Sleepy Hollow Holidays from £1,068

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Your Sleepy Hollow Holiday

Lock in a custom holiday package to Sleepy Hollow and get ready for your next great escape. Stay in the neighbourhood of Northwest Yonkers, which is great for nature and culture, for a real taste of this interesting city. Lyndhurst Mansion, Tarrytown Music Hall and Sleepy Hollow Cemetery are just some of the many sights worth checking out during your trip to Sleepy Hollow. Whatever your travel plans or budget, organising a tailored Sleepy Hollow holiday is a walk in the park with Expedia.

Top Sleepy Hollow Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Uscale 2BR Escape in the Heart of NYC

Uscale 2BR Escape in the Heart of NYC

2 out of 5
Bryn Mawr
Price was £1,326, price is now £1,068 per person
£1,068
per person
6 Sept - 11 Sept
found 1 day ago
Return flight included
Edinburgh (EDI) to White Plains (HPN)
8/10 Very good! (1 review)
The house was very clean and the areas was quiet too. We had a nice spot to park the car. The staff was calling and checking on me if I didn’t have any issues with the check in. They were available all the time. The only thing we will need next time if possible is the washer and dryer and extra towels because we were 5 and only got 3 towels. But overall we enjoyed the stays.

Reviewed on 21 Feb 2026

The Armon Stamford Hotel & Conference

The Armon Stamford Hotel & Conference

2.5 out of 5
Ridgeway-Bullshead
Price was £1,781, price is now £1,070 per person
£1,070
per person
6 Sept - 11 Sept
found 1 day ago
Return direct flight included
Glasgow (GLA) to White Plains (HPN)
7.8/10 Good! (864 reviews)
Everything was very nice and clean, but the tile in the bathroom was cracked. When trying to check out in the morning, there was no one at the front desk to help us. We waited a few minutes, looked around, called out and finally left, figuring check out was just one of those final things you don’t really need to do anymore. That is unless I had things racked up on my room charges, which I have to say this hotel was good about letting you know if you did have anything charged to you.

Reviewed on 29 Jul 2026

3BR Prime Luxury NY - Free Parking

3BR Prime Luxury NY - Free Parking

2 out of 5
Save 100% on your flight
Price was £2,687, price is now £1,979 per person
£1,979
per person
6 Sept - 11 Sept
found 1 day ago
Return flight included
Edinburgh (EDI) to White Plains (HPN)
6/10 (1 review)
Check-in was confusing and poorly organized, which made the start of the stay frustrating. The room itself was fine and comfortable, but the photos on the website were misleading and didn’t match what we saw in person. Overall, an okay room but not the experience we expected.

Reviewed on 30 Mar 2026

Luxury Apartments by Hyatus White Plains

Luxury Apartments by Hyatus White Plains

4.5 out of 5
Price was £2,463, price is now £2,047 per person
£2,047
per person
12 Oct - 19 Oct
found 1 day ago
Return direct flight included
London (LHR) to White Plains (HPN)
10/10 Exceptional! (1 review)
Brand new space. Our room was so clean!! Smelled clean. The location is perfect and walkable to restaurants, bars, grocery store. The game room was so much fun. Our host was the absolute best. Excellent communication from start to finish. Excited to return.

Reviewed on 28 Mar 2026

Sonesta White Plains Downtown

Sonesta White Plains Downtown

4 out of 5
Price was £1,304, price is now £1,103 per person
£1,103
per person
20 Sept - 26 Sept
found 1 day ago
Return flight included
Glasgow (GLA) to White Plains (HPN)
8.8/10 Excellent! (1,326 reviews)

Things to do near Sleepy Hollow

Sleepy Hollow offers a delightful blend of outdoor activities and family-friendly attractions, perfect for a romantic getaway. Visitors can enjoy shopping at local centres, catch live music performances, and explore new attractions through fun tours. Don't miss the chance to experience the vibrant block parties and engage in scenic sightseeing that this charming town has to offer.

Shopping

In Sleepy Hollow, you can explore charming local shops for unique gifts. If you're up for a drive, visit New Roc City (20.9km away), Westfield Garden State Plaza (25.7km away), or Stamford Town Center (27.4km away) for a wider range of shopping and entertainment options.

Recreation

At Doral Arrowwood Golf Club, enjoy a day on the lush greens, perfect for unwinding amidst nature. For a touch of culture, visit Lehman Center for the Performing Arts, where captivating performances create a romantic and engaging atmosphere, ideal for family outings or a night out.

Adventure

Experience the thrill of Palisades Climb Adventure, a zipline and ropes course located 8.0km from Sleepy Hollow, perfect for outdoor enthusiasts. For family fun, visit Legoland Discovery Center Westchester, an arcade and adventure zone situated 12.9km away. Finally, explore the scenic Orange Trailhead, 3.2km from Sleepy Hollow, ideal for hiking.

