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The Best Hotels for a Weekend Getaway in Berkshires

The Berkshires, MA The Berkshires, MA

Berkshires, Massachusetts is a fantastic city to visit for a weekend getaway, and finding the right hotel can make your trip even more enjoyable. Whether you're traveling as a couple, a family, or solo, we've analyzed all of the hotels in the area to help you decide where to stay for a weekend in Berkshires. There are many affordable options for a hotel here, from cozy bed and breakfasts to large chain hotels. When considering where to stay in Berkshires for your long weekend escape, make sure to look for amenities that will help you relax and unwind, such as a fitness center, spa, or pool. And don't forget to consider location - finding a hotel near restaurants and other things to do can make your stay much more enjoyable. Berkshires is a great city for sightseeing, and there are plenty of things to do for families or couples during a weekend escape, including museums or outdoor activities which are perfect for a 2-day or 3-day trip. So if you're looking for a weekend getaway in Berkshires, one of these wonderful hotels will help you take advantage of everything on offer.

(Prices are listed in U.S. Dollars.)

Wyndham Bentley Brook

Hancock, Massachusetts
3-star Hotel with prices starting at $131 (before taxes) - See All Prices
Perfect Hotel for a 3-day trip in Berkshires
  • Great Value: the price is lower than average for 3-star hotels.
  • High Quality: guest ratings are higher than average.
  • Outdoor pool
  • Spa
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Located at 1 Corey Road, Wyndham Bentley Brook has great rooms from $131 (before taxes). It offers an outdoor pool, skiing, a fitness center, hiking, and rooms with kitchens. It has a terrific 9.00 rating out of 10 from previous guests who have stayed here. Only 6 miles from the city center, visitors will especially love a hot tub, a game room, a spa, an indoor pool, and free parking at this convenient hotel. Don't forget that there's a kitchen in the room to cook your meals, too. The price of this hotel is less than average for weekend trip hotels, which makes it a great value.

Weekend Trip Hotel Amenities
  • Outdoor pool
  • Skiing
  • Kitchen
  • Hot tub
  • Spa
  • Indoor pool
  • Kid-friendly
  • Airport shuttle
  • Golf
  • Spa/Wellness
More Great Amenities
  • Fitness center
  • Hiking
  • Game room
  • Free parking
  • Family rooms
  • Fitness room
  • Tennis
  • Microwave
  • Refrigerator
  • Playground
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Wheatleigh

Stockbridge, Massachusetts
5-star Hotel with prices starting at $1816 (before taxes) - See All Prices
A Great Stay for a Weekend Trip to Berkshires
  • High Quality: guest ratings are higher than average.
  • Outdoor pool
  • Pets allowed
  • Spa
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A great place to stay is Wheatleigh which has nice rooms starting at $1816. Offering an outdoor pool, room service, a restaurant, a fitness center, and a bar, it also has a great guest rating of 9.99 out of 10 from many previous guests. It's located at Hawthorne Road. This fun hotel is also nice because it offers breakfast, hiking, child care, laundry services, and a free breakfast which weekend visitors will enjoy. Also, it's just 13.1 miles from the city center. The service at the restaurant is terrific, and so is the food.

Weekend Trip Hotel Amenities
  • Outdoor pool
  • Room service
  • Breakfast included
  • Free breakfast
  • Pets allowed
  • Spa
  • Golf
More Great Amenities
  • Restaurant
  • Fitness center
  • Bar/Lounge
  • Hiking
  • Babysitting / Child Care
  • Laundry service
  • Free parking
  • Tennis
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The Red Lion Inn Stockbridge

Stockbridge, Massachusetts
3-star Hotel with prices starting at $268 (before taxes) - See All Prices
A Great Hotel for the Ultimate 3 Days in Berkshires
  • Great Value: the price is lower than average for weekend trip hotels.
  • Family-Friendly
  • Outdoor pool
  • Pets allowed
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We found The Red Lion Inn Stockbridge to be a great place to stay, and the price starts at $268. We loved that is has an outdoor pool, skiing, room service, a restaurant, and a fitness center, and it also has a terrific guest rating of 8.40 out of 10 from previous guests. It's located at 30 Main Street. You'll also find a bar, hiking, child care, laundry services, and golf which weekend travelers will love. And this comfortable hotel is just 17 miles from the center of town. The swimming pool is fantastic and lots of fun, too. It's a great value, too, because it's less than the average price for weekend trip hotels.

