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Top The Berkshires hotels

Hotel On North

Hotel On North

3.5 out of 5
297 North Street Pittsfield MA
Fully refundableReserve now, pay when you stay
$179 nightly
The price is $200 total per night from Jun 16 to Jun 17
$200 total
Jun 16 - Jun 17
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the business center. There's ...
"Aside from minor housekeeping issues like tissues and body wash ruining out, stay was great. Staff is very friendly and helpful. Hotel is well maintained and updated. Good central location in Pittsfield with lots of good restaurants and shops within walking distance."

Reviewed on Jun 15, 2026

Opens in a new windowHotel On North
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
$111 nightly
The price is $124 total per night from Jun 16 to Jun 17
$124 total
Jun 16 - Jun 17
Total with taxes and fees
This hotel features an outdoor pool and an indoor pool. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. ...
"Yes, to all"

Reviewed on Jun 13, 2026

Opens in a new windowThe Yankee Inn
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 out of 5
190 Meadow Street South Lee MA
Fully refundable
$152 nightly
The price is $169 total per night from Jun 17 to Jun 18
$169 total
Jun 17 - Jun 18
Total with taxes and fees
This hotel features 2 outdoor pools, 2 indoor pools, and a poolside bar. There's fun for all ages with mini golf and a playground, and families will appreciate ...
"Rooms are large, beds are comfortable, everything clean. Plenty to do on the property and beautiful nearby towns to visit. Style and amenities are a bit dated, but that hardly matters,considering the value. Ideal for families."

Reviewed on Jun 14, 2026

Opens in a new windowHoliday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$155 nightly
The price is $173 total per night from Jun 16 to Jun 17
$173 total
Jun 16 - Jun 17
Total with taxes and fees
This lodge features an indoor pool and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, ...
"The staff was very helpful. It was very clean and the bed was comfortable. We would stay there again."

Reviewed on Jun 15, 2026

Opens in a new windowBerkshire Mountain Lodge
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $151 total per night from Jun 16 to Jun 17
$151 total
Jun 16 - Jun 17
Total with taxes and fees
A restaurant and a bar/lounge are featured at this lodge. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a lobby ...
"I stayed for a short time, this had everything I needed and was reasonably priced. Room was a clean, had a comfy bed, was quiet, and very friendly staff to greet me both when I checked in and out… with yummy coffee in the morning. It’s a basic stay, but everything you need. Would definitely ..."

Reviewed on Jun 15, 2026

Opens in a new windowBerkshires Untold
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
Fully refundable
$170 nightly
The price is $190 total per night from Jun 30 to Jul 1
$190 total
Jun 30 - Jul 1
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 2 conference rooms, free WiFi in public areas, and express ...
"This is a wonderful modern hotel in a very center of North Adams. A view from 7th floor is picturesque. It is very clean. The room is spacious; the beds are comfortable. The pool looks good, although we didn't try that. There are a coupe of nice art exhibitions on the first floor. The coffee is good, ..."

Reviewed on Jun 15, 2026

Opens in a new windowHotel Downstreet, an Ascend Collection Hotel
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
$136 nightly
The price is $152 total per night from Jun 16 to Jun 17
$152 total
Jun 16 - Jun 17
Total with taxes and fees
This condo features an outdoor pool and an indoor pool. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks ...
"I enjoy staying here . The front desk staff was very friendly . I like the hours of outdoor and indoor pool . My only complaints is the rooms are very very outdated and had to go to front desk every day because keys didnt work ."

Reviewed on Jun 15, 2026

Opens in a new windowVacation Village in the Berkshires
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
$192 nightly
The price is $214 total per night from Jul 7 to Jul 8
$214 total
Jul 7 - Jul 8
Total with taxes and fees
This historic hotel includes 3 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in ...
"The Red Lion Inn has so much history and character, it was a wonderful Experience to say the least. With modern amenities, it still Managed to keep its old world charm Food at the Wolf Den Tavern offered some of the best clam chowder I have ever had Enjoyed the hot tub but both hot tub and pool were ..."

Reviewed on Jun 15, 2026

Opens in a new windowThe Red Lion Inn
Quality Inn Great Barrington

Quality Inn Great Barrington

2.5 out of 5
372 Main Street Great Barrington MA
Fully refundable
$94 nightly
The price is $105 total per night from Jun 17 to Jun 18
$105 total
Jun 17 - Jun 18
Total with taxes and fees
A gym, free self parking, and free newspapers are featured at this hotel. Guests will appreciate free perks like on-the-go breakfast and WiFi in public areas. ...
"Staff was courteous and professional. The room was clean and comfortable. Parking was ample and close to our room."

