Hotels in Stockbridge

4.91 out of 5 average rating, 115 reviews

An outdoor area is illuminated by string lights, creating a warm ambiance. Several wooden Adirondack chairs are arranged around a central fire pit. The grassy space is bordered by a low building, featuring large windows and a welcoming exterior.

Hotel room in Copake

King Room - Boutique Berkshires Lodge in Copake NY

Situated in the foothills of the Berkshires in beautiful Columbia County NY, the Alander is a newly renovated boutique lodge perfectly located for everything this vibrant area offers. Countless activities such as hiking, biking, skiing and shopping await, including nearby Copake Lake for water activities. With the Berkshires and the Hudson Valley both at your doorstep, there is so much to explore and experience. The owners are knowledgeable and passionate about the area and love to share tips!

A cozy room features a spacious bed with pillows and a colorful throw. Two lamps provide warm lighting on either side. A coffee table holds decorative items, surrounded by a plush couch and area rug, enhancing the aesthetic with wall-mounted shelves displaying art.

Hotel room in Arbor Hill

4.73 out of 5 average rating, 278 reviews

Chic-romantic, center-city, hotel-style apartment.

Nestled in the heart of the city, our Airbnb exudes an enchanting charm with its stylish and romantic decor. Positioned on a vibrant city street, immerse yourself in the lively urban atmosphere. This energetic environment will carry some background noise. We prioritize your comfort and recommend bringing earplugs for light sleepers to ensure a restful stay. Corner store -1 min Airport, bus & train station -15 min. Outdoor cameras $250 indoor smoking violation fee $250 pet cleaning fee, no pets

Private room in Sheffield

The rustic timber structure is surrounded by a vibrant forest, showcasing autumn foliage in shades of gold and red. Large, multi-pane windows provide a view of the inviting interior, while a welcoming porch extends from the front entrance.

4.98 out of 5 average rating, 56 reviews

Sheffield Lodge - Ramblewood Master

The Sheffield Lodge is a warm and inviting rustic Bed and Breakfast secluded from city life nestled in a pine forest. Enjoy your home-away-from-home where there is always friendly service, delicious breakfasts, afternoon treats. The lodge features an inviting fireplace, large screen TV, game table for board games or cards and a quiet reading/living room, and ample parking. Outdoor recreation is within minutes in every direction. There are museums, shops and many great restaurants nearby.

Hotel room in Great Barrington

A well-appointed room is presented with two spacious beds, complemented by premium linens. A round dining table with chairs is positioned near a window, allowing natural light to fill the space. A wall-mounted TV is visible, enhancing the room's functionality.

5 out of 5 average rating, 6 reviews

Prime Berkshires Gem|Sleeps 4|WiFi|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.

Hotel room in Spencertown

The exterior of the Spencertown Inn is showcased across a serene pond, reflecting the building's modern architecture. Lush green grass surrounds the property, while trees and ornamental plants line the landscape, contributing to a tranquil setting.

4.67 out of 5 average rating, 3 reviews

Spencertown Inn Suite 5

The Spencertown Inn is Columbia County’s newest all-suite luxury Inn. With just 5 suites in total, the Inn offers quiet and private accommodations in a country setting, yet is just minutes away from local restaurants and attractions. The Spencertown Inn is located in the historic town of Spencertown, New York, just minutes from Chatham, New York’s charming downtown Main Street and a short drive to the Cultural Berkshires of Massachusetts. (Room furniture and décor may differ from photos.)

The exterior of the resort features a three-story building with multiple balconies and a light-colored facade. A well-maintained grassy area surrounds the building, and a small pond reflects the structure while rocks are scattered along the water's edge.

4.75 out of 5 average rating, 4 reviews

Great Place|2 BD|Kitchen| Pool 

After a day of mountain adventures , our Resort in the Berkshires is the perfect New England-y place to unwind and kick off those hiking boots. Take the whole family for a relaxing indoor swim, enjoy a flick at our onsite movie theater, and end your evening with a toast at the Beartree Bar. • Pools, Gym, Movie Theater and mini golf  • Accommodate up to 6 people  • One guest in the party, must be at least 21 y/o or older.    * U$10 PER NIGHT OF RESORT FEE.  **Additional charge 

A resort-style building features three levels with balconies, framed by lush green grass and a serene pond reflecting the structure. The surrounding area is dotted with a few rocks and landscaping, creating a peaceful outdoor environment.

