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Holiday rentals in Sleepy Hollow

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Quick stats about holiday rentals in Sleepy Hollow

  • Total holiday rentals

    Explore 10 holiday rentals in Sleepy Hollow

  • Nightly prices starting at

    Sleepy Hollow holiday rentals start at $65 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,190 verified reviews to help you choose

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    10 of Sleepy Hollow holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Sleepy Hollow rentals

  • 4.9 Average rating

    Sleepy Hollow stays are highly rated by guests – averaging 4.9 out of 5!

Top-rated holiday rentals in Sleepy Hollow

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
A modernist house is surrounded by vibrant autumn foliage, showcasing a blend of red, orange, and green leaves. The structure features large glass windows and a roof that floats above the walls, offering scenic views of the lush forest.
Home in Rye
4.91 out of 5 average rating, 143 reviews

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!

Top guest favourite
A soft, textured sofa in a light neutral tone is positioned against a warm, smooth wall. A single floor lamp provides gentle lighting beside a small black side table. An adjacent window is dressed with sheer curtains, allowing natural light to filter softly into the space.
Cottage in Warwick
4.99 out of 5 average rating, 128 reviews

Ranch in the Woods | A Peaceful Designer Retreat

Welcome to @ranch_inthewoods No cleaning fee STR permit #34035 This newly built ranch-style home with thoughtfully designed wabi-sabi interiors sits in the woods of the Warwick Valley. It's located a short drive away from several lakes, hiking trails, breweries, and dining experiences. It features forest/creek views, designer furniture, modern appliances (dishwasher, washer/dryer, gas cooktop), smart 4k TV, gym & yoga studio, gas firepit, and ample deck with an outdoor kitchen & dining area.

Superhost
The exterior of the house is set among lush greenery and features a large elevated deck that wraps around the structure. Large windows provide natural light, and the building is supported by a prominent boulder, blending harmoniously with the surrounding forest.
Home in Ossining
4.84 out of 5 average rating, 164 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.

Guest favourite
A spacious living room featuring a comfortable sectional sofa adorned with decorative pillows. A large area rug anchors the seating arrangement, which includes two lounge chairs. Natural light filters through multiple windows, highlighting the neutral color palette and decorative wall art.
Home in White Plains
4.91 out of 5 average rating, 171 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!

Top guest favourite
A stylish living area features a light-colored sofa with patterned cushions. Decorative wall plates and art are displayed above a sleek TV console. Two comfortable chairs, adorned with soft throws, invite relaxation, while a geometric area rug enhances the room's aesthetic.
Flat in Tarrytown
4.99 out of 5 average rating, 96 reviews

2 BRs, Easy Walking in Tarrytown and Sleepy Hollow

This special place, newly 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...

Top guest favourite
A hammock is suspended between two trees, providing a relaxing spot beside the lake. Vibrant autumn leaves in shades of orange and yellow frame the serene water view, while a wooden dock is visible in the background, inviting guests to enjoy the tranquil setting.
Home in Putnam Valley
4.99 out of 5 average rating, 179 reviews

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

Guest favourite
An outdoor area is illuminated by a vibrant red fireplace, surrounded by cozy seating arrangements with cushions and throws. Potted flowers add color, while string lights gently glow above, enhancing the serene atmosphere of the deck. A natural stone backdrop is visible in the distance.
Cottage in Greenwood Lake
4.98 out of 5 average rating, 385 reviews

Luxury Cottage with Spectacular Lake Views

Ultra Chic Cottage set high above Greenwood Lake with Private beach and lake front community access. Minutes away from Mountain Creek Ski Resort, Spa & Water park, Mt. Peter Ski & Tubing, Warwick creameries, breweries & vineyards & apple picking. 1 BR, 1 Bath, play/office/common room. Huge wrap around fenced in deck with Mid century modern fireplace allows for scenic dining, lounging and around the fire gatherings. #LakeViewCottage_GWL Town of Warwick Short Term Rental Permit #P25-0245

Top guest favourite
Flat in Stony Point
4.97 out of 5 average rating, 107 reviews

Gorgeous Suite w/ Private Entrance

Welcome to your private upstairs retreat with its own private entrance and bathroom. This charming efficiency offers a queen bed for restful nights, plus a loveseat sleeper sofa perfect for an adult or two small children. Enjoy the convenience of a mini fridge, coffee maker, and microwave. Step outside your door to our porch sitting area with a grill. Thoughtfully set up to feel both private and inviting, it’s a peaceful space to relax, recharge, and feel right at home during your stay.

