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The Berkshires, MA accommodations
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4010 Lodgings in The Berkshires, MA

Best The Berkshires, MA accommodation with a balcony

The Owl & Firefly  Family Cabin In The Southern Berkshires - The Berkshires, MA
10 3 reviews

The Owl & Firefly Family Cabin In The Southern Berkshires

apartment, Otis
This Otis cabin, set among pines and stone walls, is located a short drive from the Appalachian Trail and Otis Reservoir, offering a secluded experience with proximity to Hayes Pond (10560 feet) and Otis Reservoir (13 minutes).
This 1920 sq ft, 3-bedroom, 3-bathroom apartment accommodates up to 10 guests and features a kitchen with a fridge, microwave, and dishwasher, air conditioning, a terrace/balcony, garden, and internet, ideal for families seeking outdoor activities and après-ski relaxation near Jacob's Pillow and Bidwell House Museum.
353 M² House ∙ 4 Bedrooms ∙ 12 Guests - The Berkshires, MA
9.4 63 reviews

353 M² House ∙ 4 Bedrooms ∙ 12 Guests

house, Monterey
This luxurious lakefront home in the Berkshires offers stunning, uninterrupted views of Lake Garfield and is conveniently located near attractions such as the Berkshire Botanical Gardens and Jiminy Peak Mountain Resort, though precise distances aren't specified.
The four-bedroom, four-bathroom residence sleeps up to twelve guests and boasts a spacious layout including a main living area, a second living room with kitchenette, a sunroom, and a large deck with a BBQ grill; amenities include a swimming pool, hot tub, sauna, and various games.
Lakefront Retreat With Stunning Views | Forget-me-not By Avantstay - The Berkshires, MA
9.4 14 reviews

Lakefront Retreat With Stunning Views | Forget-me-not By Avantstay

apartment, Monterey
This Monterey apartment is a Berkshires retreat located on the shores of Lake Garfield, offering stunning lake views and easy access to the region's natural beauty and cultural attractions. The property has earned a very good user rating, making it a popular choice for travelers seeking a comfortable and enjoyable stay.
The home has four bedrooms and four bathrooms, comfortably accommodating up to 12 guests. Enjoy a range of amenities, including a private hot tub, sauna, tennis court, and access to the lake for swimming, fishing, and kayaking.
Lake Garfield Waterfront Home And Boathouse - The Berkshires, MA
10 4 reviews

Lake Garfield Waterfront Home And Boathouse

cottage, Monterey
This Monterey cottage rental is located 2.8 miles from the Bidwell House Museum and within 6 miles of Dry Hill, McLennan Reservation, Lake Buel, and Les Trois Emme Winery.
This three-bedroom, one-bathroom house sleeps six, features on-site laundry, and offers amenities including Wi-Fi, air conditioning, a washing machine, hairdryer, and iron/ironing board.

Popular Family Lodgings in The Berkshires, MA

These family-friendly lodgings in The Berkshires, MA offer plenty of room with trails and fresh air right outside your door.

Berkshires Cabin In Woods With Mountain Views - The Berkshires, MA
10 138 reviews

Berkshires Cabin In Woods With Mountain Views

cabin, Sandisfield
This charming cabin is located in Sandisfield, a short 20-minute drive from Great Barrington and Lee, offering easy access to the Berkshires' scenic beauty and attractions. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The cabin features three bedrooms and one bathroom, comfortably accommodating two guests. Enjoy the fully equipped kitchen, outdoor fire pit, screened-in porch, and expansive views from the balconies.
Little Longbow Lakefront Chalet - The Berkshires, MA
9.8 35 reviews

Little Longbow Lakefront Chalet

chalet, Becket
This Becket waterfront cabin is located within two miles of Pyramid Lake, Jacob's Pillow Dance Festival, and October Mountain State Forest, offering easy access to swimming, boating, hiking, and world-class dance performances.
The 2-bedroom, 2-bathroom house sleeps five, features a private garden, terrace, spa, and on-site barbecue grills, plus amenities like air conditioning, internet, and a fully equipped kitchen including a microwave and refrigerator.
Serene Berkshires Home On 5+ Acres, Rustic & Chic - The Berkshires, MA
9.5 72 reviews