Weekend Trip Hotel Amenities
  • Outdoor pool
  • Skiing
  • Room service
  • Pets allowed
  • Hot tub
  • Bicycle rental
  • Family-Friendly
  • Golf
More Great Amenities
  • Restaurant
  • Fitness center
  • Bar/Lounge
  • Hiking
  • Babysitting / Child Care
  • Laundry service
  • Free parking
  • Family rooms
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Holiday Inn & Suites Pittsfield-Berkshires

Pittsfield, Massachusetts
3-star Hotel with prices starting at $146 (before taxes) - See All Prices
Perfect for 2 Days in Berkshires
  • Great Value: the price is lower than average for 3-star hotels.
  • Outdoor pool
  • Spa
  • Heated pool
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With terrific rooms from $146, Holiday Inn & Suites Pittsfield-Berkshires, at One West Street provides an outdoor pool, room service, a restaurant, parking, and mountain views. Its terrific guest rating is 7.70 out of 10 from previous guests staying here. Travelers will really like this relaxing hotel which also offers golf, city views, a hot tub, a spa and wellness center, and a spa. It's located just 5.4 miles from the city center, too. You'll love relaxing in the heated pool after a busy day exploring. It's a great value, as the price is less than the average for weekend trip hotels.

Weekend Trip Hotel Amenities
  • Outdoor pool
  • Room service
  • Parking
  • Hot tub
  • Spa
  • Indoor pool
  • Horse riding
  • Golf
  • Spa/Wellness
More Great Amenities
  • Restaurant
  • Fishing
  • Heated pool
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The White Hart Salisbury

Salisbury, Connecticut
Inn with prices starting at $320 (before taxes) - See All Prices
A Great Weekend Getaway Hotel
  • Great Value: the price is lower than average for 4-star hotels.
  • High Quality: guest ratings are higher than average.
  • Pool
  • Pets allowed
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The White Hart Salisbury has a great guest rating of 8.90 out of 10, and offers a pool, room service, a restaurant, a bar, and breakfast. The great rooms here start at $320 before taxes and depending on the season. It can be found at 15 Undermountain Road. Furthermore, it also offers a free breakfast, pet-friendly rooms, free parking, laundry facilities, and bicycle rental, which is nice for visitors. Just 38.3 miles from the city center, this terrific hotel is a terrific choice. We love the convenience of room service, and it's really nice here.

Weekend Trip Hotel Amenities
  • Pool
  • Room service
  • Breakfast included
  • Free breakfast
  • Pets allowed
  • Bicycle rental
  • Golf
More Great Amenities
  • Restaurant
  • Bar/Lounge
  • Free parking
  • Family rooms
  • Coffee shop
  • Refrigerator
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Apple Tree Inn Lenox

Lenox, Massachusetts
Inn with prices starting at $345 (before taxes) - See All Prices
A Terrific Hotel for a Long Weekend in Berkshires
  • Outdoor pool
  • Heated pool
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The great guest rating of Apple Tree Inn Lenox is 7.80 out of 10. This place has an outdoor pool, a restaurant, a bar, hiking, and mountain views. Prices for the terrific rooms are from $345, and it's located at 10 Richmond Mountain Road. We also love the golf, a free breakfast, free parking, family rooms, and a heated pool which are great for weekend visitors. And since it's just 12.7 miles from the center of the town, the location is great, too.

Weekend Trip Hotel Amenities
  • Outdoor pool
  • Free breakfast
  • Golf
More Great Amenities
  • Restaurant
  • Bar/Lounge
  • Hiking
  • Free parking
  • Family rooms
  • Heated pool
  • Tennis
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The Old Inn On The Green

New Marlborough, Massachusetts
Inn with prices starting at $329 (before taxes) - See All Prices
A Great Stay for a Weekend Escape
  • Great Value: the price is lower than average for 4-star hotels.
  • Outdoor pool
  • Pets allowed
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A cool place is The Old Inn On The Green because it has great rooms that start at $329. It has an outdoor pool, room service, a restaurant, a bar, and breakfast, it also earned a great guest rating of 8.60 out of 10 from people who have stayed here before. It's found at 134 Hartsville New Marlborough Road. Only 27 miles from the city center, weekend travelers will especially love hiking, a free breakfast, pet-friendly rooms, free parking, and air-conditioning at this fun hotel.

