Hotels in Berkshires

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Top-rated hotels in Berkshires

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Superhost

A charming motel exterior is showcased, featuring a white building with blue accents. Five guest rooms are visible, each with a door framed by small windows. Neatly trimmed hedges line the walkway, complementing the natural surroundings. A clear sky is seen in the background.

Hotel room in Fort Montgomery

4.78 out of 5 average rating, 130 reviews

Bear Mountain Bridge Motel (Rooms 1, 2, 4, 5)

We are a small family owned and operated 5 room motel looking to welcome you like a long lost friend. We live in a home on the property so you will get great customer service. The motel is on 9W and within walking distance of many great food options. We are 2m away from West Point Military Academy and 1 mi away from Bear Mountain and Harriman State Parks. There are many beautiful hiking options .We offer an Appalachian Trail shuttle to and from the trail and our motel. We welcome sleepy guests!

Guest favourite

A serene sleeping area features a spacious bed with a light quilt and coordinating pillows. Soft light emanates from bedside lamps on dark nightstands. A wooden bench sits at the foot of the bed, while a large window offers views of the exterior.

Hotel room in Hunter

4.93 out of 5 average rating, 27 reviews

Perfect Lodge /w Gameroom Center of Hunter MT 3

Matterhorn's Lodge is located right in front of Hunter Mountain, with every unit having Hunter Mountain Trails Views right from there window!! Making it the perfect destination for a truly indulgent getaway with family & friends!Step into a world of relaxation. Catskills also has some of the best hiking trails in North America! Game Room added!! We are located only 7 mins from historical Tannersville. Just 10 minutes from North South Lake one of the most popular destinations in North America.

Guest favourite

A cozy room features a plush Queen bed with a stylish upholstered headboard. Nightstands with lamps are positioned on either side. A small armchair adds seating, and two framed botanical prints adorn the walls. Warm wood flooring complements the room's inviting design.

Hotel room in Tannersville

4.94 out of 5 average rating, 17 reviews

Standard Main Lodge Room

Our cozy Standard Main Lodge rooms offer a plush Queen bed and a private bathroom equipped with either a walk-in shower or a jet tub/shower combination. These rooms are on the 1st or 2nd floor of the main lodge (accessible via stairs.) All of our Main Lodge rooms feature comfortable, high-quality bedding, blackout privacy curtains, a mini-fridge, a flat-panel HD TV with DVD player and DirecTV. Our rooms showcase woodsy architectural details, original art, and curated books for an inspired stay.

Guest favourite

A cozy room is presented with a queen bed covered in a light quilt. Natural light filters in through two windows, flanked by neutral curtains. Two bedside tables with lamps are positioned beside the bed, and a small chair is placed against the wall.

Hotel room in Chester

4.94 out of 5 average rating, 32 reviews

Quaint Queen Room & Private Bath

Enjoy a private room & bathroom with tub in the historic Chester Inn, circa 1780. This charming property is conveniently located on Main St in walking distance to restaurants, shops & galleries (please see guidebook for recommendations!). Public hiking/snowshoeing trails can be entered right through the backyard & Okemo mountain is just a short drive away! EV charging is close by (in the public lot on Cobleigh St) Although the building is bed & breakfast style we do not provide breakfast.

Guest favourite

The entrance reveals a cozy room featuring a king-sized bed with a decorative quilt. A warm hue emanates from a pendant light above, illuminating a wooden table and a comfortable armchair. Natural light filters through the window, enhancing the inviting ambiance of the space.

Hotel room in Manchester

4.94 out of 5 average rating, 52 reviews

6 Bam Boo! Cozy escape in the heart of Vermont

6 Bam-Boo! is your cozy escape in the heart of Vermont just minutes to Manchester Center. Stay in the center of the action at this one-of-a-kind whimsical room w King-sized bed, a comfy armchair, a table with chairs, flat-screen TV with streaming services, a mini-fridge + freezer and coffee maker. Be sure to grab a snack or coffee / tea from the Snack Lounge, open 24 hours. Bam-Boo 6 is the perfect spot to unwind and recharge after exploring the Green Mountain State. Come stay with us!

Guest favourite

A brightly painted room features a spacious queen bed adorned with a colorful patterned throw. Wooden flooring complements a decorative rug. Natural light enters through nearby windows, and a ceiling fan enhances air circulation. A small bedside lamp and framed artwork add character to the space.

