Places to stay in Sleepy Hollow, NY

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Sleepy Hollow, NY place to stay
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12 Best places to stay in Sleepy Hollow, NY

Best family friendly Sleepy Hollow, NY lodging

Among the 9 accommodations in Sleepy Hollow, NY, here are the 4 best for families

Charming 3br Walk To Town & Train - Sleepy Hollow, NY
10 13 reviews
Sleepy Hollow, NY
30/09 – 07/10
SG$408/nighttotal: SG$2856 (7 )

Charming 3br Walk To Town & Train

1 2
apartment , Pleasantville
This Pleasantville family-friendly railway carriage, located a short walk from Pleasantville's shops, parks, and restaurants, offers easy access to NYC via the train station.
The three-bedroom, one-bathroom dwelling boasts a fully equipped kitchen, living room with fireplace, a bluestone patio, and parking for two cars, comfortably accommodating up to six guests.
Stylish Tarrytown Studio - Walk To Train & Main St - Sleepy Hollow, NY
9.8 18 reviews
Sleepy Hollow, NY
06/11 – 08/11
SG$537/nighttotal: SG$1074 (2 )

Stylish Tarrytown Studio - Walk To Train & Main St

1 2
studio , Tarrytown
This Tarrytown apartment is conveniently located less than 1.6km from Tarrytown Music Hall and Pierson Park, and under 1.6km from Philipsburg Manor and the Old Dutch Church of Sleepy Hollow.
The self-catering flat sleeps four, boasting a fully equipped kitchen, a jacuzzi, garden, parking, and a terrace, all within a smoke-free environment.
Pool/hottub - Close To Nyc - Sleepy Hollow, NY
9.8 21 reviews
Sleepy Hollow, NY
26/06 – 04/07
SG$1039/nighttotal: SG$8312 (8 )

Pool/hottub - Close To Nyc

1 5
apartment , Ossining
This charming Tudor house is located in Ossining, Westchester County, just 1.6 kilometres from both the Croton/Harmon and Ossining train stations, offering easy access to New York City. The property has received excellent ratings for its cleanliness, location, and overall user experience.
This four-bedroom, two-bathroom dwelling can comfortably accommodate up to eight guests. The property features a private pool and hot tub, a well-equipped kitchen, multiple working spaces, a spacious garden with a playground, and a unique Alice in Wonderland-themed bedroom.
Close To New York City With Bridge View & Parking - Sleepy Hollow, NY
9.6 169 reviews
Sleepy Hollow, NY
30/09 – 07/10
SG$1090/nighttotal: SG$7630 (7 )

Close To New York City With Bridge View & Parking

1 2
apartment , Sleepy Hollow
This four-bedroom duplex is located in a lively neighbourhood in Sleepy Hollow, just a short walk from the Metro-North train station and the town's main street. The accommodation has received excellent ratings for location, cleanliness and overall experience.
The home is spacious and comfortably accommodates up to 10 guests. It comes equipped with modern amenities like high-speed Wi-Fi, smart TVs, a fully equipped kitchen and a private garden. Guests can enjoy easy access to local attractions, activities and restaurants.

Best Sleepy Hollow, NY lodgings with a pool

Among the 9 accommodations in Sleepy Hollow, NY, here are the 4 best ones with a pool

1br W/ Workspace, Gym & Outdoor Grill - Sleepy Hollow, NY
8.7 24 reviews
Sleepy Hollow, NY
27/06 – 04/07
SG$338/nighttotal: SG$2366 (7 )

1br W/ Workspace, Gym & Outdoor Grill

1 2
resort , White Plains
This one-bedroom flat is situated in Downtown White Plains, a short train journey from Manhattan and a quick drive to the Hudson River. It has received excellent ratings for location, cleanliness, and overall experience.
The flat comfortably accommodates up to three guests, and boasts a range of amenities including a swimming pool, fitness centre, and garden. There is also a dog wash station, making it ideal for pet owners.
Soccer Fans Dream Home-just 30 Minutes To Stadium - Sleepy Hollow, NY
Sleepy Hollow, NY
26/06 – 04/07
SG$16618/nighttotal: SG$132944 (8 )

Soccer Fans Dream Home-just 30 Minutes To Stadium

1 5
apartment , Norwood
This six-bedroom residence is located in Norwood, approximately 48 kilometres from the soccer stadium.
This expansive dwelling accommodates up to 16 guests and features a heated in-ground swimming pool with spa, a dedicated man cave with 12 televisions, an outdoor fire pit, and an included pool table.
Minutes To Hospitals, Hpn & Metro-north - Sleepy Hollow, NY
8.9 49 reviews
Sleepy Hollow, NY
27/06 – 04/07
SG$338/nighttotal: SG$2366 (7 )

