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Sleepy Hollow Vacation Rentals

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Nov 23 - Nov 24
Tomorrow
Nov 24 - Nov 25
Next weekend
Nov 28 - Nov 30
In two weeks
Dec 5 - Dec 7

Vacation Rentals in Sleepy Hollow

Deluxe Studio Suite, 1 King Bed, Balcony | Balcony view
Global Luxury Suites at The Arches

Global Luxury Suites at The Arches

2.5 star property
Bronx
6.8 out of 10, (529)
"Enjoyed our stay , would stay again "
United States
Dawnae
$206 nightly
The price is $240
Nov 24 - Nov 25
Total with taxes and fees
Global Luxury Suites at The Arches
Lobby
Stamford Suites

Stamford Suites

4.0 star property
Downtown Stamford
6.2 out of 10, (75)
"It was great"
United States
Natalie
$120 nightly
The price is $138
Nov 24 - Nov 25
Total with taxes and fees
Stamford Suites
2 bedrooms, iron/ironing board, travel crib, WiFi
Beautiful cozy two bedroom apartment in great location of NYC!!

Beautiful cozy two bedroom apartment in great location of NYC!!

Manhattan
8.6 out of 10, Excellent, (41)
"It was cute and close to Yankee Stadium "
United States
Christina C.
Beautiful cozy two bedroom apartment in great location of NYC!!
Smart TV, fireplace, video games, DVD player
3-bedroom condo in Central Park, Manhattan, Times Square!

3-bedroom condo in Central Park, Manhattan, Times Square!

Manhattan
9.0 out of 10, Wonderful, (20)
"The apartment was spacious and close to public transportation and Central Park. We enjoyed our stay! "
United States
Liliana C.
3-bedroom condo in Central Park, Manhattan, Times Square!
Exterior detail
Cozy vintage studio in New York City brownstone!

Cozy vintage studio in New York City brownstone!

Manhattan
9.8 out of 10, Exceptional, (8)
"Neighborhood was quiet at night. Subway was only a few blocks away. Parking garage was around the corner. We enjoyed our stay."
United States
Heidi R.
$278 nightly
The price is $304
Nov 24 - Nov 25
Total with taxes and fees
Cozy vintage studio in New York City brownstone!
Lounge
Luxury Apartments by Hyatus at The Asher

Luxury Apartments by Hyatus at The Asher

4.5 star property
Downtown Stamford
10.0 out of 10, Exceptional, (19)
"Clean and had everything you need for longer stay Comfortable "
United States
christine
Luxury Apartments by Hyatus at The Asher
Living area
Tranquil 4-bedroom apartment in Manhattan perfect for large groups

Tranquil 4-bedroom apartment in Manhattan perfect for large groups

Manhattan
10.0 out of 10, Exceptional, (4)
"Our host was helpful, quick to respond and made check in/out easy. "
United States
Natalie S.
Tranquil 4-bedroom apartment in Manhattan perfect for large groups
Fridge, microwave, stovetop, coffee/tea maker
Modern 1-bedroom Garden Apartment with Backyard, up to 25 mins to Times Square

Modern 1-bedroom Garden Apartment with Backyard, up to 25 mins to Times Square

2.0 star property
Manhattan
10.0 out of 10, Exceptional, (61)
"Great place. Very clean, quiet, really nice patio, and close to the subway. Much better than getting a hotel room. "
United States
Christopher C.
Modern 1-bedroom Garden Apartment with Backyard, up to 25 mins to Times Square
Terrace/patio
3BR Prime Luxury near NYC w Arcade Room

3BR Prime Luxury near NYC w Arcade Room

2.0 star property
Southeast Yonkers
8.0 out of 10, Very Good, (1)
"We thought we rented the entire property, but was half of it. expect a lot of stairs. No bath tubs but two showers. some door knobs and locks need maintenance, but overall nice clean rooms."
United States
Anonymous traveler
$687 nightly
The price is $769
Nov 24 - Nov 25
Total with taxes and fees
3BR Prime Luxury near NYC w Arcade Room
Reception
Global Luxury Suites White Plains

