Holiday rentals in Sleepy Hollow

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Top-rated holiday rentals in Sleepy Hollow

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

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Top 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 Highlands
4.93 out of 5 average rating, 154 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, 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...

Guest favourite
Flat in Nyack
4.88 out of 5 average rating, 77 reviews

Home Away From Home

The best of both worlds just 32 miles north of New York City: a cozy studio apartment steps away from bustling downtown Nyack. The studio features a comfortable queen-sized bed, a kitchenette, and a modern bathroom with a shower. Enjoy bars, restaurants, antique shops, specialty stores, and boutiques all within less than a five minute walk. The Hudson River and Nyack Beach State Park are also just a short distance away, making it easy to enjoy all the outdoor activities the area has to offer.

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, 500 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
Flat in Newburgh
4.89 out of 5 average rating, 239 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
Flat in Little Falls Township
5 out of 5 average rating, 10 reviews

NEW* Apartment in Little Falls

Welcome to your perfect home away from home in charming Little Falls, NJ! This beautifully designed studio apartment offers everything you need for a relaxing stay just minutes from the city✨ 🌆 Location Highlights 🚆 1-minute walk to the Little Falls train station — Direct line into NYC’s Penn Station in under 45 minutes ✈️ Just 25 minutes to Newark Liberty International Airport (EWR) 🛍️ 15 minutes to American Dream Mall 🌊 Nestled next to a beautiful waterfall

Top 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, 270 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
An elegant balcony is presented with a wooden dining table and six matching chairs, accompanied by a comfortable sectional sofa. Lush greenery and the serene Hudson River are visible in the background, framed by a colorful sunset sky that enhances the outdoor space.
Flat in Yonkers
4.89 out of 5 average rating, 198 reviews

Elegant Riverfront Getaway with Beautiful Views

Enjoy stunning Hudson River views from your private balcony in this elegant, historic one-bedroom featuring a resort-style spa bath with steam room and jetted tub, and a warm, relaxing ambiance—perfect for a romantic getaway, a peaceful family vacation, or a tranquil weekend. Located just a few blocks from the Greystone Metro-North, you can reach NYC in under 45 minutes. A free designated parking spot is included.

Superhost
Home in Sleepy Hollow
4.67 out of 5 average rating, 3 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!

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, 303 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

Guest favourite
A light-filled living room features a comfortable sofa adorned with several cushions, providing a casual seating area. Two windows with patterned curtains invite natural light, while a decorative piece sits atop a classic cabinet in the background, adding character to the space.
Home in Dobbs Ferry
4.94 out of 5 average rating, 194 reviews

Beautiful Hudson River Bungalow in Dobbs Ferry

Serene and modern home. Newly renovated historic home on Main Street in the heart of the Village of Dobbs Ferry. Convenient to Manhattan and the Hudson Valley, the Old Croton Aqueduct trail is directly behind the home. This private apartment is on the second floor of a house with a separate entrance, offering complete privacy. Easy check-in with code.

Guest favourite
A rustic cottage is nestled amidst lush greenery, featuring a weathered wooden exterior and a large window that reflects the surrounding forest. Vibrant foliage and flowers adorn the landscaped yard, creating a peaceful natural setting.
Barn in Mount Kisco
4.91 out of 5 average rating, 593 reviews

NY Rustic Cottage Getaway

Just 50 min North of NYC (Metro North 5 min away) great for artists, writers, yogi's and creative types or people just wanting to get away from the hustle and bustle, city amenities near by. (Photo Shoots, Seminars, Workshops welcome-Call For different Rates) Tag & Follow Nina’s Cottage on Insta! @ninas_airbnb

Popular amenities for Sleepy Hollow holiday rentals

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 1,150 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!