Hotel room in Rhinebeck

4.94 out of 5 average rating, 87 reviews

The Gables of Rhinebeck Inn, Sugarloaf Suite

The Gables of Rhinebeck, a 4-suite Inn located 1 block from main street. This historic Inn is a fifteen-gable 1860 Gothic Revival Victorian in the heart of Rhinebeck Village. Guests have full access to our half-acre fenced-in yard with perennial and ornamental gardens, + plenty of indoor space. "Sugarloaf" is a 1BR Suite at The Gables of Rhinebeck. About Your Room: -Queen Bed, Cable TV, Full Bath on the 2nd floor with claw foot tub. AC'd in the summer https://www.TheGablesRhinebeck.com/

Superhost

Hotel room in Townshend

4.88 out of 5 average rating, 8 reviews

Stratton Room at River & Rye in Jamaica, VT

This hip spot offers more than just distinctive decor.River & Rye is an inn, restaurant, bar, and gathering place in the center of Jamaica's village. The inn, a renovated 1820s farmhouse, has six bedrooms with minimalist Scandinavian design, gorgeous stone and tile bathrooms, and access to beautiful views no matter the season. The inn is connected to our restaurant and bar, which offers Americana classics and crafted cocktails, and features produce, cheese, and meats from local farmers.

Guest favourite

A large wooden Adirondack chair is positioned on a well-maintained grassy area in front of the Howard Johnson Inn. The building's welcoming entrance is marked by a prominent sign, with a flag flying in the breeze against a bright blue sky dotted with clouds.

Hotel room in Rocky Hill

4.75 out of 5 average rating, 48 reviews

Near Hartford Downtown @rockyhill hotel (1 BED)

Howard Johnson Inn ( Hotel) -Exit 24 off 91, All rooms come with Microfridge, Great Wi fi Light breakfast with coffee, juice, cereal and oatmeal. PLEASE KNOW THERE IS $50 DEPOSIT DUE AT CHECK IN - WHICH IS REFUNDABLE WHEN YOU CHECK OUT. NO Pets secure with 24/7 desk clerk. Ten minutes from Downtown Hartford, XL Center, Hartford Hospital, Connecticut Convention Center, Bushnell Theater, Town of Glastonbury. Walking distances to Taco Bell and On The Border Mexican Restaurant.

Superhost

The exterior of the Courtyard by Marriott Shelton is showcased, featuring a modern, multi-story structure with large windows. The entrance is prominent, framed by landscaped greenery and a spacious parking area. The building is complemented by soft evening lighting.

Hotel room in Shelton

4.8 out of 5 average rating, 118 reviews

Close to Yale University + The Bistro. Pool. Gym.

Settle into comfort at Courtyard by Marriott Shelton, located near I-95 with easy access to Yale, Downtown New Haven, and area parks. Fuel up with Starbucks® drinks at The Bistro, unwind in the indoor pool, or stay productive in the 24/7 fitness center. Free parking and Wi-Fi keep things simple, while nearby hiking trails, restaurants, and local attractions make it easy to explore. Whether you're in town for work or a weekend escape, this stay makes it feel effortless.

Guest favourite

Hotel room in Hobart

5 out of 5 average rating, 22 reviews

Book Village Inn - Dickinson Room Queen Bed

Dickinson Room – Queen Bed, Spacious & Bright Inspired by the poetic spirit of Emily Dickinson, this upstairs suite offers a spacious and luminous retreat. Bathed in natural light, the room’s airy layout and serene décor create an inviting haven perfect for quiet reflection and leisurely mornings. Enjoy the calm, uplifting ambiance as you relax and let your thoughts wander in this uniquely inspiring space. Restaurant: The BVI Bar is open Thu-Sun 4PM-10pm

Guest favourite

A charming white building features a green roof and large front doors surrounded by symmetrical windows. A staircase on the left leads to a second-floor entrance. Lush flowerbeds with blooming plants line the stone pathway, enhancing the welcoming appearance.

Hotel room in Townshend

4.87 out of 5 average rating, 15 reviews

North Loft at Windham Hill Inn

Extremely private, this expansive loft room has its own private staircase and entrance on the second floor of our Barn building. Decorated in peaches and cream tones with shades of blue and gray, North Loft offers a true retreat from the everyday. Amenities include a four-poster king bed, sitting areas with a couch and winged-back chair, a brick surround gas fireplace, spacious deck, and private bath with Jacuzzi and shower.

Guest favourite

A cozy corner room features a queen-sized bed with a textured headboard, complemented by blue accent pillows. A plaid wall adds a pop of color, while a vibrant area rug lies beneath. Natural light brightens the space through a window, creating a warm ambiance.

Hotel room in Woodstock

4.95 out of 5 average rating, 20 reviews

Room 6 - Second Floor - Twin Gables of Woodstock

Guests seeking utter tranquility often request this light peaceful corner room that offers an ambiance of serenity, double exposure windows, queen-sized bed, butterfly sling chair, and a petite private bath. Please note that this is our smallest guest room and offers a super cozy stay with access to the second floor back door.