Global Luxury Suites White Plains

3.5 star property
White Plains
6.8 out of 10, (33)
"Being in an apartment building for an actual stay instead of a house was a first for myself and the family but overall a good stay."
United States
Ramon
Global Luxury Suites White Plains
Interior
✨ New Luxe 2BR 2BA – King Bed, Fast Wi-Fi, 15 Mins to Times Square

✨ New Luxe 2BR 2BA – King Bed, Fast Wi-Fi, 15 Mins to Times Square

Bronx
9.8 out of 10, Exceptional, (6)
"My friends and I stayed here for two nights and fell in love! It is a beautiful two bedroom apartment with lovely decora very clean! Host was kind enough to leave us beverages stocked in the fridge! Conveniently locked near the train station. Lovely restaurants next door, we a convenient store two doors down. Perfect location if you plan to travel all around nyc. "
United States
hillina
$657 nightly
The price is $717
Nov 27 - Nov 28
Total with taxes and fees
✨ New Luxe 2BR 2BA – King Bed, Fast Wi-Fi, 15 Mins to Times Square
Property grounds
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

Greenwich
9.6 out of 10, Exceptional, (21)
"Perfect place to rest. Excellent service! "
Mexico
Lucymar
$205 nightly
The price is $232
Nov 24 - Nov 25
Total with taxes and fees
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
Private kitchen
Luxury & Elegance @ Large Private HOME, 3baths, CentralAC, Washer/Dryer, Parking

Luxury & Elegance @ Large Private HOME, 3baths, CentralAC, Washer/Dryer, Parking

2.0 star property
Bronx
8.8 out of 10, Excellent, (8)
"I am writing to provide a review for the property we recently stayed at. It was truly an amazing place with a perfect location that suited all of our needs. The property had everything we needed to make our stay comfortable and enjoyable.Everything was to the tea, amazing and up to date, furniture, and appliances and moreFurthermore, the host provided excellent correspondence throughout our stay, which was greatly appreciated. I highly recommend staying here again and would enthusiastically give...
United States
Dianna D.
$577 nightly
The price is $630
Dec 1 - Dec 2
Total with taxes and fees
Luxury & Elegance @ Large Private HOME, 3baths, CentralAC, Washer/Dryer, Parking
Smart TV
Luxury New-Build 2BR w King Bed, Designer Finishes + Ultra-Fast WiFi & AC

Luxury New-Build 2BR w King Bed, Designer Finishes + Ultra-Fast WiFi & AC

Bronx
9.8 out of 10, Exceptional, (13)
"Everything was very clean and cozy.We have enjoyed our stay there. "
United States
LORAINE L.
Luxury New-Build 2BR w King Bed, Designer Finishes + Ultra-Fast WiFi & AC
Fridge, microwave, oven, stovetop
Spacious 4-bedroom apartment in delightful NYC Manhattan sleeps 9

Spacious 4-bedroom apartment in delightful NYC Manhattan sleeps 9

Manhattan
8.6 out of 10, Excellent, (20)
"Ethan made the stay a very memorable "
United States
Raul G.
Spacious 4-bedroom apartment in delightful NYC Manhattan sleeps 9
Property grounds
Large 1-bedroom apartment in New York City- Manhattan

Large 1-bedroom apartment in New York City- Manhattan

Manhattan
Large 1-bedroom apartment in New York City- Manhattan
2 bedrooms, in-room safe, WiFi
Elegant 2BR Modern Oasis Brand-New Build, Luxe Touches & Lightning-Fast WiFi, AC

Elegant 2BR Modern Oasis Brand-New Build, Luxe Touches & Lightning-Fast WiFi, AC

Bronx
9.0 out of 10, Wonderful, (8)
"We really enjoyed our stay at this apartment. It was very spacious and nice. The only small thing they needed to add was a bath mat for the tub, it was very slippery, and maybe a small step stool for shorter people to reach some items in the cupboard. I'm only 5'4". Other than that, we had an excellent stay. We did get to meet the owner, because we initially had trouble getting into the apartment and he was a very friendly person. The neighborhood was very nice and clean, would definitely...
United States
Eddie S.
Elegant 2BR Modern Oasis Brand-New Build, Luxe Touches & Lightning-Fast WiFi, AC
Fridge, microwave, oven, stovetop
Marvelous 5-bedroom house with AC in Yonkers

