Pittsfield Vacation Rentals

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Vacation Rentals in Pittsfield

Fridge, microwave, oven, stovetop
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
2.0 star property
7.8 out of 10, Good, (6)
"Very clean and spacious! We enjoyed our stay with our small pup!"
Ann C.
$434 nightly
The price is $485
Oct 20 - Oct 21
Total with taxes and fees
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Exterior
Hancock Village Inn at Jiminy Peak
Hancock Village Inn at Jiminy Peak
10.0 out of 10, Exceptional, (14)
"Amazing Inn. Cozy and everything we needed. "
Price F.
$969 nightly
The price is $1,047
Oct 21 - Oct 22
Total with taxes and fees
Hancock Village Inn at Jiminy Peak
Smart TV
Chic corporate apartment in wonderful Pittsfield with AC, WiFi
Chic corporate apartment in wonderful Pittsfield with AC, WiFi
2.0 star property
2.0 out of 10, (1)
"THIS. PLACE. IS. A. DUMP. Do NOT STAY HERE under any circumstances."
Michael
$182 nightly
The price is $203
Oct 31 - Nov 1
Total with taxes and fees
Chic corporate apartment in wonderful Pittsfield with AC, WiFi
Terrace/patio
Sugar Shack - 300 square feet of pure sweetness.
Sugar Shack - 300 square feet of pure sweetness.
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. "
Sue G.
$320 nightly
The price is $361
Oct 20 - Oct 21
Total with taxes and fees
Sugar Shack - 300 square feet of pure sweetness.
Restaurant
Huttopia Berkshires
Huttopia Berkshires
1.0 star property
10.0 out of 10, Exceptional, (5)
"Perfect place for a relaxing getaway! We loved everything! "
Cammie
Huttopia Berkshires
2 bedrooms, desk, iron/ironing board, free WiFi
HunnyHAUS: Deluxe TINY*private spa*walk to town
HunnyHAUS: Deluxe TINY*private spa*walk to town
10.0 out of 10, Exceptional, (9)
"No stone left unturned. The hot tub was clean and perfectly situated. the house was clean, with very sweet finishing touches. Within walking distance to shops. Hosts were very responsive. I highly recommend."
Jamie F.
$349 nightly
The price is $394
Oct 20 - Oct 21
Total with taxes and fees
HunnyHAUS: Deluxe TINY*private spa*walk to town
Lobby
Vacation Village in the Berkshires
Vacation Village in the Berkshires
3.0 star property
8.8 out of 10, Excellent, (2076)
"Clean and great pool and hot tub facilities "
Alyce
$112 nightly
The price is $125
Oct 30 - Oct 31
Total with taxes and fees
Vacation Village in the Berkshires
Terrace/patio
Charming 2-bedroom house in beautiful countryside of Cummington, Ma
Charming 2-bedroom house in beautiful countryside of Cummington, Ma
2.0 star property
$269 nightly
The price is $284
Oct 20 - Oct 21
Total with taxes and fees
Charming 2-bedroom house in beautiful countryside of Cummington, Ma
TV
Florida Mountain Log Cabin!
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."
Tristan e.
$377 nightly
The price is $399
Oct 23 - Oct 24
Total with taxes and fees
Florida Mountain Log Cabin!
Game room
Park Street Penthouse Apartment
Park Street Penthouse Apartment
9.6 out of 10, Exceptional, (11)
"Adams is a beautiful town and looks and feels like the appalachian trail! "
judy r.
$174 nightly
The price is $195
Oct 27 - Oct 28
Total with taxes and fees
Park Street Penthouse Apartment
Exterior
Jiminy Peak Mountain Resort
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (981)
"This is our second time staying here. We love the property, the suites work for us as there is a bedroom which is separate from the living space. There are plenty of things to do on the property and in the surrounding area. Mt. Greylock, antiquing, great breakfast spots! The Country Store on the property has great sandwiches and things needed for your stay."
Amy
$146 nightly
The price is $164
Oct 19 - Oct 20
Total with taxes and fees
Jiminy Peak Mountain Resort
Interior
Charming 3-bedroom Cabin for nature lovers
Charming 3-bedroom Cabin for nature lovers
8.0 out of 10, Very Good, (1)
