Pittsfield Vacation Rentals

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Our top choices for Pittsfield vacation rentals

$279 nightly
The price is $312
Jan 20 - Jan 21, 2026
Total with taxes and fees
3-bedroom house in beautiful Berkshires, close to amenities!

Vacation Home in Hancock

Hancock Village Inn Near Jiminy Peak
10.0 out of 10, Exceptional, (16)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
$971 nightly
The price is $1,050
Jan 6 - Jan 7, 2026
Total with taxes and fees
Hancock Village Inn Near Jiminy Peak
7.8 out of 10, Good, (6)
"Very clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
$442 nightly
The price is $494
Jan 3 - Jan 4, 2026
Total with taxes and fees
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
2.0 out of 10, (1)
"THIS. PLACE. IS. A. DUMP. Do NOT STAY HERE under any circumstances."
United States
Michael
$183 nightly
The price is $204
Dec 29 - Dec 30
Total with taxes and fees
Chic corporate apartment in wonderful Pittsfield with AC, WiFi
10.0 out of 10, Exceptional, (6)
"We loved this property. All the bells and whistles as far as amenities go for a Vrbo! Great location and place to unwind, unplug ,and reconnect!"
United States
scott B.
$330 nightly
The price is $372
Jan 5 - Jan 6, 2026
Total with taxes and fees
BLUSH: Boutique TINY home*private spa*walk to town
2.0 star property
10.0 out of 10, Exceptional, (3)
"By far one of my favorite rentals. Everything was perfect and the details were amazing. Not only do I highly recommend, I amSURE I will be returning soon. "
United States
Sue G.
$332 nightly
The price is $374
Jan 7 - Jan 8, 2026
Total with taxes and fees
Sugar Shack - 300 square feet of pure sweetness.
10.0 out of 10, Exceptional, (9)
"Huny House was the most artistically created space we stayed in on our entire trip! We were sooo impressed and appreciated the attention to detail!"
Canada
Patti S.
$366 nightly
The price is $413
Jan 13 - Jan 14, 2026
Total with taxes and fees
HunnyHAUS: Deluxe TINY*private spa*walk to town
3.0 star property
8.8 out of 10, Excellent, (2188)
"Awesome for ski"
United States
Lazar
$126 nightly
The price is $141
Jan 4 - Jan 5, 2026
Total with taxes and fees
Vacation Village in the Berkshires
10.0 out of 10, Exceptional, (3)
"Dillon was very helpful and detailed in his communication and the apartment was as advertised. We loved the small deck to enjoy our morning coffee. The kitchen setup was helpful as well."
United States
Matt E.
$229 nightly
The price is $244
Jan 3 - Jan 4, 2026
Total with taxes and fees
Berkshires Apartment at the Stephentown Hotel
10.0 out of 10, Exceptional, (1)
"The cabin was exactly what my daughter and I were looking for. Everything was clean, organized and family friendly. A bonus was the property connects to Bessie Woods and we were able to go for a hike on the trails without even having to leave the property. If you love quiet and the sounds of nature, this is the perfect place for you. We can’t wait to stay there again soon."
United States
Georgia M.
$165 nightly
The price is $183
Dec 29 - Dec 30
Total with taxes and fees
Taborton Harvest Timber Trails Unique cabin experience

Vacation Home in Great Barrington

Home in Great Barrington
9.8 out of 10, Exceptional, (26)
"Great stay in a cool, new space, totally walkable to Railroad St. I would definitely go back to GB and would try to stay here again. "
United States
Cameron M.
$224 nightly
The price is $250
Jan 26 - Jan 27, 2026
Total with taxes and fees
Home in Great Barrington
10.0 out of 10, Exceptional, (5)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
$335 nightly
The price is $374
Jan 4 - Jan 5, 2026
Total with taxes and fees
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
9.4 out of 10, Exceptional, (40)
"It’s a nice comfortable apartment with a good kitchen. We were traveling to see a concert and some art at Mass MOCA. Patrick is a friendly and welcoming host."
United States
Roy
$189 nightly
The price is $208
Jan 2 - Jan 3, 2026
Total with taxes and fees
Charming Apt in 18th c Berkshire Farmhouse
9.6 out of 10, Exceptional, (10)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
$351 nightly
The price is $392
Jan 4 - Jan 5, 2026
Total with taxes and fees
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
2.0 star property
9.6 out of 10, Exceptional, (13)
"Adams is a beautiful town and looks and feels like the appalachian trail! "
United States
judy r.
$219 nightly
The price is $245
Jan 2 - Jan 3, 2026
Total with taxes and fees
Penthouse Apartment on Park Street

Vacation Home in Florida

Florida Mountain Log Cabin
2.0 star property
10.0 out of 10, Exceptional, (4)
"Place was super clean. Beds were comfortable. Location was great."
United States
Tristan e.
$339 nightly
The price is $365
Jan 4 - Jan 5, 2026
Total with taxes and fees
Florida Mountain Log Cabin
10.0 out of 10, Exceptional, (2)
"Cozy home on the lake."
United States
Terry O.
$330 nightly
The price is $366
Jan 4 - Jan 5, 2026
Total with taxes and fees
Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace
10.0 out of 10, Exceptional, (1)
"Very nice house and the stay was unproblematic!"
United States
Noah K.
$378 nightly
The price is $422
Jan 3 - Jan 4, 2026
Total with taxes and fees
Riverbend Berkshire East Basecamp - 3 bedrooms available

Condo resort in Hancock

Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (987)
"nice and clean, good customer service, but the room is smell. "
United States
Huang
$212 nightly
The price is $237
Jan 5 - Jan 6, 2026
Total with taxes and fees
Jiminy Peak Mountain Resort
9.8 out of 10, Exceptional, (35)
"Great cottage - well appointed and very clean. No air conditioning so a bit warm when it’s hot out, but all in all a great stay"
United States
Lindsey E.
$420 nightly
The price is $469
Jan 5 - Jan 6, 2026
Total with taxes and fees
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
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

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 $141 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.

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?

Hancock Village Inn Near Jiminy Peak: Visitors give good reviews to this Pittsfield vacation home rental, which is located on a river and has a fireplace, a private yard, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a library and a hot tub. Our travelers also rate Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table as a favorite home for rent in Pittsfield.

How many vacation rentals are there in Pittsfield?

With 40 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.