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

Carriage House Apartment Close to Legoland NY

Immerse yourself in history in our newly renovated Carriage House, originally a historic horse barn, ensconced with hand hewn, exposed beams. This unique accommodation boasts modern amenities such as central air conditioning, a cozy fireplace, private laundry, and a fully working kitchen. Situated just a 4-minute drive from the renowned Legoland and opposite the prestigious Goshen Historic Race Track, we are perfectly positioned for both convenience and entertainment. @parkwayhousegoshen

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!

Cheery & Peaceful Farm Cottage, 10 Min to LEGOLAND

When you're looking to get away from it all and experience some peace and quiet surrounded in nature, this Cottage fits the bill. Whether it's enjoying fireflies over the field at dusk or enjoying cheerful birds in the morning, this beautiful Cottage sets the stage for you to be refreshed and renewed by the time you check out. While it feels like a secluded oasis, this place is also 10 minutes from LEGOLAND, Target, and all your other favorite conveniences. We look forward to hosting you.

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 1–6 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.

Luxurious New Countryside Home

Welcome to your luxurious retreat nestled in the serene woods of Warwick. This brand new home offers unparalleled comfort and style. Inside you'll discover a haven of modern elegance, where heated floors and designer upgrades greet you. The open layout boasts four bedrooms, each with its own private bathroom for ultimate convenience and privacy. Whether you're seeking a peaceful retreat or an adventure-filled getaway, this exquisite house offers the perfect setting for your next escape.

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.

Fairway Retreat - Montgomery, NY

Spacious Luxury Retreat with 6 Bedrooms, Luxury Kitchen, Walk-Out Patio, and Scenic Surroundings! Welcome to your perfect getaway! Nestled in a scenic, tree-lined setting, this stunning 6-bedroom home combines luxury with the serenity of nature, making it the ideal retreat for families, groups, or business gatherings. Book your stay today and experience the perfect blend of luxury and natural beauty at this one-of-a-kind retreat!

Goshen Retreat w/ Hot Tub & Pool 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!