Your Comprehensive Guide to the Boutique Hotels of the Hudson Valley

The Herwood Inn / Photo by Winona Barton-Ballentine, Shelter Upstate

Whether you’re dreaming of an upstate escape or a local staycation, the Hudson Valley’s charming hotels and inns are the perfect place to spend the night.

What comes to mind when you think of escape? In the Hudson Valley, escape is as much of a lifestyle as it is a concept. It’s woven into the landscape of forests and mountains, sprinkled across babbling brooks and rivers, and scattered throughout the effortlessly charming collection of towns that comprise the region.

Because of the Valley’s natural beauty, it’s no surprise that it holds such an allure for locals and visitors alike. Whether in normal times or socially distanced ones, people look to the Hudson Valley and its chic, boutique hotels for one-of-a-kind stays that allow them to disconnect, unwind, and recharge. Fortunately for all, the region’s hotels are experts when it comes to crafting unforgettable overnights that are just as beautiful and relaxing as they are safe and socially distant.

Without further ado, scroll below to discover the most marvelous boutique hotels in the Hudson Valley.

Eastwind Hotel & Bar

5088 Route 23, Windham

Anyone dreaming of a retreat to Hunter or Windham Mountain will want to bookmark Eastwind, the boutique hotel led by a hospitality professional and his wife. The 20-acre property is scenic, secluded, and filled with everything guests might need to enjoy a one-stop stay in the Hudson Valley. Rooms range from standard spaces to private lushnas, or Scandinavian-style camping units that take glamping to new heights. When it’s safe to do so, Eastwind opens its bar for socializing and cocktails. Outside, it offers bikes, hammocks, and a sauna, not to mention outdoor yoga, to guests who want to spend time in the great outdoors during the warmer months. During winter, meanwhile, it’s a no-brainer destination for skiers and snowboarders who want to make the most of slopeside staycations in the Hudson Valley.

Foxfire Mountain House

72 Andrew Lane, Mount Tremper

With a bohemian atmosphere that thrives on vintage details and natural touches, Foxfire Mountain House is a craveable escape in Ulster County. The boutique hotel resides upon 10 acres, which also play host to a pond, lily pool, bonfire pits, gardens, bocce ball court, and horseshoes. There are 11 rooms inside the 100-year-old inn, and all are equally sumptuous thanks to fresh linen bedding, cozy décor, and a pandemic welcome package that includes weekend happy hours, breakfasts, and dinners with full safety protocol in place.

Hasbrouck House

3805 Main Street, Stone Ridge

Hasbrouck House dates back to the 18^th century, when it was a Dutch colonial stone mansion in the Hudson Valley. Nowadays, the boutique hotel treats guests to romantic escapes in its 25 bedrooms spread across four buildings. While the welcoming interior is a temptation, so too are the 100-year-old landmark pool and the 50-plus acres complete with a private lake. Plus, visitors would be remiss to pass up a meal at Butterfield, the inn’s restaurant, bar, and lounge that tempts with all those farm-to-table flavors the Hudson Valley does so well.

The Herwood Inn

148 Tinker Street, Woodstock

Anyone craving a close-to-home vacation in Woodstock won’t want to pass up a night at The Herwood Inn. With its hip, socially conscious vibe, the boutique hotel is a creative retreat in the heart of Ulster County. Rooms are cheery and bright, with desirable details that include everything from clawfoot soaking tubs and private outdoor patios to open kitchenettes and pet-friendly spaces. Plus, for couples who want to plan something small, Herwood offers elopements that are intimate and romantic.

Hotel Kinsley

301 Wall Street, Kingston

Hotel Kinsley is a hotel, but not in the way you might think. Instead, the Kingston venue is more of a concept, one that operates across multiple historic venues around town. The Wall Street building, which dates back to the 1860s, is the flagship, with 10 rooms and an effortlessly cool vibe, thanks in large part to its former life as the New York State Bank. A stay there pairs perfectly with a meal at Restaurant Kinsley, the farm-to-table, new American eatery that’s a little retro, a little hipster, and 100-percent a must-visit. Nearby, the Pearl Street building is a 1770 stunner that’s now open for overnights. Coming soon, the Fair Street Building, opening in spring 2021, and the John Street Building, opening in winter 2021, will add to Kinsley’s stop-and-stay experience in the Hudson Valley.