4.85 out of 5 average rating, 13 reviews

Great place for family |2 BD|Kitchen| Pool

Top guest favorite

A three-story building is set amidst a grassy area with scattered rocks. A small pond reflects the clear sky and nearby greenery, enhancing the serene landscape that surrounds the resort.

5 out of 5 average rating, 12 reviews

Beautiful place|2 BD|Kitchen| Pool

Hotel room in Pittsfield

1 BD • Forest Views • Sleeps 4 • Kitchen • Pool

Experience the best of the Berkshires from this comfortable one-bedroom apartment. It offers beautiful forest views and a convenient location near Lenox, Massachusetts. Explore the region's rich culture, vibrant arts scene, and natural beauty throughout the seasons. Area Attractions : • Bousquet Ski Area • Hancock Shaker Village • Tanglewood Music Center • The Mount • Jiminy Peak Mountain Resort • Norman Rockwell Museum • Mount Greylock State Reservation • Naumkeag Museum

A spacious resort building is set against a clear blue sky, surrounded by lush green grass and strategically placed boulders. A small pond reflects the structure and the nearby trees, offering a serene outdoor atmosphere.

Great place|2 BD|Kitchen| Pool 

4.82 out of 5 average rating, 100 reviews

A cozy sleeping area features a spacious bed with a floral-patterned coverlet. There are two bedside tables, each topped with lamps. The room is flanked by windows dressed with plaid curtains, while framed artwork adorns the walls, adding a welcoming touch.

Hotel room in Cummington

Singing Bridge Harmony Room

Great views of the Berkshire hilly forests, and hiking trails along a scenic river. Couples, families, and pets feel right at home in our recently renovated kitchen and warm, and friendly lodge with four bedrooms, electric baseboard heat and queen-sized beds. The sunny loft has a comfy queen. Gas heat. Call an hour before arrival if you don't have AT&T or Verizon cell service- other carriers may be inconsistent in the area. Wifi enabled. Pets are welcome for a $25 fee.

The room features two full-size beds dressed in plaid comforters with coordinating pillows. A simple wooden bench is positioned at the foot of the beds. Natural light enters through a bright window adorned with light blinds.

Hotel room in Hillsdale

Walk to the Slope - Catamount Ski In/Out

Welcome to Catamount! Just steps away from the slopes, our rooms feature exceptional views, unparalleled access, and ideal privacy. You'll also be in the perfect jumping off point for further adventures in Hudson, NY and the rest of the Hudson Valley, or to Great Barrington, MA and the Berkshires beyond. Welcome to the best kept secret in the New York Berkshires!

Popular amenities for Stockbridge hotels

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly hotels

4.6 out of 5 average rating, 53 reviews

A bright guest room features a double bed with a patterned blanket. Natural light enters through a window, accompanied by a view of the surroundings. A large cityscape photograph decorates the wall, and two bedside lamps are positioned beside the bed.

Hotel room in Latham

1 Double Bed, Non Smoking Room

The exterior of the Catskill Motor Court is displayed, featuring a prominent sign indicating 'Vacancy.' The grassy area in front is maintained, with tall trees providing shade in the background. The layout includes a nearby one-story building with a simple design.

Private room in Catskill

Catskill Motor Court - Room 5

4.76 out of 5 average rating, 21 reviews

A cozy sitting area features a dark blue accent wall and a plush sofa with checkered pillows. A coffee table is positioned on a plaid rug, accompanied by an open book. A large potted plant adds a natural touch, complemented by warm lighting from a pendant lamp.

Hotel room in Catskill

Modern hotel room by Kaaterskill Falls + Catskill

Top guest favorite

A cozy suite is showcased with a spacious bed featuring decorative pillows and a textured blanket. A comfortable seating area is provided with a sofa and chairs. Natural light filters through large windows, and decorative plates adorn the wall above the bed.

Hotel room in Kingston

4.97 out of 5 average rating, 100 reviews

Grace and Favor - welcoming one bedroom suite

The exterior of the Microtel Inn by Wyndham is depicted, showcasing a two-story building with light-colored siding. A welcoming entrance is highlighted by a central portico. Lush green shrubs are arranged along the front, with clear blue skies above and a flagpole displaying the American flag.

Hotel room in Latham

4.51 out of 5 average rating, 100 reviews

1 Queen Bed with Microwave & Fridge

Hotel room in Williamstown

4 out of 5 average rating, 6 reviews

1 Queen BD • Kitchen • Patio •Pool

A multi-story building is depicted, featuring a light-colored facade with dark shutters. Snow blankets the ground and trees in the foreground, creating a serene winter scene. The structure offers several balconies, enhancing its mountain resort appeal.