Weekend Trip Hotel Amenities
  • Outdoor pool
  • Room service
  • Breakfast included
  • Free breakfast
  • Pets allowed
  • Golf
More Great Amenities
  • Restaurant
  • Bar/Lounge
  • Hiking
  • Free parking
  • Coffee shop
View Prices and Reviews


The Barrington

Great Barrington, Massachusetts
Bed & Breakfast with prices starting at $363 (before taxes) - See All Prices
A Nice Option for a Weekend Retreat
  • High Quality: guest ratings are higher than average.
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The Barrington offers room service, a bar, mountain views, laundry services, and golf which we really like. The terrific rooms here start at $363 (before taxes). It's located at 281 Main St. And has earned a guest rating of 9.40/10. This comfortable hotel is also nice because it offers city views, free parking, laundry facilities, family rooms, and air-conditioning which travelers will enjoy. Also, it's just 23.6 miles from the city center.

Weekend Trip Hotel Amenities
  • Room service
  • Golf
  • Spa/Wellness
More Great Amenities
  • Bar/Lounge
  • Laundry service
  • Free parking
  • Family rooms
  • Refrigerator
View Prices and Reviews


Wainwright Inn

Great Barrington, Massachusetts
3-star Hotel with prices starting at $213 (before taxes) - See All Prices
Perfect Hotel for a 3-day trip in Berkshires
  • Great Value: the price is lower than average for 3-star hotels.
  • High Quality: guest ratings are higher than average.
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Located at 518 Main Street, Wainwright Inn has great rooms from $213 (before taxes). It offers skiing, hiking, rooms with kitchenettes, free parking, and kids meals. It has a terrific 9.40 rating out of 10 from previous guests who have stayed here. You'll also find family rooms, air-conditioning, a 24-hour desk, a microwave, and a refrigerator which visitors will love. And this relaxing hotel is just 24.1 miles from the center of town. We always love being able to prepare simple meals in a hotel room, and the kitchenette here was teriffic. It's a great value, as the price is less than the average for weekend trip hotels.

Weekend Trip Hotel Amenities
  • Skiing
  • Golf
  • Spa/Wellness
More Great Amenities
  • Hiking
  • Kitchenette
  • Free parking
  • Family rooms
  • Microwave
  • Refrigerator
View Prices and Reviews


The Cornell Inn

Lenox, Massachusetts
Bed & Breakfast with prices starting at $245 (before taxes) - See All Prices
A Great Stay for a Weekend Trip to Berkshires
  • Great Value: the price is lower than average for weekend trip hotels.
  • High Quality: guest ratings are higher than average.
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A great place to stay is The Cornell Inn which has nice rooms starting at $245. Offering a restaurant, a bar, breakfast, rooms with kitchens, and rooms with kitchenettes, it also has a great guest rating of 9.30 out of 10 from many previous guests. It's located at 203 Main St.. Weekend visitors will really like this terrific hotel which also offers golf, a free breakfast, free parking, horse riding, and bicycle rental. It's located just 11.1 miles from the city center, too. We found the price of this hotel to be a great value because the price is less than average for weekend trip hotels.

Weekend Trip Hotel Amenities
  • Breakfast included
  • Kitchen
  • Free breakfast
  • Horse riding
  • Bicycle rental
  • Golf
  • Spa/Wellness
More Great Amenities
  • Restaurant
  • Bar/Lounge
  • Kitchenette
  • Free parking
  • Family rooms
  • Coffee shop
  • Microwave
  • Refrigerator
  • Breakfast in the room
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Also, take a look at the Weekend Trip hotels in nearby destinations: Albany, Saratoga Springs, Manchester, Clifton Park, and Pittsfield.

For more terrific hotel ideas in Berkshires, make sure you also see Best Pet-Friendly Hotels in Berkshires, Best Hotels for First Time Visitors in Berkshires, Best Hotels for One Week in Berkshires, Best Hotels for One Night in Berkshires, Best Romantic Hotels for Couples in Berkshires, or Best Business Hotels in Berkshires.


How much do hotels for a weekend visit cost in Berkshires?

Berkshires Average Weekend Trip Hotel Price
$318

Travelers to Berkshires, Massachusetts will have a large number of terrific weekend trip accommodation options with a variety of great prices. The price of weekend trip hotels here can vary by amenities, dates, and the neighborhood. Based on thorough data from 23 weekend trip hotels, their average price is a very reasonable $318. If you're interested in more information about hotels here, see our guide to hotel prices in Berkshires.

The average prices of our suggested weekend trip hotels by star rating:

  • 5-star hotels: $1816
  • 4-star hotels: $336
  • 3-star hotels: $225


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