Pittsfield Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Tonight
Jan 12 - Jan 13
Tomorrow
Jan 13 - Jan 14
This weekend
Jan 16 - Jan 18
Next weekend
Jan 23 - Jan 25

Our top choices for Pittsfield vacation rentals

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

Vacation Home in Pittsfield

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
2.0 star property
7.8 out of 10, Good, (7 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
United States
Liz V.
$441 nightly
The price is $493
Jan 14 - Jan 15
Total with taxes and fees
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Outdoor dining
Hancock Village Inn Near Jiminy Peak

Vacation Home in Hancock

Hancock Village Inn Near Jiminy Peak
10.0 out of 10, Exceptional, (16 reviews)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
$969 nightly
The price is $1,048
Jan 13 - Jan 14
Total with taxes and fees
Hancock Village Inn Near Jiminy Peak
Smart TV
Chic corporate apartment in wonderful Pittsfield with AC, WiFi

Apartment in Pittsfield

Chic corporate apartment in wonderful Pittsfield with AC, WiFi
2.0 star property
2.0 out of 10, (1 review)
"THIS. PLACE. IS. A. DUMP. Do NOT STAY HERE under any circumstances."
United States
Michael
$183 nightly
The price is $204
Jan 13 - Jan 14
Total with taxes and fees
Chic corporate apartment in wonderful Pittsfield with AC, WiFi
Dining
Sugar Shack - 300 square feet of pure sweetness.

Mobile Home in Chatham

Sugar Shack - 300 square feet of pure sweetness.
2.0 star property
10.0 out of 10, Exceptional, (3 reviews)
"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.
$303 nightly
The price is $342
Jan 13 - Jan 14
Total with taxes and fees
Sugar Shack - 300 square feet of pure sweetness.
Exterior
Huttopia Berkshires

Camping in Williamstown

Huttopia Berkshires
1.0 star property
10.0 out of 10, Exceptional, (7 reviews)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
$166 nightly
The price is $186
Jan 25 - Jan 26
Total with taxes and fees
Huttopia Berkshires
Fridge, microwave, oven, stovetop
HunnyHAUS: Deluxe TINY*private spa*walk to town

Mobile Home in Chatham

HunnyHAUS: Deluxe TINY*private spa*walk to town
10.0 out of 10, Exceptional, (9 reviews)
"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
Total with taxes and fees
HunnyHAUS: Deluxe TINY*private spa*walk to town
Lobby
Vacation Village in the Berkshires

Condo in Williamstown

Vacation Village in the Berkshires
3.0 star property
8.8 out of 10, Excellent, (2,204 reviews)
"I great place to stay!!"
United Kingdom
Maricel
$126 nightly
The price is $141
Jan 13 - Jan 14
Total with taxes and fees
Vacation Village in the Berkshires
Exterior
Jiminy Peak Mountain Resort

Condo resort in Hancock

Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (989 reviews)
"nice and clean, good customer service, but the room is smell. "
United States
Huang
$219 nightly
The price is $245
Jan 13 - Jan 14
Total with taxes and fees
Jiminy Peak Mountain Resort
Outdoor dining
Little Longbow Lakefront Chalet

Chalet in Becket

Little Longbow Lakefront Chalet
9.8 out of 10, Exceptional, (21 reviews)
"Absolutely perfect quiet get away to relax and recharge will be back! "
United States
Dana V.
$457 nightly
The price is $510
Jan 16 - Jan 17
Total with taxes and fees
Little Longbow Lakefront Chalet
TV
Florida Mountain Log Cabin

Vacation Home in Florida

Florida Mountain Log Cabin
2.0 star property
10.0 out of 10, Exceptional, (4 reviews)
"Place was super clean. Beds were comfortable. Location was great."
United States
Tristan e.
$316 nightly
The price is $339
Jan 14 - Jan 15
Total with taxes and fees
Florida Mountain Log Cabin
Pool
Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor

Apartment in Hancock

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"The host communicated everything and ensured we had all the necessary information for our arrival. The room was super clean and everything was new. Really enjoyed our stay and had plenty of room and closets for storage. Would definitely stay again and truly a premiere host!! Angelica "
United States
Jeffrey R.
$247 nightly
The price is $276
Jan 13 - Jan 14
Total with taxes and fees
Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
Exterior
The Allen House historic North Adams Home in the Berkshire Mountains

