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Holiday rentals in Sleepy Hollow

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Top-rated holiday rentals in Sleepy Hollow

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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
5 out of 5 average rating, 105 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.

Guest favourite
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
4.85 out of 5 average rating, 158 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.

Top guest favourite
A small flock of chickens is seen in a lush, green outdoor space surrounded by fencing. The chickens, displaying a variety of colors and patterns, roam on the ground among tall grass and scattered foliage. A branch is positioned in the background.
Guest house in Hastings-on-Hudson
4.92 out of 5 average rating, 906 reviews

★Tiny House Cottage 35 min to NYC on Hudson River★

Please read the entire listing to set expectations. Super charming, slightly quirky, never perfectly perfect, totally private Shangri-La with side yard chickens in the artistic and quaint Rivertowns, 35 min to NYC along the Hudson River. The Tiny House escape is reminiscent of sleep away camp, yet tastefully curated with eclectic art and furnishings that can change depending on “finds.” Sleeping loft nest with 8-step ladder or pull-out sofa bed. Fenced-in yard. FREE 24/7 street parking.

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, 492 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. $25 cleaning with or without pets.

Top guest favourite
A view of the exterior of the property is framed by lush greenery, featuring a stone wall with a potted plant. Beyond, expansive views of the lake and surrounding mountains are visible beneath a clear sky.
Home in Sterling Forest
5 out of 5 average rating, 204 reviews

Spectacular Lake Views from Every Room & Garden

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

Top guest favourite
The cottage is nestled among lush trees, highlighted by a distinctive stone chimney. Expansive glass doors reflect the surrounding greenery, inviting natural light inside. The structure is surrounded by verdant shrubs, creating a harmonious connection with nature.
Guest house in Pound Ridge
4.95 out of 5 average rating, 111 reviews

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.

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
4.93 out of 5 average rating, 268 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!

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
4.98 out of 5 average rating, 124 reviews

French Guest House in Waccabuc

A private, European-style retreat just 60 minutes from NYC. Set on an eight-acre gated French estate with its own lake, this guest house feels like a mini Versailles with 18th-century statuary, fountains and manicured gardens. Designed by David Easton, it features heated stone floors, a heated towel rack, luxury linens, gold fixtures, fast WiFi, and a private entrance. Minutes from Waccabuc Country Club and the Katonah train station.

Top guest favourite
A comfortable suite is featured, showcasing a spacious bed with crisp bedding and two decorative pillows. A compact sofa is positioned adjacent to a lift-top coffee table, with a kitchenette visible in the background, including a microwave and mini-fridge.
Guest suite in Haverstraw
4.94 out of 5 average rating, 395 reviews

Haverstraw Hospitality Suite

Quiet & cozy suite, with a comfortable full bed & private bathroom in newly renovated garden (basement) level of a single-family home. WiFi/air conditioning & heat unit/FiOS cable - roku TV. Coffee/tea available. Rollaway available for an extra bed. The neighborhood is quiet, and parking is available in the driveway. Feel free to come and go as you please -- we hope our guests feel like this is their home away from home:)

Top guest favourite
A cozy bedroom corner is featured, showcasing a spacious bed with neatly arranged pillows and blankets. A 50" 4K TV displays a calming fireplace scene, illuminating the room softly. The entryway to the bathroom is visible in the background.
Flat in Croton-on-Hudson
4.98 out of 5 average rating, 369 reviews

Luxury 2bd⭐Comfort+Style⭐

45 min train to Grand Central. Apt is 1.9mi to train, supermarket. Free PARKING. Two 4K TVs, 4K Blu-ray library, NFLX/AMZN/HBO/Apple TV. XBOX 1X. Fast WIFI. SS APPL, stocked kitchen. Bd1: adjustable queen, 50" 4K TV. Bd2: adj queen. Office area (desk, fast wifi), private porch. Sidewalks. 7 min walk to cafes, a bar, and restaurants. Car rental is 16 min walk. Hiking, kayaking. I LIVE NEARBY IN ANOTHER APT.

