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, 276 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.)

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

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 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, 9 reviews

Beautiful place|2 BD|Kitchen| Pool

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.

4.92 out of 5 average rating, 39 reviews

Great Place |2 BD|Kitchen| Pool 

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, 99 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.

Hotel room in Pittsfield

4 out of 5 average rating, 4 reviews

1 BD • Berkshires Apartment • Full Kitchen/Pool

Discover a perfect retreat in the heart of the Berkshires. Berkshires Mountain Lodge is moments away from the charming town of Lenox. Our retreat is an ideal base for exploring this cultural arts haven year-round. 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

5 out of 5 average rating, 5 reviews

A spacious room features light-colored walls and a high ceiling, creating an airy ambiance. A king-size bed with white linens is positioned in the center, flanked by wooden nightstands with decorative lamps. A vibrant piece of wall art complements the space, while a window allows natural light to fill the room.

Hotel room in Adams

The Trail in Adams - Deluxe Room

Welcome to "The Trail in Adams" - Berkshires’ Art Hotel on the Ashuwillticook Rail Trail in Adams. Jon is a 288 square feet deluxe room on the second floor with a king-size bed, a 13.5-foot ceiling, a walk-in closet, an ensuite bathroom with spa tub (indoor), south and east-facing windows, and a view of Pleasant St.

Popular amenities for Stockbridge hotels

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-Friendly hotels

4.94 out of 5 average rating, 49 reviews

An outdoor patio area is enclosed by a wooden pergola, providing shade. Below, outdoor furniture, including lounge chairs and a table, is arranged for relaxation. Potted plants add greenery, and a staircase leads to the second floor, blending the outdoor space with the building.

Hotel room in Saugerties

Village Inn - Chelsea suite - Saugerties NY

4.75 out of 5 average rating, 20 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

4.98 out of 5 average rating, 97 reviews

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

Grace and Favor - welcoming one bedroom suite

5 out of 5 average rating, 6 reviews

A cozy sleeping area features a queen brass bed adorned with a floral patterned quilt. Antique furniture, including a side table and a trunk, complements the oak paneling. Plush seating is arranged around a small antique table, all illuminated by warm lighting from vintage lamps.

Hotel room in Saugerties

Catskills Getaway - Spacious Comfortable Room

A spacious bedroom features a large bed adorned with a light green quilt and decorative pillows. Bedside tables with lamps provide soft lighting. A tasteful artwork hangs above the bed, while a patterned area rug complements the hardwood flooring.

Hotel room in Jacksonville

4.93 out of 5 average rating, 169 reviews

The Engel House Room 3: Mt Snow/Wilmington VT Area

Private room in Rhinebeck

The comfortable sitting area features a brown leather sofa, accentuated by soft throws, facing a modern fireplace. A large bed is positioned near the window, providing natural light, while a wall-mounted TV is located above the fireplace. A small coffee table complements the space.

5 out of 5 average rating, 3 reviews

The Harlow House: Chateau Suite

4.07 out of 5 average rating, 14 reviews

A cozy sleeping area features a colorful quilt displayed over the bed. Natural light filters through the nearby windows, offering a glimpse of the lush greenery outside. The walls are adorned with rustic wooden cabinets, enhancing the space's inviting feel.

Private room in Catskill

Rustic remodeled private camper by the pond

4.93 out of 5 average rating, 135 reviews

A view from a cozy sleeping area is shown, framed by a large window with white trim. A textured blanket covers the bed, complemented by soft pillows in shades of pink and blue. The exterior view features a brick building and a glimpse of outdoor space.

Hotel room in Hudson

Nest Hudson Boutique Hotel - Two Bedrooms

Hotels with a pool

A corner room features a Queen bed adorned with a sheer net canopy and vintage-style throw pillows. A small table with breakfast items sits beside the bed, while a cozy fireplace is visible. Leaded glass windows allow natural light to brighten the walls of patterned green.

Hotel room in Lenox

5 out of 5 average rating, 4 reviews

★ Vintage Romance with Fireplace & Spa Tub

A light-colored resort building with multiple balconies overlooks a serene pond, reflecting the structure and nearby greenery. Lush grass and scattered rocks frame the water's edge, while trees provide a natural backdrop in the distance.

Great Place |2 BD|Kitchen| Pool 

New place to stay

Bright 2BR Condo – Perfect for Family or Friends

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 

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

Hotel room in Stockbridge

Heart of Stockbridge + Dining. Bike-Friendly. Pool

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.

5 out of 5 average rating, 3 reviews

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

Hotels with a patio

5 out of 5 average rating, 3 reviews

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 three-story building features balconies overlooking a serene pond. The surrounding green lawn is accented by scattered rocks, reflecting the structure and blue sky in the water. Trees provide a natural backdrop to the peaceful setting.

Great place|2 BD|Kitchen| Pool 

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.