Apartment in North Adams

The Allen House historic North Adams Home in the Berkshire Mountains
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"The Allen House was a wonderful stay for my family and we cannot wait to go back! The view was incredible; the host was very approachable for questions; and there were lots of nice touches like ample dishes and silverware.Very spacious, clean and cared for location. "
United States
Annemarie M.
$283 nightly
The price is $316
Jan 20 - Jan 21
Total with taxes and fees
The Allen House historic North Adams Home in the Berkshire Mountains
Exterior
Bear Creek Cabin

Cabin in Charlemont

Bear Creek Cabin
10.0 out of 10, Exceptional, (43 reviews)
"We enjoyed our stay!!"
United States
Hillary S.
$536 nightly
The price is $599
Jan 13 - Jan 14
Total with taxes and fees
Bear Creek Cabin
TV, fireplace, DVD player, books
Berkshires farm, 30+ guests, 50 acres

Cottage in New Lebanon

Berkshires farm, 30+ guests, 50 acres
2.0 star property
10.0 out of 10, Exceptional, (1 review)
$1,812 nightly
The price is $1,837
Feb 4 - Feb 5
Total with taxes and fees
Berkshires farm, 30+ guests, 50 acres
Exterior
Getaway Near Mass MoCA, Great Hiking, Scenic Views

Apartment in Stamford

Getaway Near Mass MoCA, Great Hiking, Scenic Views
10.0 out of 10, Exceptional, (28 reviews)
"Nice property for a quick and simple check-in. Near MassMOCA, the Clark Art Institute and much more."
United States
Mario R.
Getaway Near Mass MoCA, Great Hiking, Scenic Views
House (3 Bedrooms) | Interior
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

Cottage in Stephentown

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
$499 nightly
The price is $554
Jan 13 - Jan 14
Total with taxes and fees
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
TV, fireplace
A stunning, modern Lodge with rustic charm at June Farms!

Cabin in West Sand Lake

A stunning, modern Lodge with rustic charm at June Farms!
10.0 out of 10, Exceptional, (4 reviews)
"2nd time staying at The Lodge , had a wonderful relaxing few days ! Enjoyed long walks , and the animals . The weather was perfect , couldn't have asked for anything more! Thank you !"
United States
LisaL
$633 nightly
The price is $703
Jan 14 - Jan 15
Total with taxes and fees
A stunning, modern Lodge with rustic charm at June Farms!
Living area
Penthouse Apartment on Park Street

Apartment in Adams

Penthouse Apartment on Park Street
2.0 star property
9.6 out of 10, Exceptional, (14 reviews)
"Adams is a beautiful town and looks and feels like the appalachian trail! "
United States
judy r.
$218 nightly
The price is $244
Jan 13 - Jan 14
Total with taxes and fees
Penthouse Apartment on Park Street
TV, fireplace, books
Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike

Chalet in Charlemont

Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike
2.0 star property
$579 nightly
The price is $647
Jan 20 - Jan 21
Total with taxes and fees
Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike
Exterior
Taborton Harvest Boulder Pines Cabin in the woods

Cabin in Sand Lake

Taborton Harvest Boulder Pines Cabin in the woods
10.0 out of 10, Exceptional, (13 reviews)
"Loved the earthiness and serenity of the cabin and great room. Everything built and made and maintained by the Adamos- truly a haven "
United States
Joanna R.
$165 nightly
The price is $183
Jan 13 - Jan 14
Total with taxes and fees
Taborton Harvest Boulder Pines Cabin in the woods
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pittsfield Hotel Reviews

Hotel On North

Hotel On North

10/10 Excellent
"Very clean hotel. Staff was so friendly and helpful. Location is perfect and own parking lot was great. "
Ashley 2-night trip
Posted 18 hours ago
Hotel On North

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.

Explore a world of travel with Expedia

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?

Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!: Visitors like this Pittsfield vacation home rental. It offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub.

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 Guido's Marketplace.

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.