Holiday rentals in Mechanicstown

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Top-rated holiday rentals in Mechanicstown

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite

A charming two-story cottage is surrounded by vibrant landscaping, featuring a mix of colorful flowers. The exterior is painted in green with maroon shutters adorning the windows. A wooden staircase leads to the upper entrance, while a welcoming front door is accented by a small planter.

Guest suite in Montgomery

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.

4.94 out of 5 average rating, 585 reviews

Guest favourite

Home in Wurtsboro

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.

5.0 out of 5 average rating, 23 reviews

Top guest favourite

Farm stay in Middletown

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

5.0 out of 5 average rating, 14 reviews

Guest favourite

Home in Slate Hill

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!

4.96 out of 5 average rating, 28 reviews

Guest favourite

A cozy living area is showcased with two accent chairs, one in a warm terracotta tone and another in vibrant red, featuring a playful design. The wooden floor complements the inviting atmosphere, while framed artwork adorns the walls, adding visual interest to the space.

Guest suite in Chester

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.

4.94 out of 5 average rating, 412 reviews

Guest favourite

A charming two-story villa is set amidst lush greenery, showcasing light blue siding and large windows. A circular driveway leads to a spacious garage, while outdoor seating is arranged with four chairs near a small table, inviting gatherings in the serene surroundings.

Villa in Bloomingburg

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.

4.87 out of 5 average rating, 118 reviews

Guest favourite

A spacious living area highlights a brown leather sectional sofa, accompanied by two wooden coffee tables with decorative inlays. A dining area is visible in the background, featuring a wooden table and chairs. Natural light fills the room through large windows under a vaulted ceiling.

Home in Middletown

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.

4.9 out of 5 average rating, 91 reviews

Top guest favourite

A red house is surrounded by vibrant autumn foliage, highlighting orange and yellow leaves on trees. A gravel path leads to the home, with two chairs visible in the outdoor seating area. Natural landscaping complements the serene wooded setting.

Home in Middletown

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.

4.98 out of 5 average rating, 224 reviews

Guest favourite

Home in Monroe

NEW Luxury Lakefront Retreat | Pool, Boats & Games

Welcome to our newly renovated luxury lakefront retreat the perfect escape for relaxation, adventure, and unforgettable memories. Enjoy direct lake access with paddleboats, canoes, right from the backyard. Spend your days by the private pool, relax around the fire pit, or unwind on two spacious porches with beautiful nature views. Inside features 4 bedrooms plus 2 additional sleeping/lounge rooms, a game room, stylish living spaces, full kitchen, and room for up to 12 guests

5.0 out of 5 average rating, 19 reviews

Guest favourite

A modern kitchen area is presented with open wooden shelves displaying dishes, glassware, and decorative items. Below, a gas stove and black refrigerator are complemented by a light fixture and a collection of utensils, offering a functional and organized space.

Cottage in Goshen

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.

4.92 out of 5 average rating, 386 reviews

Superhost

A welcoming countryside retreat is showcased, featuring a two-car garage at the front. The surrounding area is filled with lush green trees and a well-maintained lawn that creates a serene atmosphere. A long driveway leads up to the entrance of the home.

Home in Bloomingburg

Blooming Bnb (close to Legoland & much more)

Welcome to our tranquil countryside retreat, where you can unwind amidst picturesque greenery. Immerse yourself in the ambiance of our spacious, elegantly appointed deck, complete with an outdoor dining area, a fire pit, and a propane grill. The fully equipped kitchen features a spacious refrigerator, oven, and gas range, ensuring your culinary needs are met during your stay. Additionally, we provide ample dishware to accommodate both you and your guests.

4.75 out of 5 average rating, 16 reviews

Top guest favourite

The historic estate features a grand facade highlighted by multiple gabled roofs and a striking red front door. Soft lighting glows from the windows, and lush greenery surrounds the stone steps leading to the entrance, emphasizing the peaceful atmosphere of the property.

Villa in Goshen

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!

5.0 out of 5 average rating, 26 reviews