Sleepy Hollow Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Jul 3 - Jul 5
In two months
Aug 14 - Aug 16
In three months
Sep 11 - Sep 13
In four months
Oct 9 - Oct 11

Our top choices for Sleepy Hollow vacation rentals

Property grounds

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Greenwich
9.8 out of 10, Exceptional, (39 reviews)
"Beautiful space, excellent communication from the hosts. Would stay again!"
United States
Crystal
The price is ￥27,401
￥51,381 total
includes taxes & fees
Jun 22 - Jun 23
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Fridge, oven, stovetop, coffee/tea maker

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.8 out of 10, Exceptional, (21 reviews)
"Convenient stay in Highland Falls for events at West Point. Well appointed and decorated. It’s a little tight for 2 adults and 2 young adults but it served our needs well for a quick 2-night stay. Coffee bar with fixings was a nice treat. Host was very nice and quick to respond to our questions. We will definitely stay here again if available next time. "
United States
Maria L.
The price is ￥18,428
￥49,173 total
includes taxes & fees
Jun 16 - Jun 17
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Property grounds

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Waterside
9.8 out of 10, Exceptional, (15 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is ￥33,458
￥63,955 total
includes taxes & fees
Jun 18 - Jun 19
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Property grounds

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (138 reviews)
"The space was comfortable and clean with a great view of the Hudson River valley. Perfect for 2 people on a weekend getaway. "
United States
Meredith C.
The price is ￥31,728
￥52,433 total
includes taxes & fees
Jun 16 - Jun 17
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
TV, books, offices

Bright&Comfy 2bed/1ba in quiet White Plains duplex

Bright&Comfy 2bed/1ba in quiet White Plains duplex
White Plains
9.0 out of 10, Wonderful, (7 reviews)
"Location was great! Clean house! Comfy beds! Great space! "
United States
Montana M.
The price is ￥37,656
￥67,215 total
includes taxes & fees
Jun 17 - Jun 18
Bright&Comfy 2bed/1ba in quiet White Plains duplex
Property grounds

Piermont Oasis

Piermont Oasis
Piermont
9.8 out of 10, Exceptional, (18 reviews)
"Great place to stay! "
United States
Megan D.
The price is ￥21,632
￥36,765 total
includes taxes & fees
Jun 30 - Jul 1
Piermont Oasis
Smart TV

Modern Luxe 1BR Apt in Downtown Stamford

Modern Luxe 1BR Apt in Downtown Stamford
Downtown Stamford
9.6 out of 10, Exceptional, (5 reviews)
"Our family stayed in the hotel(s) next door. It was so nice to have our own personal space!"
United States
Jill G.
The price is ￥25,638
￥70,024 total
includes taxes & fees
Jul 8 - Jul 9
Modern Luxe 1BR Apt in Downtown Stamford
Living area

Stamford Hideaway w/ Fire Pit

Stamford Hideaway w/ Fire Pit
Cove - East Side - Shippan
The price is ￥23,507
￥58,321 total
includes taxes & fees
Jul 8 - Jul 9
Stamford Hideaway w/ Fire Pit
Interior

Harriman Outdoor Center - Mountain Laurel Cabin

Harriman Outdoor Center - Mountain Laurel Cabin
Haverstraw
The price is ￥31,407
￥36,405 total
includes taxes & fees
Jun 16 - Jun 17
Harriman Outdoor Center - Mountain Laurel Cabin
Offices

Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Downtown Stamford
9.2 out of 10, Wonderful, (11 reviews)
"Perfect apartment and location. Amazing communication. Thank you!!"
United States
Ryan F.
The price is ￥23,075
￥50,252 total
includes taxes & fees
Jun 28 - Jun 29
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Terrace/patio

Nice Cozy Room By Empire City Casino And Cross County Shopping Center

Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Southeast Yonkers
7.8 out of 10, Good, (19 reviews)
"Great location"
United States
Jordan S.
The price is ￥15,143
￥21,607 total
includes taxes & fees
Jun 16 - Jun 17
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
2 bedrooms, WiFi

