
Holiday rentals in Upper Nyack
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Top-rated holiday rentals in Upper Nyack
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2 BRs, Easy Walking in Tarrytown and Sleepy Hollow
This special place, recently renovated and lovingly decorated, has a private entrance, off-street parking, and a washer/dryer. Close to everything the Sleepy Hollow/Tarrytown area offers: a short walk to both downtowns, the Metro North train to NYC, Hudson River parks, the Jazz Forum, the Tarrytown Music Hall, a Saturday farmers market. A mile walk to the incomparable Rockefeller Park Preserve, 1.5 miles to Kykuit, 2 miles to Lyndhurst. The list of attractions and destinations goes on and on...
4.99 out of 5 average rating, 104 reviews
Large 3BR Sleepy Hollow Apt, Walk to Legend Sites
Welcome to Rock Hollow Loft, a spacious 2,200 sq ft apt steps from the legend that gave Sleepy Hollow its name. Walk 7-8 min to Philipsburg Manor & Old Dutch Church, Cemetary, setting of Irving’s “Legend of Sleepy Hollow.” RiverWalk 15 min on foot, near downtown shops & restaurants. Walking distance to train NYC 40 min Vaulted ceilings, cozy wood burning stove fill the open living space. Kitchen & dining seat 8-10. Sleeps 8: king, full & two twin beds across 3 bedrooms, plus a living room couch.
5.0 out of 5 average rating, 4 reviews
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!
4.91 out of 5 average rating, 178 reviews
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.
4.84 out of 5 average rating, 170 reviews
The Hollow Inn at Sleepy Hollow
The Hollow Inn, a charming retreat nestled in the heart of historic Sleepy Hollow—just 45 minutes from NYC and a 15-minute stroll from the Tarrytown train station. Whether you're planning a festive fall getaway with a large family or a peaceful couples’ retreat, this cozy spot is the perfect home base. October is truly magical here, Sleepy Hollow comes alive with Halloween festivities, haunted hayrides, lantern-lit cemetery tours, and more. Book your stay and experience the legend for yourself!
4.95 out of 5 average rating, 21 reviews
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.
4.86 out of 5 average rating, 165 reviews
Hudson Valley Escape
This sun-infused Queen Victorian home with front wisteria-draped porch and stunning Hudson River views will charm you. The home offers a library, two living rooms, renovated kitchen with butlers pantry and back staircase, 4 bedrooms and 2.5 baths. This home has many entertainment possibilities with 2 covered porches for dining, BBQ or just lounging and admiring the river views. A pleasant 10 minute walk to the train station. Just 45 minutes by gorgeous riverside train ride to Grand Central.
4.87 out of 5 average rating, 67 reviews
Hudson River Peaceful Getaway, Explore from here
Self Check-In/Private Entrance. House trained Dogs and declawed Cats are Welcome (No additional pet fee). Driveway Parking for two cars. Peaceful, private flat on the Hudson River. Train to NYC (Scarborough Station) 10 min walk through historic neighborhood. Arcadian Mall (Grocery Store, Starbucks, etc) 7 min walk. Lots to explore in the area. Panoramic Rivers views from inside and out. Two televisions. Coffee/Condiments/Cooking Essentials provided. $19 cleaning with or without pets.
4.96 out of 5 average rating, 559 reviews
Group Retreat | Pool, Hot Tub & Gourmet Kitchen
*POOL IS OPEN* Enjoy warm weather at this peaceful mountain retreat just an hour from NYC. Lounge on the patio with a BBQ, fire pit, hot tub, or spacious backyard with stunning views, or cool off in the pool. Inside, bright living spaces filled with natural light, a full gourmet kitchen, and cozy bedrooms with sparkling clean bathrooms make it perfect for families or groups. Explore nearby trails, relax outdoors, or unwind with games and movies indoors. Great for the whole group!
4.91 out of 5 average rating, 55 reviews
Relaxing Family Retreat
Come relax with your family in this peaceful home. It’s a beautiful split family ranch with the top floor completely private to guests. En suite master bedroom boasts both a soaking tub and a standing shower. Located a 5-minute drive from the Palisades Center, a 5-minute drive from Rockland Lake State Park, and a 10-minute drive from the bustling downtown Nyack, you will find something for everyone in the family to enjoy. Or enjoy the deck, barbecue, and pool at home.
4.75 out of 5 average rating, 28 reviews
Bright Retreat in Nyack
Charming, Sunlit Apartment in the Heart of Nyack Nestled in the vibrant and scenic town of Nyack, this cozy yet bright apartment offers an inviting and tranquil retreat. Perfect for anyone seeking a peaceful, well-lit atmosphere, the apartment combines modern comfort with a cozy, intimate feel. Just steps from Nyack’s charming cafes, boutiques, and the stunning Hudson River views, this apartment is a perfect balance of cozy living and vibrant surroundings!
4.91 out of 5 average rating, 47 reviews
Stylish Tarrytown Studio | Walk to Train & Main St
Modern designer studio 1 block from Main St, 8-min walk to Metro-North (35 mins to NYC). Private entrance, fast Wi-Fi, full kitchen, Queen bed + King sofa bed. Small front yard for a breath of fresh air. Walk to restaurants, cafes, and Hudson River parks. Ideal for couples, solo travelers, and remote workers. Explore charming Tarrytown, Sleepy Hollow, Rockefeller trails, and the Hudson Valley. A stylish, comfortable base for your next getaway!
4.92 out of 5 average rating, 291 reviewsPopular amenities for Upper Nyack holiday rentals
Other great holiday rentals in Upper Nyack

The cozy den
4.73 out of 5 average rating, 74 reviews
Sleepy Hollow Private Apartment Airbnb
4.97 out of 5 average rating, 69 reviews
Rated Coolest Small Town of New York
5.0 out of 5 average rating, 10 reviews
Nyack- Private Studio Steps from downtown
4.73 out of 5 average rating, 11 reviews
Cozy private apartment
5.0 out of 5 average rating, 4 reviews
Modern and quiet gateway
5.0 out of 5 average rating, 10 reviews
Walk to Town, Relax at Home
4.97 out of 5 average rating, 58 reviews
Waterfront Luxury in Town
4.94 out of 5 average rating, 81 reviewsDestinations to explore
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- Times Square
- Central Park Zoo
- Mountain Creek Resort
- Jones Beach
- Columbia University
- American Dream
- Yankee Stadium
- MetLife Stadium
- New York City Center
- Rockefeller Center
- United Nations Headquarters
- Bear Mountain State Park
- Empire State Building
- Bryant Park
- Barclays Center
- Citi Field
- Statue of Liberty
- Grand Central Terminal
- Minnewaska State Park Preserve
- Brooklyn Bridge
- Radio City Music Hall
- Astoria Park
- Fairfield Beach
- Thunder Ridge Ski Area