Reviewed on Jun 14, 2026

Opens in a new windowQuality Inn Great Barrington
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Cheap The Berkshires hotels

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top reasons for your vacation to The Berkshires

  • Breathtaking Scenery: The Berkshires offers stunning mountain views and picturesque landscapes, providing the perfect backdrop for outdoor activities and leisurely walks.
  • Cultural Delights: Immerse yourself in the region's rich cultural heritage by visiting museums, theaters, and art galleries that showcase a diverse range of artistic expressions.
  • Outdoor Adventures: From hiking trails to skiing slopes, The Berkshires caters to outdoor enthusiasts of all ages, offering endless opportunities for adventure and exploration.
  • Family-Friendly Fun: With its wide range of family-friendly activities and attractions, The Berkshires is an ideal vacation spot for families looking to bond and create lasting memories.
  • Convenient Location: Located near New York, The Berkshires provides easy access to both city life and the tranquility of nature, making it a versatile and convenient destination.

Find your favorite hotels in The Berkshires

If you're planning a vacation in the Berkshires, you'll find a range of hotel accommodations to suit your needs. From luxury hotels with upscale amenities and stunning views to boutique retreats with unique charm, there are options for every traveler. Whether you're looking for a top-rated hotel with impeccable service or a cozy inn nestled in the heart of nature, the Berkshires has something for everyone. These accommodations provide the perfect base for exploring the area's natural beauty and cultural attractions.

Hotel nameTypeStarsDescription
Life House BerkshiresLodge3.5This 3.5-star Lodge is located 16.4 miles away from The Berkshires. It offers a comfortable stay with its distinctive affinities and accessible facilities.
The Black Swan Lee - Lenox, Ascend Hotel CollectionHotel3.0This 3.0-star Hotel is conveniently located close to the lake, offering beautiful views. It is also near snowmobile riding, snowboarding, cross-country skiing, kayaking, and other outdoor activities. With its friendly staff and various amenities, it's a great option for your outdoor vacation. It is 12.1 miles away from The Berkshires.
The Yankee, Trademark Collection by WyndhamHotel2.5As a 2.5-star Hotel, The Yankee is situated in close proximity to friendly people, indoor and outdoor pools, nature, skiing, hiking, and more. It offers connecting rooms, a hot tub, and concierge services. With a distance of 17.4 miles from The Berkshires, it provides a convenient base for your outdoor adventures.

Explore the best activities and sights in The Berkshires

The Berkshires in Massachusetts is the perfect destination for an outdoor vacation with your family. With its close proximity to baseball, hiking, skiing, and other outdoor activities, there's something for everyone to enjoy. You can also explore the local entertainment scene, visit museums, and take in the stunning scenery. For a unique experience, check out the opera and theater performances or visit the nearby university. Don't miss out on the blue vistas, golf clubs, colonial landmarks, and curated experiences that The Berkshires has to offer. And for some extra magic, you might even find a touch of Disney here.

  1. Times Square: Times Square is a modern square point of interest featured with theaters, urban skyscrapers, entertainment, art, scenery, museums, architecture, natural parks, and friendly people. It offers a vibrant and energetic city experience with its dazzling lights, bustling crowds, and iconic billboards. Immerse yourself in the lively atmosphere as you explore the various theaters and art galleries. Admire the stunning architecture of the surrounding skyscrapers and enjoy the picturesque scenery of the area. Times Square is a must-visit destination for anyone seeking a taste of the vibrant city life.
  2. Central Park: Central Park is an urban park point of interest featured with museums, urban entertainment, art, shopping, scenery, theaters, dining, monuments, and skyscrapers. It offers a unique blend of nature and city experience. Wander through the lush greenery and take in the serene beauty of the park. Visit the various museums and art installations scattered throughout the park for a cultural experience. Enjoy a leisurely stroll or bike ride along the park's pathways, or have a picnic in one of the designated areas. Central Park is the perfect place to unwind and escape the hustle and bustle of the city while still being in the heart of it all.
  3. Statue of Liberty: The Statue of Liberty is a statue point of interest featured with urban skyscrapers, scenery, entertainment, theater, art, museums, friendly people, monuments, and natural parks. It offers a unique cultural experience. Marvel at the grandeur of this iconic symbol of freedom and democracy. Take a ferry ride to Liberty Island and explore the museum to learn about the statue's rich history. Enjoy panoramic views of the city skyline from the observation deck, and appreciate the picturesque scenery surrounding the statue. The Statue of Liberty is a must-visit attraction for its historical significance and breathtaking views.