"Very nice place to stay for our 3 day hike on the AT. The view from the deck is amazing and the living room is huge with an old stone fireplace which we didn’t use because it was 90 degrees each day. The Mexican restaurant in town (Norte Azul) has an extensive menu and a good variety of beer on tap. Highly recommend visiting Mt Greylock in MA, about 30 mins away. It has an even better restaurant on top (you need reservations) and is right on the Appalachian Trail so you will meet all sorts on...
John O.
$264 nightly
The price is $293
Oct 19 - Oct 20
Total with taxes and fees
Charming 3-bedroom Cabin for nature lovers
Exterior
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
10.0 out of 10, Exceptional, (8)
"Great location. Howie is very communicative. Wish we could have stayed longer. "
Una D.
$219 nightly
The price is $245
Oct 20 - Oct 21
Total with taxes and fees
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
TV, DVD player, books
Must See Jurassic Jiminy Suite Country Inn - Sleeps 4 Ski On/Off Mountain
Must See Jurassic Jiminy Suite Country Inn - Sleeps 4 Ski On/Off Mountain
10.0 out of 10, Exceptional, (3)
"We had a great stay! The kids absolutely loved the room. Great location and lots to do. Thanks again!!"
Jen B.
$219 nightly
The price is $245
Oct 20 - Oct 21
Total with taxes and fees
Must See Jurassic Jiminy Suite Country Inn - Sleeps 4 Ski On/Off Mountain
Exterior detail
Taborton Harvest Boulder Pines Cabin in the woods
Taborton Harvest Boulder Pines Cabin in the woods
10.0 out of 10, Exceptional, (12)
"Such a sweet spot in the woods! Can’t wait to come back."
Mariel
$165 nightly
The price is $183
Oct 19 - Oct 20
Total with taxes and fees
Taborton Harvest Boulder Pines Cabin in the woods
Smart TV, books
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
9.6 out of 10, Exceptional, (8)
"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."
James D.
$352 nightly
The price is $393
Oct 27 - Oct 28
Total with taxes and fees
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Outdoor dining
2-Bdr Apt In Town, By the Water
2-Bdr Apt In Town, By the Water
9.6 out of 10, Exceptional, (8)
"Lovely property, in good shape. Close to many Williamstown attractions."
Scott M.
$240 nightly
The price is $270
Oct 20 - Oct 21
Total with taxes and fees
2-Bdr Apt In Town, By the Water
Outdoor dining
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
10.0 out of 10, Exceptional, (3)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
Sharon K.
$357 nightly
The price is $399
Oct 28 - Oct 29
Total with taxes and fees
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
Indoor pool
Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat
Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat
9.8 out of 10, Exceptional, (18)
"We had a great time with our 2 kids during our stay at the Disney Magic Suite. The kids loved all of the Disney decor and surprise touches (and their stuffed animals thank you!). Location was amazing, walk to the lifts, and the ski school was one of the best we've been to. Thanks for a great stay, we'll be back!"
Debbie H.
$209 nightly
The price is $233
Oct 20 - Oct 21
Total with taxes and fees
Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat
Outdoor dining
Downtown | Waterfront | Walk to Shops
Downtown | Waterfront | Walk to Shops
10.0 out of 10, Exceptional, (6)
"Perfect setup for anyone visiting Williamstown."
Michael P.
$246 nightly
The price is $277
Nov 2 - Nov 3
Total with taxes and fees
Downtown | Waterfront | Walk to Shops
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

Berkshires Untold

Berkshires Untold

10/10 Excellent
"Room adequate for a night stay. Breakfast service was odd. A maintenance person gave us one napkin & silverware service for 2 people. Hard boiled eggs brought still in the shell w/no way to rinse off the shells once peeled. "
ELIZABETH 1-night trip
Posted 2 days ago
Berkshires Untold

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 $125 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?

Hancock Village Inn at 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 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.