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
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Sleepy Hollow vacation rentals

A motel with a blue awning and a '6 Now Open' sign.

1. 1 Queen Bed | Non-Smoking

1 Queen Bed | Non-Smoking
Elmsford
8.4 out of 10, Very good, (5 reviews)
The price is AED 410
AED 469 total
includes taxes & fees
20 Oct - 21 Oct
1 Queen Bed | Non-Smoking
A modern gym with various weightlifting equipment, including a squat rack and kettlebells.

2. The Arches Suites

The Arches Suites
2.0 star property
Bronx
The price is AED 479
AED 930 total
includes taxes & fees
17 Nov - 18 Nov
The Arches Suites
A garden with a stone wall, a wooden fence, and a gravel path.

3. Piermont Oasis

Piermont Oasis
Piermont
9.6 out of 10, Exceptional, (23 reviews)
"Great place to stay! "
United States
Megan D.
The price is AED 441
AED 773 total
includes taxes & fees
2 Nov - 3 Nov
Piermont Oasis
A modern hotel lobby with a stone wall, a coffee machine, a refrigerator, and a sign advertising a motel.

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 traveler
The price is AED 421
AED 481 total
includes taxes & fees
20 Oct - 21 Oct
1 King Bed | Non-Smoking
A stone staircase leading to a house with a stone wall and a metal gate.

5. 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, (27 reviews)
"A lovely spot, very nice accommodations.Breakfast supples thoughtfully supplied as well as champagne to enjoy. "
United States
Eva C.
The price is AED 918
AED 1,563 total
includes taxes & fees
19 Oct - 20 Oct
Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
The Stamford Suites Hotel entrance with a clear view of the building's facade, a large sign, and a parking area.

6. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (195 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
The price is AED 602
AED 693 total
includes taxes & fees
22 Oct - 23 Oct
Stamford Suites
A bedroom with a large bed, a black sofa, a mirror, and a chandelier.

7. 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 AED 347
AED 495 total
includes taxes & fees
21 Oct - 22 Oct
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
A modern kitchen with white cabinets, a stainless steel dishwasher, a black granite countertop, and a window with a view of trees.

8. Snow Days & City Escapes: Spacious Ossining Home

Snow Days & City Escapes: Spacious Ossining Home
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.
The price is AED 804
AED 2,900 total
includes taxes & fees
21 Oct - 22 Oct
Snow Days & City Escapes: Spacious Ossining Home
A hallway with hardwood flooring, a staircase, and a dining area with a chair and table.

9. Snow Days & City Escapes: Spacious Ossining Home

Snow Days & City Escapes: Spacious Ossining Home
3.0 star property
Ossining
The price is AED 1,003
AED 2,993 total
includes taxes & fees
21 Oct - 22 Oct
Snow Days & City Escapes: Spacious Ossining Home
A modern kitchen with white cabinets, a wooden countertop, and a refrigerator.

10. 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 AED 389
AED 1,090 total
includes taxes & fees
15 Nov - 16 Nov
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
A neatly made bed with a black and white duvet, a wooden headboard, and a bedside table with a lamp. There are three framed artworks on the wall above the bed.

11. '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, (3 reviews)
"Great stay!"
United States
Ann S.
The price is AED 569
AED 1,133 total
includes taxes & fees
1 Nov - 2 Nov
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
A dining table set with plates, cutlery, and glasses, with a bowl of fruit and a wine glass in the background.

12. 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)
"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 AED 652
AED 1,317 total
includes taxes & fees
3 Nov - 4 Nov
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
Interior

13. 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 AED 551
AED 994 total
includes taxes & fees
19 Oct - 20 Oct
Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!
An outdoor patio with a fire pit, green chairs, and a table.

14. 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, (12 reviews)
"Host was very polite and helpful. Excellent condition VRBO."
United States
Drew C.
The price is AED 533
AED 1,290 total
includes taxes & fees
27 Oct - 28 Oct
Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
A modern living room with a stone fireplace, a leather sofa, a yellow armchair, a flat-screen TV, and a bookshelf.

15. '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, (9 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 AED 833
AED 1,579 total
includes taxes & fees
26 Oct - 27 Oct
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
Living area

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

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
8.4 out of 10, Very good, (5 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 AED 432
AED 814 total
includes taxes & fees
17 Nov - 18 Nov
Cozy 1-bedroom retreat minutes from West Point!
A covered area with exercise equipment, chairs, and a view through large windows.

17. 1BR Queen near NYC | Trails, Biking & Sauna Bliss

1BR Queen near NYC | Trails, Biking & Sauna Bliss
Ossining
The price is AED 965
AED 1,214 total
includes taxes & fees
1 Nov - 2 Nov
1BR Queen near NYC | Trails, Biking & Sauna Bliss
An outdoor dining area with tables set for a formal event, featuring candles, glassware, and floral centerpieces.

18. 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)
"Super fun location! Host was very helpful. The house is very comfortable for large groups "
United States
natalie l.
The price is AED 1,837
AED 3,558 total
includes taxes & fees
9 Nov - 10 Nov
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
A dock with kayaks and a canoe, surrounded by trees and a calm lake.

19. 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, (45 reviews)
"Nice stay"
United States
Christopher J.
The price is AED 698
AED 1,361 total
includes taxes & fees
15 Nov - 16 Nov
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
A spacious living room with a large window, a ceiling fan, a dining area with a table and chairs, and a staircase leading to an upper level.

20. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is AED 1,883
AED 3,838 total
includes taxes & fees
3 Nov - 4 Nov
Summer Pool Oasis Custom Bar Arcade Pool Table
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

Hampton Inn & Suites Teaneck Glenpointe

Hampton Inn & Suites Teaneck Glenpointe

10/10 Excellent
"Great"
Juan 1-night trip
Posted 10 hours ago
Hampton Inn & Suites Teaneck Glenpointe

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 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 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.