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

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.
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.
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
This apartment in Otis is located by a river, offering a secluded woodland experience close to Hayes Pond (200 metres) and within 13 kilometres of Otis Reservoir and the Appalachian Trail.
This 178 square metre dwelling accommodates up to 10 guests with 3 bedrooms and 3 bathrooms, featuring a kitchen with a fridge, microwave, and dishwasher, air conditioning, a terrace or balcony, and garden access, with pets and families welcome.
Cabin W/ 3 Acres, Tennis Courts: By 4 Ski Mtns - The Berkshires
9.6 135 reviews

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

cabin, Sandisfield
This charming four-bedroom cottage is situated in Sandisfield, Massachusetts, just 26 kilometres from the Cranwell Spa & Golf Club, 27 kilometres from the Norman Rockwell Museum, and 29 kilometres from Tanglewood, offering easy access to popular attractions. The property has received excellent ratings for its location, cleanliness, and overall experience.
This 184 square metre dwelling comfortably accommodates up to 10 guests and boasts a fully equipped kitchen, a spacious living area, and a private garden. Guests can enjoy a range of amenities including a tennis court, a spa, and free Wi-Fi, ensuring a relaxing and enjoyable stay.

Best family friendly The Berkshires lodging

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

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.
Little Longbow Lakefront Chalet - The Berkshires
9.8 35 reviews

Little Longbow Lakefront Chalet

chalet, Becket
This Becket lakeside lodge is situated within 3.2km of Pyramid Lake, Jacob's Pillow Dance Festival, and 3km from October Mountain State Forest, offering easy access to swimming, boating, hiking and world-class dance performances.
Sleeping five guests, this two-bedroom, two-bathroom property boasts a private garden, terrace, spa, air conditioning, Wi-Fi, and barbecue facilities, perfect for a family getaway.
Berkshire Retreat At Cantina 229 - The Berkshires
10 18 reviews

Berkshire Retreat At Cantina 229

apartment, New Marlborough
This five-bedroom, three-bathroom house in New Marlborough, Berkshire, is situated on a five-acre plot, 24km from Great Barrington town centre.
The 2,584 sq ft property boasts a spacious layout sleeping up to 10 guests, offering a fully equipped kitchen, games room, and outdoor fire pit, with convenient parking and proximity to hiking and skiing in the Berkshires.
Berkshire Wonderland Family Home 7 Acr Lake Access - The Berkshires
9.9 81 reviews

Berkshire Wonderland Family Home 7 Acr Lake Access

apartment, Otis
This 4-bedroom apartment is situated in the Berkshire countryside, just 10km from a local lake and a short drive from Great Barrington and ski resorts. The apartment has received excellent ratings for its location, cleanliness, and overall experience.
The apartment offers a spacious and open layout, comfortably accommodating up to 11 guests. It includes a well-equipped kitchen, a cosy living room, a den with a TV, a library, and a wrap-around porch. Guests can enjoy access to the lake for swimming and fishing, as well as a canoe and kayak.

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

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
This spacious apartment, perfect for families and groups, is located in the picturesque Berkshires, within easy reach of popular attractions like Ski Butternut and Great Barrington. The accommodation has consistently received excellent ratings for its cleanliness, location and overall experience.
The apartment is spread over 167 square metres and comfortably sleeps eight guests, featuring three bedrooms and two bathrooms. Guests can enjoy a range of amenities, including a fully equipped kitchen, a garden, a fitness centre, Wi-Fi, and parking.
Iconic Lodge In The Berkshires - The Berkshires
9.7 64 reviews

Iconic Lodge In The Berkshires

cabin, Sandisfield
This four-bedroom lodge is situated in the Berkshires, a scenic region of Western Massachusetts, about 48 kilometres from Stockbridge, Great Barrington, and Otis Reservoir. The property has received excellent ratings for location, cleanliness, and user experience.
The lodge is spacious and can accommodate up to 12 guests. It offers a range of amenities, including an indoor pool, a billiards lounge, a large dining room, a well-equipped kitchen, and a private garden.
Berkshires Waterfront Fall Escape Hot Tub & Kayaks - The Berkshires
10 31 reviews

Berkshires Waterfront Fall Escape Hot Tub & Kayaks

apartment, Otis
This five-bedroom Otis, Massachusetts lakeside property, a six-minute drive (approx. 9.6km) from the ski slopes, offers direct waterfront access with kayaks and tranquil views.
Sleeping ten guests, this self-catering apartment boasts a fully equipped kitchen, three bathrooms, a jacuzzi, a basement suite with kitchenette, a game room, and extensive outdoor space including a patio with grill; essential amenities are provided.
Forget-me-not By Avantstay | Bold Lakefront Escape - The Berkshires
9.8 70 reviews