Nightlife

For an exciting nightlife experience near Sleepy Hollow, visit the Stonewall Inn and Dave & Buster's, both offering vibrant atmospheres with entertainment and romance vibes, located approximately 24 to 40.2km away. Don't forget to check out 51-53 Christopher Street for more lively pub experiences.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Sleepy Hollow

Sleepy Hollow, New York, offers a delightful mix of outdoor activities, cultural experiences, and family-friendly attractions, making it ideal for various types of vacations. Visitors can explore urban parks, modern colleges, and nature preserves, while also enjoying notable sites such as the Sleepy Hollow Cemetery and other local attractions. Whether you're seeking romance or adventure, Sleepy Hollow promises a memorable getaway in this charming locale.

  • Westchester County Center: A vibrant arts venue nestled 8.0km from Sleepy Hollow, the Westchester County Center hosts a variety of performances and events. Immerse yourself in the local culture as you enjoy concerts, exhibitions, and other artistic showcases in this lively setting.
  • Lyndhurst Mansion: Located merely 3.2km away, this historic estate boasts stunning architecture and lush grounds. Explore the grandeur of the 19th-century mansion, offering guided tours that delve into its rich history and picturesque gardens, perfect for a leisurely stroll.
  • Rye Playland: Experience family fun 20.9km from Sleepy Hollow at this classic amusement park. With thrilling rides, games, and beautiful waterfront views, Rye Playland promises an adventurous day out for all ages, ideal for creating lasting memories.

Best time to go to Sleepy Hollow

The best time to visit Sleepy Hollow can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Sleepy Hollow falls in July, when visitor numbers are average and weather is mostly sunny with light rain. The coolest average temperature in Sleepy Hollow falls in January, visitor numbers are low and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January30.6°F (-0.8°C)Light RainMostly SunnyLowSlightly Low
February32.2°F (0.1°C)Light RainMostly SunnyLowSlightly Low
March39.6°F (4.2°C)Light RainMostly SunnyAverageSlightly Low
April50.5°F (10.3°C)Light RainMostly SunnyAverageAverage
May60.8°F (16.0°C)Light RainMostly SunnyAverageAverage
June69.4°F (20.8°C)Light RainMostly SunnyAverageAverage
July76.1°F (24.5°C)Light RainMostly SunnyAverageAverage
August74.5°F (23.6°C)Light RainMostly SunnyHighAverage
September67.6°F (19.8°C)Light RainMostly SunnyHighSlightly High
October56.8°F (13.8°C)Light RainMostly SunnyHighSlightly High
November45.0°F (7.2°C)Light RainMostly SunnyAverageAverage
December36.9°F (2.7°C)Light RainMostly SunnyLowSlightly High

Tips to save on your trip to Sleepy Hollow

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling to Sleepy Hollow during the low season (January to March) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Sleepy Hollow Essential Information

Language
English
Currency
U.S dollars
Closest Airport
John F. Kennedy Intl. Airport (JFK)
Population
10,200
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Rockefeller Archive Centre, Lyndhurst Mansion and Tarrytown Music Hall

Top hotels in Sleepy Hollow

Tarrytown House Estate

Tarrytown House Estate

3.5 out of 5
49 E Sunnyside Lane Tarrytown NY
Fully refundableReserve now, pay when you stay
The price is £147 per night from 2 Aug to 3 Aug
£147
2 Aug - 3 Aug
includes taxes & fees
Tarrytown House Estate
Highbridge Hotel

Highbridge Hotel

2 out of 5
1263 Edward L Grant Highway Bronx NY
Fully refundableReserve now, pay when you stay
The price is £57 per night from 20 Aug to 21 Aug
£57
20 Aug - 21 Aug
includes taxes & fees
9.2/10 Wonderful! (4,320 reviews)
"The room was great nice and clean very spacious. The morning crew were"

Reviewed on 29 Jul 2026

Highbridge Hotel
Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford

2.5 out of 5
540 Saw Mill River Rd Elmsford NY
Fully refundableReserve now, pay when you stay
The price is £115 per night from 23 Aug to 24 Aug
£115
23 Aug - 24 Aug
includes taxes & fees
Baymont by Wyndham White Plains - Elmsford
See all 1,867 properties in Sleepy Hollow
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Stay near popular Sleepy Hollow attractions

A lighthouse with a metal bridge over water during sunset.
Photo by santosh dash
Open Photo by santosh dash

Tarrytown Lighthouse

8.4/10 (104 reviews)
This historic 1883 beacon on the Hudson River showcases a unique caisson design and maritime heritage. Climb its five stories to enjoy panoramic river views and glimpse the fascinating life of lighthouse keepers past.
See properties

