Sleepy Hollow, NY holiday rentals

Holiday Rentals in Sleepy Hollow, NY

23 available vacation rental offers

2 1
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  • plumguide
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Price per night
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Best Holiday rentals and Airbnb offers in Sleepy Hollow, NY

Hudson River Forest Marsh Setting Romantic Cozy - Sleepy Hollow, NY
9.8Excellent 173 reviews
Sleepy Hollow, NY
2 1
£291/nighttotal: £582 (2 )

Hudson River Forest Marsh Setting Romantic Cozy

studio - Piermont
This studio apartment is situated in Piermont, a charming town just 15 miles outside of Manhattan, offering a tranquil escape from the city bustle. The studio has received excellent ratings for its cleanliness, location, and overall experience, making it a popular choice for travellers.
The self-contained apartment can accommodate up to three guests and includes a fully equipped kitchen, a bathroom with a bathtub and shower, and a washer and dryer. Guests can enjoy stunning views of the Hudson River and Tallman Mountain, explore the nearby Piermont Pier, or take advantage of the recording studio, bikes, and non-toxic cleaning products available for their use.
Shadowbrook Manor - 1890's Gem - Sleepy Hollow, NY
10Excellent 2 reviews
Sleepy Hollow, NY
2 5
£3764/nighttotal: £7528 (2 )

Shadowbrook Manor - 1890's Gem

apartment - Tarrytown
Shadowbrook Manor, a classic English country manor in Tarrytown, is situated just 800 yards from nearby hotels and within walking distance of the historic district. The property enjoys excellent ratings for user experience, location, and cleanliness.
The manor offers 5 bedrooms and 1 bathroom, accommodating up to 16 guests. Guests can enjoy a fully equipped kitchen, on-site parking, and internet access, making it ideal for gatherings, film shoots, and photoshoots.
The Historic Hudson Vista With Prime River Views - Sleepy Hollow, NY
9.8Excellent 122 reviews
Sleepy Hollow, NY
2 1
£241/nighttotal: £482 (2 )

The Historic Hudson Vista With Prime River Views

apartment - Nyack
This charming Nyack apartment is situated just two blocks from the village's shops, restaurants, and public transport, offering easy access to the area's attractions, including Woodbury Commons, Sleepy Hollow, and the Hudson River historic houses. The apartment has received excellent ratings for its location, cleanliness, and overall experience.
The entire second floor is dedicated to guest use, comfortably accommodating up to three people. The apartment features a fully equipped kitchen, air conditioning, a garden, free street parking, and stunning Hudson River views from almost every window.
Brand New Private Studio In The Heart Of Tarrytown - Sleepy Hollow, NY
9.9Excellent 201 reviews
Sleepy Hollow, NY
4 1
£322/nighttotal: £966 (3 )

Brand New Private Studio In The Heart Of Tarrytown

studio - Tarrytown
This studio apartment is conveniently located in the centre of Tarrytown, just a block from Main Street and an 8-minute walk from the Metro-North Tarrytown train station. It has received excellent ratings for cleanliness, location and user experience.
The self-catering apartment has a modern, minimalist design and can comfortably accommodate up to four guests. Amenities include a fully equipped kitchen, a private entrance and front yard, air conditioning, a garden, parking and free Wi-Fi.
Enjoy Summer Living  "Stone Haven"  Hudson Valley - Sleepy Hollow, NY
10Excellent 30 reviews
Sleepy Hollow, NY
4 1
£296/nighttotal: £888 (3 )

Enjoy Summer Living "Stone Haven" Hudson Valley

- Briarcliff Manor
This self-catering apartment in Briarcliff Manor is ideally situated near hiking trails, bike paths, restaurants, and the train station to New York City, making it a great base for exploring the Hudson Valley. It has received excellent ratings for its location, cleanliness, and overall experience.
This spacious two-storey apartment can comfortably accommodate up to four guests and features a full kitchen and bathroom, offering more space and privacy than a typical hotel room. Enjoy modern amenities including a large living room with a 60" TV, a pool table, a private patio with a gas grill and fire pit, and access to a shared salt water pool with a diving board.
Beautiful & Fun Waterfront Duplex On The Hudson - Sleepy Hollow, NY
9.7Excellent 119 reviews
Sleepy Hollow, NY
4 3
£398/nighttotal: £1194 (3 )