Hotel Tivoli

53 Broadway, Tivoli

How idyllic does an upstate escape to Hotel Tivoli sound right now? With its 100-year-old history and eclectic, modern décor, the hotel does a beautiful job of merging Tivoli’s small-town charm with Brooklyn-esque pops of color. It comes part and parcel with The Corner, the hotel’s Mediterranean-focused restaurant and bar that tempts with farm-fresh ingredients and delectable cocktails designed by the team behind New York City’s Employees Only. In short, it’s just the place for foodies who crave a break upstate in one of the Hudson Valley’s loveliest little towns.

The Maker

302 Warren Street, Hudson

Yes, The Maker is a boutique hotel in the Hudson Valley. Yet it’s also so much more than that, thanks to its mixed bag of luxe attractions that include a café, lounge, restaurant, and, most recently, a fitness center. The property is owned by the co-founders of global beauty brand Fresh and, more locally, Bartlett House in Ghent. Inside, guests can immerse themselves in a world of bohemian luxury, with rooms named after different types of creatives and filled with unusual antiques and eye-catching treasures. In addition to unforgettable overnights, The Maker treats visitors to everything from house-made snacks and a dreamy library to an idyllic pool and decadent cocktails and dining at its three eating spaces. Add to all that the fact that The Maker sits squarely in the heart ever-popular Hudson, and locals have every excuse to book a staycation in the Hudson Valley.

Scribner’s Catskill Lodge

13 Scribner Hollow Road, Hunter

Deep in the heart of the Catskills, Scribner’s Catskill Lodge awaits to welcome visitors on snowy and sunshine-filled days alike. The mountainside resort is only a short drive away from Hunter Mountain, making it a delight for skiers and snowboarders. In addition to its 38 cozy rooms onsite, the lodge also treats visitors to in-room dining by Prospect, the onsite restaurant, for breakfast, lunch, and dinner as desired during the COVID-19 crisis. Plus, for guests who want a memento for the road, the gift shop stocks sweet treats, along with a curated selection of snacks.

Shandaken Inn

1 Golf Course Road, Shandaken

The one-time clubhouse for Rip Van Winkle Golf Course was revived as a delightful inn in the Catskills in 2019. It sits on over 12 acres, with 15 rooms and amenities available to keep guests happily occupied. The vibe inside is elegant and warm, with thoughtful details like Frette linens and Malin & Goetz bath products in each room. As for the extras, the fitness room with Peloton bikes, seasonal tennis court, outdoor pool, and fire pits are all exactly what guests need to revive and unwind. In regard to food, The Clubhouse is the inn’s onsite restaurant and a go-to for local cuisine on Wednesday through Sunday evenings.

Starlite Motel

5938 Route 209, Kerhonkson

Part Schitt’s Creek, part I Dream of Jeannie, Kerhonkson’s Starlite Motel delivers a dose of 1960s magic in Ulster County. With an artistic duo at the helm, the retreat delights with Wes Anderson-esque pops of color that stand out against the serene Catskills backdrop. Its handful of rooms are adorned with old Americana touches that contrast wonderfully with the modern, minimalistic design. In season, Starlite’s saltwater pool is a must-visit, as is its crackling fire pit. The motel has coronavirus safety protocol down pat, too, thanks to contactless check-in and staggered bookings.

Urban Cowboy Lodge

37 Alpine Road, Big Indian

The whispers of Ulster County’s storied resort culture past (remember the Borscht Belt?) come alive once more, this time with a hip and modern twist, in the form of Urban Cowboy Lodge. Set just a short drive from Phoenicia along the Esopus Creek, the wilderness retreat resides on 68 acres and serves as a hub for outdoor attractions like fly fishing, hiking and skiing. Onsite, the hotel welcomes guests to its 28 rooms, freestanding cabin, and cozy chalet for overnights. From there, visitors are free to explore the outdoors or stick to lounging on the private outdoor deck or soaking in one of the in-room cedar or copper tubs. Of course, Urban Cowboy isn’t just a hotel. Its eatery, aptly titled The Dining Room, is a zero-waste facility that dishes up holistic meals showcasing local ingredients. With food, relaxation, and endless things to do, it’s not a bad place to spend a weekend in the Hudson Valley, right?

