Vacation rentals in Sleepy Hollow

4.99 out of 5 average rating, 193 reviews

A panoramic view of a river valley is captured from a vantage point. A suspension bridge spans the water below, surrounded by lush hills and trees with emerging green foliage. Two individuals are seated, taking in the natural beauty of the landscape.

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

4.95 out of 5 average rating, 135 reviews

A modern coffee station is featured on a bright countertop. A sleek Keurig coffee maker sits beside a stainless steel kettle. Two canisters, labeled 'coffee' and 'tea', are presented with wooden lids, adding a touch of warmth to the kitchen space.

Apartment in Ossining

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

4.91 out of 5 average rating, 153 reviews

A spacious living area features a large projector screen displaying a streaming service interface. A colorful area rug lies on the light wood floor, complemented by wooden beams overhead. A wooden cabinet and bright seating are visible, enhancing the inviting ambiance.

Home in Yorktown Heights

Cozy getaway 1 hr from NYC!

This peaceful home is only 1 hour from NYC & Brooklyn. There are 3 bedrooms & 3 bathrooms and a POOL. A large living area, a play room, a wood burning FIREPLACE, large TRAMPOLINE, yard with babbling brook & seating area! Bedroom 1: King size bed & pack n play. Ensuite bathroom. Bedroom 2: Queen size bed, dresser. Ensuite bathroom. Bedroom 3: King size bed, pull out couch. Ensuite bathroom. Living room: Pull out couch. Pool is open Memorial Day - Labor Day. Heated by the sun- no heater.

4.95 out of 5 average rating, 229 reviews

An outdoor seating area is set among trees, featuring stone pathways and a gravel surface. A circular fire pit is surrounded by seating, and a small dining set with two chairs is positioned nearby. A grassy space adds greenery to the tranquil setting.

Guesthouse in Mahopac

Lakeview Guesthouse with Sauna

Art and light filled spacious studio with panoramic views overlooking lake Mahopac perched on a steep hill. A short 5 min walk down the hill to swimming/paddleboarding/canoeing. Walkable to an on-the-lake restaurant/ dining/ takeout options + boba tea! Drivable to farm fresh food markets, restaurants and art museums. Cedar dry Sauna on property for use. Nearby towns and hikes include Fahenstock Park, Pound Ridge, Cold Spring, Beacon, Ridgefield, or walk up the hill to trails of Volz park!

4.97 out of 5 average rating, 326 reviews

A rustic cabin is enveloped by lush greenery, showcasing ivy climbing its wooden exterior. The structure features two windows and a stone feature in the front yard, which is bordered by wild grass, enhancing the connection to the surrounding evergreen forest.

Cabin in Wurtsboro

Spring Spa on a Cascading Brook - The Water House

The brook flows through an evergreen forest creating a nourishing environment and the perfect setting for a relaxing and rejuvenating spa retreat. The living/dining room, hot tub/deck, and fire pit are set overlooking the cascading brook, ideal for entertaining, meditating or simply as an enjoyable natural muse. The soft, cozy and elegantly vintage styled interior is illuminated and warmed with central heating, ambient lighting and a home surround sound entertainment system with karaoke.

5 out of 5 average rating, 105 reviews

An inviting cabin is surrounded by trees, featuring a wooden deck with a fire pit and seating areas. Warm light emanates from the cabin's windows, creating a cozy atmosphere. The landscape showcases fall foliage, enhancing the tranquil setting by the lakeside.

Cottage in South Salem

Oscaleta Guest House: Lakefront Cabin

Escapology-A spectacular lakeside destination, designed as a luxury suite with its own dock. Close to NYC and ideal for a quick trip, remote work or an extended retreat. Glamping-A cabin in the woods on a lake surrounded by nature, but tech-enabled with all the modern perks. Artfully Designed Space-Modern retrofit thoughtfully curated with custom artwork throughout this historic 1920's cottage. Purpose built for your outdoor routine- from grill to canoe…. We recommend 3+nights if you can.

