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

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.
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.
Garfield Grounds | Lakeside  Guest Cottage  Dock - The Berkshires
10 1 review

Garfield Grounds | Lakeside Guest Cottage Dock

apartment, Monterey
This lakeside property in Monterey, Massachusetts, offers a private dock on Lake Garfield, convenient access to Otis Ridge, Les Trois Emme Winery, McLennan Reservation, and Dry Hill (distances unspecified).
The 375 square metre (approximately 4030 square feet) dwelling comprises a spacious main house with a basement TV room, a separate guest house with a wood stove sleeping two, four bedrooms, three bathrooms, and can accommodate up to ten guests, benefiting from a garden, terrace, parking, internet access, and a fully equipped kitchen including a fridge, microwave, and dishwasher.
Lakefront 3-br Retreat In The Berkshires - The Berkshires
9.6 8 reviews

Lakefront 3-br Retreat In The Berkshires

apartment, Becket
This Becket lakeside property offers direct Pyramid Lake access and is located 3.7km from Jacob's Pillow dance centre.
The 149 square metre house sleeps six, boasting three bedrooms, three bathrooms, a fully equipped kitchen with dishwasher, a jacuzzi, terrace, garden, parking, and on-site hot tub.

Best family friendly The Berkshires lodging

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

Lake Front Retreat - Stylish Berkshire  Home - The Berkshires
9.8 180 reviews

Lake Front Retreat - Stylish Berkshire Home

apartment, Becket
This renovated mid-century home is located on Long Bow Lake, a peaceful lake just 32 kilometres from Downtown Lee, with shops, hiking trails and the Otis Ridge ski area nearby. The property has excellent user, location and cleanliness ratings, making it a popular choice for travellers.
This spacious split-level house sleeps six guests and includes four bedrooms and two bathrooms. The home has a fully equipped kitchen, a garden, a tennis court, a private dock, kayaks, a ping pong table, a Weber gas grill, and a screened-in porch, perfect for enjoying the beautiful scenery and outdoor activities.
Exotic Mountain Retreat In The Berkshires. - The Berkshires
9.8 209 reviews

Exotic Mountain Retreat In The Berkshires.

cabin, Otis
This upscale log cabin is located in the Berkshire Mountains, just 24 kilometres from Butternut Ski Mountain and the town of Great Barrington, offering a peaceful escape from the hustle and bustle. It has received excellent ratings for location, cleanliness, and user experience.
The spacious five-bedroom property can accommodate up to 15 guests, making it ideal for families or groups of friends. The cabin is fully equipped with modern amenities including a full kitchen, Wi-Fi, a wood-burning stove, a gas BBQ, and air conditioning in several rooms. Guests can enjoy a range of activities in the surrounding area, including hiking, fishing, boating, and exploring the charming towns of Lenox and Lee.
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.
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.

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

Serene Berkshires Home On 5+ Acres, Rustic & Chic - The Berkshires
9.5 72 reviews

Serene Berkshires Home On 5+ Acres, Rustic & Chic

house, Otis
This spacious apartment is located in Otis, in the Berkshires, offering a tranquil setting within protected forestland, just a short drive from local attractions. The apartment has received excellent ratings for its location, cleanliness, and overall user experience.
The apartment has five bedrooms and three bathrooms, comfortably accommodating up to ten guests. It features a well-equipped kitchen, a dedicated workspace, a game room, a play area, and outdoor amenities such as a screened porch, a backyard with seating, a fire pit, and a gas grill, making it ideal for families and groups.
Contemporary Modern Mountain Retreat - The Berkshires
10 6 reviews

Contemporary Modern Mountain Retreat

apartment, Monterey
This Monterey holiday home is located in a wooded area with mountain ridge views, 800 metres from Lake Garfield and its hiking trails, and a 10-minute drive from Great Barrington's amenities.
This spacious 186-square-metre house offers accommodation for up to 10 guests with four bedrooms and three bathrooms, featuring a fully equipped kitchen, a screened-in porch, a deck with a fire pit and grill, and a king primary suite with a jacuzzi tub.
Cozy Cabin In The Berkshires - The Berkshires
10 21 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.
Garfield Grounds | Lakeside  Guest Cottage  Dock - The Berkshires
9.9 28 reviews

Garfield Grounds | Lakeside Guest Cottage Dock

apartment, Monterey
This five-bedroom, three-bathroom lakeside property is situated in the Berkshires region on Lake Garfield, offering access to canoeing and stunning lake views.
Sleeping up to ten guests, this house comprises a spacious main house and a separate cottage, boasting a private dock, open grounds with an outdoor dining area and grill, fireplaces, and a jacuzzi tub; internet, parking, and a fully equipped kitchen with fridge, microwave, and dishwasher are also included.

