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Vacation rentals in Sleepy Hollow

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Top-rated vacation rentals in Sleepy Hollow

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Apartment in Hastings-on-Hudson

4.82 out of 5 average rating, 123 reviews

Lovely Hastings home convenient to NYC.

Keep it simple at this peaceful and centrally-located home. This comfy one-bedroom apartment has everything you need for a convenient and warm stay. The kitchen is stocked with all the tools you need to make a delicious home-cooked meal. The living room features a sleeper sofa, perfect to accommodate a larger group and the master bedroom has a large comfortable queen-sized bed just perfect for a good night's sleep. Situated on the ground level of a townhome and only 2 blocks from the Metro North

Sep 17 – 24

G$25,939 GYD per night

Guest suite in Tarrytown

4.94 out of 5 average rating, 209 reviews

Brand new private Studio in the heart of Tarrytown

Brand new, Studio apartment in the heart of Tarrytown, with it’s own beautifully landscaped front yard! This newly renovated studio with it's private entrance, fully equipped kitchen and bathroom is only 1 block away from the Main Street and 8 mins walk to the Metro-North Tarrytown train station to explore both worlds, the city (35 mins express) and beautiful upstate New York. It is a cute town with lots of great restaurants, hiking trails and Hudson river views. Contactless check-in&check-out!

Aug 21 – 28

G$73,812 GYD per night

Apartment in Hastings-on-Hudson

4.93 out of 5 average rating, 112 reviews

Hastings On Hudson Garden Apartment

A 5-minute walk to Hastings On Hudson Metro North station (31-min fast train to Grand Central) and right next to the Old Croton Aquaduct for scenic walks. This apartment is located in a private house with views of the Hudson River, a landscaped garden and patio, and parking on the Old Croton Aquaduct – walking distance from a variety of restaurants, a supermarket and shops. A new renovation, the apartment features hardwood floors, central air & heating, separate bedroom and laundry facilities.

Feb 25 – Mar 4

G$32,041 GYD per night

Bungalow in Hastings-on-Hudson

4.92 out of 5 average rating, 718 reviews

★Tiny House Cottage 35 min to NYC on Hudson River★

The most popular Airbnb in the area! FREE private driveway too. A few blocks to the Hudson River. Super charming, slightly quirky, private Shangri-La w/backyard chickens in the artistic & quaint Rivertowns, 35 min. from NYC. The Tiny House escape is reminiscent of sleep away camp, though tastefully curated w/eclectic art & furnishings. Sleeping loft nest w/8 step ladder or pull out sofa bed. E-fireplace inside. Firepit outside. Stars galore. 2 patios, yard, hammock, gardens. Read on...

Jul 1 – 8

G$33,480 GYD per night

Apartment in Yonkers

4.94 out of 5 average rating, 213 reviews

Large, relaxing private 1 bedroom apartment.

Located on a quiet cul-de-sac, this self-catering 1 bedroom apartment with private driveway is located on the lower level of a private home and is perfect for anyone wishing to have a space to themselves. There is a roll-away single bed to accommodate a 3rd guest. We offer WiFi, Netflix and full cable TV access. Located near Executive Blvd and all the river towns. Plus, its only a short ride to all New York City has to offer. All reservation requests require verified Government ID.

Oct 20 – 27

G$26,859 GYD per night

Tiny home in New Paltz

4.99 out of 5 average rating, 742 reviews

Hudson Valley Tiny House

If you've been looking for the tiny house experience, look no further. Michelle and Chris built this tiny house to live as eco-friendly, comfy, and healthy as possible. Built with only non-toxic and all natural materials with a state of the art fresh-air system. Enjoy wildlife or relaxing at the river bend on our 5-acre property or explore the awesome attractions close by: county pool, winery, New Paltz downtown, “gunks” rock climbing, Minnewaska State Park, and more!

Jul 13 – 20

G$22,922 GYD per night

Apartment in Ossining

4.94 out of 5 average rating, 302 reviews

Hudson River Peaceful Getaway

Self check-in and private entrance. Parking for two cars. Peaceful apartment on the Hudson River. Train to NYC (Scarborough Station) is an 8 minute walk through historic neighborhood. Arcadian Mall (Grocery store, Starbucks, etc) 5 minute walk. Rivers views from inside and from three patios (1 on entrance side, 2 on River side). We only allow declawed cats because they can scratch and damage our expensive furniture and carpets. Most house trained dogs are welcome :)

Sep 14 – 21

G$59,716 GYD per night

Barn in Mount Kisco

4.91 out of 5 average rating, 539 reviews

NY Rustic Cottage Getaway

minimum of 3 nights during Covid-19 in order to keep things safe for guests... Prices are slightly elevated winter due to the cost of oil Just 50 min North of NYC (Metro North 5 min away) great for artists, writers, yogi's and creative types or people just wanting to get away from the hustle and bustle, city amenities near by. (Photo Shoots, Seminars, Workshops welcome-Call For different Rates) Tag & Follow Nina’s Cottage on Insta! @ninas_airbnb

