Hotels in Stockbridge

La Chambre Room at the Manor House Inn

La Chambre is a quaint, cozy room inside the magical Manor House Inn and a perfect location for weekend adventures and restful retreats in the Berkshire foothills of CT. Understated and elegant with vintage vibes, we're near hiking/biking trails, wineries/breweries, museums, and more. This listing is for La Chambre featuring an antique queen bed & ensuite bathroom with clawfoot tub. A served breakfast for two is included. Special Note: We are intentionally TV-free.

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.

New England Landmark + 4 Dining Spots Onsite. Pool

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 Berkshire Mountain Inn - Edison Room

Perfect for skiers and snowboarders, the Edison Room is a first-floor queen suite in our 1776 historic inn, offering easy comfort after a day on the slopes. Warm hardwood floors, a cozy sitting area, and modern amenities make it ideal for unwinding. Enjoy fireplace-lit common rooms, unique historic decor, and a location just ½ mile to downtown Great Barrington, minutes to Ski Butternut and Catamount Mountain Resort.

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.

The Central Downtown Inn

The Central Downtown Inn & Suites – Comfort & Convenience in the Heart of the Berkshires Welcome to The Central Downtown Inn & Suites, a modern and upscale guesthouse in the heart of Pittsfield. Whether you're here for a weekend getaway, a business trip, or a family vacation, our thoughtfully designed accommodations ensure a comfortable and hassle-free stay. Prime Location, Unmatched Convenience.

Hudson 4 at The Argus Hotel

Hudson 4 is a first floor queen room with private bathroom. Each room is equipped with a SmartTV and Apple TV as well as a desk. This room is pet friendly. Complimentary Services: Continental Breakfast Onsite Parking Electric Parking Wi-Fi & Apple TV Keyless Entry Ensuite Guest Rooms ​ Paid Services: Cocktails Meeting Space Rentals Pets (If applicable) Early Checkin (1PM) Late Checkout (12PM)

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!

Mezze Guesthouse - Two Bedroom, sleeps 4

Experience luxury contemporary lodging alongside culinary excellence at the new Mezze Guesthouse. Accessed via a separate entry directly adjacent to Mezze Bistro + Bar, ascend the stairs to this Two Bedroom Unit, which exudes stylish and calming vibes of custom, one-of-a-kind finishes by local artisans.

Wyndham Bentley Brook 2 BR

Ski-In/Ski-Out Plus Year-Round Mountainside Fun. The Wyndham Bentley Brook is situated right at the base of Jiminy Peak ski mountain, making this resort an exceptional choice for mountainside play. In winter, ski out your door and onto the lifts.

Endless Family Fun: Pools, Arcade Room & Mini Golf

Escape to the Berkshires! Experience hiking, boating, and skiing at our doorstep. Nearby, enjoy the Norman Rockwell Museum, Tanglewood, and the Appalachian Trail. Perfect for families and nature lovers.