Sleepy Hollow Holiday Rentals

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Check prices for these dates

In two weeks
20 Mar - 22 Mar
In two months
1 May - 3 May
In three months
29 May - 31 May
In four months
26 Jun - 28 Jun

Our top choices for Sleepy Hollow holiday rentals

Living area

Villa in White Plains

Luxury NYC Home Game Room Free Parking
4.0 star property
The price is HK$4,293
HK$6,073 total
includes taxes & fees
9 Mar - 10 Mar
Luxury NYC Home Game Room Free Parking
Living area

Apartment in Bryn Mawr

Luxury 3BR Family Home Game Room Parking
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"Beautiful layout. Property had everything that was needed for an awesome stay."
United States
Ashley
The price is HK$2,724
HK$4,210 total
includes taxes & fees
9 Mar - 10 Mar
Luxury 3BR Family Home Game Room Parking
Private kitchen

Apartment in Bryn Mawr

Luxury 1BR located in Prime Yonkers Area
2.0 star property
10.0 out of 10, Exceptional, (2 reviews)
"Everything was clean, good communication.. I would like to come back again for sure "
United States
Genesis
The price is HK$2,802
HK$4,298 total
includes taxes & fees
9 Mar - 10 Mar
Luxury 1BR located in Prime Yonkers Area
Living area

Apartment in Southeast Yonkers

Spacious 3BR Luxe Escape near NYC
2.0 star property
8.0 out of 10, Very good, (2 reviews)
"Room was cold. No parking lot for vehicle. Only off-street parking was available "
United States
david
The price is HK$3,512
HK$4,702 total
includes taxes & fees
9 Mar - 10 Mar
Spacious 3BR Luxe Escape near NYC
Exterior

Holiday Home in North Side

The Victorian Blue 25min to NYC
9.6 out of 10, Exceptional, (5 reviews)
"The accommodations were fantastic, with spacious rooms, modern amenities, and breathtaking views. Additionally, the host was incredibly accommodating, ensuring that every aspect of my stay was comfortable and enjoyable. I highly recommend this property to anyone looking for a perfect getaway with a gracious host!"
United States
Honna C.
The price is HK$4,956
HK$8,660 total
includes taxes & fees
8 Mar - 9 Mar
The Victorian Blue 25min to NYC
Living area

Holiday Home in Bryn Mawr

Luxury 3 BR Near NYC with Easy Parking
2.0 star property
The price is HK$3,139
HK$4,519 total
includes taxes & fees
13 Mar - 14 Mar
Luxury 3 BR Near NYC with Easy Parking
Property grounds

Holiday Home in Tuckahoe

Comfortable 1 family home in Tuckahoe that's near train
The price is HK$3,044
HK$5,494 total
includes taxes & fees
1 Apr - 2 Apr
Comfortable 1 family home in Tuckahoe that's near train
Living area

Apartment in White Plains

Luxury 3BR Home Game Room Free Parking
2.0 star property
The price is HK$1,553
HK$2,939 total
includes taxes & fees
10 Mar - 11 Mar
Luxury 3BR Home Game Room Free Parking
Property grounds

Cottage in Greenwich

Riverfront Cottage-Heated Pool-Hot Tub-Fireplace 35minutes from New York City
10.0 out of 10, Exceptional, (1 review)
"The location was perfect for our family getaway. The snow and river backdrop brought the holiday spirit out in our college age kids. There was plenty of room and the fireplace was great. All the appliances are high end and the communication was excellent. The host went out of his way to make the visit special. Would highly recommend "
United States
Scott and Linsay T.
The price is HK$4,095
HK$8,229 total
includes taxes & fees
8 Mar - 9 Mar
Riverfront Cottage-Heated Pool-Hot Tub-Fireplace 35minutes from New York City
Fridge, microwave, oven, stovetop

Holiday Home in Lake Peekskill

Contemporary Cozy Cottage
10.0 out of 10, Exceptional, (31 reviews)
"Very clean comfortable quiet place"
United States
Mauro C.
The price is HK$1,760
HK$3,265 total
includes taxes & fees
5 Mar - 6 Mar
Contemporary Cozy Cottage
TV, fireplace, books, offices

