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, 277 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

Hotel room in Great Barrington

A spacious king bed is prominently featured, adorned with a colorful decorative pillow. A wall-mounted Roku TV is visible, along with a small kitchenette featuring a mini-fridge and coffee supplies. Light filters through the window, while gray curtains frame the room.

4.75 out of 5 average rating, 4 reviews

Studio|King Bed|Wifi|Dog-Friendly|Prime Berkshires

Designed for a long weekend or intimate stay, with or without your furry family member. This is East Rock Inn's brand new King Studio, featuring a king bed, bathroom with a walk-in shower, and Roku TV. Quiet and comfortable. Our central location, 1 mile from downtown Great Barrington and 1 mile from Butternut Ski Area, means you're close to all the shops, restaurants, and outdoor activities the Berkshires have to offer. A $35/day pet fee applies. Please be sure to indicate if you have a pet.

Private room in Sheffield

A cozy bedroom is featured with warm wooden walls and soft blue curtains. A spacious bed with a white quilt and decorative pillows sits at the center, flanked by two nightstands with lamps. A framed artwork adorns the wall above the bed, adding a touch of color.

4.92 out of 5 average rating, 77 reviews

Sheffield Lodge - Greylock Room

Sheffield Lodge is a warm and inviting rustic Bed and Breakfast, secluded from the stressful city life, nestled in a forest of tall pines, maples, and birch trees. Enjoy your home-away-from-home where there is always welcoming hospitality, friendly service, and delicious breakfasts. Located just a short distance from the most popular activities and entertainment the Berkshires is known for including Tanglewood, Jacob's Pillow, skiing, stage theater, hiking, museums, and antique shopping.

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 

Top guest favourite

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

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 

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.

4.93 out of 5 average rating, 137 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

This is a 2 bedroom suite. Stay in a beautiful, modern and stylish private suite at Nest Hudson, a newly renovated boutique situated in a charming 100-year-old home. Lounge in the chic rooms featuring hardwood floors and bold blues before heading out the comfortable shared backyard, rocking chair front porch or enjoy a complimentary coffee/tea and relax on the back deck. There are 5 private, well-appointed suites available ideally located in the heart of town.

Popular amenities for Stockbridge hotels

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly hotels

The exterior of Gardner Farm Inn is shown, featuring a classic Federal style architecture. A welcoming sign stands at the entrance, with the number 59 visible. The well-maintained green lawn and surrounding trees contribute to the serene environment.

Hotel room in Troy

4.96 out of 5 average rating, 68 reviews

Gardner Farm Inn - John Waters suite

Hotel room in Williamstown

Spacious 2BD • Kitchen • Pool • Free Parking

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

4.94 out of 5 average rating, 50 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

4.76 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

Hotel room in Pittsfield

4.2 out of 5 average rating, 5 reviews

1 BD • Berkshires Apartment • Full Kitchen/Pool

Top guest favourite

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, 99 reviews

Grace and Favor - welcoming one bedroom suite

The exterior of the resort is showcased, featuring a combination of stone and siding. Multiple levels of balconies are visible, framed by manicured greenery and a gently sloping hillside. A flag can be seen waving at the front, with mountains rising in the background.

Hotel room in Hancock

4.75 out of 5 average rating, 8 reviews

Wyndham Bentley Brook * 1 Bedroom

Hotels with a pool

Hotel room in Stockbridge

New England Landmark + 4 Dining Spots Onsite. Pool

5 out of 5 average rating, 5 reviews

New place to stay

Peaceful Berkshires Escape – 2BR Resort Condo

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

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

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.

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.

Hotel room in Washington Park

Great for family|2 BD|Kitchen| Pool

A queen-sized bed with a light-colored canopy frame is centered in the room, flanked by two bedside tables with lamps. A cushioned bench sits at the foot of the bed, complementing the room's bright white walls and blue carpet.

4.88 out of 5 average rating, 8 reviews

Hudson 1 at The Argus Hotel