Beautiful & Fun Waterfront Duplex On The Hudson

apartment - Nyack
This charming waterfront property is situated in a peaceful Nyack neighbourhood, just a short distance from the bustling river towns and the bus stop for easy access to New York City. It has received excellent ratings for its location, cleanliness and overall user experience.
The apartment sleeps four guests in three bedrooms and one bathroom. Guests can enjoy a range of amenities, including a private balcony, a firepit, kayaks for river access, and a well-equipped kitchen.
Hudson River Town Comfy & Cozy Getaway Home!! - Sleepy Hollow, NY
9.8Excellent 130 reviews
Sleepy Hollow, NY
2 1
£206/nighttotal: £412 (2 )

Hudson River Town Comfy & Cozy Getaway Home!!

apartment - Ossining
This apartment is situated in the Indian Village district of Ossining, bordering Briarcliff Manor, within easy walking distance of shops and restaurants, and a short drive from the Great Jack O'Lantern Blaze and Sleepy Hollow. The property has consistently received excellent ratings for cleanliness, location, and user experience.
This one-bedroom flat comfortably accommodates two guests. Modern amenities include a large kitchen-diner, a private backyard with a BBQ, a washer-dryer, and a large-screen TV. Guests can also enjoy the nearby nature parks, trails, and bike paths, as well as stunning sunset views.
The Cozy Den - Sleepy Hollow, NY
9.4Excellent 56 reviews
Sleepy Hollow, NY
4 1
£224/nighttotal: £672 (3 )

The Cozy Den

apartment - Nyack
This one-bedroom flat is situated in a peaceful neighbourhood just a short walk from the centre of Nyack, offering stunning views of the Hudson River. It has received excellent ratings for its location, cleanliness, and overall experience.
The apartment has a private entrance and can accommodate up to four guests. It features a modern kitchen with a fridge and microwave, air conditioning, a garden, and parking.
MILLION $ MANSION Hudson Valley Oasis/Tranquility - Sleepy Hollow, NY
9.7Excellent 68 reviews
Sleepy Hollow, NY
4 7
£840/nighttotal: £2520 (3 )

MILLION $ MANSION Hudson Valley Oasis/Tranquility

house - Ossining
This luxury house in Ossining, Westchester County, is situated just 20.9 km from the Palisades Center Mall and 24.1 km from Manhattanville College, offering easy access to both shopping and educational facilities. The property boasts excellent ratings for user experience, location, and cleanliness, ensuring a comfortable and enjoyable stay.
The house features 5 bedrooms and 5 bathrooms, spanning a spacious 14 square metres. Enjoy a range of amenities including a private pool, hot tub, garden, terrace, and bar, perfect for relaxation and entertainment.
Victorian In Dobbs Ferry (Westchester) - Sleepy Hollow, NY
9.9Excellent 68 reviews
Sleepy Hollow, NY
4 3
£672/nighttotal: £2016 (3 )

Victorian In Dobbs Ferry (Westchester)

apartment - Dobbs Ferry
This recently refurbished family home is located in Dobbs Ferry, just across the street from Gould Park and a short walk from the quaint downtown area, with the train station approximately one mile away offering a 35-minute commute to downtown Manhattan. The apartment has received excellent ratings for its location, cleanliness, and overall user experience.
The property is spacious and spread across three floors, including a large backyard. It comes equipped with modern amenities like a fully equipped kitchen, air conditioning, and a terrace/balcony. You can enjoy outdoor dining, relax on the benches, and make use of the parking facilities.
Bright House For Photoshoots & Filming Only - Sleepy Hollow, NY
Sleepy Hollow, NY
4 3
£896/nighttotal: £2688 (3 )

