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

Sleepy Hollow Holiday Rentals

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Our top choices for Sleepy Hollow holiday rentals

1. The Arches Suites

The Arches Suites
2.0 star property
Bronx
9.4 out of 10, Exceptional, (3 reviews)
"I had a wonderful stay at this hotel. My room was clean, comfortable, and well-maintained. I would definitely recommend this place to others and look forward to staying here again."
United Kingdom
Darryl
The price is NZ$454
includes taxes & fees
17 Nov - 18 Nov
The Arches Suites

2. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (210 reviews)
"Very limited breakfast…bagels and coffee…help your self. One plus small kitchenette"
United States
Christine
The price is NZ$306
includes taxes & fees
18 Nov - 19 Nov
Stamford Suites

3. Piermont Oasis

Piermont Oasis
Piermont
9.6 out of 10, Exceptional, (25 reviews)
"Great place to stay! "
United States
Megan D.
The price is NZ$357
includes taxes & fees
30 Nov - 1 Dec
Piermont Oasis

4. 1 King Bed | Non-Smoking

1 King Bed | Non-Smoking
Elmsford
10.0 out of 10, Exceptional, (2 reviews)
"Our rooms felt cozy enough for two people with decent privacy due to separate bathrooms nearby too.The location suited our plan moving between airport runs & visits close by malls perfectly."
United States
Anonymous traveller
The price is NZ$232
includes taxes & fees
17 Nov - 18 Nov
1 King Bed | Non-Smoking

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
8.0 out of 10, Very good, (20 reviews)
"Great location"
United States
Jordan S.
The price is NZ$194
includes taxes & fees
16 Nov - 17 Nov
Nice Cozy Room By Empire City Casino And Cross County Shopping Center

6. Gem by the water+ firepit and all fenced backyard

Gem by the water+ firepit and all fenced backyard
Waterside
10.0 out of 10, Exceptional, (22 reviews)
"Property was exactly what we needed for our stay"
United States
Christopher E.
The price is NZ$792
includes taxes & fees
17 Nov - 18 Nov
Gem by the water+ firepit and all fenced backyard

7. Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.

Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
Croton-on-Hudson
9.6 out of 10, Exceptional, (28 reviews)
"Beautiful setting and well appointed"
United States
Marianna H.
The price is NZ$712
includes taxes & fees
16 Nov - 17 Nov
Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.

8. 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, (150 reviews)
"We had a great stay!!"
United States
Jasmine
The price is NZ$549
includes taxes & fees
16 Nov - 17 Nov
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

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

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Port Chester
10.0 out of 10, Exceptional, (34 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 NZ$706
includes taxes & fees
16 Nov - 17 Nov
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

10. Seabreeze at the beach west beach Stamford ct.

Seabreeze at the beach west beach Stamford ct.
Cove - East Side - Shippan
9.8 out of 10, Exceptional, (18 reviews)
"Fantastic place Very clean, a perfect stay !!!"
United States
bill J.
The price is NZ$1,058
includes taxes & fees
16 Nov - 17 Nov
Seabreeze at the beach west beach Stamford ct.

11. 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, (46 reviews)
"Nice stay"
United States
Christopher J.
The price is NZ$601
includes taxes & fees
18 Nov - 19 Nov
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

12. 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
8.6 out of 10, Excellent, (7 reviews)
"Amazing host I appreciate everything she did for me"
United States
CSQUARED A.
The price is NZ$521
includes taxes & fees
16 Nov - 17 Nov
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich

13. 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
10.0 out of 10, Exceptional, (14 reviews)
"Host was very polite and helpful. Excellent condition VRBO."
United States
Drew C.
The price is NZ$523
includes taxes & fees
16 Nov - 17 Nov
Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle

14. Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!

Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!
Downtown Stamford
10.0 out of 10, Exceptional, (3 reviews)
"Had a lovely stay. Close to the train station and close to things in Stamford. Lovely space and owner was super helpful!"
United States
Marisa C.
The price is NZ$459
includes taxes & fees
22 Nov - 23 Nov
Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!

15. Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Ossining
8.8 out of 10, Excellent, (10 reviews)
"It's an elegant older house with lots of room for company. Family friendly. The pool was great. My family enjoyed it."
United States
Karen O.
The price is NZ$1,370
includes taxes & fees
16 Nov - 17 Nov
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

16. Local Artist Inspired | Walk to WestPoint + King Bed

Local Artist Inspired | Walk to WestPoint + King Bed
Highland Falls
9.6 out of 10, Exceptional, (21 reviews)
"Great location! Easy checkin, checkout process. We would stay again"
United States
Morgan S.
The price is NZ$752
includes taxes & fees
19 Nov - 20 Nov
Local Artist Inspired | Walk to WestPoint + King Bed

17. 3BR Near West Point | Coffee Bar | Sleeps 6

3BR Near West Point | Coffee Bar | Sleeps 6
Highland Falls
9.6 out of 10, Exceptional, (4 reviews)
"Clean and convenient near West Point golf course"
United States
mario b.
The price is NZ$733
includes taxes & fees
17 Nov - 18 Nov
3BR Near West Point | Coffee Bar | Sleeps 6

18. 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, (95 reviews)
"The host, Maria, was excellent in staying in touch and personally met me upon check-in and checkout. The location is very convenient for walking around downtown or easily drive to nearby outings."
United States
Margaret S.
The price is NZ$642
includes taxes & fees
18 Nov - 19 Nov
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food

19. "Apt C " - Next to Hiking Trail - Second Floor

"Apt C " - Next to Hiking Trail - Second Floor
Northwest Yonkers
10.0 out of 10, Exceptional, (3 reviews)
"Place was very cozy and had everything we needed.Would definitely recommend!"
United States
Sandra A.
The price is NZ$731
includes taxes & fees
23 Nov - 24 Nov
"Apt C " - Next to Hiking Trail - Second Floor

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

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.2 out of 10, Wonderful, (25 reviews)
"Exactly what we needed for two people prior to an early morning touring West Point. "
United States
Andrew L.
The price is NZ$476
includes taxes & fees
16 Nov - 17 Nov
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
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

Find out more about Sleepy Hollow

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Sleepy Hollow holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Sleepy Hollow. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Sleepy Hollow. Seeing all the best attractions is bound to make you fall in love with Sleepy Hollow. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Sleepy Hollow short-term rentals, that won’t be hard to do.

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Frequently asked questions

Can I find a holiday rental in Sleepy Hollow?

Yes, there are holiday rentals close to the most popular sights in Sleepy Hollow, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Sleepy Hollow has to offer?

Modern Luxury Home w GameRoom & Parking: This holiday home rental outside of 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 that you can cook with friends or family.

How many holiday rentals are there in Sleepy Hollow?

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

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 holiday rentals like in Sleepy Hollow?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Sleepy Hollow. Holiday rentals feature extras such as hot tubs, fire pits and patios so you'll have all the comforts of home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for a family trip.