Name: The Yankee, Trademark Collection by Wyndham
Rating: 9.2

Question 1

What is the best area to stay in Pittsfield?

Accepted Answer

The best area to stay in Pittsfield is the downtown district, particularly along North Street, for its central location and access to local attractions.

Downtown Pittsfield is the city's commercial and cultural heart, characterized by its historic architecture and a walkable layout. North Street is the main thoroughfare, featuring a variety of shops, restaurants, and entertainment venues. The Colonial Theatre and the Beacon Cinema are prominent landmarks in this area.

For couples looking for a convenient and engaging stay, downtown Pittsfield is an excellent choice. You'll find a selection of local eateries for dining out, and evening entertainment is easily accessible within walking distance. The proximity to cultural venues like the Berkshire Museum also provides options for daytime activities.

Travelers seeking a blend of convenience and access to the outdoors might consider accommodations closer to the city's eastern edge, near the entrance to the Pittsfield State Forest.

Question 2

What are the best hotels in Pittsfield that travelers recommend?

Accepted Answer

For highly recommended hotels in Pittsfield, consider the Hotel On North, Holiday Inn & Suites Pittsfield-Berkshires by IHG, Hilton Garden Inn Lenox Pittsfield, Best Western Plus Berkshire Hills Inn & Suites, and Berkshire Mountain Lodge.

The 3.5-star Hotel On North, with an outstanding 9.6 rating, offers comfortable and beautiful rooms with premium bedding, fireplaces, and the option of connecting rooms. Guests frequently praise its excellent restaurant, exceptional staff, and super convenient parking. It is also well-located near the Colonial Theater, Berkshire Museum, and Berkshire Athenaeum.

The 3-star Holiday Inn & Suites Pittsfield-Berkshires by IHG, rated 8.0, features beautiful and clean rooms, a fun pool, and helpful staff. Its fantastic location places it very close to the Colonial Theater, Berkshire Museum, and Berkshire Athenaeum.

The 3-star Hilton Garden Inn Lenox Pittsfield, with a strong 9.2 rating, provides comfortable and clean rooms, often including suites with deep soaking bathtubs and kitchens. The hotel boasts an indoor pool and is praised for its central location, nice staff, and great bar. It is conveniently located near Bousquet Ski Area and Guido's Marketplace.

The Best Western Plus Berkshire Hills Inn & Suites, rated 8.6, offers comfortable and clean rooms, some with fireplaces and suites. Guests enjoy the free buffet breakfast, excellent amenities, and friendly, helpful staff.

The 3-star Berkshire Mountain Lodge, with a 9.0 rating, features clean and spacious rooms, an excellent indoor pool, and a beautiful central location. Guests appreciate the nice service and great amenities. It is situated near Bousquet Ski Area and Guido's Marketplace.

Question 3

What are the best family hotels in Pittsfield?

Accepted Answer

For family accommodations in Pittsfield, consider the Holiday Inn & Suites Pittsfield-Berkshires by IHG, Holiday Inn Express & Suites Pittsfield - Berkshires by IHG, Best Western Plus Berkshire Hills Inn & Suites, Hilton Garden Inn Lenox Pittsfield, and Berkshire Mountain Lodge.

The 3-star Holiday Inn & Suites Pittsfield-Berkshires by IHG, with an 8.0 rating, offers family-friendly amenities such as free rollaway extra beds, sofa beds, connecting rooms, and free cribs. Guests often highlight the beautiful and clean rooms, fun pool, and amazing staff. Its fantastic location places it within 0.1 miles of the Colonial Theater and Berkshire Museum.

Another excellent option is the Holiday Inn Express & Suites Pittsfield - Berkshires by IHG, which has a 9.2 rating. This hotel provides free cribs, rollaway extra beds, connecting rooms, and a pool. Families will appreciate the complimentary breakfast and buffet breakfast. It is conveniently located 1.0 mile from Bousquet Ski Area.

The Best Western Plus Berkshire Hills Inn & Suites, rated 8.6, offers sofa beds, cribs, and complimentary breakfast, including a buffet. Guests consistently praise the friendly and helpful staff, comfortable and clean rooms, and excellent breakfast.

The 3-star Hilton Garden Inn Lenox Pittsfield, with a 9.2 rating, provides a pool, connecting rooms, sofa beds, and free cribs. Families can also benefit from free self-parking, free toiletries, and free wired internet in public areas. Reviewers frequently mention the comfortable and clean rooms, kind staff, and central location. It's located 1.0 mile from Bousquet Ski Area.

Finally, the 3-star Berkshire Mountain Lodge, with a 9.0 rating, is a great choice for families. It features sofa beds, free cribs, an indoor pool, and kitchens in the rooms. Free WiFi and free self-parking are also available. Guests often praise the clean and big rooms, central location, and excellent pool. It is just 0.8 miles from Bousquet Ski Area. Find more child-friendly accommodations in Pittsfield

Question 4

What hotels in Pittsfield offer free breakfast?

Accepted Answer

For hotels in Pittsfield that offer complimentary breakfast, consider the Best Western Plus Berkshire Hills Inn & Suites and the Holiday Inn Express & Suites Pittsfield - Berkshires by IHG.

