Hotels in Lenox

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

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

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 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

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, 11 reviews

Beautiful place|2 BD|Kitchen| Pool

A resort building with three levels features a light-colored exterior, surrounded by green grass and natural landscaping. A calm pond reflects the structure and greenery, enhancing the peaceful outdoor setting. Nearby trees and pathways are visible, providing an inviting 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.

Hotel room in Pittsfield

4.2 out of 5 average rating, 5 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 Lenox hotels

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly hotels

A well-lit room features two full-size beds with patterned bedding and dark wood frames. A lamp beside one bed casts a warm glow. Large sliding doors open to a natural view, while framed photographs adorn the walls.

4.94 out of 5 average rating, 163 reviews

#32 Top Floor-Newly Renovated! Room 32-Horizon Inn

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

4.76 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

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

This ground-level room features a spacious king-size bed with patterned bedding. Two framed photographs adorn the green walls, while a small table with two chairs is positioned nearby. A refrigerator, microwave, and Keurig are also included, along with a desk and chair.

4.93 out of 5 average rating, 114 reviews

#13 Newly renovated! Horizon Inn (Room #13)

A room features two full-size memory foam beds dressed in gray bedding with a subtle branch pattern. Natural light enters through sliding glass doors that lead to a small balcony. Artwork adorns the walls, and a lamp stands beside one of the beds.

4.92 out of 5 average rating, 145 reviews

#34 Top Floor-Newly Renovated! Horizon Inn Room 34

A spacious room is shown with a king-size bed dressed in a patterned gray comforter. A piece of wall art is displayed above the bed, while large glass doors provide access to an outdoor area, allowing natural light to fill the room.

4.94 out of 5 average rating, 177 reviews

#27 Top Floor-Newly Renovated! Horizon Inn-room 27

Hotels with a pool

Hotel room in Stockbridge

New England Landmark + 4 Dining Spots Onsite. 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

New place to stay

Bright 2BR Condo – Perfect for Family or Friends

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

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

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 

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

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 

The exterior of a well-maintained two-story building is featured, showcasing a light-colored facade with decorative window features. The entrance is approached by a wide pathway, bordered by neatly trimmed shrubs and flower beds. A balcony area is visible on the rooftop, surrounded by trees.

Hotel room in Pittsfield

Home a while

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.