Vacation rentals in Sleepy Hollow

4.96 out of 5 average rating, 56 reviews

Condo in Vernon

New Luxury Ski Condo-2 Full Bathrooms

This newly renovated Great Gorge Village condo, the perfect getaway to be active or just relax with the whole family. There is so much to explore during every season. It's heaven for golfers, leaf peepers, skiers, snowboarders, hikers, bikers and water park explorers. For those looking to relax and unwind it's a great area to explore wineries, breweries and top- notch restaurants. Please note: the unit is located on the second floor. Also, the master bedroom loft suite is up a spiral staircase

5 out of 5 average rating, 10 reviews

Home in Roxbury

Zoom In Map To 5*Roxbury "Painter Hill" PoshPadsCT

PoshPadsCT - Private 4-5-Bedroom hilltop retreat on a serene brook - a perfect getaway. New Hot Tub, Terrace, Trampoline. Located on a 3 acre property near historic estates, Maple Bank farm stand and Toplands Farm and just 1.5 hours from NYC. The house features beautiful fields, views, a large terrace with a gas grill, a firepit. Nearby hiking trails & Washington restaurants, shopping, distilleries, vineyards, breweries, and more! Ski Mohawk Mountain or Swim Lake Waramaug State Beach.

4.89 out of 5 average rating, 141 reviews

Chalet in Goshen

The Goshen Glass Chalet

A vacation house furnished decorated 1 large master bedroom down stairs and full bathroom.2 bedrooms 1 full size bed upstairs & 2 twin size beds upstairs with a full bathroom bathroom .1 well stocked & equipped kitchen 1 large spacious combined living and a dining room with fireplace and large screened TV.A beautiful outdoor deck that sits 6 people for dining outside 1 screened in porch with a beautiful large patio with a barbecue & stunning woods view, 10 minute drive to Woodridge Lake.

4.94 out of 5 average rating, 114 reviews

A spacious outdoor dining area features a large wooden table surrounded by matching chairs. Sunlight illuminates the area, showcasing a well-maintained yard with a manicured hedge and a small garden shed visible in the background.

Home in Northport

Cool pad, Private Rms, Walk to village, Wtr view

Beautiful pad on a tranquil street and walkable neighborhood. 5-10 minute walk to the village and 2-minute walk to the cliffs overlooking the bay and sound. Water view from one bedroom, great outdoor yard - very private. Updated amenities, marble bathroom, cozy indoor living area and very comfortable beds. The rental space is private and is the entire first floor of the home. The home is a two-story duplex with a shared entrance and private locking doors to each space. Wonderful location.

Cottage in Greenwood Lake

A contemporary open-concept kitchen and living area features large windows that frame scenic views. A central dining table complements the kitchen with dark cabinetry and modern appliances. A comfortable couch with decorative pillows enhances the inviting space, while a vibrant potted plant adds natural greenery.

4.98 out of 5 average rating, 336 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

4.98 out of 5 average rating, 118 reviews

A spacious living area features wooden beams and warm lighting. A large brown sectional sofa is paired with a patterned armchair, creating a comfortable seating arrangement. A colorful area rug complements the hardwood floor, while an open staircase leads to the upper level.

Chalet in Monticello

Riverfront Ski Chalet

Escape to the country air at Sean & Brad's riverfront chalet on the Neversink River. Formerly a popular ski shop and yoga studio, this fully renovated property offers you every possible amenity. Walk across the street to launch your kayak or toss a line into some of the best trout fishing around, roast s'mores around the fire or visit the Resorts World Casino, just 5 minutes away. Golf, hiking, mountain biking, local breweries and distilleries...all just a short distance as well.

4.95 out of 5 average rating, 355 reviews

A serene saltwater pool is framed by lush greenery, providing a tranquil escape. Comfortable lounge chairs are positioned around the patio, inviting relaxation. The setting is peaceful, surrounded by trees that enhance the private atmosphere.

