Pittsfield Vacation Rentals from $159: Search Short-Term Rentals

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

Berkshire Village Carriage House - Super Private!! : You might want to consider this vacation home rental near Pittsfield, which is located in the mountains and has a garden, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the books in this rental home to help you unwind.

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Vacation Rentals in Pittsfield

"Nicely decorated and clean. It had everything we needed, including kitchen supplies and detergent for the washer/dryer. Great rental for our family getaway."

Indoor pool, outdoor pool, pool umbrellas

"ease of use"

includes taxes & fees

$178 per night

Jul 28 - Jul 29

"Only stayed a night but kids liked the pool and it was close to the adventure park "

includes taxes & fees

$144 per night

Jul 29 - Jul 30

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"We loved our time, very cozy cabin"

"I really loved my stay at this beautiful property surrounded by nature and peacefulness in the Berkshire mountains. The owners were great too with communication and making things easy for check in and check out. Highly recommend this place!"

"Nice house with fenced yard. Nice and quiet. Inside of house was well maintained but, the outside area needs some repairing."

"Loved everything about the cabin. It looks a bit dated from outside but very modern and convenient inside. Everything important is there and working, no clutter, very clean. The lake is perfect!"

"Be aware they will not proactively provide you with a local host name or contact info. It was very difficult to get Vacasa support to help me get this info to resolve wifi issue - like hours long to get them to just give me the property managers info and even then, they wouldn't give it to me, just had them contact me. Otherwise, amazing pool and great location. Outdated indoors but clean to the extent that it could be. Utensils were dirty and tons of flies in the house upon arrival - like 50...

"Wonderful accommodation."

"lovely property."

"This house was the perfect get away house for out family! The place was clean and the kitchen well stocked! We had wonderful large family dinners and enjoyed heading into town for meals and fun too. We had the best hikes with are wonderful dog that we got to include, it was a very special week. Great location and the most peaceful and amazing views from the deck and the dock. Would stay here again for sure! Thank you for sharing your home."

"Pictures are accurate. Very clean. Bed was comfy."

includes taxes & fees

$259 per night

Aug 18 - Aug 19

"The house is on a very quiet and lovely setting. The “pond room” is the perfect place to enjoy the many species of birds (we saw/heard about 25 different species!) that visit the pond across the road. The house is lovely and cozy, stocked with everything we needed to eat, sleep and shower. You have to close the shower curtain completely, or the water will leak and cause it to “rain” in the dining room. That was the only setback. Overall, we had a wonderful time and would stay again."

"We made great meals and enjoyed them on the deck. Hiked Otis Forest (very buggy and sadly, many trees are blighted.) Fabulous hike at Greylock! House is a comfortable space."

"Very well thought out rental home. Everything you could possibly need for cooking and all thought out to reduce your time cleaning and more time on the river. No issues and we had a great time. Thanks again,"

includes taxes & fees

$539 per night

Jul 28 - Jul 29

"Thank you so much for sharing your Otis home with us. From the moment we walked through the door, we could feel the warmth and energy of great memories shared in this home. Growing up visiting Otis as a kid, it was incredibly special to celebrate my Grandmother's 85th birthday and send off my brother, who is starting his PhD program at Harvard University in Boston. My grandmother and the rest of our family will forever cherish this trip, full of laughter, swimming, and using our boat, which we...

"The cottage was perfect for us , walking distance to a small beach with kayaking available . Check in was super easy ! We enjoyed our stay !"

"Hot tub was dirty with a lot of debris. Bathtub and shower bases had mold on them and smelled moldy also. There were delays in being able to utilize the clubhouse (pools and gym) and the boats at the lake a 1/2 mile away. Other than that the rental was well appointed with everything and is situated in a gorgeous location with lots of cultural and outdoor activities nearby. Twin beds in 2 of the 4 rooms were massage/multi position types. Manager and owner nearby were responsive. ."

"Our group had a great time. The place is a bit dated but has room for plenty of people."

"Thoroughly enjoyed our stay. This is our 2nd year at Nana's Place & we plan to return next year. Beautiful view of the lake. Spacious home provides a wonderful gathering place for our daughters & their families who live in Albany & Ballston Lake. Chris is a great host and very responsive. Communications are excellent."

