Places to stay in The Berkshires

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The Berkshires place to stay
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4010 Best places to stay in The Berkshires

Best The Berkshires accommodations with a balcony

Peaceful, Post And Beam Loft, Sleeps 9 - The Berkshires
9.7 122 reviews

Peaceful, Post And Beam Loft, Sleeps 9

apartment, New Marlborough
This New Marlborough apartment is situated just 8km from Ski Butternut, 7km from Dry Hill, and 25km from Tanglewood, making it an ideal base for exploring the region's natural beauty and cultural attractions. The property has received excellent ratings for user experience, location, and cleanliness, ensuring a comfortable and enjoyable stay.
The self-catering property spans 198 square metres and comfortably accommodates up to nine guests. It offers a range of amenities including a fully equipped kitchen, a spacious living area, a tranquil bathroom with a double-headed shower and a Jacuzzi, a private bedroom with a queen bed, a loft with two queen beds, a full-size bed and a queen-size air bed, a terrace, a garden, parking for six vehicles, and a washer and dryer.
Lake Garfield Waterfront Home And Boathouse - The Berkshires
10 4 reviews

Lake Garfield Waterfront Home And Boathouse

cottage, Monterey
This Monterey cottage, located 4.5km from the Bidwell House Museum and within 10km of Dry Hill and McLennan Reservation, offers easy access to Lake Buel and Les Trois Emme Winery.
The three-bedroom self-catering property sleeps six, includes a bathroom, laundry facilities (washing machine, hairdryer, iron), Wi-Fi, and air conditioning; nearby activities include wine tasting and exploring local attractions.
Little Longbow Lakefront Chalet - The Berkshires
9.0 1 review

Little Longbow Lakefront Chalet

house, Becket
This lakefront chalet in Becket offers direct access to a private beach and is located 20.9 kilometres from Cranwell Spa & Golf Club and 24.1 kilometres from Tanglewood.
This spacious 2-bedroom holiday home, covering 117 square metres, accommodates up to 9 guests and features a balcony with lake views, a well-equipped kitchen, air conditioning, WiFi, and barbecue facilities, with skiing, fishing, and hiking nearby.
Forget-me-not By Avantstay - The Berkshires
No reviews

Forget-me-not By Avantstay

house, Monterey
Forget-Me-Not by AvantStay, a lakefront property in Monterey, California, is situated 23-35km from attractions including the Cranwell Spa & Golf Club, the Norman Rockwell Museum, Haystack Mountain State Park, and Great Falls.
This one-bedroom house boasts four bathrooms, sleeps sixteen guests, and features a fully equipped kitchen, Jacuzzi, sauna, parking, and a terrace; enjoy lakefront views, water activities, and a fireplace.

Best family friendly The Berkshires lodging

Among the 4010 accommodations in The Berkshires, here are the 4 best for families

Heated Pool, Hot Tub, Game Room, Sauna! - The Berkshires
9.9 36 reviews

Heated Pool, Hot Tub, Game Room, Sauna!

house, New Marlborough
Casa Mia is a spacious holiday home located in New Marlborough, just 10 kilometres from Great Barrington and 5 kilometres from Ski Butternut, offering a peaceful retreat in the quiet countryside. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
This five-bedroom property, with a capacity for 12 guests, is designed with an open layout, providing ample space for families and groups. Guests can enjoy a range of amenities, including a swimming pool, hot tub, sauna, and a fully equipped kitchen, as well as entertainment options like a games room and a bocce court.
Beaver Lodge - The Berkshires
10 83 reviews

Beaver Lodge

apartment, Monterey
This three-bedroom cottage is situated in the Berkshires, just a short distance from Tanglewood, Lake Garfield, and Ski Butternut.
The property boasts a spacious layout, accommodating up to six guests, and offers a range of amenities including a fully equipped kitchen, a wood-burning fireplace, and high-speed internet.
The Pinnacle House At Otis Ridge Ski Area! - The Berkshires
9.8 178 reviews

The Pinnacle House At Otis Ridge Ski Area!