Bright House For Photoshoots & Filming Only

apartment - Nyack
This charming three-bedroom house is situated in Nyack, a picturesque town just 20 miles north of Manhattan, offering easy access to both the bustling city and the scenic Hudson River. It's located on a spacious double lot within walking distance of the town centre, providing a peaceful retreat while still being close to all the action.
The home offers a comfortable and spacious layout, ideal for accommodating up to 16 guests. It comes equipped with a fully-equipped kitchen, parking, and internet access, ensuring a convenient and enjoyable stay.
1br Apt In Hartsdale, Steps From The Train To Nyc! - Sleepy Hollow, NY
Sleepy Hollow, NY
2 1
£184/nighttotal: £368 (2 )

1br Apt In Hartsdale, Steps From The Train To Nyc!

apartment - Hartsdale
This one-bedroom flat is situated in a charming village in Westchester County, just a block from the train station offering express service to NYC, a 25-minute ride away. The apartment is perfect for exploring the city without the hassle of driving or navigating city traffic, whilst also offering a tranquil escape from the hustle and bustle.
The flat is equipped with a kitchen, a microwave oven, and a fridge, and can accommodate up to three guests. It features air conditioning, a swimming pool, and easy access with an elevator.

Other types of accommodation in Sleepy Hollow, NY

Best Sleepy Hollow, NY holiday rentals with a pool

Among the 23 accommodations in Sleepy Hollow, NY, here are the 1 best rentals with a pool

Memorial Day Retreat - Pool, Jacuzzi, Firepit, Bbq - Sleepy Hollow, NY
Sleepy Hollow, NY
4 7
£823/nighttotal: £2469 (3 )

Memorial Day Retreat - Pool, Jacuzzi, Firepit, Bbq

apartment - Briarcliff Manor
This spacious home is located in Ossining, a short distance from Briarcliff Manor, just a 15-minute walk from Sing Sing Correctional Facility and a 12-minute walk from Old Croton Aqueduct State Park. The surrounding area offers a mix of historical sites and natural beauty, providing a range of activities for visitors.
This seven-bedroom apartment, spanning 127 square metres, comfortably accommodates up to 13 guests. The property features a private pool, a garden with a fire pit, a fully equipped kitchen, a laundry room, and covered parking, ensuring a relaxing and comfortable stay.

Best family friendly Sleepy Hollow, NY holiday rentals

Among the 23 accommodations in Sleepy Hollow, NY, here are the 5 best family friendly rentals

Cheerful Bright Child Friendly 4 Bdrm In S. Nyack. - Sleepy Hollow, NY
9.3Excellent 42 reviews
Sleepy Hollow, NY
4 4
£314/nighttotal: £942 (3 )

Cheerful Bright Child Friendly 4 Bdrm In S. Nyack.

apartment - South Nyack
This four-bedroom apartment is situated in South Nyack, a short seven-minute walk from the centre of Nyack and directly linked to the Esposito Trail. The apartment has consistently received excellent ratings for its location, cleanliness, and overall guest experience.
This spacious home comfortably accommodates up to six guests and includes a fully equipped kitchen, air conditioning, and parking. Guests can enjoy the fresh river breeze on the outdoor living area, take advantage of the pet-friendly features, and explore the nearby Esposito Trail for scenic walks and bike rides.
Gorgeous 1 Br W/high End Finishes, Heated Ba Floor - Sleepy Hollow, NY
9.9Excellent 100 reviews
Sleepy Hollow, NY
4 1
£225/nighttotal: £675 (3 )

Gorgeous 1 Br W/high End Finishes, Heated Ba Floor

apartment - Ossining
This peaceful apartment is located just a short walk from downtown Ossining and the Hudson River waterfront parks, offering easy access to shops, restaurants, and scenic views. The apartment has received excellent ratings for cleanliness, location, and user experience.
The apartment has one bathroom and can accommodate up to four guests. It features modern amenities such as a dishwasher, microwave, and air conditioning, as well as contactless entry and off-street parking.
Cozy Farm House In Scarsdale - Sleepy Hollow, NY
Sleepy Hollow, NY
2 4
£1088/nighttotal: £2176 (2 )

