Vacation rentals in Sleepy Hollow

5 out of 5 average rating, 121 reviews

Home in Greenwood Lake

Summer is calling! Lakefront/Hot-tub/1 hour to NYC

Lakefront, fully renovated and ready for guests to experience lake living at its best from the inside out. The modern gas fireplace and cozy sectional sofa make the living room the perfect place to perch over crisp autumn evenings. Or take a steaming soak in the backyard hot tub after a day of hiking or exploring all of neighboring Warwick’s wineries, breweries and local farms.With direct access to the lake from the property our location is ideal for kayaking. All within a 1 hour drive from NYC!

Cottage in Greenwood Lake

A wooden home is surrounded by lush greenery and manicured gardens. Flower beds with colorful blooms are visible in the foreground, while the house features a large deck. Mature trees provide a natural backdrop, enhancing the serene outdoor atmosphere.

4.96 out of 5 average rating, 48 reviews

5 bedroom 7 beds Cottage Sauna, Hike, Winery & Ski

Rental ID# 23-67 4 Season Home for relaxation with cedar sauna, hiking, wineries & skiing! Bring the whole family to this great home with lots of room for fun. This house has it all! The community children’s playground is steps from house. There is a basketball hoop on property & plenty of trees. Passes (6) provided for public beach with lifeguards, lake to swim, BBQ pits with playground & shower facilities on site. We have beach towels, rolling cooler, and beach chairs available for guests.

4.76 out of 5 average rating, 127 reviews

A welcoming entryway is seen, featuring a simple 'hello' sign mounted on the wall. A potted plant is positioned on the floor beside a textured mat, with wood railing guiding the view up the staircase.

Home in Poughkeepsie

Newly Renovated & Comfortable Home-Vassar/Marist

Leave the busy city and the hustle and bustle behind. Relax and rejuvenate yourself in the Hudson Valley. This retreat has all the amenities (fully equipped kitchen, spacious deck/backyard, fire pit, grill, and parking on premises available). Take a walk or bike ride at the Hudson Valley Rail Trail, hike at Mt. Beacon, explore Dutchess Wine Trail c/o Clinton Vineyards, shop at the Poughkeepsie Galleria, or relax at Hand and Stone Massage. There is so much for you, family and friends to do.

4.95 out of 5 average rating, 43 reviews

The entrance to the cabin is framed by vibrant greenery, featuring a wooden deck with railings and a welcoming sign. Potted flowers add a touch of color, while a pebbled pathway leads towards the cabin, surrounded by a peaceful natural setting.

Home in Greenwood Lake

Secluded Cottage on the Lake with Hot Tub

Enjoy the fresh air and surrounding nature over Greenwood Lake in our 2-bedroom cottage located on the 28-acre private property of Timber Hill Estates. This property is secluded and peaceful. Enjoy the brand new hot tub overlooking the lake. There is indoor gas fireplace, outdoor grill and an outdoor fireplace. In the summer, this unique property also includes lake access and a private boat launch and slip. This amenity is an additional charge and is available upon request May-September.

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.

4.96 out of 5 average rating, 425 reviews

The bathroom features wooden walls and beams, accented by a tiled shower area with a gray curtain. A bathtub is situated near a window that allows natural light to enter, complementing the rustic decor of the cabin.

Cabin in Greenwood Lake

"Cabinessence" on Greenwood Lake, 60 mi from NYC

"Cabinessence" is Year Round Comfort in a Chestnut Cabin by Greenwood Lake with a little touch of "glamping". Hiking, biking, strolling, paddle boarding, kayaking , canoeing. Restaurants, shopping, Drive-in movies, antiquing in nearby Warwick. Fall color, apple picking, gas fireplace (in season). Winter, ski, snowboard, tubing. Spring is watching the natural world wake up :) Hanging at the cabin- year round- is special here! Every season has its magic! ( + Covid Enhanced cleaning!)

5 out of 5 average rating, 39 reviews

The living room is designed with a stone fireplace as the centerpiece. Two light-colored sofas face each other, accompanied by brown armchairs and a coffee table. Large windows provide ample natural light and views of the yard, enhancing the spaciousness.

Home in New Paltz

Luxury Home with Mountain Views

This sprawling home with a spectacular Mohonk view is minutes from the shops and restaurants in the Village of New Paltz. It is within walking distance of the River to Ridge Trail and Mohonk Preserve, offering hundreds of acres of outdoor recreation. This house is designed for entertaining and lounging, with plenty of room for everyone. Perfect for those seeking a vacation with family or friends, it allows for gathering and privacy. The house is impressive inside and out.

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.

4.94 out of 5 average rating, 145 reviews

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.

4.98 out of 5 average rating, 66 reviews

A screened-in porch is showcased with a well-maintained hot tub and two wooden Adirondack chairs. Surrounding greenery is visible through the screens, creating a serene and private atmosphere.

