Sleepy Hollow Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Sleepy Hollow vacation rentals

A modern interior with a wooden ceiling, large glass doors leading to a living area with a sofa, chairs, and a dining table.

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
$220 nightly
The price is $255
Dec 16 - Dec 17
Total with taxes and fees
The Arches Suites
A modern hotel room with a large window, a sofa, a coffee table, and a decorative statue.

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
$149 nightly
The price is $171
Nov 22 - Nov 23
Total with taxes and fees
Stamford Suites
A garden pathway with stepping stones, surrounded by dense foliage and a stone wall.

3. Piermont Oasis

Piermont Oasis
Piermont
9.6 out of 10, Exceptional, (25 reviews)
"Great place to stay! "
United States
Megan D.
$180 nightly
The price is $200
Nov 30 - Dec 1
Total with taxes and fees
Piermont Oasis
A kitchenette with a water dispenser, microwave, coffee machine, and snack vending machine.

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
$112 nightly
The price is $128
Nov 17 - Nov 18
Total with taxes and fees
1 King Bed | Non-Smoking
A bedroom with a patterned bedspread, a headboard, bedside tables, and a window with curtains.

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.
$91 nightly
The price is $107
Nov 16 - Nov 17
Total with taxes and fees
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
A gated outdoor area with a wooden fence, a metal gate, and a small table with a lamp.

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.
$390 nightly
The price is $445
Nov 17 - Nov 18
Total with taxes and fees
Gem by the water+ firepit and all fenced backyard
A wooden deck with a railing overlooking a body of water and trees.

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.
$353 nightly
The price is $404
Nov 16 - Nov 17
Total with taxes and fees
Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
A house with a view of a bridge and mountains.

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
$257 nightly
The price is $304
Nov 16 - Nov 17
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
A living room with a sofa, a glass coffee table, a fireplace, and a TV mounted above it.

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.
$341 nightly
The price is $390
Nov 16 - Nov 17
Total with taxes and fees
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
An outdoor seating area with tables and chairs, surrounded by planters with flowers, and a modern building in the background.

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.
$515 nightly
The price is $587
Nov 16 - Nov 17
Total with taxes and fees
Seabreeze at the beach west beach Stamford ct.
A dock with kayaks and a canoe, surrounded by trees and a calm lake.

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.
$293 nightly
The price is $333
Nov 18 - Nov 19
Total with taxes and fees
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
A wooden staircase leading to a gazebo in a forested area with a metal railing.

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.
$254 nightly
The price is $289
Nov 16 - Nov 17
Total with taxes and fees
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
An outdoor patio with a fire pit, green chairs, and a table.

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.
$253 nightly
The price is $289
Nov 16 - Nov 17
Total with taxes and fees
Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
Living area

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.
$226 nightly
The price is $258
Nov 22 - Nov 23
Total with taxes and fees
Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!
A rectangular swimming pool with a brick wall and a basketball hoop.

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.
$746 nightly
The price is $763
Nov 16 - Nov 17
Total with taxes and fees
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
A modern kitchen with stainless steel appliances, white cabinetry, a coffee station, and a dining area with a wooden table and bench.

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.
$390 nightly
The price is $393
Nov 16 - Nov 17
Total with taxes and fees
Local Artist Inspired | Walk to WestPoint + King Bed
A hallway with a wooden door, a black table with a sign, and large green plants.

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.
$388 nightly
The price is $391
Nov 16 - Nov 17
Total with taxes and fees
3BR Near West Point | Coffee Bar | Sleeps 6
A dining table set with plates, cutlery, and glasses, with a bowl of fruit and a wine glass in the background.

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.
$311 nightly
The price is $356
Nov 18 - Nov 19
Total with taxes and fees
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
A modern living room with a grey sectional sofa, a round wooden coffee table, a hanging woven light fixture, and a green plant wall.

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.
$342 nightly
The price is $403
Nov 16 - Nov 17
Total with taxes and fees
"Apt C " - Next to Hiking Trail - Second Floor
A modern kitchen with white cabinets, a wooden countertop, and a refrigerator.

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.
$261 nightly
The price is $263
Nov 16 - Nov 17
Total with taxes and fees
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

A modern reception area with a wooden reception desk, a blue accent wall, and a large glass door leading to an outdoor seating area.
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
Hawthorne

10/10 Excellent

The room was very clean and the hotel itself looked very clean. Beds were comfortable and the room was very spacious. I would definitely recommend this hotel to anyone staying in this area.
United States
Lorena
Reviewed December 27, 2023
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

Find out more about Sleepy Hollow

Everything you need to know about Sleepy Hollow vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Sleepy Hollow vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Sleepy Hollow vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Sleepy Hollow vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Sleepy Hollow. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Sleepy Hollow in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $107 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Sleepy Hollow rentals

At Expedia, we put the best Sleepy Hollow vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Sleepy Hollow rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Sleepy Hollow vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Sleepy Hollow. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.

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