Holiday rentals in Sleepy Hollow

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Top-rated holiday rentals in Sleepy Hollow

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Superhost

Flat 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

17–24 Sep

€ 133 per night

Guest favourite

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!

13–20 Sep

€ 381 per night

Guest favourite

Flat in Ossining

4.95 out of 5 average rating, 100 reviews

Gorgeous 1 BR w/High End Finishes, Heated BA Floor

Unwind at this peaceful retreat a short walk from downtown Ossining and Hudson River front parks. Designed with end to end comfort, beautifully decorated, and featuring a gorgeous open kitchen and entertaining room, in this space you can relax and step away from it all. Highlights include: 2nd floor walk-up High End Appliances and all Finishes Heated bathroom floors Contactless entry Off-street parking 1/2 block from multiple parks Weekly discount available Come stay here! You’ll love it

27 Sep – 4 Oct

€ 243 per night

Guest favourite

Bungalow in Hastings-on-Hudson

4.91 out of 5 average rating, 716 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...

8–15 Nov

€ 161 per night

Superhost

Guest suite in Piermont

4.85 out of 5 average rating, 381 reviews

Cozy private apartment with Hudson River views

This cozy apartment just one block from the Hudson River, is on the ground level of a house, with a separate entrance offering complete privacy. This modern space has a fully equipped kitchen, beautiful bathroom, comfy queen bed, reading chair, books galore, and a desk. Located in the adorable town of Piermont, it has the feel of a country retreat, a waterfront town, and it's an easy commute to Manhattan. As of Nov. 2022, the WIFI has been upgraded and it is now RELIABLE & HIGH-SPEED.

Guest favourite

Flat in Ossining

4.94 out of 5 average rating, 298 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 :)

15–22 Sep

€ 283 per night

Guest favourite

Barn in Mount Kisco

4.91 out of 5 average rating, 538 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

21–28 Feb

€ 160 per night

Guest favourite

Earthen home in Ossining

4.87 out of 5 average rating, 143 reviews

The Babbling Brook

Unique 2 room and 3rd room ( full bath) with backyard and babbling brook with 5 minute ride to train into NYC and 45 minute car ride to midtown Manhattan (with no traffic, lol) Totally renovated with gorgeous large bedroom overlooking backyard and brook. Private entrance with patio. Private driveway with parking spot. For 1 night only guests add $15.00 cleaning fee. Here is a 2 minute Video of "THE BABBLING BROOK" https://www.youtube.com/watch?v=CRUac3qSOm0

8–15 May

€ 125 per night

Guest favourite

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:)

17–24 Oct

€ 83 per night

Guest favourite

Guest house in Peekskill

4.94 out of 5 average rating, 206 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

28 Oct – 4 Nov

€ 137 per night

Guest favourite

Home in Dobbs Ferry

4.92 out of 5 average rating, 306 reviews

Small cozy room in historic 1828 Dobbs Ferry home.

This is a sweet warm room with twin bed chest of drawers, desk and hanging closet with shelves. I have a 2nd larger room with two twin beds in it, listed separately, and also a very small bedroom with a slightly narrower bed with a curtain across the doorway. Please note: I have one cat. So if you are allergic, maybe not a good choice for you.

10–17 Jan

€ 62 per night

Superhost

Flat in Ardsley

4.9 out of 5 average rating, 379 reviews

Lovely and well-appointed suite with full privacy

Charming suite with a private entrance, bathroom, indoor parking and dining area with kitchen amenities. Conveniently located in Westchester, and is accessible by the I-87, Henry Hudson, Sprain and Saw Mill Parkways; only a thirty minute drive to NYC. Near a deli, grocery, bakery, Carvel, CVS and a selection of restaurants.

12–19 Feb

€ 110 per night