Home in New Paltz

Spacious, Quiet 4 Bedroom + All Season Hot Tub

Modern, clean, family-friendly home on a quiet dead-end street. There is a well-maintained hot tub is on a screened-in porch for year-round use, with a large fenced-in backyard, patio, and Weber grill. There are 4 queen beds with brand new luxury mattresses + a pullout sofa in the den. The two living rooms each have 55" Smart TVs + puzzles, games, and a record player. The kitchen is fully stocked with everything you could ever need. Central heat + A/C + Wifi.

An outdoor swimming pool is surrounded by a spacious deck, featuring several lounge chairs and orange umbrellas. Lush greenery and trees provide a natural backdrop, while a clear blue sky enhances the inviting atmosphere of the pool area.

4.95 out of 5 average rating, 133 reviews

Sunsets at Mountain Creek! Walk to ski slopes!

Your whole family will love this stylish, centrally located hotel condo at the base of the mountain! Awesome 1 bedroom condo on the 3rd floor of the majestic Appalachian hotel. You’ll be in the middle of all the action - true ski in / out, mountain bike, zip line, water park, hiking, golf and much much more. Festivals, races, year round special events, hiking, wineries, Appalachian Trail, short drive to historic Warwick, NY. Enjoy pool, hot tub, sauna and more.

An outdoor swimming pool is surrounded by landscaped areas with large rocks and greenery. Several lounge chairs are placed around the pool, with a hot tub situated nearby, creating an inviting space for relaxation.

4.77 out of 5 average rating, 154 reviews

1 Bedroom Condo @ Appalachian Resort Hotel

A perfect space at a perfect location! That’s the Appalachian @ Mountain Creek Want to get away for a week or even for a weekend? Load up the golf clubs, put the skis on the roof rack and don’t forget the mountain bikes, hiking boots, swim wear, or fishing gear! Chill out and relax at this comfortable, 1-bedroom, 1-bathroom condominium, perfect for up to 4 guests.

4.95 out of 5 average rating, 39 reviews

The outdoor deck showcases a spacious dining table surrounded by wooden chairs, featuring soft lighting from string lights overhead. Relaxing seating areas are arranged alongside a large umbrella, enhancing the inviting space for gatherings under the treetops.

Home in Vernon Township

Lakeside Spring Retreat: Hike, Kayak, Relax

Unwind and reconnect with nature in our charming cabin, nestled just one block from the tranquil shores of the main lake. This idyllic getaway offers the perfect blend of rustic charm and modern comforts, making it an ideal retreat for couples, families, or groups of friends seeking a peaceful escape.

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

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

Philipsburg Manor6 locals recommend

Coffee Labs Roasters Inc.15 locals recommend

The Taco Project4 locals recommend

Lefteris Gyro10 locals recommend

Bridge View Tavern5 locals recommend

Muddy Water Coffee & Cafe8 locals recommend

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 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, 355 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, 131 reviews

A grand lobby area is highlighted by a large chandelier suspended from the ceiling. Dark wooden panels and marble accents create a sophisticated atmosphere. A reception desk is positioned in the foreground, while a staircase is visible in the background, providing access to the upper level.

Hotel room in Great Neck

Boutique Hotel in the heart of the North Shore

4.74 out of 5 average rating, 170 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

4.82 out of 5 average rating, 28 reviews

2 Double-Beds with Balcony Views in Boutique Hotel

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Other great vacation rentals in Sleepy Hollow

4.94 out of 5 average rating, 141 reviews

Apartment in Wallkill

Log Cabin Apartment Great for Outdoor Enthusiasts

4.92 out of 5 average rating, 97 reviews

A wooden deck features two chairs and a small table, surrounded by lush greenery. The spacious backyard is visible in the background, with a variety of trees and shrubs providing natural shade.

Home in Beacon

Beacon 2BR house w/ backyard, easy walk to main st

4.93 out of 5 average rating, 161 reviews

Home in Garrison

Hudson Valley Mountaintop Riverview

An open living area is presented with a spiral staircase leading to an upper level. A dining table with dark placemats and a vase of fresh flowers is centrally located. Cozy seating options include a textured sofa and an accent chair, while a television is mounted on the wall.

4.95 out of 5 average rating, 76 reviews

Peaceful Mountain Retreat

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.

5 out of 5 average rating, 24 reviews

A large outdoor pool is surrounded by a stone patio, equipped with several lounge chairs. Lush greenery lines the perimeter, providing a natural backdrop. Soft sunlight reflects off the water, enhancing the inviting atmosphere of the spacious area.

Home in Dix Hills

Nice getaway with your family.

4.94 out of 5 average rating, 203 reviews

An outdoor wedding ceremony is set against a scenic landscape, featuring rows of white chairs arranged on a grassy area. The couple is positioned at the front, surrounded by guests seated in a semicircle. Lush greenery and trees frame the background, enhancing the ambiance.

Home in Vernon Township

Luxury Mountain Retreat Condo - Skiing & More!