Holiday rentals in Bedford Hills

Cozy 1 Bdrm Apt; Privt Entry; 5 min walk to train

This cozy apartment is on the lower level of a house, a 5 minute walk to town and the Harlem Line, Metro North Train stop. A separate entrance to the apt offers complete privacy. This gorgeous space has a fully equipped kitchen, bathroom, comfy twin beds . Located in the adorable town of Mt. Kisco, allowing you to take strolls to access restaurants, boutique shops, library, park and bars. It has the feel of a country retreat, a quaint town, and it's an easy commute to White Plains or NYC.

The Cottage on Maple Grove Farm

Escape to this charming historic cottage on the border of artsy Pound Ridge and bucolic Bedford, NY. Maple Grove Cottage features a light-filled kitchen with French doors, beamed living room with working stone fireplace, a cozy bedroom with full bath and attached front sitting room. Enjoy your morning coffee sitting on the small deck outside the kitchen which overlooks a newly planted vineyard, watch the sun set over the adjacent field. Half mile from 5000 acre Ward Pound Ridge Preserve.

The Magic Red Barn with Heated Salt Pool

Experience country magic one hour from NYC! Our heated saltwater pool offers a perfect retreat. Enjoy nearby farmers' markets, Muscoot Farm, and scenic orchards. Stay in a renovated 1,000 sq ft luxury loft on the second floor of a private barn that includes: 1 king , 2 queen , and 1 toddler beds, a full kitchen (half-size fridge, mini freezer), microwave, and full-size oven. Ideal for guests who need to « escape ». Enjoy privacy—no other guests. Good Wi-Fi and full-house generator.

The River Loft

Escape to The River Loft, a private riverfront retreat in Weston, CT. Built in 2015 by a visionary local architect, The River Loft open-air design seamlessly integrates the outdoors with the interior space. As you step inside this 750 sf small home, you'll be instantly captivated by the layout that makes it feel spacious. Sitting on over 2 acres of forested land with private river access. Book now for an unforgettable experience. For more images & videos visit insta @the.riverloft

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.

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**

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.

A nice place to getaway

Situated on a serene neighborhood surrounded by trees. It gives you such a relaxing feel staying there. This property is lower level of a private house with living room, full kitchen ,1 bedroom and a 1 full bath. Very close to multiple parks, hiking spots and fruit picking farms. Perfect for a runaway weekend. Far enough from the city for a peaceful atmosphere and close enough to drive after a working day. Give it a try and enjoy it.

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 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.

Peaceful Light-Filled Guesthouse 1 Hour From NYC

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. Perfect for families, small groups, or couples seeking a peaceful nature retreat.

Clean,Comfy & Convenient. Private 1Bed Village Apt

Occupying the entire 2nd floor of a 2 unit home, above a chiropractors office in the heart of the "Big Little Village" Mt Kisco . You will be within a short walk to Northern Westchester Hospital, Metro North train station (for a less than 1 hr ride to Mid-Town Manhattan) along with a slew of high end restaurants, bars, cafes, boutique shops, hiking and outdoor activities abound.