Other types of properties in Pittsfield you may be interested in

"I had a quiet stay & everything was clean and tidy. The only thing I didn’t like was that I had to park down the street at the bank. But besides that I was satisfied with my room. "

includes taxes & fees

$131 per night

Aug 25 - Aug 26

Fridge, microwave, stovetop, coffee/tea maker

"We arrived after dark on Tuesday and checked out Wednesday morning; so we didn't get to experience much. Compared to some we've seen the rooms are modern, enormous, and comfortable. Staffing is efficient (no overnight front desk; guests strip beds and put out trash when leaving). The full kitchen was impressive; but we didn't bring food, so had to look elsewhere for breakfast."

includes taxes & fees

$205 per night

Jul 29 - Jul 30

Desk, iron/ironing board, free WiFi, bed sheets

"We had a peaceful night's rest and felt secure. Our room was clean, beds comfy, and bathroom updated. The outside appearance and the room doors could use some help. "

includes taxes & fees

$79 per night

Jul 28 - Jul 29

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 $159 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?

Berkshire Village Carriage House - Super Private!!: You might want to consider this vacation home rental near Pittsfield, which is located in the mountains and has a garden, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the books in this rental home to help you unwind.

How many vacation rentals are there in Pittsfield?

With 37 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 Pittsfield State Forest and Housatonic River are a couple of great spots to enjoy the outdoors. Other places in town to visit include Colonial Theater 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.

Recent reviews of Pittsfield properties
Expedia verified reviews

5/5 Excellent

"A great college inn. Service, dining and location cannot be beat. "

A verified traveler stayed at The Williams Inn

Posted 1 day ago

5/5 Excellent

"We stayed at the Constance Inn on a hot Tuesday night after going to a concert at Tanglewood. The room had great air conditioning, which was the most important thing that night! Otherwise, the room was small but nicely decorated and clean, with a very comfortable bed. The TV was, of course, far too difficult to use, but that has been the case in the last three hotels we've stayed at. I guess we're old. The downstairs was charming and a relaxing place to sit and chat with our friends who were also staying there. The continental breakfast was delicious with bagels, muffins, fresh fruit, cereal, and even some gluten free options. The Inn was within easy walking distance of Lenox's great restaurants and town center, but NOT within walking distance of Tanglewood. That's okay as we would rather walk to the restaurants. Finally, we had selected the Inn for its relatively low price. It was not a luxury resort with a gourmet breakfast, but we were extremely satisfied and will be returning. "

A verified traveler stayed at The Lenox Collection

Posted 2 days ago

The Black Swan Lee - Lenox, Ascend Hotel Collection

5/5 Excellent

A Splendid Stay!

"My friend & I enjoyed two days here & loved the setting overlooking the lake where we were able to relax. We slept well because the inn is quiet & the beds are comfortable. The room was clean. The location is excellent for activities in Lenox. We enjoyed a delicious dinner of Indian food at the on site restaurant with a view of the lake. I’ll be back to stay here, for sure!"

A verified traveler stayed at The Black Swan Lee - Lenox, Ascend Hotel Collection

Posted 3 days ago

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

5/5 Excellent

Parking Could Be Better!!!

"I had a quiet stay & everything was clean and tidy. The only thing I didn’t like was that I had to park down the street at the bank. But besides that I was satisfied with my room. "

A verified traveler stayed at Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

Posted 4 days ago

Pittsfield Vacation Rental Travel Info

Number of vacation rentals	9
Popular accommodation	Pittsfield private vacation homes
Known landmarks	Bousquet Ski Area, Berkshire Museum and Colonial Theater
International airport	Albany, NY (ALB-Albany Intl.)

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Pittsfield Vacation Rentals

Check Pittsfield vacation rental availability

Vacation Rentals in Pittsfield

Chic Pittsfield Home With A View!

Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

Pristine Home In Becket Woods

Peace and quiet on the lake

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Tree-lined Home, Large Yard, Pool, & Dog-Friendly.

Serene Acreage - Pond - Hiking Trails Nearby

Private Estate, Heated YEARROUND Outdoor Pool

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Berkshire Village Carriage House - Super Private!!

Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort

Berkshires Cabin 2 Mi to Appalachian Trail!

Bear Creek Cabin

Private Island - Largest Fresh Water Reservoir in Mass....

Berkshire Lake access

Fox Hollow Luxury Ranch Laurel Lake

Beautiful Estate! Upon booking, a Reduced Rate applies for 8/25 - 8/30! Hurry!

3 Bedroom Lakefront Home with Hot Tub & Fireplace

Other types of properties in Pittsfield you may be interested in

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

Berkshire Mountain Lodge

FairBridge Inn Express

Frequently asked questions

Recent reviews of Pittsfield propertiesExpedia verified reviews

The Williams Inn

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Pittsfield Vacation Rental Travel Info

Recent reviews of Pittsfield properties
Expedia verified reviews