4.96 out of 5 average rating, 436 reviews

A colorful sunset is displayed over the Hudson River, with vibrant hues of orange and pink reflecting on the water. Silhouettes of trees frame the image, accentuating the serene beauty of the landscape.

Apartment in Ossining

Hudson River Peaceful Getaway, Explore from here

Self Check-In/Private Entrance. House trained Dogs and declawed Cats are Welcome (No additional pet fee). Driveway Parking for two cars. Peaceful, private flat on the Hudson River. Train to NYC (Scarborough Station) 10 min walk through historic neighborhood. Arcadian Mall (Grocery Store, Starbucks, etc) 7 min walk. Lots to explore in the area. Panoramic Rivers views from inside and out. Two televisions. Coffee/Condiments/Cooking Essentials provided. $25 cleaning with or without pets.

4.95 out of 5 average rating, 255 reviews

A serene pond is framed by rustic stone edging and lush green plants, including hostas and grasses. A gentle waterfall is visible, creating a peaceful sound. Colorful koi fish can be seen swimming in the dark water, adding to the tranquil atmosphere of the outdoor space.

Apartment in Yonkers

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.

4.94 out of 5 average rating, 130 reviews

A serene gathering area is nestled among lush greenery, featuring four dark wood chairs arranged around a small fire pit. A gentle stream flows nearby, surrounded by diverse trees and foliage, creating a peaceful atmosphere for relaxation in nature.

Apartment in Suffern

Renovated Forest Oasis with Pool & Fire-pit

Get away from it all in this nature lovers retreat! Serenity abounds in this fully renovated 1 bedroom apartment with private entrance. Located on a 5 acre property abutting Harriman State Park with direct access to hiking trails. Guests are welcome to use the pool and hot tub (Memorial day through Labor day), or sit and enjoy a fire pit by the babbling brook. Fenced dog run for your furry friend. Just 30 minutes from the GWB and minutes from the train and bus.

4.93 out of 5 average rating, 219 reviews

A serene view of the Hudson River during sunset, showcasing vibrant hues of orange and pink reflecting on the water. Silhouettes of trees and hills frame the scene, creating a peaceful setting. The landscape reveals a quiet area with foliage and distant trees along the riverbank.

Home in Wappingers Falls

Tranquil Tree-House on the beautiful Hudson River

Take it easy at this unique and tranquil getaway. Be our guest at our beautiful home located on the widest part of the Hudson River. Enjoy a private room with a queen size bed and a large screen smart tv. The full bathroom is located across the hallway. Enjoy a warm fire in the sitting area. There is a work area and a high table to enjoy some tea/coffee or wine with dinner while enjoying the view of the Hudson through the large windows and sliding door.

4.83 out of 5 average rating, 127 reviews

A pair of sliding glass doors, framed in white, opens to a softly lit bedroom area. The spacious bed is centered against a neutral wall, with bedside lamps placed on either side. A textured area rug adds warmth to the wooden floor.

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.

4.92 out of 5 average rating, 203 reviews

A calm waterfront scene is captured with soft mist hovering over the tranquil water. Vivid autumn foliage is visible on the distant shoreline, providing a serene backdrop to the stillness of the lake and creating a peaceful ambiance.

Cottage in Mohegan Lake

The Pearl of Westchester

Welcome to the Paradise! This Pearl of Westchester are nested with a Main house on private 2 acres of direct waterfront estate. Offering a private dock and beach in a flawless natural paradise. Enjoy swimming, fishing, boating or barbecuing on a private porch. Hiking in walking distance Located less than an hour away from NYC. Peekskill Metro North is 15 min away.

Vacation rentals for every style

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Apartments

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A space thats all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Sleepy Hollow vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Boutique hotel rooms in Sleepy Hollow

4.7 out of 5 average rating, 43 reviews

An inviting porch is furnished with wicker seating and colorful cushions. A small table is adorned with a fresh flower vase. Natural light filters through the overhead ceiling fan, casting soft shadows on the polished wooden floor, which is bordered by lush greenery.

Hotel room in Summit

The Vestibule-Full Room with External Private Bath

A bedside table is equipped with a modern lamp featuring a textured shade. Next to the lamp, a remote control lies on the dark surface, indicating ease of access for guests. The background shows part of a bed with muted bedding.