What to do in Sleepy Hollow

LEGOLAND® Discovery Center Westchester Tickets

LEGOLAND® Discovery Center Westchester Tickets

£23
per adult
88% of travellers recommend
LEGOLAND® Discovery Center Westchester Tickets
Helicopter landing in a field in New York

Introductory Helicopter Flight Lesson from Westchester

£981
per traveller
Introductory Helicopter Flight Lesson from Westchester
See all activities in Sleepy Hollow

Frequently asked questions

Why should I book my Sleepy Hollow holiday with Expedia?
Choose Expedia to arrange your next big escape simply and all in one convenient place. Our top tip for bagging an unbeatable deal on a Sleepy Hollow getaway? Bundle your hotel, flights and/or hire car into a package holiday. Then add a couple of fun tours and activities. Most bookings also have flexible cancellation policies, so there's no need to worry if you have to switch up your travel itinerary. Round-the-clock help with amending and cancelling your trip is available via our Customer Service Portal link.
When is the best time of year to holiday in Sleepy Hollow?
April, September and November are the busiest months in Sleepy Hollow, while January, February and October are generally a lot quieter. With daytime average temperatures of 0ºC, January is the coolest period in Sleepy Hollow. The warmest month is July, when you can experience averages of 24ºC during the day. Whatever the temperature, you'll find a whole lot to keep you busy here.
What is the top hotel for my holiday in Sleepy Hollow?
Offering many of the creature comforts of home, SpringHill Suites by Marriott Tarrytown Westchester County will make the ideal base for your Sleepy Hollow trip.
How do I get a cheap holiday to Sleepy Hollow?
Combine your flight and hotel bookings, toss in extras such as a hire car or activities, and save with a Sleepy Hollow holiday. You won't just score amazing discounts on your adventure — you'll have loads of choice too. When you book with Expedia, you can choose from more than 400 airlines and 321,000 properties all over the world. Your next big adventure begins right here, right now! Learn more about how you can save money on your next holiday when you book a flight and hotel together with Expedia.
What should I do on my Sleepy Hollow holiday?
Make sure your next holiday in Sleepy Hollow is one to remember by taking in its leading attractions. Sleepy Hollow Cemetery, Tarrytown Music Hall, Lyndhurst Mansion and Kykuit are among the things you must see while you're here.
What is the best area to stay in when on holiday in Sleepy Hollow?
There's loads to do in Sleepy Hollow, so stay near its best sights and allow yourself more time sightseeing. Sleepy Hollow Cemetery is one place that should be on your itinerary.
Do I need a visa for my Sleepy Hollow holiday?
Visa requirements for Sleepy Hollow vary based on your nationality and the reason for your visit. It's best to check official government websites to determine if you need a visa for your holiday. Here you'll also find the most up-to-date information, including details about application procedures and any supporting documentation you may need. Enquire about your visa requirements well in advance to ensure a smooth travel experience. Also check to see that your passport has at least six months validity from your date of return.
What should I wear on my Sleepy Hollow holiday?
Although everyone's fashion style varies, it can be helpful to have some guidelines for what type of clothes to wear during your holiday in Sleepy Hollow. Consider searching style blogs before you leave so you can blend in like a local. Pack your luggage with confidence by checking the forecast in Sleepy Hollow. July brings the warmest temperatures, with daytime averages of 24ºC, while January days average 0ºC, making it the coolest time of year.
What does an Expedia Sleepy Hollow holiday include?
Hotels, flights and a reliable car for your road trip adventures. Simply mix and match your preferred bundle and gain access to great discounts. Once you've made your booking, add on a few tours and experiences and watch your savings pile up. When it comes to planning your Sleepy Hollow holiday, you're in charge! See if there are any available private holiday homes in Sleepy Hollow as they are the most popular property type here. You can also look up other great stays on Expedia and tailor a one-of-a-kind travel experience.
Does Expedia offer Book Now, Pay Later Sleepy Hollow holidays?
Expedia has partnered with online lender Klarna to make your next trip a little easier on the wallet. Paying by instalment means you can spread the costs of your next dream escape, leaving you with more cash to splash while you're away. Klarna has several payment plans to choose from, so you're sure to find one that fits your budget. Check out these flexible payment options:

  • Pay monthly holidays: Jet off on that dream holiday sooner with Klarna's easy payment plans. If paying across multiple instalments sounds right for you, pick this option during the checkout process.
  • No-deposit holidays: If not paying upfront for your trip makes hitting that "book now" button easier, consider a no-deposit holiday plan with Klarna so that you can Book Now, Pay Later!

Can I choose my airline with a Sleepy Hollow Expedia holiday?
Definitely. Expedia has more than 400 partner airlines to choose from worldwide. With all that choice, finding the right carrier to take you to Sleepy Hollow will be a snap.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.