Hotel room in Hancock

4.87 out of 5 average rating, 15 reviews

Wyndham Bentley Brook ** 2BR Deluxe

An outdoor deck features wooden flooring and a cozy seating area with a fire pit. Lounge chairs and tables are positioned under shaded umbrellas, surrounded by greenery and the vibrant colors of nearby vintage caravans. The setting offers an inviting space for relaxation.

Hotel room in Amenia

4.61 out of 5 average rating, 31 reviews

1967 Hotel Caravana: For Those Who Want Amazing

Hotels with a pool

5 out of 5 average rating, 5 reviews

New place to stay

Bright 2BR Condo – Perfect for Family or Friends

A spacious room features a 4-poster bed with a light quilt, complemented by a cozy seating area with a beige sofa and a small table. A gas fireplace adds warmth, while soft lighting enhances the tranquil blue walls and decorative artwork.

Hotel room in Lenox

★ Romantic King Room w/ Double Jacuzzi & Fireplace

A large, multi-story building showcases a blend of red and white siding, topped with a distinctive clock tower. Lush greenery surrounds the property, offering a spacious driveway leading up to the entrance, with decorative lamp posts adding to the inviting exterior.

Resort in Pittsfield

Berkshire Mass. Resort, 1bdrm 8/27-9/03 $1050

Resort in Hancock

New place to stay

Slope view ski-in/out 1br condo hotel @Jiminy Peak

A spacious room features a large bed adorned with a decorative blanket. A rustic bench is positioned at the foot of the bed. Natural light enters through a window, and a vanity area can be seen in the background, complemented by modern bathroom fixtures.

Endless Family Fun: Pools, Arcade Room & Mini Golf

A soft, white robe is displayed on a wooden hanger against a dark wall. A small emblem is positioned on the robe's front. A door with a window and a minimalist handle is visible in the background.

Hotel room in Hillsdale

Little Cat Lodge -King room

The resort area showcases a multi-story building, surrounded by green grass and landscaping. A small pond reflects the structure, while rocks line the water's edge. Trees provide additional greenery, creating a serene outdoor setting.

4.93 out of 5 average rating, 40 reviews

Great Place |2 BD|Kitchen| Pool 

The resort's exterior features a multi-story building with a light-colored facade, surrounded by landscaped grass and rocky accents. A calm pond reflects the structure, while a few trees offer greenery. Clear skies facilitate a serene atmosphere.

Great Place - 2BD/2BA

Hotels with a patio

A mid-century building features a wooden balcony overlooking a vibrant green lawn. Surrounding colorful foliage, including tall evergreens and rich red bushes, adds to the landscape's beauty under a clear blue sky. Natural stone accents provide a rustic touch to the exterior.

Hotel room in Red Hook

The Reclaimed Motel, Hudson Valley - Three Farmers

A spacious resort building is set against a clear blue sky, with soft morning light illuminating its exterior. A serene pond reflects the structure, surrounded by green grass and scattered rocks. Lush trees provide a natural backdrop for this tranquil environment.

Great place|2 BD|Kitchen| Pool 

A multi-story resort building is framed by well-maintained lawns and trees. The structure features a light exterior with balconies, reflecting a classic New England style. A peaceful pond with gentle ripples adds to the serene atmosphere, surrounded by rock landscaping.

Great Place|2 BD|Kitchen| Pool 

A multi-story resort building is depicted, featuring a light-colored exterior and a cupola on the roof. Surrounding green lawns are visible, with decorative rocks lining a small pond reflecting the building and foliage in the background.

Great for family|2 BD|Kitchen| Pool

Hotel room in Norfolk

La Chambre Room at the Manor House Inn

A white dog stands in an expansive green lawn, holding a pink toy. The background features a grand brick building with large windows and a terrace, where guests are gathered, enjoying the outdoor space.

Hotel room in Lenox

Near all lodging alternative cln

A three-story building with a light-colored exterior is surrounded by a grassy area and trees. A small pond reflects the structure, with rocks lining the water's edge. Four gabled roof structures are seen in the background under a clear blue sky.

Great place|2 BD|Kitchen| Pool

The exterior of the resort is showcased, featuring three floors with light-colored siding and distinctive cupolas. A lush green lawn surrounds the building, and a small pond reflects the structure, adorned with rocks along its edge.