Hotel room in Union City

4.69 out of 5 average rating, 107 reviews

Private bedroom Boutique Hotel 10 mins from NYC

The lobby area features modern furnishings and a warm color palette. Plush seating is arranged around a circular coffee table on a rich red rug. A stylish front desk is visible, complemented by an elegant fireplace and an open staircase in the background.

Hotel room in Midtown Manhattan

4.81 out of 5 average rating, 355 reviews

Sonder Chambers | Queen Room

Hotel room in Cold Spring

A well-lit hallway features smooth marble flooring and soft green walls. A small refrigerator stocked with drinks is positioned next to a door marked with the number three. Decorative mirrors and wall sconces add to the inviting atmosphere.

4.84 out of 5 average rating, 98 reviews

Room 1 Cold Spring Hotel (Main St.)

4.77 out of 5 average rating, 133 reviews

A welcoming entrance is highlighted by a covered awning, featuring the establishment's name prominently displayed. Potted plants add greenery along the pathway, while an American flag gently waves nearby, indicating the welcoming atmosphere of the entrance to the hotel.

Hotel room in Great Neck

Boutique Hotel in the heart of the North Shore

4.74 out of 5 average rating, 173 reviews

The exterior of the Warwick Inn is showcased, featuring classic white siding and intricate architectural details. A central entrance with double doors is framed by dark shutters, while the building's name is elegantly displayed above. Lush greenery is positioned near the entrance, adding to the inviting appearance.

Hotel room in Warwick

The Warwick Inn Boutique Bellvale Room 2

Hotel room in Greenwood Lake

A scenic view of Greenwood Lake is depicted, featuring several boats docked along the wooden piers. Lush green hills rise in the background, under a sky dotted with fluffy white clouds. The calm water reflects the natural beauty of the environment.

4.71 out of 5 average rating, 45 reviews

Unique lakeside lodging steps from Greenwood Lake

Hotel room in Midtown Manhattan

The lobby features modern seating arrangements with plush armchairs and a decorative rug. Unique art pieces, including a large ornamental sculpture, add character to the space. A shimmering chandelier provides illumination, while the reception area is marked by a contemporary design and welcoming atmosphere.

4.87 out of 5 average rating, 136 reviews

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Other great vacation rentals in Sleepy Hollow

4.94 out of 5 average rating, 142 reviews

A welcoming entrance features a brown door, adorned with a window showcasing a sheer curtain. A potted plant sits on a metal stand beside the door, while a decorative welcome mat lies on the wooden floor, adding charm to the rustic log home facade.

Apartment in Wallkill

Log Cabin Apartment Great for Outdoor Enthusiasts

4.98 out of 5 average rating, 118 reviews

An airy loft space is highlighted by wooden beams and warm-toned walls. A mix of seating options, including a green lounge chair and blue dining chairs, are arranged around a table. Natural light filters through a window, illuminating the polished wooden floor.

Chalet in Monticello

Riverfront Ski Chalet

4.73 out of 5 average rating, 112 reviews

The entrance of Minerals Resort and Spa is showcased, featuring a prominent sign surrounded by vibrant autumn foliage and colorful flower beds. The building's stone accents and unique architecture complement the natural scenery of the lush mountains in the background.

Condo in Vernon Township

200 yds Minerals - great for hotel weddings

4.96 out of 5 average rating, 56 reviews

Condo in Vernon

New Luxury Ski Condo-2 Full Bathrooms

4.94 out of 5 average rating, 205 reviews

Home in Vernon Township

Luxury Mountain Retreat Condo - Skiing & More!

4.83 out of 5 average rating, 100 reviews

Home in Cornwall

State Forest Getaway

5 out of 5 average rating, 40 reviews

A spacious living room features a high stone fireplace as its focal point, surrounded by tall windows that allow natural light to fill the space. A modern chandelier hangs from the cathedral ceiling, while comfortable seating options are arranged for relaxation and conversation.

Home in New Paltz

Luxury Home with Mountain Views