Minutes To Hospitals, Hpn & Metro-north

1 2
resort , White Plains
This apartment is located in Downtown White Plains, just a short train ride from Manhattan and a quick drive up the Hudson River. The apartment has received excellent ratings for location, cleanliness, and user experience.
This one-bedroom, one-bathroom flat can comfortably accommodate up to three guests. You'll enjoy a range of amenities including a swimming pool, fitness centre, and a garden, as well as a dog wash station and a children's playroom.
Modern City Studio In Heart Of White Plains, 2 Units - Sleepy Hollow, NY
Sleepy Hollow, NY
27/06 – 04/07
SG$833/nighttotal: SG$5831 (7 )

Modern City Studio In Heart Of White Plains, 2 Units

2 2
studio , White Plains
This modern White Plains city apartment is centrally located near the Westchester County Center.
The 63-square-metre (678 square-foot) self-catering apartment sleeps eight, offering two bedrooms, two bathrooms, free Wi-Fi, air conditioning, and access to a hotel swimming pool and fitness centre.

Frequently asked questions about accommodations in Sleepy Hollow, NY

  • What are the must-see sites in or near Sleepy Hollow, NY?

    Sleepy Hollow is brimming with history and charm. You absolutely have to visit the iconic Sleepy Hollow Cemetery, where Washington Irving, the author of The Legend of Sleepy Hollow, is buried. The Old Dutch Church is also a must-see, and you can even take a tour of the Old Dutch Church and Cemetery. If you want to delve deeper into the legend, the Headless Horseman Hayride is a thrilling experience.
  • What are the best accommodations in Sleepy Hollow, NY?

    Among the accommodations in Sleepy Hollow, NY, Castle Hotel & Spa - Luxury Hotel Near Nyc, Relaxing & Great Location & Minutes From New York and Aleida'house On Beautiful Town are the most popular ones.

  • How can travelers reach Sleepy Hollow, NY?

    Sleepy Hollow is easily accessible. The nearest airport is Westchester County Airport, about 30 minutes away. If you're driving, it's about an hour from New York City. The Metro-North Railroad also offers a convenient route from Grand Central Terminal in Manhattan, with the station just a short walk from the village centre.
  • What are the best accommodations with a pool in Sleepy Hollow, NY?

    Castle Hotel & Spa - Luxury Hotel Near Nyc and (New To Airbnb) Charming Westchester Townhome are the best accommodations with a pool in Sleepy Hollow, NY.

  • What outdoor activities can visitors enjoy in and around Sleepy Hollow, NY?

    Sleepy Hollow is a haven for outdoor enthusiasts. You can explore the scenic trails of the Rockefeller State Park Preserve, just a short drive away. The 1600-acre park offers hiking, biking, and even horseback riding. For a more laid-back experience, you can stroll along the Hudson River or enjoy a picnic at the Sleepy Hollow Waterfront Park.
  • What are the best accommodations with a jacuzzi in Sleepy Hollow, NY?

  • When is the ideal time to plan a trip to Sleepy Hollow, NY?

    The best time to visit Sleepy Hollow is during the autumn months, from September to November, when the leaves turn vibrant colours. The village comes alive with Halloween festivities, including the famous Headless Horseman Hayride. Spring and summer are also lovely, with pleasant weather and plenty of outdoor activities.
  • What are the best accommodations for families and kids in Sleepy Hollow, NY?

  • What are the best walking or cycling routes in Sleepy Hollow, NY?

    For a leisurely walk, the Sleepy Hollow Cemetery is a great option. The historic cemetery is beautifully maintained and offers stunning views of the Hudson River. For a longer bike ride, you can follow the Old Croton Aqueduct Trail, which runs for 26 miles along the former aqueduct, offering picturesque scenery and access to several parks.
  • What are the best pet friendly accommodations in Sleepy Hollow, NY?

  • What nearby towns or cities can be explored from Sleepy Hollow, NY?

    Sleepy Hollow is ideally situated for exploring the surrounding area. You can easily visit Tarrytown, just a short drive away, known for its charming shops and restaurants. A bit further afield, you can explore the vibrant city of New York, which is just a short train ride away.
  • What are the best accommodations with parking in Sleepy Hollow, NY?

  • What amenities can travelers expect from accommodations in Sleepy Hollow, NY?

    Sleepy Hollow offers a range of accommodation options, from charming bed and breakfasts to modern hotels. Most accommodations include amenities like Wi-Fi, parking, and breakfast. Some also offer additional amenities like swimming pools, fitness centres, and restaurants. You can find something to suit your budget and preferences.