apartment, Otis
This four-bedroom apartment is located just a short distance from popular Berkshire destinations like Jacob's Pillow, Tanglewood, and the Norman Rockwell Museum, offering a peaceful escape in the tranquil surroundings of Otis Ridge Ski Area. It has consistently received excellent ratings for cleanliness, location, and overall user experience.
The spacious apartment comfortably accommodates up to eight guests and features a well-equipped kitchen, a private garden, and parking. Guests can enjoy outdoor meals on the patio with a gas grill, relax in the living area, or explore the nearby hiking trails, swimming spots, and local restaurants.
Spacious Lakeside Berkshire Home Close To Tanglewood And Jacob's Pillow - The Berkshires
10 127 reviews

Spacious Lakeside Berkshire Home Close To Tanglewood And Jacob's Pillow

apartment, Monterey
This family-friendly holiday home is situated near Monterey, within a 3km radius of Beartown State Forest and Bidwell House Museum, and within 10km of Ashintully Gardens and McLennan Reservation. The property has received excellent ratings for its cleanliness, location and user experience.
The accommodation has four bedrooms and a floor area of 288 square metres. Guests can enjoy a range of amenities, including a fully equipped kitchen, a fireplace, a patio with a barbecue grill, a fitness centre, and a garden.

Frequently asked questions about accommodations in The Berkshires

  • What are the top attractions and must-see sites in Monts Berkshire?

    The Berkshires is bursting with things to see. You simply must visit the Clark Art Institute in Williamstown, a stunning museum with beautiful gardens, and the Berkshire Museum in Pittsfield, which has a fantastic collection of art and natural history exhibits. If you're a theatre fan, a trip to Tanglewood in Lenox for a performance is a must. And don't forget to explore the charming towns of Stockbridge and Lenox, with their beautiful architecture and quaint shops.
  • What are the best places to stay in The Berkshires?

  • Which cultural festivals and seasonal events should visitors attend in Monts Berkshire?

    The Berkshires is a hub for cultural events. The Jacob's Pillow Dance Festival in Becket is a world-renowned dance festival, and the Shakespeare & Company in Lenox offers excellent theatre productions. For autumn foliage, visit in October, and for winter fun, there's the Berkshire Winter Festival in February. You'll find something to enjoy no matter when you visit.
  • What are the best places to stay with a pool in The Berkshires?

  • What are the most convenient modes of transportation within Monts Berkshire?

    The Berkshires is best explored by car. The roads are scenic and well-maintained. However, if you're staying in a town like Lenox or Williamstown, you can easily get around on foot or by bicycle. There are also public buses, but they're not as frequent as in larger cities.
  • What are the best places to stay with a jacuzzi in The Berkshires?

  • What outdoor activities and adventures are popular in and around Monts Berkshire?

    The Berkshires is a haven for outdoor enthusiasts. Mount Greylock, the highest peak in Massachusetts, offers hiking and stunning views. You can also go kayaking on the Housatonic River, explore the Appalachian Trail, or take a scenic drive along the Mohawk Trail. For winter fun, there's skiing at Butternut and Jiminy Peak.
  • What are the best places to stay for families and kids in The Berkshires?

  • What types of accommodations are available in Monts Berkshire?

    You'll find a wide range of accommodation options in the Berkshires, from charming bed and breakfasts to luxurious hotels. There are also plenty of vacation rentals, including cabins and cottages, for those who prefer a more secluded experience. If you're on a budget, there are some motels and inns available.
  • What are the best pet friendly places to stay in The Berkshires?

    The best pet friendly places to stay in The Berkshires are Holiday Inn Express Great Barrington By Ihg, The Little Lion and Peace And Quiet On The Lake.

  • When is the best time to visit Monts Berkshire?

    The best time to visit the Berkshires depends on your interests. If you want to enjoy the vibrant cultural scene, summer is ideal. For stunning autumn foliage, visit in October. Winter offers skiing and snowshoeing, while spring brings beautiful wildflowers and fresh air.
  • What are the best places to stay with parking in The Berkshires?

  • What local dishes and culinary experiences are a must-try in Monts Berkshire?

    The Berkshires is known for its farm-to-table cuisine. You'll find plenty of restaurants featuring locally sourced ingredients, including fresh produce, meats, and cheeses. Try a Berkshire pork chop, a local specialty, or sample some of the delicious apple cider donuts. Don't miss the chance to visit a local farmers market for a taste of the region's bounty.
  • In which part of Monts Berkshire should you consider renting accommodation?

