Cottage vacation rentals in Sleepy Hollow

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Top-rated cottage rentals in Sleepy Hollow

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Guest favorite

Cottage in Greenwood Lake

4.93 out of 5 average rating, 181 reviews

Cozy home in the Village of Greenwood Lake

Adorable country retreat under an hour from NYC - perfect for a romantic couples getaway or a family of 4. Located in the village, our quaint cottage is walkable to everything; Restaurants, bars, grocer, cvs, bagels, bus stop and even the public beach!! Minutes away from TONS of local attractions; drive-in, skiing, renaissance fair, wineries, shopping, lake activities, orchards, creameries, parks, Appalachian trail, spa, rafting, golf, water park, & so much more. Pets welcome! Permit #21-07603

Top guest favorite

Cottage in Cortlandt

4.99 out of 5 average rating, 190 reviews

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

Top guest favorite

Cottage in Warwick

5 out of 5 average rating, 213 reviews

Cottage at Millpond Falls - Romantic Luxury Escape

Looking for a romantic getaway? Relax in this cozy cottage overlooking a waterfall in a private setting. We offer a 5-star premium experience! Super-clean and luxurious. One hour from NYC. Our most frequent review: "We can't wait to come back!" Nearby wineries, craft breweries. Minutes from Warwick village, restaurants, bars, antiques, shopping, Appalachian Trail, and Greenwood Lake. Apple picking, skiing and water park nearby. Close to LegoLand and Jehovah's Witness Headquarters.

Superhost

Cottage in Gardiner

4.9 out of 5 average rating, 161 reviews

Little Cottage Under the Ridge

Visit the cottage for an upscale retreat in the rock climbing epicenter of New York’s famous Shawangunk ridge. our mountain top paradise sits on a dead end road amongst untouched nature, only minutes to town, with a small chef’s kitchen, breakfast bar, and brand new everything. As the last property before Minnewaska’s protected preserve land, the cottage offers unmatched peace and quiet. Enjoy a private campfire beneath mature maple & oak trees that decorate our secluded five acre property.

Guest favorite

Cottage in Cornwall

4.93 out of 5 average rating, 148 reviews

Newly Built Cottage in Housatonic Valley

This newly built modern cottage is located on a historic railroad street nestled in a charming village within the Housatonic River Valley. There are beautiful river views from the front porch, deep woods off the back deck, a white marble kitchen with new appliances, and a dedicated parking spot. Escape the city and surround yourself in this quiet valley and the calm of small village life, located just 2 hours from NYC. This location offers year-round access to nature & outdoor activities.

Guest favorite

Cottage in Vernon Township

4.94 out of 5 average rating, 190 reviews

Rustic Chic Lake view cottage 50 miles from NYC

Cozy lake view cottage 50 miles from NYC. Nestled in nature with swimming, fishing , hiking and biking with beautiful lake views. 5 beaches to choose from. Lovely walking or jogging around the lake, Appalachian trail nearby. Highland Lakes is a very scenic, peaceful area easily accessible. 3 of the best golf courses in the US , Mountain Creek water park and resort minutes away.Apple and pumpkin picking comes fall. Beautiful village of Warwick NY is nearby with restaurants and shopping .

Guest favorite

Cottage in Greenwood Lake

4.98 out of 5 average rating, 337 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

Guest favorite

Cottage in New Milford

4.95 out of 5 average rating, 196 reviews

The Cottage on Babbling Brook

A cozy, rustic cottage beautifully overlooking Wimsink Brook. Custom designed & handcrafted woodwork throughout the home. An all around great spot for families and friends. A magical, peaceful and relaxing space. Conveniently located on the Connecticut/New York border, just a 1 ½ hour drive or metro north from NYC. The area is a prime location, as it offers some of the most stunning and scenic hikes & drives in the country. Only a 10 minute drive from Kent, New Milford or Pawling.

Guest favorite

Cottage in Goshen

4.94 out of 5 average rating, 123 reviews

Country Cottage in Goshen

Quaint country cottage, with beautiful hardwood floors, screened in porch, claw foot bathtub and lots of antiques set on a naturally landscaped 1 acre property. The original cottage was built in 1932, but was completely renovated in the last 5 years. 650 square feet with a bedroom, bathroom, lounge on the 2nd floor loft, and an open floor plan with living area, dining area and kitchen on the first floor. French doors lead from the dining area to a large screened in porch.

Guest favorite

Cottage in Goshen

4.92 out of 5 average rating, 310 reviews

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Picture this... You escape to a relaxing, picturesque, and peaceful country cottage and enjoy some of your favorite convenience amenities like 1 Gig Wifi and your favorite streaming sources. Just 10 minutes to LEGOLAND, 3 miles to the famous Orange Heritage Trail, and less than 20 minutes to America's oldest winery, Brotherhood, this cottage has something to offer for everyone. You'll be minutes from conveniences like Target but taking in the views, you'd never know it.

Guest favorite

Cottage in Walden

4.96 out of 5 average rating, 108 reviews

Cute, Cozy, Lakefront cottage

Cute, cozy lakefront cottage on private lake. Deck with an unobstructed view of the lake. Stunning sunrises, pinewood floors in bedroom/living room/kitchen. Queen size bed in bedroom. Situated on the same lot as owner occupied main house. Quiet, residential area. Near wineries, breweries, hiking. WIFI. No TV. Unfortunately, due to severe pet allergies I am unable to host any kind of animals including emotional support and service dogs and cats of any kind.

Guest favorite

Cottage in Pawling

4.98 out of 5 average rating, 119 reviews

Twin Lakes Designer A-frame Stone Cottage

*Twin Lakes Cottage* Stunningly restored 1930s a-frame stone cottage located on a private lake in West Mountain State Forest with a new deck, patio, soaring high skylights, and 21’ tall wood-burning fireplace. Resting on a hillside with 180 degree views of two lakes, this breathtaking retreat is a one-of-a-kind experience. Surrounded by mature oaks, ferns, and the soothing songs of birds, this remarkable home offers unmatched tranquility.