning to enjoy a day in NYC, we are only 1hr away either by car or train (New Canaan or Katonah Train Station are 15 min away). We have renovated the entire place with a lot of care and special touches for an incredible stay. We hope you love it!

Pound Ridge Paradise: Your Private Cottage Retreat

Escape to our serene Pound Ridge cottage, surrounded by nature's embrace and surrounded by quaint new england towns: New Canaan, Ridgefield,CT and Bedford, NY. Near renowned attractions like Jean-Georges' Inn, Grace Farms, and The Glass House, it's an idyllic retreat. With 2 bedrooms, a full kitchen, and a cozy porch, it's perfect for relaxation or family visits. Hiking trails, charming towns, and outdoor adventures await – Book your stay today and experience the magic for yourself.

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.

Cozy 1 Bd Private Entrance In-law Suite & Hot Tub

Charming Getaway in Norwalk, CT - Discover comfort and convenience in this cozy low ceiling short-term rental located just 5 minutes from local markets, dining spots, Norwalk River Valley Trail, Norwalk Hospital and shopping centers. Perfect for single travelers, work related or weekend adventurers, this space offers a warm, inviting atmosphere with modern amenities. Enjoy easy access to local attractions and scenic spots, the perfect base for exploring coastal Connecticut!

A Lovely Cottage in the Woods

Welcome to our cottage located just 1 hour north of NYC! It is nestled into 2.7 acres of beautiful gardens, mossy groves, and lovely woods. Nature abounds: The property abuts the 4000 acres of the Ward Pound Ridge Reservation. A trailhead begins right across the driveway. The cottage is equipped with a stone fireplace, spacious kitchen, living room area, table for dining and working, and a sleeping loft. During the summer, a private salt water pool is available.

The Perch, a luxe cottage in the woods 1h from NYC

"The Perch is a peaceful, thoughtfully appointed woodland haven." - Elyssa The Perch, our luxe cottage nestled in the woods with a heated saltwater pool in Bedford, NY is the perfect country getaway. Surrounded by nature, this charming retreat is the perfect getaway in any season for those seeking peace and quiet, in the heart of Bedford with all the surrounding amenities just 1 hour from NYC. **Pool closed for the season, will re-open late May 2026**

Guest suite with private enter

Private room with private enter and bathroom attached dedicated work space and privat parking. On a 1.5 acres property. With fast internet. Located 5 minutes of walking distance from ASML office park, 5 minutes drive from Norwalk corporate park, 9 minutes drive from Wilton Downtown and 15 min drive from Norwalk train station. Close to a lot of restaurants, coffee shops, stores and parks. The owners live in other part of the house. Family owns cats.

Oscaleta Lake House: Modern Lux

Escapology-A spectacular destination, designed as a luxury Lakehouse with its own dock and 120' private lakefront. Close to NYC and ideal for a quick trip, remote work or an extended retreat. Artfully Designed Space-Modern retrofit thoughtfully curated with custom artwork and furniture throughout this historic 1940's gem. Purpose built for your outdoor routine, Canoeing, Swimming, Hiking, Grilling etc We recommend 3+ nights if you can.

French Guest House in Waccabuc

A private, European-style retreat just 60 minutes from NYC. Set on an eight-acre gated French estate with its own lake, this guest house feels like a mini Versailles with 18th-century statuary, fountains and manicured gardens. Designed by David Easton, it features heated stone floors, a heated towel rack, luxury linens, gold fixtures, fast WiFi, and a private entrance. Minutes from Waccabuc Country Club and the Katonah train station.

Pound Ridge Cottage

Take it easy at this private and tranquil getaway. A mile from town. We have two dogs, one a Newfoundland and the other a 60lb mixed breed. They mostly stay by the main house and are further controlled by an electric fence. Please don’t feed them anything or they likely will move in with you. They’re friendly but we don’t want other dogs there for obvious reasons: they’re dogs!