12 Holiday rentals and Airbnb in Sleepy Hollow, NY
10 7 reviews
Sleepy Hollow, NY
23/10 – 26/10
A$3514/nighttotal: A$10542 (3 )
Clean And Large Family Home In Nyc Suburbs
5 6
apartment , Scarsdale
This spacious apartment is located in Scarsdale, a short walk from the Metro North train station, offering a 45-minute ride to Grand Central Station in NYC. It benefits from excellent user, location and cleanliness ratings. The property is ideal for families or groups of up to 10 guests, and features a private garden, a fully equipped kitchen, laundry facilities and ample storage space. Guests can enjoy a relaxing outdoor space and benefit from a peaceful, residential setting with easy access to shops, restaurants and amenities in Scarsdale Village.
Sleepy Hollow, NY
27/06 – 04/07
A$4643/nighttotal: A$32501 (7 )
Fifa Lakefront Oasis
1 2
apartment , New City
This apartment is situated in New City, offering a tranquil lake view without specifying a district or precise distances to landmarks. This residence accommodates up to 12 guests and features a kitchen, air conditioning, swimming pool, jacuzzi, and fitness centre, with on-site activities including golf, hockey, and barbecuing, plus a "FIFA SPECIAL" offering.
9.9 38 reviews
Sleepy Hollow, NY
17/08 – 27/08
A$589/nighttotal: A$5890 (10 )
Piermont Landmark House - Garden Suite
1 3
apartment , Piermont
This two-bedroom flat is situated in a historic Greek Revival house, just across the street from the Hudson River in Piermont, a short walk from the town centre and the pier. It has consistently received excellent ratings for location, cleanliness, and user experience. The apartment can accommodate up to four guests and features a kitchenette with a microwave, mini fridge, and electric kettle. Guests can enjoy a private garden oasis with a patio, lounge chairs, a hammock, and a BBQ, as well as direct access to the Hudson River for scenic walks.
Sleepy Hollow, NY
23/10 – 26/10
A$1206/nighttotal: A$3618 (3 )
Spacious 3br Home / Free Parking / Perfect For Families & Groups
3 6
apartment , White Plains
This three-bedroom flat in White Plains is located in a peaceful residential area, offering easy access to amenities and attractions such as Bowlero White Plains and Silver Lake Park, situated approximately 1.6 kilometres away. This private residence accommodates up to 16 guests with four queen beds, featuring a fully equipped kitchen, air conditioning, complimentary on-site parking, and is professionally cleaned with fresh linens and towels provided.
9.3 78 reviews
Sleepy Hollow, NY
27/06 – 04/07
A$294/nighttotal: A$2058 (7 )
Cozy Apartment W/private Entrance In Ossining Home
1 2
apartment , Ossining
This one-bedroom flat is located in Ossining, New York, just a 1.6km walk from the Ossining Train Station, providing easy access to New York City via a 40-minute train ride. The apartment has received excellent ratings for its location, cleanliness, and overall user experience. The flat is ideal for couples or solo travellers and offers a private entrance, a backyard, and a quiet setting. Guests can enjoy basic amenities, Wi-Fi, light cooking facilities, and access to local shops and the public library.
8.0 3 reviews
Sleepy Hollow, NY
27/06 – 04/07
A$374/nighttotal: A$2618 (7 )
Fully Furnished, Cozy 1br In White Plains
1 2
resort , White Plains
This apartment is situated in Downtown White Plains, a short train journey from Manhattan and a quick drive up the Hudson River, making it a convenient base for exploring the area. It has received excellent ratings for location, cleanliness, and overall user experience. The flat is a one-bedroom, one-bathroom property with a capacity for three guests. Guests can enjoy a range of amenities, including a swimming pool, fitness centre, and a garden, as well as a fully equipped kitchen and laundry facilities.
9.9 66 reviews
Sleepy Hollow, NY
08/08 – 13/08
A$348/nighttotal: A$1740 (5 )
Idyllic & Chic In Piermont, 20 Min From Gw Bridge
2 2
apartment , Piermont
This Piermont holiday home enjoys a prime village location, a short 0.8 km stroll from the Hudson River and Tallman Park, and is within 3.2 km of the George Washington Bridge. The two-bedroom, one-bathroom property sleeps four guests and features a fully equipped kitchen, living room with TV, in-unit laundry, and outdoor space; amenities include Wi-Fi, cable TV, and access to streaming services such as Netflix, Amazon Prime Video, and HBO Max.
