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
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Sleepy Hollow vacation rentals

Property grounds

1. Piermont Oasis

Piermont Oasis
Piermont
9.6 out of 10, Exceptional, (19 reviews)
"Great place to stay! "
United States
Megan D.
The price is ￥20,305
￥34,359 total
includes taxes & fees
Sep 1 - Sep 2
Piermont Oasis
Desk, WiFi (free), bed sheets

2. '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 ￥21,532
￥44,969 total
includes taxes & fees
Aug 3 - Aug 4
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
Luxury Apartment | Private kitchen

3. Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking
2.0 star property
White Plains
The price is ￥28,191
￥55,695 total
includes taxes & fees
Aug 3 - Aug 4
Elegant Hideaway with Free Parking
Property grounds

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

Garden Loft with Patios & Green Space · Westchester Retreat
Scarsdale
9.2 out of 10, Wonderful, (5 reviews)
"It was excellent!! "
United States
Henry C.
The price is ￥30,536
￥55,629 total
includes taxes & fees
Aug 31 - Sep 1
Garden Loft with Patios & Green Space · Westchester Retreat
1 bedroom, iron/ironing board, WiFi (free), bed sheets

5. 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 ￥14,874
￥21,224 total
includes taxes & fees
Aug 10 - Aug 11
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Terrace/patio

6. 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, (8 reviews)
"We had such a nice and peaceful stay! Shelton’s place was super clean, quiet, comfortable, and had everything we needed. Would definitely stay here again! "
United States
Katie M.
The price is ￥23,925
￥56,532 total
includes taxes & fees
Aug 17 - Aug 18
Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
Apartment (1 Bedroom) | Interior

7. 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 ￥22,351
￥45,632 total
includes taxes & fees
Aug 3 - Aug 4
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
Luxury Apartment | Living area

8. NY Luxury Apt Free Parking in PRIME Area

NY Luxury Apt Free Parking in PRIME Area
3.0 star property
Southeast Yonkers
5.8 out of 10, (7 reviews)
"Everything about this place is amazing. Great location, very safe, cozy, clean. Will be back soon!"
United States
Paola
The price is ￥17,140
￥42,628 total
includes taxes & fees
Aug 7 - Aug 8
NY Luxury Apt Free Parking in PRIME Area
Property grounds

9. 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
7.6 out of 10, Good, (4 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 ￥15,866
￥22,661 total
includes taxes & fees
Aug 3 - Aug 4
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
Interior

10. 1BR Queen near NYC | Trails, Biking & Sauna Bliss

1BR Queen near NYC | Trails, Biking & Sauna Bliss
Ossining
The price is ￥32,424
￥41,369 total
includes taxes & fees
Aug 3 - Aug 4
1BR Queen near NYC | Trails, Biking & Sauna Bliss
TV

11. 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 ￥34,628
￥64,989 total
includes taxes & fees
Aug 3 - Aug 4
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Offices

12. 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)
"loved walking the city. pizza was good."
United States
michelle b.
The price is ￥22,666
￥49,676 total
includes taxes & fees
Aug 3 - Aug 4
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Property grounds

13. 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, (141 reviews)
"We had a great stay!!"
United States
Jasmine
The price is ￥31,165
￥52,060 total
includes taxes & fees
Aug 3 - Aug 4
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Smart TV, video games, DVD player, books

14. '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, (7 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 ￥32,865
￥63,331 total
includes taxes & fees
Aug 6 - Aug 7
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
Coffee/tea maker, fridge, microwave, stovetop

15. 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 ￥28,332
￥45,929 total
includes taxes & fees
Aug 3 - Aug 4
The Subterranean Haven
Dining

16. 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 ￥42,309
￥74,853 total
includes taxes & fees
Aug 7 - Aug 8
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
Smart TV

17. Spacious 3BR Home / Free Parking / Perfect for Families & Groups

Spacious 3BR Home / Free Parking / Perfect for Families & Groups
White Plains
The price is ￥84,854
￥141,696 total
includes taxes & fees
Aug 3 - Aug 4
Spacious 3BR Home / Free Parking / Perfect for Families & Groups
Smart TV

18. Spacious 2 Bedroom Home / Parking Included / Near NYC

Spacious 2 Bedroom Home / Parking Included / Near NYC
Bryn Mawr
The price is ￥42,356
￥88,424 total
includes taxes & fees
Aug 3 - Aug 4
Spacious 2 Bedroom Home / Parking Included / Near NYC
TV

19. Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
10.0 out of 10, Exceptional, (3 reviews)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is ￥23,056
￥40,786 total
includes taxes & fees
Aug 4 - Aug 5
Cozy 1-bedroom retreat minutes from West Point!
Property grounds

20. Beautiful, spacious, and centrally located - 25 minutes from the heart of NYC.

Beautiful, spacious, and centrally located - 25 minutes from the heart of NYC.
Getty Square
9.8 out of 10, Exceptional, (12 reviews)
"Very clean and spacious apartment, close to the city and to great restaurants in Yonkers. Our host was responsive and accommodating. I would recommend renting this place."
United States
Andras M.
The price is ￥42,498
￥109,720 total
includes taxes & fees
Aug 3 - Aug 4
Beautiful, spacious, and centrally located - 25 minutes from the heart of NYC.
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

DoubleTree by Hilton Fort Lee - George Washington Bridge

DoubleTree by Hilton Fort Lee - George Washington Bridge

8/10 Good
"Hotel was approx $140 per night. 20 min drive to Times Square. Parking free at hotel. Nice clean modern rooms. Breakfast for a fee of $25 which was adequate. I would stay here again if on a budget. Near a busy highway but good for getting right on road to manhattan. Rooms were quiet I would stay here again. No pool and the run a shuttle bus to nyc for $10 but not sure of times"
Angela 3-night trip
Posted less than an hour ago
DoubleTree by Hilton 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?

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.: This vacation home rental outside of Sleepy Hollow is equipped with a garden, air-conditioning, and a Smart TV to help you feel comfortable during your stay. Kitchen amenities include a fridge, a stovetop, and a microwave.

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 Sportime USA, 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.