Marvelous 5-bedroom house with AC in Yonkers

2.0 star property
Bryn Mawr
2.0 out of 10, (1)
"Cancelled my stay at check out time while I was at the NY airport— said there was a “power outage”. “Upgraded” me to a luxury property that turned out to be a dirty 3rd floor walk up. When I asked for a refund, they lied to VRBO and said I never showed up. I had to prove to VRBO with texts and phone records that they cancelled me. I suspected a bait and switch. Also, VRBO had to start an investigation because the phone number from the owner was an unknown number—my information had been...
United States
Amy L.
Marvelous 5-bedroom house with AC in Yonkers
Interior
Iconic Views, Ideal Location: Your Perfect NYC Apartment for 6 people

Iconic Views, Ideal Location: Your Perfect NYC Apartment for 6 people

Manhattan
10.0 out of 10, Exceptional, (6)
"Great location. Very clean. Close to subway "
United States
Ahmad-Shaker S.
$646 nightly
The price is $705
Nov 30 - Dec 1
Total with taxes and fees
Iconic Views, Ideal Location: Your Perfect NYC Apartment for 6 people
1 bedroom, iron/ironing board, WiFi, bed sheets
Elevated City Views: Modern & Stylish Retreat near Times Square

Elevated City Views: Modern & Stylish Retreat near Times Square

Manhattan
10.0 out of 10, Exceptional, (5)
"Beautiful views - the property is high up. The kitchen was nice to make some food at and had supplies. Check in instructions were clear. The place was clean as well. There is free parking on the street - just read the signs. One downside - The AC in the bedroom was pretty loud if you can’t sleep with loud noises. Quiet building though you can hear outside noises."
United States
Kimberly M.
Elevated City Views: Modern & Stylish Retreat near Times Square
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.
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Top Sleepy Hollow Hotel Reviews

Highbridge Hotel

Highbridge Hotel

10/10 Excellent
"The room was spotless, staff were amazing and warm. Breakfast was on point. The rate was affordable too and it was easy getting by with transportation. Keep the amazing work up! I’ll definitely visit again soonest!❤️😘"
Harris 1-night trip
Posted 3 days ago
Highbridge Hotel

Find out more about Sleepy Hollow

Everything you need to know about Sleepy Hollow vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Sleepy Hollow vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Sleepy Hollow vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Sleepy Hollow vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Sleepy Hollow. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Sleepy Hollow in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $138 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Sleepy Hollow rentals

At Expedia, we put the best Sleepy Hollow vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Sleepy Hollow rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Sleepy Hollow vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Sleepy Hollow. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Sleepy Hollow?

Yes, there are vacation rentals near the most popular sights in Sleepy Hollow, or you can go with a more secluded option if you're looking for relaxation. Sleepy Hollow is known for its churches and local tours. Make sure you have time to check out the riverfront and restaurants during your trip.

What are some of the best vacation rentals in Sleepy Hollow?

3BR Prime Luxury near NYC w Arcade Room: This vacation home rental outside of Sleepy Hollow is near the airport and offers free WiFi to help you feel perfectly comfortable in your new surroundings. This vacation rental also comes with free parking to give you added peace of mind.

What can I see and do in Sleepy Hollow?

While exploring the area, visit family-friendly sights like Legoland Discovery Center Westchester, or get outside and enjoy nature at Rockefeller State Park Preserve. Other places in town to visit include Philipsburg Manor and Old Dutch Church of Sleepy Hollow.

What are vacation rentals like in Sleepy Hollow?

Vacation rentals are private accommodations you can reserve for several days or longer in Sleepy Hollow. Vacation rentals offer extras such as patios, hot tubs, and fire pits so your stay will be comfortable. If you're concerned about cleanliness, a vacation rental can offer a sense of safety away from shared hotel elevators and bustling concierge desks while still allowing you to travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental a popular choice for a family trip or a small group gathering.