Guest favourite
A bright sleeping area features a spacious bed with light bedding, positioned beneath a vaulted ceiling. Floor-to-ceiling windows provide views of the woods, while a small desk and chair are set against one wall for workspace. A television is mounted for entertainment.
Guest house in Greenwich
4.95 out of 5 average rating, 105 reviews

The Cottage in Greenwich

Brand new, light-filled private cottage guesthouse overlooking the woods in the heart of Greenwich, CT. Floor to ceiling windows, radiant heat bathroom floors, queen Casper mattress, a dedicated parking spot, Wi-Fi, TV, kitchenette with full fridge, Keurig coffee maker, microwave, toaster and induction stovetop and all utensils. Perfect for a weekend getaway or a quiet place to work.

Guest favourite
An open studio layout features a dining island with black chairs, a cozy couch in the corner, and a spacious bed made with neutral bedding. Decorative walls showcase intricate designs, while numerous pendant lights hang from the ceiling, illuminating the area. Large windows provide natural light.
Guest house in Peekskill
4.93 out of 5 average rating, 301 reviews

Peekskill Carriage House Downtown Studio

Located close to the center of town, this is the perfect launchpad to experience local restaurants, coffee houses, the Paramount Theater, shopping, etc. and a short drive to stunning hikes, the Hudson Valley and beyond. The apartment is ideal for one or two and features a kitchenette, bathroom, dining island, comfortable queen bed, and couch. peekskillcarriagehouse.com

Popular amenities for Sleepy Hollow holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Sleepy Hollow's top sights

Rockefeller State Park Preserve

69 locals recommend

Tarrytown Music Hall

31 locals recommend

Philipsburg Manor

23 locals recommend

Other great holiday rentals in Sleepy Hollow

Top guest favourite
The living area showcases a light-colored sofa adorned with patterned throw pillows, set next to a dark wooden coffee table. A dining area is visible, featuring a kitchen island with seating, and modern appliances can be seen in the well-lit space.
Guest house in Mount Kisco
5 out of 5 average rating, 35 reviews

White Cedar Cottage

Guest favourite
A spacious kitchen area features warm wooden cabinetry and a large island countertop. Natural light enters through multiple windows, which are framed by soft green curtains. In the adjacent living space, a light-colored sofa and a minimalist coffee table create a welcoming setting.
Flat in Sleepy Hollow
4.84 out of 5 average rating, 19 reviews

Large apt close to Tarrytown & NYC

Superhost
The entrance to the studio apartment is framed by a neat garden and stone pathway. A white door with a glass panel is flanked by two windows adorned with shutters. Lush greenery and flowering plants contribute to the inviting exterior.
Guest suite in Ossining
4.73 out of 5 average rating, 66 reviews

Comfortable Studio Apartment

Top guest favourite
A cozy living area features a leather sofa draped with a soft fur throw, set against floral-patterned wallpaper. Large windows allow natural light to illuminate the space, complemented by wooden beams and a plush area rug beneath a low coffee table.
Guest house in Bedford
5 out of 5 average rating, 51 reviews

Red Coat Cottage

Top guest favourite
A charming cottage is shown adorned with warm string lights, set against a backdrop of freshly fallen snow. The exterior features light blue trim, with windows illuminating the serene winter scene, while delicate branches are dusted with snowflakes.
Cottage in Ossining
5 out of 5 average rating, 25 reviews

Charming 18th-Century Farm Cottage

Guest favourite
A living area is presented with a dark sectional sofa, a large mirror, and a side chair. Windows allow natural light to fill the space, complemented by neutral-toned walls and wooden flooring. A soft rug is positioned under the seating arrangement, adding comfort to the room.
Flat in Tarrytown
4.89 out of 5 average rating, 112 reviews

2 bedroom apartment in Tarrytown/Sleepy Hollow

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
4.9 out of 5 average rating, 71 reviews

Peaceful Forest Cabin

Guest favourite
Home in Croton-on-Hudson
5 out of 5 average rating, 14 reviews

Hudson Valley Bungalow Retreat ~1 hr from NYC

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.

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 £37 per night before taxes and fees

  • Verified guest reviews

    Over 1,080 verified reviews to help you choose

  • 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!

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