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Holiday houses in Sleepy Hollow

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Top-rated holiday 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

4.81 out of 5 average rating, 130 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

Guest favourite

Guest suite in Tarrytown

4.94 out of 5 average rating, 213 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!

Guest favourite

Bungalow in Hastings-on-Hudson

4.91 out of 5 average rating, 730 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...

Guest favourite

Apartment in Yonkers

4.94 out of 5 average rating, 219 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.

Guest favourite

Tiny home in New Paltz

4.99 out of 5 average rating, 745 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!

Guest favourite

Apartment in Ossining

4.94 out of 5 average rating, 316 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 :)

Guest favourite

Barn in Mount Kisco

4.91 out of 5 average rating, 540 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

Guest favourite

Apartment in Brookfield

4.94 out of 5 average rating, 189 reviews

Peaceful apartment on 3.5 acres w/ Artist studio.

Welcome to our cozy apartment! This fully enclosed apartment is attached to our main house on a beautiful 3.5-acre property in Brookfield. Enjoy a kitchen, comfortable living and bedroom area, and a clean bathroom. Guests have access to a shared 32 ft, 10 ft deep pool, artist studio, pool table,, garden, fire space, and outdoor seating. We provide a guidebook for your convenience. Book now and experience a perfect blend of comfort, creativity, and relaxation.

Earthen home in Ossining

4.87 out of 5 average rating, 144 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

Guest favourite

Guest suite in Haverstraw

4.95 out of 5 average rating, 301 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:)

Guest favourite

Guesthouse in Peekskill

4.94 out of 5 average rating, 213 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

Guest favourite

Apartment in Ardsley

4.9 out of 5 average rating, 385 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.

Holiday 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 accommodation and amenities

Popular amenities for Sleepy Hollow holiday rentals

Free parking on premises

Air conditioning

Stay near Sleepy Hollow's top sights

Tarrytown Music Hall23 locals recommend

Bridge View Tavern10 locals recommend

Scenic Hudson RiverWalk Park at Tarrytown7 locals recommend

Lefteris Gyro10 locals recommend

Philipsburg Manor16 locals recommend

Pierson Park5 locals recommend

Other great holiday rentals in Sleepy Hollow

Guest favourite

Apartment in Hastings-on-Hudson

5.0 out of 5 average rating, 111 reviews

Spacious apartment in Hastings-on-Hudson near NYC

Guest favourite

Apartment in Hastings-on-Hudson

4.92 out of 5 average rating, 114 reviews

Hastings On Hudson Garden Apartment

Guest favourite

Home in Croton-on-Hudson

4.96 out of 5 average rating, 162 reviews

The Carriage House: Vacation Home & Retreat

Guest favourite

Home in New Paltz

4.97 out of 5 average rating, 684 reviews

Victorian Haven

Guest favourite

Apartment in Milford

4.97 out of 5 average rating, 517 reviews

Water front studio apartment with fireplace.

Guest favourite

Guest suite in Sleepy Hollow

4.98 out of 5 average rating, 44 reviews

Sleepy Hollow Private Apartment Airbnb

Guest favourite

Apartment in Hastings-on-Hudson

4.99 out of 5 average rating, 92 reviews

30min>Manhattan/on Hudson River/Small town living!

Guest favourite

Home in Hastings-on-Hudson

4.91 out of 5 average rating, 11 reviews

Rivertown Retreat 25 mins to NYC

Quick stats about accommodation in Sleepy Hollow

Total rentals
10 properties
Popular amenities
Lake access, Gym and BBQ grill
Wi-Fi availability
10 properties include access to Wi-Fi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Total number of reviews
810 reviews
Nightly prices starting at
$76 AUD before taxes and fees

Destinations to explore