The Best Western Plus Berkshire Hills Inn & Suites, with an 8.6 rating, is highly regarded for its excellent and fantastic breakfast offerings, which are always free. Guests also frequently compliment the friendly and helpful staff, as well as the comfortable and clean rooms. It also provides free WiFi and free parking.

Another excellent choice is the Holiday Inn Express & Suites Pittsfield - Berkshires by IHG, which has a strong 9.2 rating. This hotel also provides a free buffet breakfast daily. It is conveniently located near Herman Melville's Arrowhead, just 0.9 miles away, and Guido's Marketplace, only 0.1 miles away. Guests will also appreciate the free WiFi and free self-parking. Find more hotels with free breakfast in Pittsfield

Question 5

What are the top pet-friendly hotels in Pittsfield?

Accepted Answer

For top pet-friendly hotels in Pittsfield, consider the Hotel On North, the Hilton Garden Inn Lenox Pittsfield, or the Holiday Inn & Suites Pittsfield-Berkshires by IHG.

The 3.5-star Hotel On North, with an outstanding 9.6 rating, is highly recommended for travelers with pets, offering food and water bowls, free toiletries, free WiFi, and free self-parking. Guests consistently praise its comfortable and beautiful rooms, excellent restaurant, and exceptional staff. It is conveniently located near the Berkshire Athenaeum, the Berkshire Museum, and the Colonial Theater.

Another excellent option is the 3-star Hilton Garden Inn Lenox Pittsfield, rated 9.2, which welcomes both dogs and cats and offers suites for extended stays. Guests appreciate the comfortable and clean rooms, the kind staff, and the central location. It's also very close to Bousquet Ski Area and Guido's Marketplace.

The 3-star Holiday Inn & Suites Pittsfield-Berkshires by IHG, with an 8.0 rating, is another good choice that permits dogs. Guests frequently mention the beautiful and clean rooms, the fun and amazing pool, and the helpful staff. Its fantastic location places it within a short walk of the Colonial Theater, the Berkshire Museum, and the Berkshire Athenaeum.

Finally, the Best Western Plus Berkshire Hills Inn & Suites, rated 8.6, is also a great pet-friendly option, offering a dedicated dog exercise area and welcoming dogs. It provides a free buffet breakfast, and guests often compliment the friendly and helpful staff, comfortable rooms, and excellent breakfast. See more pet-friendly hotels in Pittsfield

Question 6

What are the best budget hotels in Pittsfield?

Accepted Answer

For budget-friendly accommodations in Pittsfield, consider the Hilton Garden Inn Lenox Pittsfield and the Holiday Inn Express & Suites Pittsfield - Berkshires by IHG.

The 3-star Hilton Garden Inn Lenox Pittsfield, with a 9.2 rating, offers free WiFi and complimentary self-parking. Guests frequently praise the comfortable and clean rooms, the nice and kind staff, and its central location. It is conveniently located just steps from Guido's Marketplace and less than a mile from Herman Melville's Arrowhead.

Another excellent choice is the Holiday Inn Express & Suites Pittsfield - Berkshires by IHG, which also boasts a 9.2 rating. This hotel provides free WiFi, complimentary buffet breakfast, and free self-parking. It is located very close to Guido's Marketplace and under a mile from Herman Melville's Arrowhead.

Other popular options include the Best Western Plus Berkshire Hills Inn & Suites, rated 8.6, which offers free WiFi, free buffet breakfast, and free parking, and the 3-star Holiday Inn & Suites Pittsfield-Berkshires by IHG, rated 8.0, which features free WiFi and is just 0.1 miles from the Berkshire Museum. View all budget hotels in Pittsfield

Question 7

What are the most romantic hotels in Pittsfield for couples?

Accepted Answer

For a romantic stay in Pittsfield, two highly-rated options for couples are the Berkshire Mountain Lodge and the Holiday Inn & Suites Pittsfield-Berkshires by IHG.

The 3-star Berkshire Mountain Lodge, with a 9.0 rating, offers spacious rooms with fully equipped kitchens, providing a comfortable and convenient experience. Guests often highlight the excellent indoor pool and the overall cleanliness and size of the rooms. The lodge is also conveniently located just 0.8 miles from Bousquet Ski Area.

Another excellent choice for couples is the 3-star Holiday Inn & Suites Pittsfield-Berkshires by IHG, rated 8.0. This hotel is praised for its beautiful, clean rooms and helpful staff. It is centrally located, just 0.1 miles from the Colonial Theater and 0.4 miles from the Barrington Stage Company, making it ideal for those looking to enjoy local entertainment. See all romantic hotels in Pittsfield

Question 8

What are the best hotels in Pittsfield near Pleasant Valley Wilderness Sanctuary?

Accepted Answer

For hotels in Pittsfield near Pleasant Valley Wilderness Sanctuary, consider the Hilton Garden Inn Lenox Pittsfield or the Holiday Inn Express & Suites Pittsfield - Berkshires by IHG.