Holiday Home in Cove - East Side - Shippan

New Beach Home near Stamford Downtown/Shippan
10.0 out of 10, Exceptional, (24 reviews)
"Great stay!"
United States
Kyra S.
The price is HK$2,870
HK$6,820 total
includes taxes & fees
6 Mar - 7 Mar
New Beach Home near Stamford Downtown/Shippan
Living area

Apartment in Bryn Mawr

Luxe 1BR Oasis - Prime NY Stay
2.0 star property
The price is HK$2,724
HK$4,210 total
includes taxes & fees
10 Mar - 11 Mar
Luxe 1BR Oasis - Prime NY Stay
Living area

Apartment in Bryn Mawr

Uscale 2BR Escape in the Heart of NYC
2.0 star property
8.0 out of 10, Very good, (1 review)
"The house was very clean and the areas was quiet too. We had a nice spot to park the car. The staff was calling and checking on me if I didn’t have any issues with the check in. They were available all the time. The only thing we will need next time if possible is the washer and dryer and extra towels because we were 5 and only got 3 towels. But overall we enjoyed the stays."
United States
Adj Fatou
The price is HK$2,724
HK$4,288 total
includes taxes & fees
13 Mar - 14 Mar
Uscale 2BR Escape in the Heart of NYC
TV

Apartment in Port Chester

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
10.0 out of 10, Exceptional, (30 reviews)
"Super cute with everything we needed! We had a great time during our stay and this was the perfect spot for a little getaway! Highly recommend!"
United States
Christina
The price is HK$1,721
HK$3,015 total
includes taxes & fees
5 Mar - 6 Mar
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Private kitchen

Holiday Home in Southeast Yonkers

3BR Prime Luxury near NYC w Arcade Room
2.0 star property
8.0 out of 10, Very good, (1 review)
"We thought we rented the entire property, but was half of it. expect a lot of stairs. No bath tubs but two showers. some door knobs and locks need maintenance, but overall nice clean rooms."
United States
Anonymous traveller
The price is HK$4,675
HK$6,237 total
includes taxes & fees
9 Mar - 10 Mar
3BR Prime Luxury near NYC w Arcade Room
Private kitchen

Apartment in White Plains

Elegant Hideaway with Free Parking
2.0 star property
The price is HK$1,553
HK$2,939 total
includes taxes & fees
10 Mar - 11 Mar
Elegant Hideaway with Free Parking
TV, stereo

Apartment in Downtown Stamford

Luxurious 3BR/2BA Modern Haven Downtown Stamford
10.0 out of 10, Exceptional, (3 reviews)
"This was a fantastic spot near restaurants (especially the Japanese grocery store) and the waterfront and was just a lovely place to stay. It was well appointed and easy to negotiate and really enjoyed the stay."
United States
Lisle N.
The price is HK$2,576
HK$4,784 total
includes taxes & fees
20 Mar - 21 Mar
Luxurious 3BR/2BA Modern Haven Downtown Stamford
Property grounds

Holiday Home in Waterside

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
10.0 out of 10, Exceptional, (11 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is HK$1,232
HK$2,551 total
includes taxes & fees
5 Mar - 6 Mar
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Property grounds

Holiday Home in Greenwich

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
9.8 out of 10, Exceptional, (27 reviews)
"Beautiful space, excellent communication from the hosts. Would stay again!"
United States
Crystal
The price is HK$1,007
HK$2,065 total
includes taxes & fees
9 Mar - 10 Mar
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Outdoor banquet area

Holiday Home in Ossining

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
9.2 out of 10, Wonderful, (7 reviews)
"Super fun location! Host was very helpful. The house is very comfortable for large groups "
United States
natalie l.
The price is HK$4,059
HK$7,990 total
includes taxes & fees
19 Mar - 20 Mar
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
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

Crowne Plaza Saddle Brook by IHG

Crowne Plaza Saddle Brook by IHG

10/10 Excellent
"r.everytvhing was great "
Bria 3-night trip
Posted 23 hours ago
Crowne Plaza Saddle Brook by IHG

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
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  • 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 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?

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

What can I see and do in Sleepy Hollow?

While exploring the area, visit family-friendly sights like Westchester Skating Academy, 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.