Sleepy Hollow, NY
23/10 – 26/10
A$573/nighttotal: A$1719 (3 )
Updated Victorian In The Heart Of Nyack
3 6
apartment , Nyack
This Victorian property in Nyack offers spectacular Hudson River views from a peaceful, tree-lined street, providing convenient access to local amenities and a 10-minute walk to the shuttle stop for easy travel. This 3-bedroom, 2-bathroom apartment accommodates up to 6 guests and features a private backyard courtyard, balcony terrace, WiFi, and central air conditioning, making it ideal for those seeking a comfortable stay with modern conveniences.
9.8 87 reviews
Sleepy Hollow, NY
30/09 – 07/10
A$218/nighttotal: A$1526 (7 )
Home Away From Home
1 2
apartment , Nyack
This Nyack studio apartment boasts a central downtown location, a short walk from shops and restaurants, and approximately 51 kilometres north of New York City, offering easy access to the Hudson River and Nyack Beach State Park. The self-contained unit sleeps two guests, includes a queen-sized bed, kitchenette with fridge and freezer, and modern bathroom, plus features such as remote keyless entry, fast Wi-Fi, and in-room TV and wireless charging.
9.2 89 reviews
Sleepy Hollow, NY
30/09 – 07/10
A$242/nighttotal: A$1694 (7 )
The Luxe Nook: Premier Studio In Scenic Congers
1 2
apartment , Congers
This Congers, New York studio suite is conveniently located near Rockland Lake State Park and Congers Lake, offering easy access to outdoor recreation and scenic views, within a reasonable driving distance of Hudson Valley and New York City attractions. The meticulously remodelled self-catering unit features a full kitchen, queen-size bed, sofa bed (sleeping up to three guests), a private porch, and ample on-site parking; nearby amenities include a vending machine and Rockland Lake State Park provides swimming, boating and hiking opportunities.
9.0 2 reviews
Sleepy Hollow, NY
08/08 – 13/08
A$644/nighttotal: A$3220 (5 )
Modern 2br In Downtown| Clubhouse + Gym | Parking
2 2
apartment , White Plains
This White Plains apartment is situated a 6-minute walk from White Plains Metro-North Railroad Station, less than 1.6km from White Plains Hospital Center and Pace University Law School, and within a 15-minute walk of The Galleria at White Plains and Westchester County Center. The 93 square metre flat offers three bedrooms, two bathrooms, sleeps five guests, and includes a fully equipped kitchen, free Wi-Fi, a swimming pool, fitness centre, concierge service, parking, and is close to numerous shops and entertainment venues.
9.7 20 reviews
Sleepy Hollow, NY
08/08 – 13/08
A$1836/nighttotal: A$9180 (5 )
Hudson River Views: Briarcliff Manor Home W/ Deck
4 2
apartment , Briarcliff Manor
This Briarcliff Manor holiday home provides extensive views of the Hudson River and Palisades, situated a short drive from Historic Sleepy Hollow and Rockefeller State Park Preserve. This spacious 385 square meter residence accommodates up to 12 guests with four bedrooms and six bathrooms, featuring a well-appointed games room, outdoor entertaining areas with a pizza oven, multiple fireplaces, and eight dedicated home office spaces, plus an EV charger.
Best family friendly Sleepy Hollow, NY holiday rentals
Among the 9 accommodations in Sleepy Hollow, NY, here are the 4 best family friendly rentals
Sleepy Hollow, NY
08/08 – 13/08
A$984/nighttotal: A$4920 (5 )
Five Bedroom Family Home In Larchmont - Guest Suite And Large Yard
5 2
apartment , New Rochelle
This Larchmont holiday home, situated within 5km of Iona College and Harbor Island Park and 10km of Monroe College and Hudson Park and Beach, offers convenient access to New Rochelle's key attractions. This spacious 233 square metre property sleeps up to 10 guests, boasting 4 bedrooms, 2 bathrooms, a fully equipped kitchen, fitness centre, garden, terrace, parking, and free Wi-Fi.