Best The Berkshires accommodations with a kitchen

The Southfield Spot - The Berkshires
9.9 53 reviews

The Southfield Spot

apartment, New Marlborough
This apartment is located in New Marlborough, a short distance from the Southfield Store and Old Inn On the Green, with hiking trails and waterfalls within easy reach. The property has received excellent ratings for cleanliness, location, and user experience.
The home is a spacious three-bedroom property with two bathrooms, comfortably accommodating up to six guests. The apartment features a well-equipped kitchen, air conditioning, a private garden, and parking, as well as a large deck with comfortable furniture, perfect for enjoying the beautiful Berkshire scenery.
Modern Escape In The Woods Of The Berkshires - 4br - The Berkshires
9.7 49 reviews

Modern Escape In The Woods Of The Berkshires - 4br

apartment, Monterey
This four-bedroom apartment is located in the Berkshires, a scenic region of western Massachusetts, a 320km drive from Monterey and just 10 minutes from Ski Butternut. It has received excellent ratings for location, cleanliness, and overall user experience.
The apartment has three bathrooms and can accommodate up to eight guests. It offers a modern kitchen, a private pool, a garden, a fitness centre, and a range of outdoor activities, including hiking and horseback riding.
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.
Bosworth Tap Room - The Berkshires
9.9 101 reviews

Bosworth Tap Room

apartment, Sandisfield
This historic house is located in the southeast corner of the Berkshires, around 48 kilometres from the nearest shopping centre, offering a peaceful retreat in the beautiful countryside. The property has received excellent ratings for its location, cleanliness, and overall experience.
The house has four bedrooms and one bathroom, comfortably accommodating up to six guests. The house features a fully equipped kitchen, a garden, and air conditioning, alongside modern amenities while retaining its authentic colonial charm.

Top-rated The Berkshires accommodations

Cozy Berkshire Cottage - The Berkshires
10 6 reviews

Cozy Berkshire Cottage

cottage, Otis

Best pet friendly The Berkshires places to stay

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

Family Cabin W/ Climbing Wall, Games. Near Great Barrington, Butternut, Lakes - The Berkshires
10 3 reviews

Family Cabin W/ Climbing Wall, Games. Near Great Barrington, Butternut, Lakes

apartment, Otis
Cozy Cabin Retreat In The Berkshires - The Berkshires
8.5 17 reviews

Cozy Cabin Retreat In The Berkshires

cabin, Otis
Berkshire Retreat At Cantina 229 - The Berkshires
10 18 reviews

Berkshire Retreat At Cantina 229

apartment, New Marlborough
Cabin W/ 3 Acres, Tennis Courts: By 4 Ski Mtns - The Berkshires
10 1 review

Cabin W/ 3 Acres, Tennis Courts: By 4 Ski Mtns

cottage, Sandisfield

Best The Berkshires lodgings with a pool

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

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

Berkshires Oasis Retreat: Art Meets Nature

apartment, 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

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.

Forget-me-not By Avantstay | Bold Lakefront Escape - The Berkshires
9.8 70 reviews

Forget-me-not By Avantstay | Bold Lakefront Escape

house, Monterey
Hilltop Escape With Views & Hot Tub - The Berkshires
No reviews

Hilltop Escape With Views & Hot Tub

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

Sunset Falls Estate, 167 Private Acres, Berkshires

house, New Marlborough
353 M² House ∙ 4 Bedrooms ∙ 12 Guests - The Berkshires
9.4 63 reviews

353 M² House ∙ 4 Bedrooms ∙ 12 Guests

house, Monterey
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