The 3-star Hilton Garden Inn Lenox Pittsfield, with a 9.2 rating, is located just 2.0 miles from Pleasant Valley Wilderness Sanctuary. This hotel offers a pool, free WiFi, and complimentary self-parking. Guests frequently mention the comfortable and clean rooms, as well as the nice staff.

Another excellent option is the Holiday Inn Express & Suites Pittsfield - Berkshires by IHG, which also has a 9.2 rating and is 2.0 miles from Pleasant Valley Wilderness Sanctuary. This hotel provides a pool and offers free breakfast, including a buffet option, which is convenient for families.

Question 9

What hotels are near Pittsfield, MA (PSF-Pittsfield Municipal)?

Accepted Answer

For hotels near Pittsfield, MA (PSF-Pittsfield Municipal), consider the Best Western Plus Berkshire Hills Inn & Suites.

This hotel, rated 8.6, is conveniently located just 1.2 miles from Pittsfield, MA (PSF-Pittsfield Municipal). Guests consistently highlight the friendly and helpful staff, as well as the comfortable and clean rooms. The complimentary breakfast, featuring a buffet, is frequently described as excellent and fantastic, adding great value to your stay. The hotel also offers amenities such as sofa beds and cribs, making it a family-friendly option.

Question 10

When is the best time to go to Pittsfield?

Accepted Answer

The best time to go to Pittsfield is during the summer and early autumn months, from June to October, for pleasant weather and a full calendar of activities.

For those looking to enjoy outdoor activities and cultural events, July and August offer warm temperatures and peak season for attractions. You'll find many festivals, farmers' markets, and opportunities to explore the natural beauty of the Berkshires. This period is ideal for travelers who enjoy hiking, biking, and outdoor concerts.

Couples often find September and October particularly appealing. The weather is cooler and comfortable, superb for scenic drives to view the fall foliage. Local orchards are open for apple picking, and many cultural institutions in the area host special autumn programs.

Question 11

Can I cancel my hotel reservation on Expedia?

Accepted Answer

You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Pittsfield.

Question 12

How can I save on a Pittsfield hotel booking with Expedia?

Accepted Answer

With Expedia, you earn OneKeyCash™* on eligible Pittsfield hotel bookings for every dollar you spend – just join our One Key™ travel rewards program to get started. It’s free to join, and you’ll unlock our lowest Member Prices as soon as you’re signed in. On top of this, you could also save significantly by bundling your hotel and flights together on Expedia.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.

Question 13

How much is the nightly rate at a Pittsfield hotel?

Accepted Answer

Prices for hotels in Pittsfield often vary, but you can find a great deal from $75 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	22.6°F (-5.2°C)	Light Rain	Mostly Cloudy	Average	Average
February	24.6°F (-4.1°C)	Light Rain	Mostly Cloudy	Average	Average
March	32.4°F (0.2°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
April	44.2°F (6.8°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
May	56.3°F (13.5°C)	Light Rain	Mostly Sunny	Average	Average
June	64.0°F (17.8°C)	Light Rain	Mostly Sunny	Slightly High	Average
July	70.3°F (21.3°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
August	68.4°F (20.2°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
September	61.3°F (16.3°C)	Light Rain	Mostly Sunny	Average	Average
October	50.0°F (10.0°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly High
November	37.6°F (3.1°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
December	29.3°F (-1.5°C)	Light Rain	Mostly Cloudy	Slightly Low	Average

Find hotels in Pittsfield, MA from $75

Upfront pricing

Treat yourself

Be picky

Go beyond your typical stay in Pittsfield

Check prices for these dates

Filter by

Our top choices for Pittsfield hotels

Berkshire Mountain Lodge

Berkshires Untold

Holiday Inn & Suites Pittsfield-Berkshires by IHG

The Yankee Inn

Hotel On North

Best Western Plus Berkshire Hills Inn & Suites

The Black Swan Lee - Lenox, an Ascend Collection Hotel

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

Element Lenox Berkshires

The Cornell Inn, Lenox & The Berkshires

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Hampton Inn & Suites Berkshires-Lenox

Berkshire Inn

Courtyard by Marriott Lenox Berkshires

Hilton Garden Inn Lenox Pittsfield

Howard Johnson by Wyndham Lenox

The Ponds at Foxhollow

Brook Farm Inn

Club Wyndham Bentley Brook

The Red Lion Inn

Where to stay in and around Pittsfield

Lenox

Hancock

Stockbridge

Lee

Lanesborough

Stay near popular attractions in and around Pittsfield

The Mount

Hancock Shaker Village

Learn more about Pittsfield

Top Pittsfield Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

More cheap stays in Pittsfield

Quality Inn Great Barrington

Hotels in Pittsfield with star-rating

Find out more about Pittsfield

Top reasons to visit Pittsfield

Find great hotels in and around Pittsfield

Where to stay near Pittsfield

Things to do in Pittsfield

Booking tips and Expedia advantages for Pittsfield

Find the best attractions in and around Pittsfield

Best time to go to Pittsfield

The nearest major airports for your trip to Pittsfield

Frequently asked questions

Explore a world of travel with Expedia

Go further with the Expedia app