Vanderbilt Lakeside

161 Main Street, Philmont

If you’ve never heard of a Victorian lakehouse before, don’t be surprised. Columbia County’s Vanderbilt Lakeside might just be the only one in existence. The Hudson Valley hotel resides on an enviable plot of land with its very own lake. Of course, that means the property is a delight for guests, who are free to sit waterside or picnic outdoors in the warmer weather. Inside, the bohemian, hipster hotel calls to mind literary characters like Jay Gatsby and Dorian Gray, thanks in large part to its moodily romantic décor. There are eight rooms in total, and they all come with private bathrooms. During the COVID-19 crisis, the hotel is open for full private rentals only. When it’s safe to do so, it offers complimentary Hudson Valley breakfasts each morning. Also on the grounds, the hotel’s eponymous restaurant, which is temporarily closed due to the pandemic, is just as much a local favorite for its flavor-driven menu as it is for its curated bar offerings.

The Villa at Saugerties

159 Fawn Road, Saugerties

Does a villa count as a boutique hotel? Yes, if you’re looking for one of the most indulgent overnight locations in the Hudson Valley. The Saugerties retreat resembles a European escape, even though it’s just a short drive from the center of town. As for the four rooms, they’re a study in elegance, with thoughtful details like plush beds, gas fireplaces, cozy robes, and full stocked mini fridges. During the warmer months, guests are welcome to lounge away on private patios or skip on over to the picturesque pool to swim a few laps. The experience is unforgettable as is, and even more so when paired with one of the owners’ homemade, farm-to-table breakfasts. Just-baked muffins and fresh frittatas, anyone?

Wm. Farmer and Sons

20 S Front Street, Hudson

Sure, you could just stop by Wm. Farmer and Sons for a delectable farm-to-table meal. Yet when the Hudson hotspot comes with its very own boutique hotel, it seems a shame to pass up a visit here without planning an overnight to go with it. Visitors from both near and far will fall in love with the medley of rooms available across the venue’s historic handful of buildings. The main building, which dates back to the 1830s, houses seven guest rooms, while The Merchant House next-door comes with four unique rooms that offer access to a serene garden. On the opposite side, The Annex Suites are a go-to for families that crave additional space or a longer stay in the Hudson Valley.

The Woodhouse Lodge

3807 County Route 26, Greenville

Did someone say hidden retreat in the Catskills? Because that’s precisely what The Woodhouse Lodge is. With 10 rooms to its name, the 1962 hotspot is just as striking outside as it is within, due in part to its partial A-frame construction and mid-century modern décor. The property sits on four airy acres featuring fire pits, hammocks, and scenic views. The rooms, meanwhile, are designed to help guests unwind, with everything from beds that are almost too lovely to tuck into to bathrooms stocked with Woodhouse Provisions products. During the COVID-19 crisis, room service from The Tavern, the lodge’s restaurant, is available to guests. The restaurant reopens to the public in March 2021, making it the perfect place to go for a meal made with local ingredients and a glass of natural wine to pair with it.

Woodstock Way Hotel

10 Waterfall Way, Woodstock

Located a hop and skip away from the heart of town, Woodstock Way is eye-catching from the start. The hotel sits just behind a waterfall, where it channels a contemporary aesthetic that pairs perfectly with its conscious and sustainable sensibilities. Guests can choose to stay the night inside the hotel’s medley of cabins, rooms, and suites, which range from standard queens and kings with tubs to standalone retreats so welcoming that they’re nearly impossible to leave. While the rooms are an attraction in themselves, equally enjoyable is The Tannery, the hotel’s historic lobby space that once served as a tannery in the 1800s. Today, it’s a stopping point for refreshments, art, and artisan wares. And did we mention the wellness offerings? Woodstock Way is ready to help visitors turn each stay into an experience, thanks to in-room massage therapy, private yoga instruction, and individualized spiritual healing sessions upon request.