Hotels in Lenox

Welcome to Woodford Rest!

You won’t want to leave this charming, one-of-a-kind place. Our centrally located private suite is perfect for the outdoor enthusiast. Woodford Rest is located 1 mile from Prospect Mountain Ski Area, 2 miles from the Appalachian Trail/Long Trail, near snowmobile entry points, and 8 miles from Bennington. Toy hauler parking included! Enjoy an outdoor fire nestled in the national forest or relax in our cozy suite with all of our upgraded amenities. We look forward to seeing you at Woodford Rest!

Prime Berkshires Gem|Sleeps 4|WiFi|Near Tanglewood

Perfect for a family or friend getaway, this property features two luxury pillow-top queen beds, premium linens, a dining table and chairs for work or eating, a sparkling clean bathroom with a shower and a separate sink/vanity area, Roku Smart TV, and individually controlled AC and heat. Quiet, comfy, and comes with full access to East Rock Inn's outdoor dining tables and Adirondack chairs for lounging or enjoying your morning coffee while listening to birdsong. Only 1 mile to Ski Butternut.

The Gables of Rhinebeck Inn, Sugarloaf Suite

The Gables of Rhinebeck, a 4-suite Inn located 1 block from main street. This historic Inn is a fifteen-gable 1860 Gothic Revival Victorian in the heart of Rhinebeck Village. Guests have full access to our half-acre fenced-in yard with perennial and ornamental gardens, + plenty of indoor space. "Sugarloaf" is a 1BR Suite at The Gables of Rhinebeck. About Your Room: -Queen Bed, Cable TV, Full Bath on the 2nd floor with claw foot tub. AC'd in the summer https://www.TheGablesRhinebeck.com/

1 Double Bed, Non Smoking Room

Budget-friendly and clean place with a 1 Double bed for long term guests with many other room types! We are in Latham, near Albany, Troy, Schenectady, Clifton Park, Rensselaer East Greenbush area! Albany airport, -Amtrak Train Station. We are easy to access to Government offices, Medical treatment places, the major colleges in the area, as well as highway Rt 7, Rt 2, I-87, I-90, and 787. We are a short drive to CNY fertility, the Regeneron pharmaceutical Co & the Government offices.

The Trail in Adams - Entire Inn (9 guest rooms)

Welcome to "The Trail in Adams" - Berkshires’ Art Hotel on the Ashuwillticook Rail Trail in Adams. "The Trail in Adams" is a 9-room boutique inn located in the heart of Adams. Nestled among world-renowned arts institutions, our artist-decorated boutique inn offers an intimate lodging experience that connects the art, culture, and nature of the Berkshires. Each guest room has its own ensuite bathroom and electronic door lock. Find out more about us on social media @theTrailinAdams

#23 *Newly Renovated!* Two-room SUITE! Horizon Inn

This stylish suite has a living room with couch and a 50” Roku TV with kitchenette! Although no stovetop, there’s an air-fryer, toaster, crock-pot, blender and microwave! A private bedroom space is the second room with two full-size beds and a desk. There’s a queen-size murphy-bed, plus the couch! The Horizon Inn is being renovated, so the outside, is getting some final touches, and the lobby is closed. Construction will not effect your stay!

Springs Motel Honeymoon Suite

Experience retro charm and modern comfort in our Honeymoon Suite at The Springs Motel. This beautifully designed suite features a spacious king bedroom, a cozy living area with a pull-out couch, and a dining space, all adorned with unique vintage decor. Enjoy the convenience of two full retro-tiled bathrooms, a private patio, and access to our seasonal front lawn lounge. You’ll love the stylish decor of this charming place to stay.

Walkable Stockbridge + Headed Pool & Bike Rentals

Step into a living legend at The Red Lion Inn—welcoming travelers since 1773. In the heart of walkable Stockbridge, you're just 2 miles from the Norman Rockwell Museum, minutes to local shops, and surrounded by art, live music, and unforgettable food. Sip tea on the iconic front porch, dip into the year-round heated pool, catch a speakeasy show downstairs, or bike through town. It's all here—classic New England with a twist.

The Dutchman Room in Catskill Hotel

Enjoy access to the best of the Hudson Valley and Catskills from our prime location just 8 mins outside the Village of Catskill. Our hotel offers 13 stylish & sparklingly clean rooms with a contactless check-in process. The Dutchman Room is inspired by Henry Hudson's voyage up the Hudson River on his famous ship, the Half Moon. This cozy and clean space is the perfect launch pad for your next Catskill adventure!

Hudson Whaler Hotel - Queen Deluxe 103

Beautifully designed with a queen bed, desk, modern bathroom with a multi-spray spa shower and bathtub. All of our suites have an electric fireplace, Smart TV, Cable, Complimentary WiFi, Refrigerator, Keurig Coffeemaker, In-room Safe, Heat/AC and an Iron/board. Enjoy Soap/Shampoo/Conditioner, Lux Bedding, Towels, En-suite Bathrooms, firm euro-pillow top mattress, and in-room amenities for purchase.

The Reclaimed Motel, Hudson Valley - Three Farmers

Moving the past forward The Reclaimed Motel was built in 1960, and we wanted to respect its mid-century bones while making thoughtful modern upgrades. And the list of upgrades was long! From a new roof, to all new plumbing and electric, we've kept the integrity of this Red Hook landmark while investing in meaningful improvements to make this motel appealing and memorable for the modern traveler.

Little Cat Lodge -King room

Merging the rustic charm of an alpine lodge with the magic of mid-century Berkshires, our 400 sq. ft. King rooms are lined in mushroom wood, outfitted with a custom twin daybed, and accented by original artwork. Built in storage and a private terrace or patio ensure you can make the most of your mountain stay. Mini fridge and Keurig included!