Where to stay in The Berkshires

Welcome to the beautiful Berkshires in western Massachusetts, a perfect destination for your outdoor vacation! Immerse yourself in the stunning Berkshire Mountains, where you can enjoy hiking trails with breathtaking scenery. Explore the charming countryside escape and indulge in outdoor activities such as skiing and baseball. Don't miss the opportunity to visit the numerous museums and theaters for a cultural experience. The Berkshires are conveniently located near New York, making it an ideal getaway for families seeking adventure and relaxation. Get ready to create unforgettable memories in this idyllic destination!

  1. Lenox: Lenox is a popular city located 14.8 miles away from The Berkshires. It is known for its beautiful gardens, museums, yoga studios, live music venues, and entertainment options. Families can enjoy exploring the local art and architecture scene, as well as hiking in the scenic surroundings. The city also offers a well-stocked library for book lovers. Lenox is a great choice for outdoor enthusiasts and families looking for a mix of cultural and natural experiences.
  2. Pittsfield: Located 20.2 miles away from The Berkshires, Pittsfield is a vibrant city with a strong sports culture. Families can enjoy watching baseball games, as well as exploring the city's entertainment options, theaters, and opera houses. Museums offer educational experiences for all ages, and biking enthusiasts will find great trails to explore. Pittsfield's historical sites and proximity to lakes and ski resorts make it an ideal destination for families seeking both adventure and cultural experiences.
  3. Great Barrington: Great Barrington, only 11.1 miles away from The Berkshires, is a popular city known for its rock climbing opportunities and scenic hiking trails. Families can enjoy live music performances, cafes, and dining options in the city. The area is also home to ski resorts and beautiful flower gardens. With its entertainment options and theaters, Great Barrington offers a unique experience for families looking for a mix of outdoor adventure and cultural activities.

Best times to go to The Berkshires

The travel seasons of The Berkshires

Trips to The Berkshires show no change in popularity throughout the year. The peak season to visit is from June to August, with July being the highest month. Off-peak season starts from November to January, and November sees the least travelers.

The Berkshires has something in store for you whenever you visit. January is the coldest month of the year, while July is hottest, with average temperatures up to 70.3 degrees Fahrenheit. The wettest month in The Berkshires is October, so pack accordingly.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationcloud iconCloudiness
January22.8°F (-5.1°C)Light RainMostly Cloudy
February24.6°F (-4.1°C)Light RainMostly Cloudy
March32.5°F (0.3°C)Light RainMostly Cloudy
April44.2°F (6.8°C)Light RainMostly Cloudy
May56.3°F (13.5°C)Light RainMostly Sunny
June64.0°F (17.8°C)Light RainMostly Sunny
July70.3°F (21.3°C)Light RainMostly Sunny
August68.4°F (20.2°C)Light RainMostly Sunny
September61.3°F (16.3°C)Light RainMostly Sunny
October50.0°F (10.0°C)Light RainMostly Sunny
November37.8°F (3.2°C)Light RainMostly Sunny
December29.5°F (-1.4°C)Light RainMostly Cloudy

Food and dining in The Berkshires

When visiting The Berkshires, you'll be delighted by the local culinary scene. One must-visit restaurant is Ozzie's Steak & Eggs, known for its highly rated northAmerican cuisine. Another popular spot is Friendly's, a moderately rated restaurant that specializes in northAmerican dishes. If you're looking for a taste of Berkshire style, head to Applebee's, which offers a variety of moderately rated northAmerican dishes. Don't miss the charming towns in the area, where you can find restaurants with tasting rooms and cocktail bars, offering a truly unique dining experience.

How do I find a great hotel with Travelocity?

Give your entire crew a vacation they'll never forget. When searching for the ideal accommodations, utilize our family-friendly badge to find hotels that offer additional amenities for children. Moreover, our personalized filters assist you in narrowing down hotels that are in close proximity to popular attractions, provide enhanced cleaning services, and fit within your budget.

Why should I book with Travelocity?

Conference calls, to-do lists, and, of course, football practice. Busy lives and packed schedules require trips that are hassle-free. Our aim is to provide stress-free travel every time you and your family make a booking with us. We want to minimize your worries, allowing you to create lasting memories. We will assist you in finding and planning your ideal trip, offering transparent pricing, reliable reviews, and 24/7 customer support before, during, and after your vacation.

How can I save money on my trip to The Berkshires?

If you're looking to save money on your trip to The Berkshires, consider visiting during the less popular season from November to January. You can also save by bundling your flights, hotel, and car bookings together for a discounted price. As for inexpensive local activities, you can enjoy hiking in the beautiful scenic areas, explore the various museums in the region, and catch a baseball game for some affordable family entertainment.

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