Forget-me-not By Avantstay | Bold Lakefront Escape

house, Monterey
This apartment is located in the Berkshires, a region in western Massachusetts, just 160 kilometers from Monterey, offering stunning views of Lake Garfield. It has received excellent ratings for its location, cleanliness and overall guest experience.
The property is a spacious home with a modern design, suitable for up to 12 guests. Enjoy a range of amenities, including a hot tub, sauna, a fully equipped kitchen, a large deck with a BBQ grill, a ping pong table, and a pool table for entertainment.

Best The Berkshires accommodations with a kitchen

The Lake House - The Berkshires
10 45 reviews

The Lake House

apartment, Otis
This Sandisfield apartment, a two-bedroom lakeside property in Otis, Massachusetts, is a short walk from a lake.
The self-catering house sleeps six, features a fireplace, fire pit, parking for two vehicles, and is pet-friendly.
4 Acres | Rustic-modern Berkshires Retreat - The Berkshires
9.8 159 reviews

4 Acres | Rustic-modern Berkshires Retreat

apartment, Otis
This rustic modern apartment is located in Otis, Massachusetts, just 5 kilometres from Otis Ridge Ski Area and within a 15-kilometre radius of Butternut and Catamount ski resorts, perfect for a winter getaway. The property has received excellent ratings for its cleanliness, location and overall experience.
The apartment can accommodate up to 6 guests and features a spacious layout with a modern kitchen, a cosy fireplace and a large garden. Guests can enjoy the convenience of a fully equipped kitchen, a washer and dryer, and a wrap-around deck with a gas grill, as well as access to a range of activities in the surrounding area, including skiing, hiking and exploring the Berkshires.
Quiet Comfortable Cabin 5 Min. Walk To Swimming And Boating - The Berkshires
9.6 259 reviews

Quiet Comfortable Cabin 5 Min. Walk To Swimming And Boating

cabin, Becket
This charming cabin is located in Sherwood Forest, just outside of Becket, within 10km of Pyramid Lake, Iroquis Waterfront, Jacob's Pillow, October Mountain State Forest, and Becket Land Trust Historic Quarry. It enjoys a peaceful setting, offering a tranquil escape from the hustle and bustle of town. This cabin has been rated excellent by previous guests.
The cabin spans 59 square meters and comfortably sleeps up to four guests in its two bedrooms. It boasts a range of amenities, including a fully equipped kitchen, a garden, a terrace, and a fireplace, allowing guests to enjoy both indoor and outdoor relaxation.
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.

Top-rated The Berkshires accommodations

Picturesque Cottage House With Nearby Lake And Cafe - The Berkshires
No reviews

Picturesque Cottage House With Nearby Lake And Cafe

apartment, New Marlborough

Best pet friendly The Berkshires places to stay

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

Misty Pines Cabin | Wood Stove  Sauna - The Berkshires
10 1 review

Misty Pines Cabin | Wood Stove Sauna

cabin, Monterey
Berkshire Lake At The Pillow, And Ev! - The Berkshires
9.6 21 reviews

Berkshire Lake At The Pillow, And Ev!

apartment, Becket
Berkshire Retreat With Fenced Yard On 9 Acres - The Berkshires
10 3 reviews

Berkshire Retreat With Fenced Yard On 9 Acres

apartment, Otis
The Southfield Spot - The Berkshires
9.9 53 reviews

The Southfield Spot

apartment, New Marlborough

Best The Berkshires lodgings with a pool

Among the 4010 accommodations in The Berkshires, here are the 3 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
Berkshires Modern Cabin With Babbling Brook - The Berkshires
10 14 reviews

Berkshires Modern Cabin With Babbling Brook

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

353 M² House ∙ 4 Bedrooms ∙ 12 Guests

house, Monterey

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.

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

Lakefront Otis Home W/ Stunning Views & Boats!

apartment, Otis
Mountain Refuge - The Berkshires
9.3 21 reviews

Mountain Refuge

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

Berkshire Lakefront Cabin With Modern Luxuries

apartment, Otis
Lakefront Retreat | Berkshires Escape - The Berkshires
10 7 reviews

Lakefront Retreat | Berkshires Escape

apartment, Becket
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