Top guest favourite
The exterior of the guest house is framed by manicured gardens, featuring two decorative statues positioned beside a pea gravel walkway. A small patio area includes a round table with two chairs, creating a serene spot for outdoor relaxation.
Guest house in Waccabuc
4.99 out of 5 average rating, 140 reviews

French Estate Guest House on Private Lake

A private, European-inspired guest house set on an eight-acre gated French estate, just 60 minutes from NYC. Surrounded by manicured gardens, 18th-century statuary, and a private lake, the setting feels transportive—a French countryside retreat. Designed by architect David Easton, the space blends classic elegance with modern comfort: heated stone floors, a heated towel rack, fine linens, curated finishes, and a private entrance. Perfect for a refined weekend escape or a quiet reset.

Top guest favourite
A serene view of the Hudson River at sunset, featuring vibrant orange and yellow hues reflected on the calm water. Silhouettes of trees outline the scene, creating a peaceful atmosphere with the distant hills visible against the colorful sky.
Flat in Ossining
4.96 out of 5 average rating, 541 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.

Guest favourite
A modern studio apartment features a spacious bed with a low wooden frame and cozy bedding. A sofa bed is positioned nearby, surrounded by pillows. Natural light fills the room through two windows, with soft curtains framing the view. A decorative rug enhances the inviting atmosphere.
Guest suite in Tarrytown
4.92 out of 5 average rating, 286 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!

Superhost
Home in Sleepy Hollow
4.71 out of 5 average rating, 17 reviews

7 Minutes from the train, Studio with W/D

Cozy modern studio in the heart of Sleepy Hollow! Perfect for short stays, business trips, or weekend getaways. Enjoy a comfortable bed, stylish living area, kitchenette, fast Wi-Fi, and easy self-check-in. Minutes from downtown Sleepy Hollow, Tarrytown restaurants, parks, and historic sites. Close to Metro-North for a quick NYC trip. Clean, quiet, and convenient—your ideal Hudson Valley stay!

Popular amenities for Sleepy Hollow holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Sleepy Hollow's top sights

Rockefeller State Park Preserve

70 locals recommend

Tarrytown Music Hall

32 locals recommend

Philipsburg Manor

23 locals recommend

Other great holiday rentals in Sleepy Hollow

Top guest favourite
A comfortable living room features a leather sofa with an accent throw blanket. A decorative stone fireplace serves as a focal point, complemented by a mounted television displaying a serene landscape. Light-colored curtains frame the window, allowing natural light to fill the space.
Flat in Croton-on-Hudson
4.98 out of 5 average rating, 44 reviews

Croton Quarters-Modern Amenities

Guest favourite
A spacious living area showcases a neutral color palette, complemented by a dark sofa and a decorative area rug. An air conditioning unit and wall art pieces add character, while natural light filters in through a large window. Red accent furniture enhances the inviting atmosphere.
Guest suite in Croton-on-Hudson
4.9 out of 5 average rating, 60 reviews

Forest Suite | Croton Dam Trails | 45 Min NYC

Top guest favourite
The exterior of the cottage features a charming shingled facade, with a vibrant collection of potted flowers enhancing the entrance. A small pathway lined with gravel leads to a blue door, surrounded by lush greenery and rustic decor.
Cottage in Ossining
5 out of 5 average rating, 25 reviews

Charming 18th-Century Farm Cottage

Guest favourite
Home in Sleepy Hollow
4.94 out of 5 average rating, 16 reviews

The Hollow Inn at Sleepy Hollow

Top guest favourite
The outdoor area features a grassy lawn surrounded by trees, with a rustic wooden table and chairs set for gathering. A stone pathway leads through the yard, where small trees and decorative birdhouses add charm to the tranquil natural setting.
Cabin in Carmel Hamlet
4.93 out of 5 average rating, 96 reviews

Peaceful Forest Cabin

Top guest favourite
A charming log cabin is nestled among the trees, featuring a green metal roof and large windows. The front porch showcases wooden railings and steps, providing access to the home. A manicured lawn and gravel driveway extend in front of the cabin.
Cabin in Carmel Hamlet
4.97 out of 5 average rating, 92 reviews

Cozy Log Cabin Getaway

Superhost
Barn in Mount Kisco
New place to stay

Idyllic Retreat

Top guest favourite
A cozy living area is showcased with a comfortable sectional sofa and a large flat-screen TV mounted on the wall. Soft lighting from recessed fixtures and a standing lamp creates a warm ambiance. A light-colored rug with subtle stripes adds texture to the space.
Flat in Tarrytown
4.95 out of 5 average rating, 21 reviews

Stylish, Cozy 2 BR Pied-á-terre

Frequently Asked Questions

  • What are the best places to stay in Sleepy Hollow?

