Holiday rentals in Mechanicstown

Garden View Guest Cottage

Located under 15 min. to Stewart Airport...1 mile to City Winery , nearby Angry Orchards , 1/2 hour to West Point Charming cottage setting located in the village of Montgomery, NY, Come for the day or stay for a few to take in all this historic area has to offer. Walk to some of the best restaurants in Orange County or simply read a book in the gardens... Truly a great value since it's a true "apartment " like setting..not just a room, with all the conveniences and sleeps up to 4 people.

Bashakill Hillside Cottage East

Escape to Bashakill Hillside Cottage East, a peaceful 2BR retreat on the Shawangunk Ridge in the Catskills. Steps from wetlands, hiking trails & kayak rentals at Mamakating Environmental Education Center, Blue Cliff Monastery & Bashakill Nature Preserve. Explore Wurtsboro's Main Street antiques, shops & dining. Hudson Valley vineyards & Catskills villages nearby. Ideal for NYC weekend escapes, remote work & outdoor adventures. Quiet, cozy, well-equipped. Prime birdwatching & dark sky stargazing.

Hudson Valley Horse Farm Stay | 10 min to Legoland

Escape to a private lakefront cottage just 90min from NYC. Enjoy lake access, dock, canoe, paddleboat, firepit & roaming horses. 7 min to Goshen Village. Amenities: King bed, full kitchen w/ basics, grill, beach towels, basic toiletries, parking, queen murphy bed + pack & play (upon request). Nearby: LEGOLAND, Brotherhood Winery, Goshen Historic Track, Warwick Valley Winery, Paramount Theatre. Relax, explore & make memories in the Hudson Valley. Check our IG page - behind the scenes at the

The Wooden Igloo Near Legoland NY

Unwind in tranquility at The Wooden Igloo, a unique and spacious home that is fully equipped with a touch of luxury. It's situated in a quiet, secluded area just minutes away from some of the major attractions like LEGOLAND NY Theme Park (9 miles), Soons Orchards (2.4 miles), and Orange County Arboretum (14.6 miles) for memorable outings. Indulge in shopping and dining adventures at The Galleria at Crystal Run (7.6 miles), Chester Mall (10.5 miles), Orange Plaza (6.9 miles) and much more!

Serene Victorian Guest Apartment with Clawfoot Tub

Escape to a stunningly renovated private 3rd-floor apartment in a 6000 sq ft. 1883 Victorian Manor in Blooming Grove, NY. Designed for 1–4 guests, this light-filled space offers comfort and classic charm in a peaceful country setting. Includes luxe beds, a clawfoot tub, French-door shower, and kitchenette with sunny breakfast nook. An ideal sanctuary. Views of wildflowers, quiet country, and cows next door. 3rd Floor up two staircases, rewarded with a stunning space and elevated views.

Spacious 6BR Villa | Serene Scenic Mountain Escape

Escape to this spacious 6-bedroom mountain villa, a peaceful retreat perfect for families and groups. Just about 1 hour from New York City, enjoy beautiful scenic views, comfortable living spaces, a well-equipped home, and plenty of outdoor space. Explore nearby hiking trails and local attractions, or simply relax and enjoy the quiet surroundings. Whether you're planning a family getaway or a weekend with friends, it's the perfect place to unwind, reconnect, and make lasting memories.

Historic Meets Modern 1900 Farmhouse Plus

Enjoy rest and relaxation in this historic 120 year old farm house. This house has all the character of a historic home lovingly renovated and updated. A modern living room addition features a cathedral ceiling and access to two separate decks. One is for sun and open air, another shaded with a mature wisteria over the pergola. The house is surrounded by lush gardens. Plenty of space to reconnect with family and friends or just enjoy a rest after a day of local activities.

Peace and quiet. Comfy, private house to relax in

Quiet property,almost 8 acres, of beautiful wooded property . Set back from the road. Many trails, wineries and breweries nearby. Legoland is 20 minutes away and many antique shops within 30 minutes or so. We live in the other house on the property, so we are accessible. You can take a stroll on the path by the stream or sit on the spacious 35 x 10 foot deck and enjoy the natural setting of the property. Fire pit is now available. Enjoy the night air and gaze at the stars.

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.

Forest Spa Retreat on Cascading Brook • 90 Min NYC

Tucked into an evergreen forest, The Water House is a private spa retreat set above a cascading brook—where flowing water shapes your stay. Spend slow mornings on the deck, unwind in the hot tub, and gather by the fire pit under the stars. Find a quiet moment beside the Japanese-inspired pond. Inside, soft textures and vintage style create a warm, calming atmosphere designed to reconnect you with nature while offering the restful comfort of a boutique retreat.

Goshen Historic Estate w/ Hot Tub near Legoland

Set among the rolling hills of Goshen, this historic estate blends rustic charm with a touch of luxury, creating a peaceful getaway from city life. Just 19 miles radius distance from West Point and minutes from Legoland, this beautifully preserved home places you at the center of the Hudson Valley’s best attractions. Be sure to check out the Brotherhood Winery, the oldest winery in America, for a memorable local experience!

Bright Farm House- Tranquil setting

Secluded 3-bedroom newly renovated late 1800 Farm house on a 50 acre working farm nestled in the Hudson Valley. Only 60 miles from NYC and close to everything the Hudson Valley has to offer. Many farms with seasonal apple picking and pumpkin picking ,West point , Woodbury Commons Premium outlets ,Resorts Casino. Tons of great local breweries ,Hudson Valley Wine Trail .. LegoLand Theme park is just 5 minutes away