Home in Kerhonkson

Beautiful Salt Water Pool & Fully Fenced 10 Acres

Look from the luxurious spa tub at the countryside oasis atop a rolling knoll on the edge of fir-scented forest land. Come home from a hike, farm, or award winning restaurant, & snuggle up by the fire under grand cathedral ceilings. In summer, swim in the salt water pool & enjoy the fire pit surrounded by lush landscaping & quiet. Stunning views as the seasons change, the windows showcasing rolling snowy hills or the vibrant colors of autumn leaves climbing the mountains.

4.94 out of 5 average rating, 145 reviews

A circular seating area is surrounded by red Adirondack chairs arranged around a stone fire pit. Lush greenery and flowering trees are visible in the background, enhancing the outdoor space's natural ambiance.

Condo in Vernon Township

Ski-In/Ski-Out @ Mountain Creek-Pool/Hot Tub/Sauna

NEWLY Renovated! Top floor 1 bedroom Condo with Mountain/Pool View at Mountain Creek Resort. Steps away from ski mountain & gondola ! Swim in the outdoor heated saltwater pool, relax in the sauna or soak in the hot tub while taking in mountain views, Catch the sunset from your private top floor balcony or cozy up by your gas fireplace. Visit award-winning spas, golf, breweries, wineries, farms, and fine dining at Crystal Springs & Warwick, NY--only 10 min away.

4.99 out of 5 average rating, 174 reviews

A private outdoor deck featuring a wooden floor and a shaded area. Several seating options include four light-colored lounge chairs and a dining table surrounded by additional chairs, providing ample space for relaxation and dining while enjoying the ocean views.

Apartment in Long Beach

Incredible Long Beach Private Rental

True 5 star two bedroom rental. Newly renovated and professionally designed. Stunning ocean views from private second floor deck. You have your own barbecue and fully furnished outdoor space so you can enjoy the your stay on your terms. You are just a walk to the bars and restaurants of the West End. No car required! Walk or catch the bus from the train. Only 700 feet from the ocean. Due to allergies in the home we are unable to host any animals.

5 out of 5 average rating, 211 reviews

A serene lakeside scene shows calm water reflecting vibrant fall foliage and pine trees along the shore. Light mist hovers over the surface, while a clear sky suggests a tranquil atmosphere, with the moon faintly visible in the background.

Cabin in Kingston

Lakeside Cottage: Boulder's Bluff

Come enjoy the serenity of our renovated lakeside cottage! Guests can enjoy their time relaxing fireside with panoramic views, hiking or biking 22 miles of trails running through our backyard, and let's not forget splashing around in the lake. We are sorry but we are unable to accommodate pets. Pack N Play available only when request ahead of time. Pack N Play sheets not provided.

4.94 out of 5 average rating, 264 reviews

A rustic log cabin is nestled among tall trees, showcasing a sloped roof and a prominent chimney. Autumn leaves cover the ground, contributing to a natural and serene setting. Soft light glows from a distant area, hinting at additional outdoor spaces.

Cabin in Huguenot

Tranquil Lakefront Cabin!

This Warm LAKEFRONT Home Grabs Your Soul and Forces you to Decompress Instantly. Enjoy the Large Well Appointed Screened Porch with Glass of Wine/Cup of Coffee as you Gaze over the Rustic Lake thru Stately Oak Trees and Cranberry Bogs. Boats Included!!! $50 Per Pet Per Stay After Host Approval.. Firewood Stored In The Rear Of The Tool Shed..

4.94 out of 5 average rating, 62 reviews

A welcoming living area features wooden walls and a high ceiling, illuminated by a rustic chandelier. A cozy black sofa is positioned next to a wooden coffee table on a textured rug. A white armchair and a stone fireplace add warmth to the space.

Cabin in Sparta Township

The Stonefire Cabin!