    It really depends on what you want to do! If you're interested in the arts and culture, Lenox or Williamstown are great choices. For outdoor activities, consider staying near Mount Greylock or the Housatonic River. For a more rural experience, explore the towns of Stockbridge or Great Barrington. Each area has its own unique charm and attractions.

Popular destinations

Best The Berkshires accommodations with a fireplace

Sunset Falls Estate, 167 Private Acres, Berkshires - The Berkshires
10 4 reviews

Sunset Falls Estate, 167 Private Acres, Berkshires

apartment, New Marlborough
This luxurious apartment is located in the picturesque Berkshires of western Massachusetts, 32 kilometres from Great Barrington, a town known for its cultural experiences, restaurants, and shops. The apartment offers a range of amenities including a hot tub, steam room, radiant heated floors, three fireplaces, a fully equipped chef's kitchen, a gym, a 2-car heated garage, a children's nook with books and games, a dedicated kids room with 6 queen over queen bunk beds, accommodating up to 12 guests, and a great room with a pool table, foosball, darts, arcade games, an 85” TV, and a wet bar with a wine fridge and a kegerator.
Forest Hollow | Waterfront  Kayaks  Wood Stove - The Berkshires
9.4 11 reviews

Forest Hollow | Waterfront Kayaks Wood Stove

apartment, Monterey
This three-bedroom lakefront property in Monterey, Massachusetts, within the Berkshires, offers direct access to Lake Garfield, with two docks and kayaks, and is approximately 0.8 km from the Bidwell House Museum and the Mahaiwe Performing Arts Centre.
The 185 square metre house features a cosy open-plan living area with a fireplace, a downstairs den/games room, a spacious deck, parking for three cars, and sleeps up to six guests, including children accommodated in trundle beds.
Lovely Vacation Home On Secluded Hillside With Views And Heated Pool - The Berkshires
9.7 27 reviews

Lovely Vacation Home On Secluded Hillside With Views And Heated Pool

apartment, New Marlborough
This modern barn conversion is situated on a secluded hill in New Marlborough, offering stunning mountain views and a short drive (5km) to both the charming town centre and the scenic hiking trails of the Berkshires. It has consistently received excellent ratings for its location, cleanliness, and overall guest experience.
The property has three bedrooms, two bathrooms, and can comfortably accommodate up to six guests. Guests can enjoy a heated pool, a spacious living area, a private garden, and a terrace with views of the surrounding countryside, as well as a trampoline and access to nearby hiking trails.
Berkshires Cabin 2 Mi To Appalachian Trail! - The Berkshires
9.7 46 reviews

Berkshires Cabin 2 Mi To Appalachian Trail!

cabin, Otis
The Berkshires Cabin 2 Mi to Appalachian Trail! is located in Otis, just 3.2km from the Appalachian Trail and within a short drive of attractions such as Cranwell Spa & Golf Club, Tanglewood, and Tanglewood Musical Center. The property has excellent user, location, and cleanliness ratings.
This 3-bedroom holiday home is 111 square metres and can accommodate up to 7 guests. The cabin has a fully equipped kitchen, a garden, a spa, free Wi-Fi, a flat-screen TV, and parking.

Best The Berkshires accommodations with a kitchen

Cozy Cabin In The Berkshires - The Berkshires
10 23 reviews

Cozy Cabin In The Berkshires

cabin, Sandisfield
This charming two-bedroom cabin is situated in the beautiful Berkshires, just a short drive from Sandisfield, with Butternut ski resort 40km away and Jiminy Peak 80km away. The cabin has received excellent user, location, and cleanliness ratings, making it a top choice for travellers.
The property has two bathrooms and can comfortably accommodate up to eight guests, offering plenty of space for families or groups of friends. The cabin features a fully equipped kitchen, a screened-in deck, a loft with four twin beds, a basement with a pool table and dart board, a fire pit, and a grill, ensuring a comfortable and enjoyable stay for all.
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-swimming, Canoeing - The Berkshires
9.8 16 reviews

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-swimming, Canoeing

apartment, Becket
This Becket Sherwood Forest holiday home is situated 4km from Pyramid Lake and within 10km of both Jacob's Pillow Dance Festival and the Iroquois Waterfront.
The two-bedroom property sleeps seven, boasts a jacuzzi, terrace, garden, free Wi-Fi, BBQ facilities and parking, and is perfect for families, with pets welcome.
Berkshires Modern Cabin With Babbling Brook - The Berkshires
10 14 reviews