Private 2-bedroom apartment, private entrance, MetLife Stadium World Cup 30 mins

Private 2-bedroom apartment, private entrance, MetLife Stadium World Cup 30 mins
Paterson
10.0 out of 10, Exceptional, (1 review)
"The comfort and safety "
United States
Jolena
The price is ￥19,556
￥43,743 total
includes taxes & fees
Jul 6 - Jul 7
Private 2-bedroom apartment, private entrance, MetLife Stadium World Cup 30 mins
Desk, free WiFi, bed sheets

'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway

'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
Croton-on-Hudson
10.0 out of 10, Exceptional, (2 reviews)
"Great stay!"
United States
Ann S.
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
TV

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Port Chester
10.0 out of 10, Exceptional, (31 reviews)
"Super cute with everything we needed! We had a great time during our stay and this was the perfect spot for a little getaway! Highly recommend!"
United States
Christina
The price is ￥35,253
￥66,713 total
includes taxes & fees
Jun 21 - Jun 22
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Fridge, microwave, oven, stovetop

Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (34 reviews)
"Very clean comfortable quiet place"
United States
Mauro C.
The price is ￥36,054
￥67,629 total
includes taxes & fees
Jun 16 - Jun 17
Contemporary Cozy Cottage
Living area

Cheerful Home in Yonkers NY

Cheerful Home in Yonkers NY
Lincoln Park
7.6 out of 10, Good, (4 reviews)
"Nice neighborhood,open concept.Hreat space for my entire family.Kitchen big and spacious. Beds are huge. Definitely will stay here again."
United States
Tanya J.
The price is ￥40,060
￥93,399 total
includes taxes & fees
Jun 16 - Jun 17
Cheerful Home in Yonkers NY
TV, stereo

Solara – Luxury 1BR Downtown

Solara – Luxury 1BR Downtown
Downtown Stamford
The price is ￥33,666
￥68,361 total
includes taxes & fees
Jun 18 - Jun 19
Solara – Luxury 1BR Downtown
Interior

Waterview House Walking Distance from Cove Beach

Waterview House Walking Distance from Cove Beach
Cove - East Side - Shippan
9.2 out of 10, Wonderful, (25 reviews)
"House was amazing, with a wonderful view. Hosts were responsive and helpful. Will need to come back in summer!"
United States
Scott H.
The price is ￥74,992
￥150,109 total
includes taxes & fees
Jun 19 - Jun 20
Waterview House Walking Distance from Cove Beach
Smart TV, video games, DVD player, books

'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!

'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
Croton-on-Hudson
10.0 out of 10, Exceptional, (6 reviews)
"We had an extended stay at Croton Quarters, it was great! The hosts truly are pet-friendly, the location is ideal, and the property comfortable for a longer term visit. "
United States
Mateo A.
The price is ￥32,497
￥63,193 total
includes taxes & fees
Jun 17 - Jun 18
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
Interior

Harriman Outdoor Center - Cranberry Cabin

Harriman Outdoor Center - Cranberry Cabin
Haverstraw
Harriman Outdoor Center - Cranberry Cabin
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Sleepy Hollow Hotel Reviews

Wingate by Wyndham Bronx/Haven Park

Wingate by Wyndham Bronx/Haven Park

8/10 Good
"The bar had great food. Staff is very friendly."
Ivan 2-night trip
Posted less than an hour ago
Wingate by Wyndham Bronx/Haven Park

Find out more about Sleepy Hollow

Search for holiday rentals in Sleepy Hollow on Expedia! You can easily find your home rentals, villas, holiday apartments in Sleepy Hollow using one of the methods below:

  • View our selection of featured holiday rentals in Sleepy Hollow
  • Use the map to find apartments and other holiday homes in the Sleepy Hollow neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Sleepy Hollow while they last

Look no further and take a look at our great range of rental properties in Sleepy Hollow!

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?

Cheerful Home in Yonkers NY: This vacation home rental outside of Sleepy Hollow comes with WiFi so you can feel at home during your trip.

How many vacation rentals are there in Sleepy Hollow?

Choose from 3 Expedia vacation rentals in Sleepy Hollow for a memorable vacation.

What can I see and do in Sleepy Hollow?

While exploring the area, visit family-friendly sights like Bronx Zoo, or get outside and enjoy nature at Rockefeller State Park Preserve. Other places in town to visit include Old Dutch Church of Sleepy Hollow and Tarrytown Lighthouse.

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.