Pittsfield Vacation Rentals

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Vacation Rentals in Pittsfield

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (609)
"Very clean place for a very good price "
The price is CA $105
CA $149 total
includes taxes & fees
Sep 7 - Sep 8
Berkshire Mountain Lodge

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very good, (868)
"Consistently a clean room with welcoming staff."
The price is CA $150
CA $167 total
includes taxes & fees
Sep 4 - Sep 5
Holiday Inn & Suites Pittsfield-Berkshires by IHG

FairBridge Inn Express

2.5 star property
5.4 out of 10, (775)
"Close to our target event a plus"
The price is CA $98
CA $109 total
includes taxes & fees
Sep 2 - Sep 3
FairBridge Inn Express

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.6 out of 10, Exceptional, (29)
"Do hotel, very clean we had a great day"
The price is CA $195
CA $217 total
includes taxes & fees
Sep 4 - Sep 5
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1005)
"Very clean rooms and excellent staff."
The price is CA $146
CA $163 total
includes taxes & fees
Sep 4 - Sep 5
Best Western Plus Berkshire Hills Inn & Suites

Berkshire Inn

2.0 star property
7.8 out of 10, Good, (810)
"good location....easy access to highlight destinations and downtown"
The price is CA $116
CA $130 total
includes taxes & fees
Sep 2 - Sep 3
Berkshire Inn

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (641)
"It’s a three star hotel charging 5 star prices. They should include free breakfast."
The price is CA $218
CA $244 total
includes taxes & fees
Sep 7 - Sep 8
Hilton Garden Inn Lenox Pittsfield

The Central Downtown Inn & Suites

4.0 star property
8.8 out of 10, Excellent, (312)
"Friendly staff, clean and perfect for a trip with the pups! "
The price is CA $137
CA $153 total
includes taxes & fees
Oct 1 - Oct 2
The Central Downtown Inn & Suites

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (765)
"Quite and good location to around towns"
The price is CA $218
CA $244 total
includes taxes & fees
Sep 28 - Sep 29
Hotel On North

Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more!

10.0 out of 10, Exceptional, (1)
"We loved everything about this place! It was quiet, centrally located, and everyone was friendly and helpful. We will stay here again for sure!"
Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more!

Berkshire Mountain Lodge

Berkshire Mountain Lodge

Mountain Lodge Apt!

Mountain Lodge Apt!

Heart of the Berkshires

7.2 out of 10, Good, (9)
"Was great comfy quiet "
Heart of the Berkshires
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.
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Top Pittsfield Hotel Reviews

Find out more about Pittsfield

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, cottages, cabins, villas... 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pittsfield vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pittsfield vacation rentals we have selected for you start as low as CA $135 per night. Entering your travel dates in the search wizard 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. 

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?

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table: Visitors give good reviews to this Pittsfield vacation home rental, which is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 8 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation. Our travelers also rate Hancock Village Inn at Jiminy Peak as a favorite home for rent in Pittsfield.

How many vacation rentals are there in Pittsfield?

With 38 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 Colonial Theater and Barrington Stage Company.

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.