Holiday houses in Sleepy Hollow

5 out of 5 average rating, 7 reviews

Apartment in Tarrytown

Stylish, Cozy 2 BR Pied-á-terre

Relax in a stylish Pied-á-terre in Tarrytown, NY, 50 minutes from Manhattan. This cozy, renovated apartment has a private entrance, two bedrooms, washer/dryer, and a fully equipped kitchen with a dishwasher. The living area features a comfy sectional and 65" smart TV. Just a 5-minute walk to EF School, ideal for students or visiting loved ones. Steps from Old Croton Aqueduct trail, blocks from Main Street's cafes and shops, and a 12-minute walk to Metro-North Train Station and Hudson River Walk.

4.99 out of 5 average rating, 197 reviews

Cottage in Cortlandt

The Little Cottage in the Woods

The Little Cottage in the Woods Nestled among the trees, and in close proximity to our main house, this studio cottage is newly refurbished, very private and is in a great location to access the Hudson Valley. Hiking trails are within minutes of the cottage or right out the front door. Golf courses are also minutes away. Whether you are in the area on business or just looking to escape for the weekend and enjoy the out doors. It is situated on 9 1/2 hikeable acres, all available to our guests

4.98 out of 5 average rating, 62 reviews

Apartment in Tarrytown

2 BRs, Easy Walking in Tarrytown and Sleepy Hollow

This special place, newly renovated and lovingly decorated, has a private entrance, off-street parking, and a washer/dryer. Close to everything the Sleepy Hollow/Tarrytown area offers - a short walk to both downtowns, the Metro North train to NYC, Hudson River parks, the Jazz Forum, the Tarrytown Music Hall, a Saturday farmers market. A mile walk to the incomparable Rockefeller Park Preserve, 1.5 miles to Kykuit, 2 miles to Lyndhurst. The list of attractions and destinations goes on and on...

4.84 out of 5 average rating, 37 reviews

Home in Tarrytown

Lovely Tarrytown Home in Hudson

This charming 3-bedroom, 2-bathroom home in Tarrytown offers the perfect blend of comfort and convenience. Located just few minutes from the scenic Hudson River, it features spacious living areas, modern amenities, and a cozy atmosphere, making it an ideal retreat. Easy access to historic sites, including Washington Irving’s Sunnyside and Lyndhurst Mansion, as well as parks, dining, and shopping. With the beauty of the Hudson River and NYC only 45 minutes away, this home is a true getaway.

Guest suite in Croton-on-Hudson

4.92 out of 5 average rating, 135 reviews

The Bluestone - Spacious 2 bedroom w/central air

Come stay with us! You will have the entire first floor to yourself but we will be right upstairs if you should need us! Access to tree lined back yard with fire pit. Close to metro north train to NYC. Minutes to kayaking, hiking, restaurants, cafes & historical sites. Please note: Drive, walkway and entrance accessible to full size wheelchair (see photos) however the bathroom is not accessible to a wheelchair. Guest must have ability to enter and maneuver the bathroom on thier own.

Cottage in Greenwood Lake

4.98 out of 5 average rating, 343 reviews

Luxury Cottage with Spectacular Lake Views

Ultra Chic Cottage set high above Greenwood Lake with Private beach and lake front community access. Minutes away from Mountain Creek Ski Resort, Spa & Water park, Mt. Peter Ski & Tubing, Warwick creameries, breweries & vineyards & apple picking. 1 BR, 1 Bath, play/office/common room. Huge wrap around fenced in deck with Mid century modern fireplace allows for scenic dining, lounging and around the fire gatherings. #LakeViewCottage_GWL Town of Warwick Short Term Rental Permit #33593

4.88 out of 5 average rating, 41 reviews

Cabin in Carmel Hamlet

Peaceful Forest Cabin

Nestled down a quiet dirt road, this authentic, rustic 1800s log cabin has been lovingly updated with timeless style and all-new appliances in 2023. Perfectly situated on 4 private acres with native and perennial pollinator meadows! Lower Hudson Valley and surrounded by over 1,000 acres of State Forest, it's easy to stay in and bathe in nature, read a book, and bird-watch or to explore, shop, hike and dine in nearby Katonah, Cold Spring, Beacon, Hudson, or NYC.

4.93 out of 5 average rating, 14 reviews

Apartment in Nyack

Bright Retreat in Nyack

Charming, Sunlit Apartment in the Heart of Nyack Nestled in the vibrant and scenic town of Nyack, this cozy yet bright apartment offers an inviting and tranquil retreat. Perfect for anyone seeking a peaceful, well-lit atmosphere, the apartment combines modern comfort with a cozy, intimate feel. Just steps from Nyack’s charming cafes, boutiques, and the stunning Hudson River views, this apartment is a perfect balance of cozy living and vibrant surroundings!

Apartment in Croton-on-Hudson

4.98 out of 5 average rating, 343 reviews

Luxury 2bd⭐Comfort+Style⭐

45 min train to Grand Central. Apt is 1.9mi to train, supermarket. Free PARKING. Two 4K TVs, 4K Blu-ray library, NFLX/AMZN/HBO/Apple TV. XBOX 1X. Fast WIFI. SS APPL, stocked kitchen. Bd1: adjustable queen, 50" 4K TV. Bd2: adj queen. Office area (desk, fast wifi), private porch. Sidewalks. 7 min walk to cafes, a bar, and restaurants. Car rental is 16 min walk. Hiking, kayaking. I LIVE NEARBY IN ANOTHER APT.

