
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.

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...

Bright&Comfy 2bed/1ba in quiet duplex
Bright, comfortable & quiet! Just outside downtown White Plains, this home has a relaxing living space with thoughtful touches. It offers easy accessibility to New York City (35 min Via Metro North) and Westchester (via highways and local buses). The house is set up for WFH, with great wifi via Verizon. It's an easy jump off spot for a fun weekend in Westchester. It comes with a dedicated parking spot, never worry about your vehicle! Bars, restaurants, shopping, groceries are all minutes away!

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!

The Bluestone - Spacious 2 bedroom w/central air
Come stay with us! You will have the entire first floor to yourself but we will be right upstairs if you should need us! Access to tree lined back yard with fire pit. Close to metro north train to NYC. Minutes to kayaking, hiking, restaurants, cafes & historical sites. Please note: No Kitchen!! Drive, walkway & entrance accessible to full size wheelchair (see photos) but bathroom is not accessible to a wheelchair. Guest must have ability to enter and maneuver the bathroom on thier own.

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.

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!

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!

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.

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

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.

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

Charming private 1BR apt. Easy access to NYC
Location, location, location! Private 1 bedroom unit that is part of a two-unit property. It has its own entrance, kitchen, bath, and off street parking. Walkable to Valhalla Metro North train station. (Has steps and stairs. No children under 12 years old.)
Popular amenities for Sleepy Hollow holiday rentals
Stay near Sleepy Hollow's top sights
Other great holiday rentals in Sleepy Hollow

Small cozy room in historic 1828 Dobbs Ferry home.

Bright Comfortable Room 2-A

Aleida'house on beautiful town.

Quiet room in the heart of Westchester

Private studio in home- own entrance and kitchen.

Cozy, modern apartment in the heart of Westchester

Charming Room Part Deux my Nyack House on the Hill

Sleepy Hollow Private Apartment Airbnb
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 $63 SGD 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!
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- Times Square
- Rockefeller Center
- Madison Square Garden
- Bryant Park
- Grand Central Terminal
- New York Public Library Main Branch
- Brooklyn Bridge
- New York University
- Columbia University
- Central Park Zoo
- MetLife Stadium
- Mountain Creek Resort
- Old Glory Park
- Bronx Zoo
- Ohel Chabad-Lubavitch
- Yankee Stadium
- Manhattan Bridge
- Jones Beach
- United Nations Headquarters
- Chabad Lubavitch World Headquarters
- Empire State Building
- Citi Field
- Statue of Liberty
- Radio City Music Hall