9.8 8 reviews
Sleepy Hollow, NY
08/08 – 13/08
A$291/nighttotal: A$1455 (5 )
Cozy Studio With Reading Nook
1 2
studio , White Plains
This one-bedroom flat is conveniently located in White Plains, just 1.5 kilometres from the Westchester County Center and a 20-minute walk from the Galleria at White Plains shopping centre. The area is well-connected, offering easy access to local amenities and attractions. The flat can accommodate up to 3 guests and has a fully equipped kitchen, a comfortable living area with a smart TV, and a bathroom. Enjoy modern amenities such as air conditioning, heating, and Wi-Fi, along with access to a spa, parking, and a lakefront location perfect for water activities.
Sleepy Hollow, NY
23/10 – 26/10
A$1232/nighttotal: A$3696 (3 )
Perfect Family Getaway / 5br Home / 6 Queen Beds / Free Parking
5 6
apartment , Yonkers
This expansive five-bedroom residence is situated in Yonkers' Bryn Mawr district, offering convenient access to landmarks such as the Bronx Zoo, located approximately 3.2 kilometres away, and the Untermyer Gardens Conservancy, about 2.4 kilometres distant. This private home accommodates up to 20 guests with six queen beds, featuring a fully equipped kitchen, complimentary on-site parking, and air conditioning, making it a suitable option for families and groups seeking a comfortable stay in Yonkers.
9.2 31 reviews
Sleepy Hollow, NY
23/10 – 26/10
A$1982/nighttotal: A$5946 (3 )
Westchester Summer: Pool Pet Friendly Events Games
1 6
house , Ossining
This 6000 sq ft estate in Ossining, New York, is situated just 8 kilometres from White Plains and 49 minutes by train to New York City, offering convenient access to Rockefeller State Park Preserve (800 metres away), Croton Gorge Park (6.4 kilometres away), and Sleepy Hollow (16 kilometres away). This family-friendly, pet-welcoming property accommodates up to 13 guests with 5 bedrooms and 4 bathrooms, featuring a custom bar, pool table, arcade games, a seasonal swimming pool, fully equipped kitchen, fast WiFi, and private parking for 5 vehicles.
Best Sleepy Hollow, NY holiday rentals with parking
9.7 156 reviews
Sleepy Hollow, NY
17/08 – 27/08
A$676/nighttotal: A$6760 (10 )
Beautiful & Fun Waterfront Duplex On The Hudson
1 3
apartment , Nyack
This charming waterfront property is situated in Nyack, a historic river town, with easy access to the Hudson River and the Mario Cuomo Bridge. The apartment has received excellent ratings for location, cleanliness and user experience. The dwelling has three bedrooms and one bathroom, accommodating up to four guests. Amenities include a fully equipped kitchen, a spacious living area with a fireplace, a private garden with a fire pit, and a 36 ft deck offering breathtaking views of the river and the bridge.
Sleepy Hollow, NY
17/08 – 27/08
A$797/nighttotal: A$7970 (10 )
3 Mi To Downtown: Spacious White Plains Home
1 3
cottage , Fairview
This Fairview cottage is conveniently located within a 4.8km radius of Greenburgh Public Library, Westchester County Center, Pace University Law School, The Galleria at White Plains, and Blythedale Children's Hospital. The self-catering property boasts a fully equipped kitchen with microwave and dishwasher, 2.5 bathrooms, a private balcony, garden, parking, and Wi-Fi; nearby attractions include an on-site arcade.
9.2 15 reviews
Sleepy Hollow, NY
17/08 – 27/08
A$740/nighttotal: A$7400 (10 )
3 Mi To Downtown: Spacious White Plains Home
5 3
apartment , Fairview
This Fairview property, a seven-bedroom, three-bathroom house, is situated 4.8 kilometres from White Plains city centre, 3.2 kilometres from the Bronx River Greenway, and offers easy access to New York City (51.5 kilometres away). The 298 square metre dwelling boasts a spacious layout sleeping up to twelve guests, featuring a private patio, garden with gas grill, garage parking for four vehicles, plus Smart TVs, a washer/dryer, and complimentary toiletries.