4.83 out of 5 average rating, 127 reviews

Apartment in Nyack

Nyack Retreat

This stylish apartment is tucked away but right in the center of the popular town of Nyack. Very comfortable and spacious, perfect for an amazing get away. Please note: This is a quiet multi-family home that houses four apartments. We do not allow any parties or gatherings. Please do not book this place if you plan to host an event. Only persons booked are allowed without permission. Thank you respectfully.

4.95 out of 5 average rating, 156 reviews

Home in Dobbs Ferry

Beautiful Hudson River Bungalow in Dobbs Ferry

Serene and modern home. Newly renovated historic home on Main Street in the heart of the Village of Dobbs Ferry. Convenient to Manhattan and the Hudson Valley, the Old Croton Aqueduct trail is directly behind the home. This private apartment is on the second floor of a house with a separate entrance, offering complete privacy. Easy check-in with code.

4.91 out of 5 average rating, 579 reviews

Barn in Mount Kisco

NY Rustic Cottage Getaway

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

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Other great holiday rentals in Sleepy Hollow

Private room in Dobbs Ferry

4.94 out of 5 average rating, 373 reviews

Small cozy room in historic 1828 Dobbs Ferry home.

SusanRating, 5 stars2 weeks ago

Joanna is an awesome host and person! She went above and beyond doing everything to help me and make my visit comfortable and fun. Great location too. Walk to everything. Train to NYC is super close. Highly recommend this place!

Guest suite in Haverstraw

4.94 out of 5 average rating, 365 reviews

Haverstraw Hospitality Suite

AshlynRating, 5 stars3 weeks ago

The place was really lovely and had a spacious bathroom, comfortable bed and lots of beautiful nature to explore nearby. Would definitely recommend!

Private room in Rockleigh

4.86 out of 5 average rating, 153 reviews

Secluded Rockleigh Retreat #1

GaryRating, 5 stars7 months ago

Beautiful place and setting. Loved the nautical bathroom and shower. Plenty of room.

Private room in Sleepy Hollow

4.98 out of 5 average rating, 110 reviews

Aleida'house on beautiful town.

BeatriceRating, 5 stars1 month ago

My 5 night stay at Aleida’s in Tarrytown was fantastic. Aleida was a very helpful and friendly host, I felt very at home with her. Aleida always replied to any questions promptly. The house is in a great location, only about 5 minutes walk from the station. It is also very close to the river Hudson, and you can do a beautiful riverside walk to see the Tappan Zee bridge and Sleepy Hollow lighthouse. As a woman travelling on my own, I felt very safe in Tarrytown. A couple of times I got the train back from Grand Central late at night, and I always felt comfortable walking back from Tarrytown station to the house. I also felt safe walking around the town in the evening. It’s a very safe and friendly place, and only a 50 minute train to Grand Central. There are plenty shops and things to do in the town too. I would recommend booking a show at the historic Tarrytown Music Hall - it’s really special. I will miss my chats over breakfast with Aleida and would love to come back one day.

4.88 out of 5 average rating, 8 reviews

Guest suite in Elmsford

The Hidden Gem Guest House

ÍñigoRating, 5 stars2 weeks ago

My family and I stayed at Stephanie and Oscar’s property for a couple of months, as we were renovating our home in a neighboring town. House exactly as described and as shown in the pictures, very comfortable, and perfectly equipped for any kind of stay from a couple nights to a short term like in our case. The property was spotless clean when we checked in. Beyond, the house, which perfectly fit our needs, I would like to highlight what great hosts Stephanie and Oscar are! Proactive, super attentive, responsive and uber friendly. It was such a pleasure getting to know both of then. 100% recommended property and hosts! If we ever need to find lodging in the area, we’ll no doubt reach out to Stephanie and Oscar again!

Place to stay in Spring Valley

4.72 out of 5 average rating, 18 reviews

steampunk Studio

MarinaRating, 5 stars2 months ago

Tal himself is an excellent host, very positive and responsive. Tal's place is very unique. It is a stand-alone building on Tal's premises, so he is always nearby if help is needed. The area is a quiet jewish neighborhood. Plenty of space for parking. Things to take into consideration: 1) a very steep drive-up at a sharp angle. Not a problem during the daylight and if the road is dry. Just be careful driving during the night. 2) Steep stairs to the actual loft. Again, if you travel with no luggage not a problem at all. 3) No stove or kitchen utensils. There is a microwave, so you could at least warm food up. 4) The main bed is in the attic area with another flight of steep stairs. Originally we also had a problem with LED lights throughout the loft, we couldn't switch all of them off but I did figure that it is possible (the plug is through the little door by the bed). Overall, a very interesting place thanks to the excellent host who made it with his own hands.

Guest suite in Haverstraw

4.86 out of 5 average rating, 69 reviews

Unique comfortable guest suite

JonathanRating, 5 stars2 weeks ago

Maria’s listing was a cozy step up, clean and had everything I needed over the 4 days of my stay! Maria was quick to respond to any questions or concerns I had and was able to provide clear instructions on how to check in and check out of the apt.