Destinations nearby

Best Sleepy Hollow, NY accommodations with a garden

Upscale Studio In Ny With Kitchen & Serene Setting - Sleepy Hollow, NY
9.1 57 reviews
Sleepy Hollow, NY
17/08 – 27/08
SG$223/nighttotal: SG$2230 (10 )

Upscale Studio In Ny With Kitchen & Serene Setting

1 3
apartment , Congers
This Congers, New York studio flat is situated near Rockland Lake State Park and Congers Lake, offering easy access to major highways and public transport links to New York City.
The self-contained apartment, sleeping up to three guests, features a fully equipped kitchen, private porch, and ample parking; nearby activities include swimming at Rockland Lake and birdwatching at Congers Lake.
Nyack Retreat - Sleepy Hollow, NY
9.6 161 reviews
Sleepy Hollow, NY
06/11 – 08/11
SG$352/nighttotal: SG$704 (2 )

Nyack Retreat

1 2
apartment , Nyack
This one-bedroom apartment in Nyack is ideally situated just a short walk from the town centre, offering easy access to shops, restaurants and the waterfront. It has received excellent ratings for location, cleanliness and overall experience.
The apartment comfortably accommodates up to three guests and features a well-equipped kitchen with a fridge, freezer, microwave oven and dishwasher. Enjoy a peaceful stay with amenities like air conditioning, a garden and internet access, allowing you to relax and explore the surrounding area.
557 M² Apartment ∙ 5 Bedrooms ∙ 13 Guests - Sleepy Hollow, NY
Sleepy Hollow, NY
23/10 – 26/10
SG$1970/nighttotal: SG$5910 (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.
Classic Tudor In A Prime Nyc Suburban Location. - Sleepy Hollow, NY
10 5 reviews
Sleepy Hollow, NY
27/06 – 04/07
SG$2651/nighttotal: SG$18557 (7 )

Classic Tudor In A Prime Nyc Suburban Location.

4 2
apartment , Scarsdale
This Scarsdale house, a mile (1.6km) from Scarsdale Metro-North station for easy Manhattan access, offers convenient proximity to top-rated schools and town amenities.
The spacious four-bedroom property sleeps nine, boasting a finished basement with kitchenette and large TV, a private backyard, two driveways, and access to Scarsdale's town pool and tennis courts (membership fees apply for stays over 30 days).

Best Sleepy Hollow, NY accommodations with a kitchen

2 Bedroom Apartment In Tarrytown/sleepy Hollow - Sleepy Hollow, NY
9.8 123 reviews
Sleepy Hollow, NY
06/11 – 08/11
SG$357/nighttotal: SG$714 (2 )

2 Bedroom Apartment In Tarrytown/sleepy Hollow

1 2
apartment , Tarrytown
This Tarrytown flat is situated a short walk from Broadway and Main Street, offering easy access to shops, restaurants, and entertainment, and just five minutes from the train station, with a 45-minute ride to New York City. The property has excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay. The apartment has two bedrooms and one bathroom, comfortably accommodating up to four guests. Amenities include a fully equipped kitchen, air conditioning, a garden, parking, and internet access, making it ideal for families or groups seeking a relaxing and convenient base to explore the area.
7 Minutes From The Train, Studio With W/d - Sleepy Hollow, NY
9.8 10 reviews
Sleepy Hollow, NY
06/11 – 08/11
SG$402/nighttotal: SG$804 (2 )

7 Minutes From The Train, Studio With W/d

1 2
apartment , Sleepy Hollow
This studio apartment in Sleepy Hollow offers central proximity, situated just 500 meters from the town centre and a short drive to Tarrytown's dining options, as well as being conveniently located near the Metro-North station for trips to New York City.
This self-contained unit accommodates up to three guests, featuring a comfortable bed, a kitchenette with a fridge and microwave, air conditioning, Wi-Fi, and on-site parking.
The Cozy Den - Sleepy Hollow, NY
9.4 72 reviews
Sleepy Hollow, NY
17/08 – 27/08
SG$314/nighttotal: SG$3140 (10 )

The Cozy Den

1 3
apartment , Nyack
This one-bedroom apartment is situated in a peaceful neighbourhood in Nyack, just a short stroll from the town centre, offering stunning views of the Hudson River. It has received excellent ratings for cleanliness, location, and overall user experience.
The cosy den has a private entrance and can accommodate up to four guests. The apartment is equipped with modern amenities including air conditioning, a kitchen with a fridge and microwave, internet access, and a garden.
Pet Friendly Parks & Trails Pleasantville Home - Sleepy Hollow, NY
Sleepy Hollow, NY
17/08 – 27/08
SG$737/nighttotal: SG$7370 (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.
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