Serene Berkshires Home On 5+ Acres, Rustic & Chic

house, Otis
Otis apartment is a spacious retreat nestled in the heart of the Berkshires, offering a secluded sanctuary surrounded by breathtaking natural beauty. This highly-rated apartment features five bedrooms, three bathrooms, and dedicated spaces for every need, ensuring comfort and privacy for up to 10 guests.
With its exquisite artwork and furnishings by local Berkshires artists, this apartment creates a warm and inviting atmosphere that celebrates the region's creative spirit. Guests can enjoy a variety of entertainment options, including a game room with shuffleboard and arcade games, a home gym, and a screened porch with picturesque views. The outdoor dining area, fire pit, and games allow guests to fully embrace the beauty of the Berkshires while enjoying the fresh mountain air.
Family Berkshires Cabin W/ Climbing Wall, Games - The Berkshires, MA
10 11 reviews

Family Berkshires Cabin W/ Climbing Wall, Games

apartment, Otis
This apartment in Otis offers a secluded woodland escape, nestled deep within the pine forests and stone walls of the southern Berkshires, providing 6 acres of private property.
This 3-bedroom, 3-bathroom cabin accommodates up to 10 guests with 7 beds, featuring a fully equipped kitchen, an indoor climbing wall, a record player, and a 65" Roku TV, with two pack-n-play cribs available.

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Best The Berkshires, MA accommodation with a fireplace

Stone Tudor In Monterey Village - The Berkshires, MA
9.4 96 reviews

Stone Tudor In Monterey Village

apartment, Monterey
This charming Tudor-style accommodation is located in the heart of Monterey Village, within walking distance of the Monterey General Store and a 10-minute drive from Great Barrington's amenities. It has excellent user, location, and cleanliness ratings.
The home features 3 bedrooms, 3 bathrooms, and a guest capacity of 7. It boasts a cozy and inviting interior with warm wooden floors, multiple fireplaces, and comfortable living spaces. Guests have access to a variety of amenities, including a kitchen with a fridge, freezer, and dishwasher, air conditioning, a garden, parking, and access to board games, video game consoles, and Roku streaming.
Waterfront Oasis In Heart Of Berkshires - The Berkshires, MA
10 48 reviews

Waterfront Oasis In Heart Of Berkshires

house, Sandisfield
This Sandisfield waterfront rental boasts four bedrooms and three bathrooms, sleeping seven guests, and offers easy access to Butternut Ski Area and the cultural attractions of Great Barrington and Lenox.
The home features a fully stocked, professional-grade kitchen, a spacious living room with a wood-burning stove, and a private garden, all contributing to a relaxing atmosphere.
Waterfront Cottage Retreat By Evergreen Home - The Berkshires, MA
10 2 reviews

Waterfront Cottage Retreat By Evergreen Home

apartment, Becket
This Lee, Massachusetts lakefront home is nine minutes from Becket, offering direct access to Shaw Pond and proximity to Butternut and Bousquet ski resorts (within 25 minutes' drive).
The 1190-square-foot, three-bedroom, two-bathroom house sleeps six and features a fully equipped kitchen, screened porch, fire pit, kayaks, paddle boat, and electric fireplaces in the queen bedrooms.
Spacious Lakeside Berkshire Home - The Berkshires, MA
10 127 reviews

Spacious Lakeside Berkshire Home

apartment, Monterey
This family-friendly vacation home is located on a lake in Monterey, within 2 miles of Beartown State Forest and Bidwell House Museum. It has excellent user, location, and cleanliness ratings.
The house has 4 bedrooms and 3100 square feet of floor area. It includes a patio, DVD player, fireplace, kitchen with refrigerator and oven, and a smoke-free environment. Guests can also enjoy a garden with barbecue grills, a fitness center, and parking.

Best The Berkshires, MA accommodation with a kitchen

Cozy Becket Cottage Minutes From Lake Beaches - The Berkshires, MA
9.0 4 reviews

Cozy Becket Cottage Minutes From Lake Beaches

cottage, Becket
This Becket, Massachusetts cottage is located in the Sherwood Forest neighborhood, a short 5-minute drive from Pyramid Lake and a 9-minute drive from Iroquois Waterfront Beach.
This 600-square-foot vacation home sleeps six guests and features two bedrooms, one bathroom, a fully equipped kitchen with fridge and microwave, in-house laundry, internet access, and outdoor amenities including a fire pit and grill.
Sunny Berkshire Studio Apartment - The Berkshires, MA
9.9 241 reviews

Sunny Berkshire Studio Apartment

apartment, Sandisfield
This studio apartment is located in Sandisfield, Massachusetts, just a short drive from historic sites like the Inn on the Green and Gedney Farm, and a 20-minute drive from popular Berkshire cultural destinations. This rental has earned excellent ratings for location, cleanliness, and overall experience.
The studio offers a comfortable space for up to four guests with a full-size bed, a twin futon, and an attached bedroom with a full-size bed. The studio also has a kitchen with a fridge and microwave, air conditioning, parking, and internet access, as well as a private deck and yard, making it perfect for relaxing and enjoying the surrounding nature.
The Meadows House @ Otis Ridge W/ 7-person Hot Tub - The Berkshires, MA
9.7 215 reviews