Mar 17 – 24

G$32,382 GYD per night

Guest suite in Haverstraw

4.95 out of 5 average rating, 293 reviews

Haverstraw Hospitality Suite

Quiet & cozy suite, with a comfortable full bed & private bathroom in newly renovated garden (basement) level of a single-family home. WiFi/air conditioning & heat unit/FiOS cable - roku TV. Coffee/tea available. Rollaway available for an extra bed. The neighborhood is quiet, and parking is available in the driveway. Feel free to come and go as you please -- we hope our guests feel like this is their home away from home:)

Jan 12 – 19

G$17,628 GYD per night

Home in New Paltz

4.97 out of 5 average rating, 677 reviews

Victorian Haven

Victorian Haven is located near the Shawangunk Mountains that extends for over 20 miles and reaches 2,200 feet in height at Sam's point, the highest elevation on the ridge. In addition, the Wallkill River provides unspoiled and picturesque spots for hiking, fishing and/or picnics. Gardiner has a beautiful rail trail that follows the path of the 1860's railroad and provides a great opportunity to hike, bike or ski.

Jan 21 – 28

G$27,385 GYD per night

Guesthouse in Suffern

4.91 out of 5 average rating, 112 reviews

Private Studio w/Full Kitchen & Bath

Our place is a private, stand-alone building separate from our house, and is cleaned thoroughly between guests including disinfecting all hard surfaces. Private cottage with full kitchen and bath in Suffern, NY. Quick walk to train & bus to NYC. Right off I-87, I-287 (NY & NJ), & NJ Rt. 17. Close to shopping & local restaurants. Off-Street parking & outdoor picnic area. NO CLEANING FEE!

May 18 – 25

G$22,152 GYD per night

Guesthouse in Peekskill

4.94 out of 5 average rating, 207 reviews

Peekskill Carriage House Downtown Studio

Located close to the center of town, this is the perfect launchpad to experience local restaurants, coffee houses, the Paramount Theater, shopping, etc. and a short drive to stunning hikes, the Hudson Valley and beyond. The apartment is ideal for one or two and features a kitchenette, bathroom, dining island, comfortable queen bed, and couch. peekskillcarriagehouse.com

Jul 10 – 17

G$29,680 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Cottages

Quaint homes, peaceful surroundings

Hotels

Stylish accommodations and amenities

Popular amenities for Sleepy Hollow vacation rentals

Free parking on premises

Air conditioning

Stay near Sleepy Hollow's top sights

Tarrytown Music Hall23 locals recommend

Scenic Hudson RiverWalk Park at Tarrytown7 locals recommend

Bridge View Tavern10 locals recommend

Lefteris Gyro10 locals recommend

Philipsburg Manor16 locals recommend

Pierson Park5 locals recommend

Other great vacation rentals in Sleepy Hollow

Apartment in Piermont

4.85 out of 5 average rating, 307 reviews

Piermont Oasis

Dec 19 – 26

G$24,302 GYD per night

Earthen home in Ossining

4.87 out of 5 average rating, 144 reviews

The Babbling Brook

Aug 22 – 29

G$26,775 GYD per night

Apartment in Brookfield

4.94 out of 5 average rating, 184 reviews

Peaceful apartment on 3.5 acres w/ Artist studio.

Sep 4 – 11

G$25,314 GYD per night

Apartment in Hastings-on-Hudson

5.0 out of 5 average rating, 107 reviews

Spacious apartment in Hastings-on-Hudson near NYC

Sep 4 – 11

G$44,328 GYD per night

Cottage in Cortlandt

4.99 out of 5 average rating, 159 reviews

The Little Cottage in the Woods

Aug 3 – 10

G$30,176 GYD per night

Guest suite in White Plains

4.87 out of 5 average rating, 164 reviews

1BR close to White Plains train station

Oct 14 – 21

G$31,383 GYD per night

Guesthouse in Mahopac

4.96 out of 5 average rating, 110 reviews

Sunny Lakeview Guesthouse

Jan 4 – 11

G$27,621 GYD per night

Guest suite in Sleepy Hollow

4.98 out of 5 average rating, 44 reviews

Sleepy Hollow Private Apartment Airbnb

Aug 17 – 24

G$25,062 GYD per night

Quick stats about vacation rentals in Sleepy Hollow

Total rentals
10 properties
Popular amenities
Lake access, Gym, and BBQ grill
Wifi availability
10 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Total number of reviews
810 reviews
Nightly prices starting at
G$10,428 GYD before taxes and fees

Destinations to explore