Cozy Farm House In Scarsdale

farm - Greenville
This four-bedroom country retreat is located in Scarsdale, a short distance from landmarks like the Cudner-Hyatt House Complex and Lyndhurst Mansion, offering a peaceful escape in a scenic setting. The property is ideal for families and groups, with a spacious layout that comfortably accommodates up to five guests.
The farmhouse offers a range of amenities, including a fully equipped kitchen, a garden, a spa, and ample parking. Guests can enjoy outdoor activities like fishing, cycling, and exploring the surrounding countryside.
Lux Haven- Garden & Campfire - Sleepy Hollow, NY
10Excellent 1 review
Sleepy Hollow, NY
4 3
£421/nighttotal: £1263 (3 )

Lux Haven- Garden & Campfire

apartment - Ardsley
This stylish three-bedroom apartment is situated in Ardsley, just a short walk from the train station and a 15-minute drive from Ardsley Park. It has received excellent ratings for location, cleanliness, and overall experience.
The apartment can comfortably accommodate up to seven guests and features a well-equipped kitchen, a garden, and parking. Guests can enjoy the modern amenities, including air conditioning, internet, and a dishwasher, as well as the peaceful setting.
Lovely 2br W/ Off St Parking, Privt Entr, Sleeps 6 - Sleepy Hollow, NY
9.5Excellent 15 reviews
Sleepy Hollow, NY
4 2
£199/nighttotal: £597 (3 )

Lovely 2br W/ Off St Parking, Privt Entr, Sleeps 6

apartment - Ossining
This two-bedroom flat is conveniently located in Ossining, just half a mile from the town centre, offering easy access to shops, restaurants, and attractions. The property has received excellent ratings for location, cleanliness, and overall experience.
The apartment comfortably accommodates up to six guests and features a fully equipped kitchen, laundry facilities, private entrance, and keyless entry. Guests can enjoy a tranquil escape in the nearby parks or explore the vibrant downtown area, all within walking distance.

Frequently asked questions for the holiday rentals in Sleepy Hollow, NY

Destinations nearby

Best pet friendly Sleepy Hollow, NY holiday rentals

Among the 23 accommodations in Sleepy Hollow, NY, here are the 8 best pet friendly rentals

Piermont Waterfront Villa! - Sleepy Hollow, NY
9.6Excellent 62 reviews
Sleepy Hollow, NY
4 6
£1204/nighttotal: £3612 (3 )

Piermont Waterfront Villa!

apartment - Piermont
This six-bedroom apartment is located in Piermont, a charming village just under two kilometres from Tallman Mountain State Park and the Hudson River, offering a peaceful setting with stunning views. The property has received excellent ratings for its cleanliness, location, and overall experience.
The apartment comfortably accommodates up to 14 guests, with four bathrooms and a fully equipped kitchen including a dishwasher, fridge, freezer, and microwave. Guests can enjoy a garden, terrace, and barbecue grills, making it ideal for relaxing and enjoying the beautiful Piermont weather.
Duplex Waterfront Home - Sleepy Hollow, NY
10Excellent 5 reviews
Sleepy Hollow, NY
4 3
£428/nighttotal: £1284 (3 )

Duplex Waterfront Home

apartment - Grand View-on-Hudson
This charming apartment is situated in the heart of Nyack, a historic river town just a short distance from Grand View-on-Hudson, offering easy access to the Hudson River and the Mario Cuomo Bridge. The property has received excellent ratings from previous guests, who have praised its unique character and stunning river views.
The apartment is spread over two floors, with enough space to comfortably accommodate up to six guests. Guests can enjoy a range of amenities, including a fully equipped kitchen, a spacious terrace with river views, access to kayaks, and a peaceful garden.
Briarcliff Manor Estate With Hudson River Views - Sleepy Hollow, NY
9.0Excellent 6 reviews
Sleepy Hollow, NY
4 3
£1010/nighttotal: £3030 (3 )