The Meadows House @ Otis Ridge W/ 7-person Hot Tub

apartment, Otis
This 3-bedroom apartment is located in Otis, Massachusetts, just a short walk from the Otis Ridge Ski Area and a 20-minute drive from the town of Great Barrington. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The apartment features a spacious living area with a fireplace and a pull-out couch, accommodating up to 7 guests. It comes equipped with a private hot tub, a large deck, a fully equipped kitchen, and access to a variety of outdoor activities, including hiking trails and lakes.
Berkshire Treehouse Retreat - The Berkshires, MA
9.8 178 reviews

Berkshire Treehouse Retreat

cabin, New Marlborough
This charming treehouse cabin is located in the woods near Great Barrington, Massachusetts, offering a peaceful escape just a short drive from the town center. The cabin consistently receives excellent ratings for its cleanliness, location, and overall guest experience.
The two-level treehouse features a unique design with a live tree running through its interior, accommodating up to 5 guests. Enjoy the outdoors with amenities like a gas grill, a solo stove, and an outdoor dish station, perfect for a glamping experience.

Search Luxury Lodgings in The Berkshires, MA

Upscale lodgings in The Berkshires, MA offer a premier mountain experience defined by high-end finishes and refined service.

Cozy Cottage-sunset On The Lake - The Berkshires, MA
9.8 52 reviews

Cozy Cottage-sunset On The Lake

cottage, Otis

Find the Best Pet-Friendly Lodgings in The Berkshires, MA

Your dog is as welcome as you are; each pet-friendly lodging in the mountains around The Berkshires, MA offers dog-friendly trails and plenty of room to roam.

Bidwell Landing | Lakefront  Spacious - The Berkshires, MA
9.8 109 reviews

Bidwell Landing | Lakefront Spacious

house, Monterey
Lakefront Multi-home Compound - The Berkshires, MA
9.3 12 reviews

Lakefront Multi-home Compound

apartment, Monterey
Dog/family Friendly A-frame! Walk To Lake/kayak Use In The Berkshires! - The Berkshires, MA
10 9 reviews

Dog/family Friendly A-frame! Walk To Lake/kayak Use In The Berkshires!

apartment, Becket
Lakefront Retreat | Dock, Kayaks & Fire Pit - The Berkshires, MA
9.8 17 reviews

Lakefront Retreat | Dock, Kayaks & Fire Pit

apartment, Becket

Our Favorite Lodgings with a Pool in The Berkshires, MA

A lodging with a swimming pool in The Berkshires, MA is a brilliant base for a refreshing dip after a day of hiking.

Berkshires Modern Cabin With Babbling Brook - The Berkshires, MA
10 14 reviews

Berkshires Modern Cabin With Babbling Brook

apartment, Sandisfield
Sweet Dreams Retreat - The Berkshires, MA
9.8 141 reviews

Sweet Dreams Retreat

resort, Sandisfield
Modern Escape In The Woods Of The Berkshires - 4br - The Berkshires, MA
9.7 49 reviews

Modern Escape In The Woods Of The Berkshires - 4br

apartment, Monterey
Berkshires Oasis Retreat: Art Meets Nature - The Berkshires, MA
9.9 17 reviews

Berkshires Oasis Retreat: Art Meets Nature

apartment, Otis

Discover Lodgings with a Hot Tub in The Berkshires, MA

Private hot tub access after a day in the mountains is a detail that makes any trip to The Berkshires, MA truly memorable.

Berkshires Waterfront Fall Escape Hot Tub & Kayaks - The Berkshires, MA
10 31 reviews

Berkshires Waterfront Fall Escape Hot Tub & Kayaks

apartment, Otis
Lakefront 3-br Retreat In The Berkshires - The Berkshires, MA
9.6 8 reviews

Lakefront 3-br Retreat In The Berkshires

apartment, Becket
Lakefront Otis Home W/ Stunning Views & Boats! - The Berkshires, MA
10 23 reviews

Lakefront Otis Home W/ Stunning Views & Boats!

house, Otis
Berkshire Lakefront Cabin With Modern Luxuries - The Berkshires, MA
10 93 reviews

Berkshire Lakefront Cabin With Modern Luxuries

apartment, Otis
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