House vacation rentals in Sleepy Hollow

1956 House of the Year Award. Easy commute to NYC.

Architectural masterpiece, designed by famous architect Ulrich Franzen. House of the year awarded in 1956 by Architectural Record, featured in LIFE and House and Garden magazines. Taste the unique experience of modernist living, surrounded by nature yet walking distance to the beautiful town of Rye, the beach, natural parks and 45m by train to NYC. The house is filled with light,all the rooms have forest views,you feel inmersed in nature while enjoying the magical experience of modernist living!

Family · Value · Walkability

Lower Hudson Valley Idyllic Retreat

Located 2 minutes from Teatown Nature Reserve (35 mins from NYC) on 1+ acre in the Lower Hudson Valley, this updated 2,600sf oasis is the perfect forest setting for your family or business retreat. It features an oversized gourmet chef's kitchen with adjoining dining room. There are 4 bedrooms, including a nursery/crib, additional sleeping spots, and stunning views from a perfectly perched solarium. The great room features a spectacular working fire place and floor to cathedral ceiling windows.

Value · Location · Nearby

Spacious 3b/3b Mediterranean in White Plains

Bring the whole family to this great place with lots of room for fun, relaxation or hosting! This 3bed/3bath Mediterranean is freshly renovated with stylish touches & comfy furniture. The main floor of this multi family serves as a great spot to bring the family while visiting the area. The house boasts an oversized living room, formal dining room, large chef's kitchen, and plenty of sleeping space. With heat & AC throughout the entire 2k sf unit, this house is great for anything& everything!

Value · Location · Laundry

Piermont Getaway Mt. Village Home. 30 min to NYC

Nestled at the base of Tallman Mountain lies the quaint village of Piermont where a population of 2,500 sleep, live & thrive enjoying life on the simpler side. Sip coffee on the porch overlooking the Sparkill creek. Stroll down Main Street to visit an array shops/restaurants. Fishing on the pier, dancing fireflies at night and wildlife throughout. A quick hike along the firetrail to the state park will overlook the backyard mountain, a view of the Hudson & catching a glimpse of NYC or a picnic.

Location · Value · View

Modern 3BD West Point USMA House w/ HotTub!

Our beautiful 3 bed, 2 bath contemporary home sits just 0.4 miles from West Point Military Academy. The house is equipped with super fast internet, work stations in each bedroom, cozy nectar mattresses, a 4-person jacuzzi, and of course, an incredible back yard patio with a BBQ, fire pit and outdoor dining area. Our kitchen is stocked for coffee lovers with 3 different types of machines ( Nespresso, Keurig, and Miele). There are also Samsung Smart TV's in each bedroom along with Sonos speakers!

Family · Value · Hospitality

Luxury Lake House Sauna 1h From NYC

Enjoy the lakefront from my charming home! Fish or Kayak from the private dock or relax on the large deck overlooking the water tucked away on the lake. Boats are included for all guests! Heated bathroom floors, massive TV (86in) + ample lake views. We also have a free Tesla Charger (with an adaptor you can use for other EVs). This is a relaxing retreat tucked away in one of New York's most convenient lakefronts from the city. 20 min to Bear Mountain 35 min to West Point 1 hour to NYC

Family · Location · Bathroom

Family Cottage with 4 King Beds and Fire Pit

Escape to Norwalk Cottage, a beautifully designed 4-bedroom, 2-bath home perfect for 8 guests. This family-friendly getaway features a fully stocked kitchen, cozy fireplace, and a fun basement playroom. Relax in the private backyard with a deck, grill, and fire pit. Located on the quiet Norwalk/Westport border, you're just minutes from Calf Pasture Beach, great restaurants, and the vibrant SoNo district. Enjoy central air, fast WiFi, and a dedicated workspace for the perfect year-round escape.

Location · Family · Air conditioning

Panoramic Lakeviews & Lush Garden | Beach Access

Our property boasts unparalleled views of Greenwood Lake and the mountains beyond. Our private garden features hundreds of plants and a seasonal waterfall cascading into a lily pond with fish and frogs. A shaded patio offers panoramic views and a gas grill. Guests get access to a private community beach. In winter, after skiing at nearby slopes, unwind in the claw foot tub or retreat to the cozy living room, with exposed wooden ceilings, fireplace, smart TV, record player and board games.

Family · Location · Long stay

Beautiful & Fun Waterfront Duplex on the Hudson

Enjoy a getaway to this charming historic waterfront home. Sip a glass of wine, a cup of Joe, or a refreshing cool drink from the 36 ft deck overlooking the Hudson River and Mario Cuomo Bridge beautifully lit up each evening. **PLEASE read everything in the description of "The Space" and "Other Things to Note" before booking. Thank you! Check out my "GUIDEBOOK" for my favorite picks including entertainment, shopping, eateries, and more. Non shedding pets welcome with additional fee $150.

Family · Location · Cleanliness

The Peekskill RiverView House

The Peekskill RiverView House A fully renovated dream house overlooking the historic Peekskill Bay. This 3 bedroom 3.5 bath designer house is a 5 minute walk to the train station, the train is loud, as well as the historic downtown. It’s truly the gateway to the Hudson Valley along with having the walkable access to culture, hiking, biking, culinary, spa, and entertainment activities within City limits. Expansive decks on all 3 floors with spectacular Hudson River views from every room.

Location · Value · Indoor spaces

Waterfront Lake House

Welcome to your lakeside retreat! Escape to tranquility and breathtaking views with our unique lakefront Airbnb. Nestled right into the water of Lake Peekskill, our cozy lake house promises the ultimate getaway. Adventure awaits right outside your door! Take advantage of complimentary paddleboard or kayaks for a leisurely paddle on the lake. Located just minutes from renowned hiking trails and delicious dining options, our Airbnb offers the perfect balance of serenity and convenience.

Location · Value · Nearby

Backyard Gazebo in Quiet NYC Suburban Stay

Welcome to our private split-level home with a fenced-in backyard! Enjoy this entire single-family home and never walk more than 8 steps between levels! This is a year-round perfect spot - enjoy the outdoor patio and indoor electric fireplace during your short term or midterm stay. We are located in Westchester County, just outside NYC. The house is 1.5 mi from 3 Metro-North stops and a 30-minute ride to Manhattan. Send us a message and we will let you know how far it is to your event.

Value · Family · Getting around