Briarcliff Manor Estate With Hudson River Views

house - Briarcliff Manor
This Briarcliff Manor house is a short drive from both the Palisades Center Mall and Manhattanville College, offering a convenient base for exploring the area. The property consistently receives excellent ratings for its cleanliness, location, and overall experience.
This three-bedroom, six-bathroom home spans 386 square metres and comfortably accommodates up to 10 guests. The house offers a range of amenities, including a fully equipped kitchen, a spa, a fitness centre, a garden, and parking, ensuring a comfortable and enjoyable stay.
Briarcliff Manor Estate W/ Hudson River Views - Sleepy Hollow, NY
9.0Excellent 4 reviews
Sleepy Hollow, NY
4 3
£1137/nighttotal: £3411 (3 )

Briarcliff Manor Estate W/ Hudson River Views

apartment - Briarcliff Manor
This spacious apartment is located in Briarcliff Manor, just a short distance from Sleepy Hollow Country Club and Rockefeller State Park Preserve, offering a peaceful retreat in a scenic setting. It has received excellent user ratings, indicating a high level of satisfaction from previous guests.
The apartment offers plenty of room for families or groups, with its 386 square metres of space and capacity for up to 10 guests. It boasts a range of amenities, including a fully equipped kitchen, a comfortable living area, a dedicated game room, and a spacious deck with outdoor seating, perfect for enjoying the beautiful surroundings.
Brand New Private Studio In The Heart Of Tarrytown - Sleepy Hollow, NY
10Excellent 4 reviews
Sleepy Hollow, NY
4 1
£328/nighttotal: £984 (3 )

Brand New Private Studio In The Heart Of Tarrytown

studio - Tarrytown
This studio apartment is conveniently situated in the heart of Tarrytown, just a block from the main street and an eight-minute walk from the Metro-North Tarrytown train station. It has received excellent reviews from previous guests.
The studio comfortably sleeps up to four guests and features a fully equipped kitchen with a fridge and microwave oven. Amenities include air conditioning, a jacuzzi, a garden, parking, and internet access.
2 Bedroom Apartment In Tarrytown - Sleepy Hollow, NY
10Excellent 21 reviews
Sleepy Hollow, NY
4 2
£214/nighttotal: £642 (3 )

2 Bedroom Apartment In Tarrytown

apartment - Tarrytown
This centrally located Tarrytown flat is just a 5-minute drive from the train station and a short walk to Broadway and Main Street, placing you within easy reach of the town's shops, restaurants and attractions. Guests consistently rate the property excellent for its location, cleanliness and overall experience.
The two-bedroom flat comfortably accommodates up to four guests and features a well-equipped kitchen with a fridge, freezer, microwave, and dishwasher. You'll also enjoy amenities such as air conditioning, a garden, parking, and internet access.
Hudson River Peaceful Getaway - Sleepy Hollow, NY
9.9Excellent 250 reviews
Sleepy Hollow, NY
4 2
£318/nighttotal: £954 (3 )

Hudson River Peaceful Getaway

apartment - Ossining
This charming two-bedroom flat is situated in a historic district of Ossining, just a short walk from the Scarborough train station and the Arcadian Mall. The property benefits from excellent user, location and cleanliness ratings.
The lower-level flat comfortably accommodates up to four guests and features a spacious living area with a queen-sized bed and sofa bed. Guests can enjoy a fully equipped kitchen, a private entrance, off-street parking, a large garden, two patios and a gas grill, perfect for relaxing and enjoying the outdoors.
1/2 Block From The Hudson River - Sleepy Hollow, NY
Sleepy Hollow, NY
2 1
£229/nighttotal: £458 (2 )

1/2 Block From The Hudson River

apartment - Nyack
This charming flat is located on a picturesque street in Nyack, just a short walk from the Hudson River and a five-minute stroll from the town's restaurants and cafes. The apartment is in a peaceful area, making it ideal for a relaxing getaway.
The flat has a separate entrance and can accommodate two guests. It features a comfortable queen-size bed, a well-equipped kitchen with a fridge, freezer, and microwave, and a bathroom. Guests can also enjoy access to Wi-Fi, air conditioning, and parking.