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Top 10 Boutique Hotels and BnBs in Dutchess

Date Published: November 30, 2023

Whether it's nature, culture or romance you're seeking, Dutchess County has it all. Nestled in the heart of New York's Hudson Valley only 90 miles north of Manhattan, Dutchess is easy to get to from anywhere. And with so much to see and do during all four seasons, Dutchess is the perfect destination for a weekend escape, a week-long excursion, or whatever adventure you have in mind.

Explore our Top 10 Boutique Hotels and Bed and Breakfasts (plus a couple bonus spots) for your perfect getaway.

The Dutchess Inn & Spa, Beacon

Enjoy the quiet elegance of The Dutchess Inn & Spa, a European-style hotel located in the heart of vibrant Beacon. With only 10 luxury hotel rooms, their personalized service will ensure that your visit is nothing less than stellar. The Dutchess Inn & Spa is located on Beacon's vibrant Main Street; it is within walking distance of shops, restaurants and attractions and is about a 15-minute walk or a brief ride from the Beacon Metro-North train station. 

Hotel Caravana Amenia
Hotel Caravana, Amenia

Hotel Caravana, Amenia

Glamping like never before! Book a stay at Hotel Caravana, a renovated, retro Airstream at Four Brothers Drive-In Theater in Amenia. Ranked one of the top eight world’s best vintage caravan hotels by Lonely Planet, Hotel Caravana offers a unique experience to relax under the stars and stay on-site at a drive-in movie theater. The funky decor and fun amenities will make it a stay to remember. Open seasonally.

Hotel Tivoli
Hotel Tivoli, Tivoli

Hotel Tivoli, Tivoli

Hotel Tivoli and its accompanying farm-to-table restaurant, The Corner, is a century-old building in the heart of the historic Village of Tivoli. It is owned by painters Brice and Helen Marden, who have filled the property with an eclectic collection of furniture, lighting and art. It’s a great choice for your visit to northern Dutchess.

Inn at Pine Plains, Pine Plains

Conveniently located at the crossroads of Routes 82 and 199, the Inn at Pine Plains is the perfect base for exploring the Hudson Valley. Each of the eight beautiful rooms has its own unique character. Wake up to a delicious continental breakfast with locally made breads, Pine Plains-roasted Schapira’s coffee, and their signature breakfast sandwich of local hard-boiled eggs, avocado hummus, tomatoes and organic microgreens before venturing out to explore nearby hiking, farms, shops and more!

The Millbrook Inn, Millbrook

Relax and recharge at this elegant inn tucked away in the Dutchess countryside only minutes away from the Village of Millbrook. The inn offers 10 luxurious suites, and the on-site restaurant and bar highlight the finest Hudson Valley ingredients.

Mirbeau Inn and Spa Rhinebeck
Mirbeau Inn & Spa, Rhinebeck

Mirbeau Inn & Spa, Rhinebeck

Based on the Mirbeau philosophy of balancing life with wellness and indulgence, the world-class Mirbeau Inn & Spa Rhinebeck is reminiscent of an old-world chic Parisian hotel with all the modern comforts that today’s travelers expect. Located right in the heart of Rhinebeck, Mirbeau Inn & Spa Rhinebeck is a wonderful place to re-balance one’s life through a restful yet inspiring experience.

Reclaimed Motel, Red Hook

The Reclaimed Motel is a throwback to the iconic motor lodge, boasting beautiful views of the Catskills and mid-century modern aesthetics. Each one of its eight unique rooms features hand-selected vintage items, from tiles to lighting, from doors to vinyl records, to art and mirrors. The Reclaimed Motel is the perfect jumping-off point if you're planning to explore Red Hook, Rhinebeck and Tivoli.

The Roundhouse Beacon
The Roundhouse, Beacon

The Roundhouse, Beacon

This industrial-chic boutique hotel overlooks the beautiful Beacon Falls and is within walking distance of all that Main Street has to offer. From coffee shops and vintage stores to art galleries and speciality goods, Main Street is bustling year-round. A destination itself, The Roundhouse offers outdoor patio dining, a hip restaurant and trendy bar. 

Troutbeck Amenia
Troutbeck, Amenia

Troutbeck, Amenia

Unplug in eastern Dutchess! This 250-acre estate hotel is the perfect getaway for the romantic, the locavore, the creative, the adventurous and the curious. With an on-site restaurant, wellness center, pool and gardens, Troutbeck has everything you need for a relaxing escape. 

Wing’s Castle, Millbrook

Ever thought you could stay in a castle made of 80 percent recycled materials? Well, you can! This living art project built by Peter and Toni Ann Wing is a unique and memorable experience. Tour the grounds, visit nearby Millbrook Vineyards & Winery, and stroll through the cute village of Millbrook for a trip you won’t soon forget.

Bonus options

The Gables of Rhinebeck, Rhinebeck

This historic four-room inn is a 15-gable 1860 Gothic Revival Victorian with thoughtful renovations for a comfortable stay. Enjoy the walkability to explore Rhinebeck's local shops and restaurants, or simply relax at the inn and admire the gardens and play lawn games like cornhole, ladder golf and badminton. 

Station Inn, Pawling

Dutchess is filled with charming towns, and Pawling is definitely one of them! Plan your stay at this airy, modern, sunlit inn just steps away from the beautiful village and a short walk from the Pawling Metro-North train station. Soak in scenic vistas while hiking at the nearby Appalachian Trail, shop fresh produce at the Pawling Farmers Market and dine at local favorites like McKinney & Doyle. Leave feeling refreshed and recharged.

Attached photo of Wing's Castle by AmityPhotos.com.

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