Berkshires Modern Cabin With Babbling Brook

apartment, Sandisfield
The Cabin is located in the Berkshires, a short walk from a community lake and amenities, and a short drive (around 10km) to popular ski resorts like Otis Ridge and Ski Butternut. It has received excellent ratings for location, cleanliness and overall user experience.
The accommodation has a spacious and open floor plan, ideal for families, and can comfortably sleep up to 7 guests. It offers a range of amenities including a fully equipped kitchen, a swimming pool, a garden, a wood-burning stove, and a dedicated kids' play area, as well as easy access to hiking trails, cultural attractions, and winter sports.
Newly Rebuilt Waterfront House On Otis Reservoir - The Berkshires
9.6 81 reviews

Newly Rebuilt Waterfront House On Otis Reservoir

apartment, Otis
This four-bedroom apartment is situated in Otis, right on the water in a cove, with a road separating the front yard from the water's edge. The property enjoys excellent ratings for location, cleanliness, and overall user experience.
The self-catering property sleeps up to eight guests and features a fully-equipped kitchen, two bathrooms, and a spacious deck. Guests can enjoy a private dock, boat rentals, and a peaceful garden, all within a safe and child-friendly environment.

Top-rated The Berkshires accommodations

Beautiful, Private Berkshires Retreat W Magic View! 5min To Lake Garfield Beach - The Berkshires
9.8 149 reviews

Beautiful, Private Berkshires Retreat W Magic View! 5min To Lake Garfield Beach

chalet, Monterey

Best pet friendly The Berkshires places to stay

Among the 4010 accommodations in The Berkshires, here are the 4 best ones accepting pets

Exotic Mountain Retreat In The Berkshires. - The Berkshires
9.8 209 reviews

Exotic Mountain Retreat In The Berkshires.

cabin, Otis
Enjoy Every Season The Berkshires Have To Offer. - The Berkshires
9.9 128 reviews

Enjoy Every Season The Berkshires Have To Offer.

apartment, Otis
River House - The Berkshires
10 3 reviews

River House

apartment, New Marlborough
Scribe's Stable | A/c  Screened Porch  Sleeps 6 - The Berkshires
9.9 67 reviews

Scribe's Stable | A/c Screened Porch Sleeps 6

farm, Monterey

Best The Berkshires lodgings with a pool

Among the 4010 accommodations in The Berkshires, here are the 4 best ones with a pool

Berkshires Oasis Retreat: Art Meets Nature - The Berkshires
9.9 17 reviews

Berkshires Oasis Retreat: Art Meets Nature

apartment, Otis
A Fun Country Escape For Two! Featuring A Fireplaces,hot Tub, And Ping Pong - The Berkshires
9.8 141 reviews

A Fun Country Escape For Two! Featuring A Fireplaces,hot Tub, And Ping Pong

B&B, Sandisfield
353 M² House ∙ 4 Bedrooms ∙ 12 Guests - The Berkshires
9.4 63 reviews

353 M² House ∙ 4 Bedrooms ∙ 12 Guests

house, Monterey
Hot Tub, Sauna, Game Room, Fireplaces + Heated Pool In Summer! - The Berkshires
No reviews

Hot Tub, Sauna, Game Room, Fireplaces + Heated Pool In Summer!

apartment, New Marlborough

Discover Accommodations with a Jacuzzi in The Berkshires

Private hot tub access after a day in the hills is one of those details that makes a trip to The Berkshires truly memorable.

Hilltop Escape With Views & Hot Tub - The Berkshires
10 2 reviews

Hilltop Escape With Views & Hot Tub

apartment, New Marlborough
Amazing Berkshire Mountains Cabin - The Berkshires
9.9 311 reviews

Amazing Berkshire Mountains Cabin

cabin, Monterey
Lakefront Otis Home W/ Stunning Views & Boats! - The Berkshires
10 16 reviews

Lakefront Otis Home W/ Stunning Views & Boats!

apartment, Otis
Hilltop Escape With Views & Hot Tub - The Berkshires
9.2 24 reviews

Hilltop Escape With Views & Hot Tub

apartment, New Marlborough
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