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Holiday houses in Sleepy Hollow

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Top-rated holiday rentals in Sleepy Hollow

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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
4.86 out of 5 average rating, 159 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
Home in Sleepy Hollow
5 out of 5 average rating, 11 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!

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.
Apartment in Tarrytown
4.99 out of 5 average rating, 79 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 charming cabin is nestled among vibrant trees displaying autumn foliage. A wooden staircase leads to the entrance, flanked by natural stone walls. Outdoor seating arrangements are visible on the deck, offering a peaceful retreat in a wooded setting.
Cabin in Fishkill
4.96 out of 5 average rating, 126 reviews

Secluded Hilltop Cabin near Beacon & Cold Spring

3 private acres atop small mountain. Feels like you're way upstate - check out the reviews! Hi-speed WiFi. Next to forest preserve and hiking trails. Furnished deck w grill overlooks Mt. Beacon sunsets. Loft w/queen and twin mattresses + pull out couch & twin-size mattress day bed on the porch. Perfect for 2, comfortable for 3, but 4 is probably max comfort since it's a small space. Please note that the road heading up there is steep. A car with AWD is ideal but a sedan will make it up too!

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.
Guesthouse in Hastings-on-Hudson
4.92 out of 5 average rating, 908 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.
Apartment 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.

Guest favourite
Apartment in Newburgh
4.89 out of 5 average rating, 235 reviews

Special Nest w Private Entrance River View Porches

Front and back porch, river views, spacious living areas, new & fresh kitchen, and *two* bathrooms make this apartment the ultimate landing spot for a fun vaycay! Located on a street filled with intricate historical homes, this first floor apartment offers an accessible and comfortable getaway. A large backyard is shared with other guests, and sweeping river views are only steps away from your front door. Private entrance, plus easy parking and an electric car charger if you need it!

Top Guest favourite
The studio apartment features a queen-sized bed with a teal coverlet and a vibrant red accent chair. Large windows provide natural light, and a writing desk is situated beside the bed. A plush area rug adds warmth to the hardwood flooring.
Guest suite in Pleasantville
4.84 out of 5 average rating, 83 reviews

Charming Studio Centrally Located in Pleasantville

Private Studio Apartment with private entrance. Queen-sized bed + sofa bed. Cozy-space w/ big windows in a big home centrally located in the beautiful small town of Pleasantville. 5 min walk to MetroNorth Train to NYC (45 train ride), Pace University, TONS of bars & restaurants, coffee shops, Jacob Burns Film Center, cute shops. One of the best walking towns in Westchester County. Amazing outdoor activities close by. Friendly host nearby in main house for any questions!

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
Home in Croton-on-Hudson
4.95 out of 5 average rating, 19 reviews

Private Suite in the Heart of the Hudson Valley

Private suite in Croton-on-Hudson with its own entrance, full bath, and a striking 6-ft circular window overlooking the trees. Enjoy access to an outdoor fire pit, on-site parking, and easy transit via nearby Metro-North stations. Pet friendly and close to the Hudson River, great restaurants, hiking trails, and scenic overlooks—an ideal base to explore the beauty of the Hudson Valley by day and return to a cozy retreat at night.

Superhost
Home in Sleepy Hollow
New place to stay

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!

Top Guest favourite
A bright dining corner features a small wooden table surrounded by two chairs. Decorative plates adorn the wall above, while natural light enters through the nearby window, illuminating the warm wooden flooring.
Apartment in Ossining
4.95 out of 5 average rating, 38 reviews

Lovely | Private | Historic Home | Walk to Town

Our home is located in the heart of lower Hudson Valley and a quick drive to attractions in neighboring Sleepy Hollow and Croton-on- Hudson. Set in the charming, historic Upper Village neighborhood just a stones throw from downtown Ossining this garden-view apartment occupies part of the second floor of our village colonial and has a private entrance up a set of stairs in our back garden.

Popular amenities for Sleepy Hollow holiday rentals

KitchenWi-FiPoolFree 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

Superhost
A spacious living area is presented with light hardwood flooring and modern furnishings. A light gray sectional couch and two white chairs are arranged around a glass coffee table on a patterned rug. Large windows allow natural light to fill the room, while a sleek wall mirror reflects the space.
Private room in Nyack
4.89 out of 5 average rating, 133 reviews

Cul-de-sac 1-bedroom, includes free parking.

Top Guest favourite
A modern full kitchen is equipped with stainless steel appliances, including a gas stove and fridge. A butcherblock table is positioned under natural light, with seating for two. The overall color scheme features gray cabinets and light wood flooring, enhancing functionality and style.
Home in Piermont
4.96 out of 5 average rating, 114 reviews

Piermont's Getaway Mt. Village Home. 30min to NYC

Guest favourite
Private room in Morris Park
4.94 out of 5 average rating, 185 reviews

Private room by Stella

The bedroom features a spacious bed with light-colored bedding against a backdrop of warm red and green walls. Natural light filters through multiple windows, adding brightness to the cozy space. A dark wood dresser complements the decor.
Apartment in Scarsdale
4.71 out of 5 average rating, 174 reviews

One Bedroom w/ Great Location

Guest favourite
A modern room features a spacious bed covered in a teal quilt. A wall-mounted television is visible, along with a decorative wall clock. A light fixture adds subtle color to the space. Light wood flooring enhances the room's overall brightness.
Private room in Bronx
4.88 out of 5 average rating, 102 reviews

Bright Comfortable Room 2-A

Top Guest favourite
A spacious guest room features a large bed partially covered with a light blanket. A glass side table is positioned beside the bed, topped with a small decorative item and a lamp. A comfortable chair with a patterned cushion adds to the room's furnishings. Natural light enters through sheer curtains.
Private room in Sleepy Hollow
4.98 out of 5 average rating, 121 reviews

Aleida'house on beautiful town.

Top Guest favourite
Private room in Elmsford
4.96 out of 5 average rating, 109 reviews

Quiet room in the heart of Westchester

A cozy bedroom is presented with a spacious bed dressed in soft linens, flanked by two bedside lamps. A patterned chair is situated near the bed, and a decorative area rug covers the floor. Natural light enters through a window dressed with sheer curtains.
Apartment in Ardsley
4.59 out of 5 average rating, 207 reviews

Cozy, modern apartment in the heart of Westchester

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 $74 AUD per night before taxes and fees

  • Verified guest reviews

    Over 1,150 verified reviews to help you choose

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    10 of Sleepy Hollow holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi 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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