Holiday rentals in Sleepy Hollow

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

Rustic Blues Cottage Retreat

Kick back and relax in this calm, stylish space with an escape to the picturesque Hudson Valley for a Retreat like no other! Immerse yourself in the vibrant colors of the season, surrounded by the region's most breathtaking foliage. Our curated getaway combines adventure, relaxation, and festive fun. *PULL OUT COUCH in living room* Nearby: Woodbury Commons Premium Outlets Flagship Cinemas Legoland Renaissance Faire Pure Terror Scream Park Warwick Wineries Pumpkin Picking Apple Picking Hiking

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.

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.

Clarissa's Paradise

RESERVE NOW: This ideally located five-bedroom totally renovated home is the perfect spot for a family fun vacation. Located within walking distance of the well known playground and spray ground. The home features a spacious patio, central air conditioning, baseboard heating, WiFi, and Cable tv. The open layout provides perfect gathering spaces for your family, and all bedrooms are spacious and comfortably appointed. 4 full bathrooms . Sleeps 10. PLEASE NO PARTIES ARE STRICKLY PROHIBITED

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 .

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.

Cottage with Picturesque Views

Quaint 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. 2 BR, 1 Bath private 2 car parking. Fenced in deck allows for scenic dining. Fire pit with Adirondack seating allows for around the fire gatherings. #CozzyCottage_GWL Town of Warwick Short Term Rental Permit # 34234

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.