Family-friendly holiday rentals in Port Chester

Blacksmith Bldg Guesthouse Upscale in downtown.

The Blacksmith Building built 1891, Upscale guesthouse since 2015. Enjoy peaceful evenings on this street, second-floor walk-up in the heart of downtown Yonkers. 100 meters away from the Metro North - Hudson River line. Just 30 minutes south to NYC or head north to explore the Hudson River towns, and majestic Hudson Valley. Entire 1000 sq. ft. live/work loft w/ 1 bedroom, 1 bath, sunroom and high-end kitchen. 1 queen + 2 twin beds. Walk to all, including renowned restaurants, museums, & river.

Lakefront Cottage near Hudson Valley

Named in the Top 30 U.S. Lakehouse Rentals by Refinery29 in May'21, this beautiful, secluded cottage on pristine Lake Oscawana has breathtaking views. Escape the city and enjoy the fresh country air! Extra-large great room, cathedral ceilings, loft bedroom, kitchenette, bathroom, fireplace, wall of double-height windows with spectacular lake views. Central AC/heat, hardwood floors, private large deck with BBQ. Dock nestled in a cove where you can swim or paddleboard. Only 1 hour from NYC.

Cozy Studio Getaway w/easy access to NYC/CT

Enjoy a relaxing stay with a home away from home; in this 1 bedroom studio apartment. Equipped with a comfortable bed, clean bathroom, kitchen, fridge, microwave, sink, counter top & stove. - 1 bedroom apartment with open floor plan (Fits 1-2 adults) - Private Individual Entrance (basement level) - Convenient & easy street parking - 5 minute drive from Metro North Railroad (Mount Vernon East station) which gives access to other parts of Westchester, Manhattan, and Connecticut areas.

Large, relaxing private 1 bedroom apartment.

Located on a quiet cul-de-sac, this self-catering 1 bedroom apartment with private driveway is located on the lower level of a private home and is perfect for anyone wishing to have a space to themselves. There is a roll-away single bed to accommodate a 3rd guest. We offer WiFi, Netflix and full cable TV access. Located near Executive Blvd and all the river towns. Plus, its only a short ride to all New York City has to offer. All reservation requests require verified Government ID.

Chic Vintage Cottage in Artsy Village of Nyack

Chic, cozy and adorable, our recently renovated 1929 Nyack Village cottage is a one of a kind. Located one block from Main Street and the wonderful dining, shopping and culture downtown Nyack has to offer, our home is the perfect backdrop for a beautiful weekend retreat. Traveling for work? NYC is a quick 30 mile commute with fast access to public transportation. We welcome you to come and be our guests!

Conefrey's.

Spacious, bright, comfortable, 1 bedroom apartment. Walking distance to all public transport, 10 minutes walk to Cross County Shopping Center. Only 20 minutes from Grand Central station and only 7 minutes from Sarah Lawrence College. Quite neighborhood, close to all amenities including McLean Avenue.

Private charming Studio efficiency

My apartment is centrally located, close to restaurants, (Sushi Mike's Japanese Restaurant, The Parlor and Dobbs Diner Inc.) It has a private entrance, easy access to Westchester county and NYC by train. My apartment is good for couples, solo adventurers and business travelers.

The Carriage House: Vacation Home & Retreat

Tucked away in the foothills of the lower Hudson Valley, the Carriage House offers a mountain retreat just outside the city. The meticulously designed arts-and-crafts cabin sits on a hillside in the rivertown of Croton-on-Hudson, NY, and is perfect for a quiet getaway or active retreat.

Southport, CT across from BEACH

Located at Southport beach on Westport Line, this renovated 1 bedroom apartment totally private located above the garage and includes a full kitchen with new appliance and d/w and central air. Bdrm with queen, fine cotton sheets and towels, marble bath open living room w views.