    Stays near village green spaces, riverfront paths, or historic neighborhoods are frequently suggested for convenience and local charm. Options range from private homes to family-friendly apartments throughout the area.

  • What are the best things to do in Sleepy Hollow with kids?

    Families often explore historic landmarks, hands-on museums, and nature trails in Sleepy Hollow. Seasonal festivals and interactive storytelling events add to child-friendly experiences around the village.

  • What are some of the best things to do in Sleepy Hollow?

    Explore the historic Old Dutch Church, wander scenic paths by the river, and take guided tours focused on local legends. Art galleries, seasonal events, and nature preserves add variety to your visit.

  • How is the weather in Sleepy Hollow?

    Sleepy Hollow experiences cold winters around 29–45°F (-2–7°C), with mild, humid summers near 71–86°F (22–30°C). Spring and fall bring moderate temperatures and are often recommended for outdoor exploration.

  • When is the best time to visit Sleepy Hollow?

    Many visitors favor late spring through early autumn for Sleepy Hollow, when temperatures are mild—ranging from 53°F to 81°F (12°C to 27°C)—and seasonal festivals take place. Fall is also frequently suggested, especially for those interested in the area's storied legends.

  • What are the best places to visit in Sleepy Hollow?

    Visit the Old Dutch Church and Sleepy Hollow Cemetery for a look at centuries-old history, or explore Rockefeller State Park Preserve’s walking trails. The town’s art spaces and cultural centers bring local flavor to your stay.

  • What are some hiking trails in Sleepy Hollow?

    Sleepy Hollow has tree-lined trails at Rockefeller State Park Preserve and paved paths in local parks, both suited for easy walks or family hikes. The area around the Hudson River also features scenic walking routes.

  • What are some family activities we can do in Sleepy Hollow?

    Families often enjoy touring historic landmarks, hiking local trails, and attending seasonal events with interactive experiences. Parks and riverside paths are popular for picnics and outdoor play.

  • What are some of the best day trip ideas from Sleepy Hollow?

    Explore neighboring river towns for historic estates, art museums, or hikes along the Hudson Valley. Many visitors spend a day discovering locally owned shops, gardens, or nature preserves in the region.

  • Are there any pet friendly accommodations available in Sleepy Hollow?

    Several accommodations in Sleepy Hollow welcome pets, and some properties are near green spaces where you can explore with your dog. Always check with your host for pet policies during booking.

  • What are some local tips for visiting Sleepy Hollow?

    Consider booking tours in advance during peak autumn weekends, and bring comfortable shoes for uneven historic paths. Many seasonal events fill quickly, so check local calendars for updates before planning.

  • What is Sleepy Hollow known for?

    Sleepy Hollow is known for its connection to Washington Irving’s legend, as well as its historic sites and scenic Hudson River views. The village has a tradition of autumn celebrations and cultural storytelling.

  • What are the best hidden gems to explore in Sleepy Hollow?

    Explore the Rockefeller State Park Preserve’s winding trails, or discover smaller historic sites and art galleries around the village. Locally-owned shops and riverside parks add quiet charm to a visit.

  • What are the best foods to try in Sleepy Hollow?

    Local menus feature seasonal farm-to-table dishes, regional comfort foods, and classic American fare. Bakeries and cafés are frequently suggested for enjoying homemade pastries or apple-based treats.

  • What should I bring for a trip to Sleepy Hollow?

    Pack comfortable walking shoes for exploring historic areas, and bring layers—temperatures can vary from cool mornings to warmer afternoons. Rain jackets or umbrellas are helpful during wetter months.

  • What is the nightlife in Sleepy Hollow like?

    Sleepy Hollow’s nightlife includes cozy taverns and pubs, some with live music or local craft drinks. Nearby towns feature relaxed evening venues, making the region suited for laid-back socializing.

  • What are the most popular events or festivals in Sleepy Hollow?

    Fall is known for immersive Halloween-themed events inspired by local folklore, as well as weekend festivals with family activities. Around late spring, arts and cultural celebrations also draw visitors to the village.

  • Are there family friendly vacation rentals in Sleepy Hollow?

    Sleepy Hollow has a variety of family-friendly vacation rentals, including options near parks and riverfront areas. Neighborhoods around the village are known for walkable streets and proximity to local attractions.

Destinations to explore