Sleepy Hollow, NY
17/08 – 27/08
A$1324/nighttotal: A$13240 (10 )
Historic Former Speakeasy 4 Bdrm, Walk To Train And Town: Pleasantville
4 3
apartment , Pleasantville
This Pleasantville castle, a former speakeasy, is conveniently located a short walk from restaurants, a farmer's market, and a yoga studio, and within 1.6km of Rockefeller State Park and 3.2km of Stone Barns Center for Food and Agriculture. This 372 square metre property boasts four bedrooms, four bathrooms, and accommodates up to ten guests, featuring a chef's kitchen, wood-burning fireplace, spa, terrace, garden, and parking, alongside easy access to hiking trails in Graham Hills Park and a 50-minute train journey to Grand Central Terminal in New York City.
Frequently asked questions about holiday rentals in Sleepy Hollow, NY
What are some interesting places to visit in or near Sleepy Hollow, NY?
Sleepy Hollow is steeped in history! You have to visit the iconic Sleepy Hollow Cemetery, where Washington Irving is buried, and the Old Dutch Church, which inspired his famous story. For something a little different, head to the Philipsburg Manor, a restored 18th-century estate with a working gristmill.
What are the best Airbnb and holiday rentals in Sleepy Hollow, NY?
Which walking or cycling routes are the best in Sleepy Hollow, NY?
The Old Croton Aqueduct Trail is a fantastic paved path for walking or cycling, stretching for 40 kilometres through beautiful scenery. For a shorter walk, the Sleepy Hollow Cemetery itself is a lovely place to wander, with its historic monuments and peaceful atmosphere.
What are the most popular Airbnbs in Sleepy Hollow, NY?
What sports or outdoor activites can visitors enjoy in and around Sleepy Hollow, NY?
Sleepy Hollow is perfect for outdoor enthusiasts! You can enjoy hiking and biking in the Rockefeller State Park Preserve, which borders the village. The Hudson River offers opportunities for kayaking, paddleboarding, and even fishing.
What are the best holiday rentals with a pool in Sleepy Hollow, NY?
What other towns or cities can be easily accessed from Sleepy Hollow, NY?
Sleepy Hollow is conveniently located near several other interesting places. You can easily visit Tarrytown, just across the river, which has a charming historic district and a vibrant arts scene. A little further afield, you can explore the city of Yonkers, or head into New York City, which is about an hour away by train.
What are the best rentals for families and kids in Sleepy Hollow, NY?
What amenities are commonly available in vacation rentals in Sleepy Hollow, NY?
Vacation rentals in Sleepy Hollow typically offer a range of amenities, including kitchens, laundry facilities, and Wi-Fi. Many also have outdoor spaces like patios or balconies, perfect for enjoying the fresh air. Some even come with fireplaces or hot tubs for a more luxurious experience.
What time of year is best to rent a vacation rental Sleepy Hollow, NY?
The best time to visit Sleepy Hollow depends on your preferences. Spring and autumn offer mild weather and stunning foliage. Summer is great for outdoor activities, while winter brings a magical atmosphere with snow-covered landscapes and festive events.
What are the local dishes in Sleepy Hollow, NY region?
The Hudson Valley is known for its farm-to-table cuisine. You'll find plenty of restaurants serving fresh, seasonal dishes, often featuring local ingredients. Try the Hudson Valley apple pie, a classic treat, or a hearty stew with locally sourced vegetables.
Destinations nearby
Best Sleepy Hollow, NY holiday rentals with a balcony
9.8 18 reviews
Sleepy Hollow, NY
30/09 – 07/10
A$227/nighttotal: A$1589 (7 )
Piermont Oasis
1 2
apartment , Piermont
This Piermont apartment, near Tallman Mountain State Park and Palisades Interstate Park, offers easy access to Piermont's natural beauty and cultural attractions such as the Tarrytown Music Hall (a short drive away). The self-catering flat features a private balcony overlooking mountain greenery, one bedroom, one bathroom, sleeps two guests, and includes WiFi, a kitchenette, and parking.
