Pittsfield Vacation Rentals from $121: Search Short-Term Rentals

Q: What's the top vacation rental that Pittsfield has to offer?

Peace and quiet on the lake : Visitors like this Pittsfield vacation home rental. It is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection of games in this rental home to help you unwind.

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In two weeks

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In four months

Our top choices for Pittsfield vacation rentals

Cozy cottage in the Berkshires

PITTSFIELD

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Pittsfield

Liz V.

$442 nightly

Jun 7 - Jun 8

Total with taxes and fees

Hancock Village Inn Near Jiminy Peak

Hancock

Stephanie B.

$1,060 nightly

Jun 2 - Jun 3

Total with taxes and fees

Huttopia Berkshires

Williamstown

GEORGINA

$108 nightly

Jun 1 - Jun 2

Total with taxes and fees

Sugar Shack - 300 square feet of pure sweetness.

Chatham

Sue G.

$296 nightly

Jun 1 - Jun 2

Total with taxes and fees

BLUSH: Boutique TINY homeprivate spawalk to town

Chatham

jack h.

$268 nightly

Jun 8 - Jun 9

Total with taxes and fees

Vacation Village in the Berkshires

Williamstown

Celina

$128 nightly

May 31 - Jun 1

Total with taxes and fees

Taborton Harvest Boulder Pines Cabin in the woods

Sand Lake

Lea

$165 nightly

May 31 - Jun 1

Total with taxes and fees

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Top Pittsfield Hotel Reviews

The Red Lion Inn

10/10 Excellent

"We love the laid back shabby chic comfort of the Inn. It is our third visit in 2 years and a delightful getaway. The food is excellent. Breakfast has a good choice of menu options . We also love the pool"

Vacation Village in the Berkshires

4/10 Poor

"So after answering all questions that could only lead to a “decent” review here’s what happened. Check in was fine, it was a check in; friendly and we checked in. We get to the room and I leave to grab food for our dinner, my wife calls front desk because of awful noises upstairs, people stomping around like they’re getting paid to. I get back and she’s still on the phone after desk telling her everything is fixed… okayyy but we still hear incredible stomping. Lady insisted everything is fixed it must be a kid…..right but our room sounds like an industrial zone. Do we have to beg to be moved to a new room when this place is mostly vacant? Our food is cold and we’re on the phone again noise won’t stop even though I’m listening on ALL FLOORS for the source of noise, finally agrees to move us to a top floor in a new building. We haul our stuff over, keycards maintenance brought us don’t work. He says he’ll get new ones (very nice guy btw). ONE of the two new cards works after he comes back and he tries for a few minutes to get it to slide in at the perfect angle and velocity. Finally we get to settle into our new room for the last few hours we would be awake. Thanks for a wonderful finale to our one anniversary night away from kiddos. At least there was a tub to relax in this room. This place would have been fine if it weren’t for the horrible sound enhancing construction and front desk person who tried their best not to solve an easy problem."

Berkshires Untold

6/10 Okay

"The converted motel has several appealing features — it was clean, the Le Labo products smelled wonderful, and the lobby bar is beautifully designed. Unfortunately, the level of service fell well below expectations. Two days before our arrival, I received a survey asking whether we’d like any additional amenities, which initially gave me a very positive impression of the hotel’s attention to detail. However, upon check-in, not only was the requested amenity missing, but the room was also inadequately stocked: there was only one roll of toilet paper, a nearly empty tissue box with just three tissues remaining, and only two towels for three guests. I requested additional towels, but they were never delivered. The following morning, I asked again and was met with a dismissive, somewhat snarky response that they would arrive later. By 4 p.m., we still had not received them, and when I followed up, I was told my name was “on a list,” though no one could say when the towels would actually be available. Throughout the stay, the staff came across as indifferent rather than genuinely helpful, and service was often delivered with attitude rather than hospitality. While the hotel’s location is excellent and the property itself has charm, I left feeling unconvinced that the hotel currently has the staffing or linens needed to provide a truly top-tier guest experience."

Find out more about Pittsfield

Everything you need to know about Pittsfield vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Pittsfield vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pittsfield vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Pittsfield vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pittsfield. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Pittsfield in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $121 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Pittsfield rentals

At Expedia, we put the best Pittsfield vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Pittsfield rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pittsfield vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pittsfield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Frequently asked questions

Can I find vacation rentals in Pittsfield?

Yes, we give you a choice of vacation rentals in Pittsfield near Berkshire Museum, or you can choose a more secluded option if you want a relaxing stay. Travelers who like culture and the arts say Pittsfield is known for its entertainment venues. Make sure you have time to check out the baseball games and museums during your trip.

What's the top vacation rental that Pittsfield has to offer?

Peace and quiet on the lake: Visitors like this Pittsfield vacation home rental. It is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals are there in Pittsfield?

With 39 Expedia vacation rentals, you're sure to find just the right place for your Pittsfield stay.

What can I see and do in Pittsfield?

Family-friendly attractions include Berkshire Museum and Bousquet Ski Area, whereas Housatonic River and Canoe Meadows Wildlife Sanctuary are a couple of great spots to enjoy the outdoors. Other places in town to visit include Barrington Stage Company and Hancock Shaker Village.

What are vacation rentals like in Pittsfield?

Vacation rentals are privately owned properties you can reserve for several days or more in Pittsfield. Vacation rentals feature amenities such as patios, hot tubs, and fire pits to help you enjoy your stay. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from public hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great option for a family trip or a small group gathering.

Pittsfield Vacation Rentals

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Check prices for these dates

Our top choices for Pittsfield vacation rentals

Cozy cottage in the Berkshires

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Hancock Village Inn Near Jiminy Peak

Huttopia Berkshires

Sugar Shack - 300 square feet of pure sweetness.

BLUSH: Boutique TINY home*private spa*walk to town

Vacation Village in the Berkshires

Taborton Harvest Boulder Pines Cabin in the woods

Getaway Near Mass MoCA, Great Hiking, Scenic Views

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

The Brooks Motel: Exceptional Suite

2-Bdr Apt In Town, By the Water

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Home in Great Barrington

Cozy Riverside Berkshires Retreat

Find vacation rentals that suit your style

Top Pittsfield Hotel Reviews

The Red Lion Inn

Find out more about Pittsfield

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BLUSH: Boutique TINY homeprivate spawalk to town