A wooden structure with a bridge over a body of water, surrounded by trees.

Sleepy Hollow Vacation Rentals

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Sleepy Hollow vacation rentals

Property grounds

1. Piermont Oasis

Piermont Oasis
Piermont
9.6 out of 10, Exceptional, (21 reviews)
"Great place to stay! "
United States
Megan D.
The price is ￥18,510
￥32,470 total
includes taxes & fees
Sep 24 - Sep 25
Piermont Oasis
Villa, Garden View | Living area

2. Luxury NYC Home Game Room Free Parking

Luxury NYC Home Game Room Free Parking
4.0 star property
White Plains
4.0 out of 10, (1 review)
"After flying in with four of us from Los Angeles on a Red Eye, we had to drive around for 4-5 hours until we were able to check in at 4pm, however after hours of trying to get into the property with no answer on the contact number ,we finally were able to have the local property manager come out and say that the property overbooked and had no room for us. I spent over 2 hours on the phone getting the run around by Expedia with mixed stories of our accommodations. FINALLY with now the story is...
United States
Jorge
The price is ￥76,037
￥109,856 total
includes taxes & fees
Sep 28 - Sep 29
Luxury NYC Home Game Room Free Parking
Room

3. 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 ￥14,516
￥20,713 total
includes taxes & fees
Sep 28 - Sep 29
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Room

4. '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.
The price is ￥23,878
￥47,599 total
includes taxes & fees
Sep 20 - Sep 21
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
Property grounds

5. Garden Loft with Patios & Green Space · Westchester Retreat

Garden Loft with Patios & Green Space · Westchester Retreat
Scarsdale
9.0 out of 10, Wonderful, (6 reviews)
"It was excellent!! "
United States
Henry C.
The price is ￥25,926
￥47,823 total
includes taxes & fees
Sep 29 - Sep 30
Garden Loft with Patios & Green Space · Westchester Retreat
House (5 Bedrooms) | Interior

6. Nyc-area Escape Near River, Trails & Mta!

Nyc-area Escape Near River, Trails & Mta!
3.0 star property
Ossining
The price is ￥42,110
￥125,709 total
includes taxes & fees
Sep 20 - Sep 21
Nyc-area Escape Near River, Trails & Mta!
Living area

7. '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, (8 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 ￥33,133
￥61,182 total
includes taxes & fees
Sep 24 - Sep 25
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
Private kitchen

8. NYC-Area Escape Near River, Trails & MTA!

NYC-Area Escape Near River, Trails & MTA!
Ossining
8.2 out of 10, Very good, (19 reviews)
"A family trip with teens and tweens- a perfect space! Clean, hist was friendly, the house was stocked with all we'd need! A great getaway for any family NYC trip!"
United States
Justeen P.
NYC-Area Escape Near River, Trails & MTA!
Living area

9. Cozy 1-bedroom apartment in lovely Yonkers minutes from Empire Casino and NYC

Cozy 1-bedroom apartment in lovely Yonkers minutes from Empire Casino and NYC
Dunwoodie
The price is ￥20,130
￥32,968 total
includes taxes & fees
Sep 16 - Sep 17
Cozy 1-bedroom apartment in lovely Yonkers minutes from Empire Casino and NYC
Property grounds

10. Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich

Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
Greenwich
8.0 out of 10, Very good, (5 reviews)
"This was a warm and inviting space. CC even offered me breakfast. I was a single woman in for a class reunion and had be somewhere on Sat and Sunday mornings. It was lovely coming back to relax and read. The space is small perfect for a couple with a young person. The patio over looks the river. The house is on a cul-de-sac perfect for strolling around the neighborhood. Very quiet and safe. Well lit path at night to the back, private entrance. Small fridge but holds a lot. Microwave, kurgurg...
United States
Kathleen W.
The price is ￥25,991
￥34,659 total
includes taxes & fees
Sep 28 - Sep 29
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
Property grounds

11. 2 Mi to NYC Train: WFH-Friendly Greenwich Apt!

2 Mi to NYC Train: WFH-Friendly Greenwich Apt!
Greenwich
8.0 out of 10, Very good, (4 reviews)
"Price was right for the stay! I would come back"
United States
Mark
The price is ￥41,648
￥77,758 total
includes taxes & fees
Sep 30 - Oct 1
2 Mi to NYC Train: WFH-Friendly Greenwich Apt!
Terrace/patio

12. Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle

Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
New Rochelle
9.8 out of 10, Exceptional, (10 reviews)
"Host was very polite and helpful. Excellent condition VRBO."
United States
Drew C.
The price is ￥22,675
￥54,164 total
includes taxes & fees
Oct 5 - Oct 6
Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
Dining

13. Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food

Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
CROTON HDSN
9.8 out of 10, Exceptional, (93 reviews)
"Our stay was just perfect! We chose the location based on being close-ish to family in northern Westchester and friends in the city and it was perfect. Maria is an excellent host and super attentive and helpful when needed. The apartment was the perfect size for our family and super cozy after a long day. We'd definitely stay again!"
United States
Aimee S.
The price is ￥29,431
￥57,830 total
includes taxes & fees
Oct 4 - Oct 5
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
Property grounds

14. 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, (42 reviews)
"Nice stay"
United States
Christopher J.
The price is ￥24,989
￥48,019 total
includes taxes & fees
Oct 3 - Oct 4
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Property grounds

15. 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, (19 reviews)
"Very nice location, easy check in and check out. Also very comfortable."
United States
Leslie S.
The price is ￥28,536
￥56,571 total
includes taxes & fees
Oct 7 - Oct 8
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Apartment (1 Bedroom) | Interior

16. 2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
3.5 star property
Greenwich
The price is ￥50,748
￥77,890 total
includes taxes & fees
Sep 30 - Oct 1
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
Living area

17. Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Port Chester
10.0 out of 10, Exceptional, (33 reviews)
"Exactly as described, comfy and close to the Capital and restaurants. We would definitely stay here again.Directions and parking instructions were very clear and helpful."
United States
Sarah W.
The price is ￥33,935
￥64,219 total
includes taxes & fees
Sep 20 - Sep 21
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Interior

18. Harriman Outdoor Center - Mountain Laurel Cabin

Harriman Outdoor Center - Mountain Laurel Cabin
Haverstraw
The price is ￥30,108
￥34,899 total
includes taxes & fees
Sep 28 - Sep 29
Harriman Outdoor Center - Mountain Laurel Cabin
Private kitchen

19. The Subterranean Haven

The Subterranean Haven
North Side
8.8 out of 10, Excellent, (10 reviews)
"Great space but anlittle amall, the floor dips a few spots and the space is pretty tight, but perfect for a short term stay!"
United States
Hannah R.
The price is ￥27,765
￥44,666 total
includes taxes & fees
Sep 16 - Sep 17
The Subterranean Haven
Living area

20. 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 ￥22,120
￥64,148 total
includes taxes & fees
Sep 17 - Sep 18
Modern Luxe 1BR Apt in Downtown Stamford
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

Hyatt Place Fort Lee / George Washington Bridge

Hyatt Place Fort Lee / George Washington Bridge

10/10 Excellent
"Nice Stay, friendly staff and dog friendly"
Jermaine 28-night trip
Posted 2 hours ago
Hyatt Place Fort Lee / George Washington Bridge

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?

Modern Luxury Home w GameRoom & Parking: This vacation home rental outside Sleepy Hollow is situated near the airport and has a rooftop terrace and free WiFi to help you feel content during your stay. It has 3 bedrooms as well as a kitchen with a full-sized fridge, a dishwasher, and a stovetop, so you can cook with friends or family.

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 Rockland Bakery, 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.