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
31 Jul - 2 Aug
In two months
11 Sep - 13 Sep
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Sleepy Hollow vacation rentals

Property grounds

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, (140 reviews)
"We had a great stay!!"
United States
Jasmine
The price is AED 727
AED 1,215 total
includes taxes & fees
20 Jul - 21 Jul
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Property grounds

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, (41 reviews)
"rooms were lovely and spacious and hosts were responsive and helpful. "
United States
nina a.
The price is AED 694
AED 1,276 total
includes taxes & fees
20 Jul - 21 Jul
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Property grounds

Piermont Oasis

Piermont Oasis
Piermont
9.8 out of 10, Exceptional, (18 reviews)
"Great place to stay! "
United States
Megan D.
The price is AED 569
AED 933 total
includes taxes & fees
29 Jul - 30 Jul
Piermont Oasis
TV

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 AED 571
AED 993 total
includes taxes & fees
29 Jul - 30 Jul
Cozy 1-bedroom retreat minutes from West Point!
Exterior detail

Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.4 out of 10, Exceptional, (9 reviews)
"Clean home, conveniently located to West Point. Very comfortable beds. "
United States
Danielle B.
The price is AED 1,177
AED 1,900 total
includes taxes & fees
20 Jul - 21 Jul
Fabulous 3bdrm Home w/parking!
In-room safe, iron/ironing board, travel crib, WiFi (free)

2BR House w/ Free Parking / Fully Equipped Kitchen / Spacious / Family Friendly

2BR House w/ Free Parking / Fully Equipped Kitchen / Spacious / Family Friendly
Bryn Mawr
The price is AED 975
AED 2,039 total
includes taxes & fees
20 Jul - 21 Jul
2BR House w/ Free Parking / Fully Equipped Kitchen / Spacious / Family Friendly
Interior

Harriman Outdoor Center - Mountain Laurel Cabin

Harriman Outdoor Center - Mountain Laurel Cabin
Haverstraw
The price is AED 830
AED 957 total
includes taxes & fees
22 Jul - 23 Jul
Harriman Outdoor Center - Mountain Laurel Cabin
Coffee/tea maker, fridge, oven, stovetop

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

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.6 out of 10, Exceptional, (23 reviews)
"Exactly what we needed for two people prior to an early morning touring West Point. "
United States
Andrew L.
The price is AED 422
AED 1,127 total
includes taxes & fees
26 Jul - 27 Jul
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Offices

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 AED 588
AED 1,223 total
includes taxes & fees
7 Aug - 8 Aug
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
TV

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 AED 808
AED 1,517 total
includes taxes & fees
21 Jul - 22 Jul
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Coffee/tea maker, fridge, microwave, dishwasher

3 Mi to Downtown: Spacious White Plains Home

3 Mi to Downtown: Spacious White Plains Home
White Plains
9.2 out of 10, Wonderful, (16 reviews)
"Great place for a short visit to the city "
United States
Jeremy S.
The price is AED 606
AED 2,714 total
includes taxes & fees
22 Jul - 23 Jul
3 Mi to Downtown: Spacious White Plains Home
House (5 Bedrooms) | Interior

3 Mi to Downtown: Spacious White Plains Home

3 Mi to Downtown: Spacious White Plains Home
3.0 star property
White Plains
The price is AED 779
AED 2,619 total
includes taxes & fees
22 Jul - 23 Jul
3 Mi to Downtown: Spacious White Plains Home
Coffee/tea maker, fridge, microwave, oven

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Highland Falls
10.0 out of 10, Exceptional, (7 reviews)
"Location was perfect for West Point visit. The space was clean and recently updated, the beds very comfortable, and perfect layout and spacious for 3-4 people. The host was welcoming and responsive."
United States
Maria L.
The price is AED 1,041
AED 1,638 total
includes taxes & fees
29 Jul - 30 Jul
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Dining

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 AED 569
AED 1,209 total
includes taxes & fees
21 Jul - 22 Jul
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
3 bedrooms, desk, iron/ironing board, travel crib

Local Artist Inspired | Walk to WestPoint + King Bed

Local Artist Inspired | Walk to WestPoint + King Bed
Highland Falls
9.4 out of 10, Exceptional, (18 reviews)
"Sweet abode. Cozy, clean and amazing location. The cute coffee bar was a nice bonus. Would definitely stay there again. "
United States
Danica J.
The price is AED 606
AED 1,745 total
includes taxes & fees
21 Jul - 22 Jul
Local Artist Inspired | Walk to WestPoint + King Bed
Terrace/patio

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 AED 558
AED 1,307 total
includes taxes & fees
6 Aug - 7 Aug
Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
Coffee/tea maker, fridge, microwave, oven

Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (35 reviews)
"Our stay was very nice and described as listed! We recommend anyone who is interested to stay! "
United States
Aj L.
The price is AED 918
AED 1,672 total
includes taxes & fees
2 Aug - 3 Aug
Contemporary Cozy Cottage
Interior

Private Garden Getaway: Cozy & Chic , Near Subway

Private Garden Getaway: Cozy & Chic , Near Subway
Manhattan
10.0 out of 10, Exceptional, (3 reviews)
"Great stay, excellent location and our host was so helpful and immediately responsive to any of my husband's requests while he was there. We would most definitely stay here again! "
United States
Robin C.
Private Garden Getaway: Cozy & Chic , Near Subway
1 bedroom, iron/ironing board, WiFi (free), bed sheets

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 Jul - 22 Jul
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
TV

The Classic Suite: 2BR close to NYC

The Classic Suite: 2BR close to NYC
Paterson
10.0 out of 10, Exceptional, (1 review)
"The property has everything we needed for a two night stay. Driving to NYC is approximately 40 mins. We like how this apartment was modernly designed. The check in and check out process was easy - detailed instruction provided. Would stay again. "
United States
Yue Z.
The price is AED 701
AED 1,300 total
includes taxes & fees
10 Aug - 11 Aug
The Classic Suite: 2BR close to 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

Hyatt Regency Greenwich

Hyatt Regency Greenwich

10/10 Excellent
"Q"
Jeff 1-night trip
Posted 2 hours ago
Hyatt Regency Greenwich

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 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.