Escape to a cozy log cabin retreat, beautifully restored and landscaped. This charming 2BR + Loft + pet-friendly home boasts style and comfort, with easy access to delicious restaurants, shops, and top attractions. Mention your furry friends at booking and pay a small fee to bring them along. Stay connected with fast 1G internet

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Houses

A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Popular amenities for Sleepy Hollow vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Sleepy Hollow's top sights

Kykuit, the Rockefeller Estate36 locals recommend

Philipsburg Manor16 locals recommend

Coffee Labs Roasters Inc.15 locals recommend

Sleepy Hollow Cemetery15 locals recommend

The Taco Project13 locals recommend

Tarrytown - Train Station12 locals recommend

Boutique hotel rooms in Sleepy Hollow

4.69 out of 5 average rating, 42 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 modern bathroom sink area is featured, highlighting a sleek white countertop and a stylish faucet. White toilet paper is visibly mounted on a holder next to the sink, emphasizing convenience and accessibility.

Hotel room in Union City

4.69 out of 5 average rating, 105 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, 352 reviews

Sonder Chambers | Queen Room

Hotel room in Cold Spring

A charming cafe exterior is visible, featuring a red awning with the name 'Silver Spoon Café.' Outdoor seating is arranged along a green railing, where guests are gathered. The building showcases a mix of light green and beige siding, adding to the inviting atmosphere of the village.

4.84 out of 5 average rating, 97 reviews

Room 1 Cold Spring Hotel (Main St.)

4.76 out of 5 average rating, 130 reviews

The lobby features a striking mural above a seating area with plush chairs and sofas. A stylish bar is visible in the background, and a grand chandelier hangs from the ceiling, illuminating the open space and highlighting the elegant decor.

Hotel room in Great Neck

Boutique Hotel in the heart of the North Shore

4.73 out of 5 average rating, 169 reviews

The entryway welcomes guests with polished marble flooring and a large chandelier overhead. A lighted reception desk stands to the left, accompanied by decorative wall sconces. A grand staircase with elegant wooden detailing rises in the background, framed by warm gold walls.

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

A modern interior features a well-equipped kitchenette with sleek cabinetry and appliances. Comfortable seating is provided at two bar stools near the counter. The open layout includes warm wood flooring and decorative plants, contributing to a cozy dining atmosphere. A spacious bed is positioned in the foreground.

Hotel room in Long Island City

4.81 out of 5 average rating, 27 reviews

2 Double-Beds with Balcony Views in Boutique Hotel

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Other great vacation rentals in Sleepy Hollow

5 out of 5 average rating, 14 reviews

A serene backyard setting is surrounded by tall trees, showcasing a mix of open grassy space and partial woodland. Five white adirondack chairs are arranged around a firepit, with a dining table visible nearby, inviting outdoor gatherings.

Home in South Fallsburg

Renovated & Spacious 3BR Catskills Retreat

4.94 out of 5 average rating, 141 reviews

Apartment in Wallkill

Log Cabin Apartment Great for Outdoor Enthusiasts

5 out of 5 average rating, 48 reviews

Cabin in Cornwall

Beautiful Cabin in Cornwall CT.

4.91 out of 5 average rating, 33 reviews

A two-story house is set on a sloping waterfront, surrounded by trees. The exterior features large decks on both floors, with seating and umbrellas visible. A dock extends into the water with additional seating, and a sandy area is positioned nearby.

Home in Vernon Township

Highland Bluffs Lake House, 50 miles from NYC

4.9 out of 5 average rating, 269 reviews

A wooden deck features a seating area with two white cushioned chairs and a matching table. Blue accent pillows add a touch of color. Lush green trees surround the deck, creating a natural backdrop that enhances the outdoor setting.

Home in Kerhonkson

Perfect Country Cabin getaway. Large Fenced yard.

4.96 out of 5 average rating, 118 reviews

Home in Chester

Millionaire Mansion Countryside Stay w/ Lrg Hottub

4.73 out of 5 average rating, 111 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