Sleepy Hollow, NY
23/10 – 26/10
A$2180/nighttotal: A$6540 (3 )
557 M² Apartment ∙ 5 Bedrooms ∙ 13 Guests
5 6
apartment , Ossining
This large property is located in Ossining, Westchester, a short distance from Sleepy Hollow, making it ideal for experiencing the region's autumn colours. This 557 square meter residence offers five bedrooms, four bathrooms, and can accommodate thirteen guests, featuring a fully equipped kitchen, a custom in-house bar, a pool table, smart TVs, fast WiFi, air conditioning, a swimming pool, a terrace, a garden, a spa, and parking, with pets welcome.
9.7 292 reviews
Sleepy Hollow, NY
08/08 – 13/08
A$1085/nighttotal: A$5425 (5 )
Modern 4bd/3ba W/parking & Deck & 29 Min>nyc
3 2
apartment , Yonkers
This family-friendly house is located in Yonkers, a short drive from Hastings-on-Hudson and close to attractions like Untermyer Gardens Conservancy and the Hudson River Museum. The property has excellent user, location, and cleanliness ratings. The house has three bedrooms and is 102 square metres in size. It offers a range of amenities including a swimming pool, tennis court, and a fully equipped kitchen, perfect for a comfortable and enjoyable stay.
10 2 reviews
Sleepy Hollow, NY
08/08 – 13/08
A$2304/nighttotal: A$11520 (5 )
Hudson River Views Briarcliff Manor Home With Deck
4 2
house , Briarcliff Manor
This Briarcliff Manor estate is situated just 11 miles from The Palisades Center Mall and 14 miles from Manhattanville College, offering stunning Hudson River views and a peaceful setting. The property has received excellent ratings for user experience, location, and cleanliness. The 3-bedroom home provides ample space for families or groups, with a floor area of 386 square metres and a guest capacity of 10. Enjoy modern amenities such as free Wi-Fi, cable TV, a washing machine, a fully equipped kitchen, a spa, a fitness centre, and a garden.
Best pet friendly Sleepy Hollow, NY holiday rentals
Among the 9 accommodations in Sleepy Hollow, NY, here are the 4 best pet friendly rentals
Sleepy Hollow, NY
17/08 – 27/08
A$816/nighttotal: A$8160 (10 )
Pet Friendly Parks & Trails Pleasantville Home
1 3
apartment , Pleasantville
This Pleasantville flat offers a prime location, a 15-minute walk from the Jacob Burns Film Centre and within 5 kilometres of Rockefeller State Park Preserve and St John's River Side Hospital. This property provides complimentary Wi-Fi, in-unit washing machines, Smart TVs, and fully equipped kitchens, making it ideal for a convenient stay with pets welcome.
Sleepy Hollow, NY
27/06 – 04/07
A$466/nighttotal: A$3262 (7 )
Global Luxury Suites White Plains
1 2
apartment , White Plains
This apartment is conveniently located in White Plains, just one kilometre from the city centre, making it easy to explore the area's attractions. The apartment is suitable for up to two guests and includes a kitchen with a microwave oven and dishwasher, as well as a garden and an outdoor pool. You can also enjoy free Wi-Fi, a laundry facility and a business centre during your stay.
Sleepy Hollow, NY
27/06 – 04/07
A$2225/nighttotal: A$15575 (7 )
Spacious Yonkers Home Sleeps 16 Game Room Gazebo Perfect For Groups
3 2
apartment , Yonkers
This three-bedroom residence is situated in Yonkers' Bryn Mawr district, offering a swift commute to New York City and convenient access to local amenities, with the city centre approximately 24 kilometres away. This property accommodates up to 16 guests, featuring a fully equipped kitchen, a dedicated game room, a private gazebo with outdoor space, and fast WiFi, making it ideal for large family gatherings or group holidays.
9.4 10 reviews
Sleepy Hollow, NY
30/09 – 07/10
A$754/nighttotal: A$5278 (7 )
Charming Dobbs Ferry (Westchester) Victorian Home
1 2
apartment , Dobbs Ferry
This Dobbs Ferry apartment, situated opposite Gould Park, is 0.8km from the village centre and 1.6km from the train station, offering easy access to Manhattan via a 35-minute train journey. Sleeping up to nine guests, this four-bedroom, one-bathroom Victorian house boasts a spacious layout with two king-size and one single bed, a second living area, full kitchen, BBQ, laundry facilities, and ample street parking; it also benefits from a large garden and is available for short or discounted long-term lets.