Pittsfield Vacation Rentals

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Tonight
Jul 14 - Jul 15
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Jul 15 - Jul 16
This weekend
Jul 18 - Jul 20
Next weekend
Jul 25 - Jul 27

Vacation Rentals in Pittsfield

Berkshire Village Carriage House - Super Private!!
Enjoy cooking in this well-equipped kitchen with a central island, sink, and ample seating for two.

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (252)
"One of the best properties i've ever stayed at "
$262 nightly
The price is $293
Jul 31 - Aug 1
Total includes taxes and fees
Berkshire Village Carriage House - Super Private!!
NEW RENO Historic Creamery in Berkshires w/hot tub
Relax in a spacious outdoor living area with a comfortable sofa set and sheltered seating options.

NEW RENO Historic Creamery in Berkshires w/hot tub

10.0 out of 10, Exceptional, (1)
"We used all amenities (besides hot tub) full kitchen and only brought food which worked well."
$470 nightly
The price is $474
Jul 15 - Jul 16
Total includes taxes and fees
NEW RENO Historic Creamery in Berkshires w/hot tub
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Enjoy cooking in this well-equipped kitchen with a central island, stainless steel appliances, and a window with a view.

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

2.0 star property
9.0 out of 10, Wonderful, (4)
"Very clean and spacious! We enjoyed our stay with our small pup!"
$593 nightly
The price is $662
Aug 4 - Aug 5
Total includes taxes and fees
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Hancock Village Inn at Jiminy Peak
Charming two-story house with a historic facade, featuring a prominent address and star symbol, set amidst a serene winter landscape.

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (12)
"Very kinda hosts, and wonderful house."
$1,015 nightly
The price is $1,100
Jul 28 - Jul 29
Total includes taxes and fees
Hancock Village Inn at Jiminy Peak
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
Enjoy al fresco dining and socializing on this tranquil outdoor deck, complete with a barbecue grill and comfortable seating.

Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

$371 nightly
The price is $414
Jul 28 - Jul 29
Total includes taxes and fees
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
North Getaway Cottage
Stunning two-story house with a central entrance and lush green surroundings.

North Getaway Cottage

9.6 out of 10, Exceptional, (20)
"Claudia is such a considerate and thoughtful host! We felt so welcome and at ease."
$403 nightly
The price is $450
Jul 15 - Jul 16
Total includes taxes and fees
North Getaway Cottage
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Cozy living room with a comfortable sofa, throw blanket, and fireplace.

Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

10.0 out of 10, Exceptional, (5)
"My wife, two kids, and chocolate lab spent a few days at the cottage to enjoy the snow and hot tub. Everything was set up exactly as described and Nicole was very friendly and proactive. We had a great time and would do it again "
$458 nightly
The price is $512
Aug 6 - Aug 7
Total includes taxes and fees
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Hummingbird Haven is a Berkshires retreat surrounded by nature and local charm.
Relax on the covered porch with two comfortable rocking chairs overlooking a serene grassy area surrounded by trees.

Hummingbird Haven is a Berkshires retreat surrounded by nature and local charm.

10.0 out of 10, Exceptional, (3)
"This property was amazing! Very clean and spacious, perfect location for a nice peaceful getaway. Kendra was very communicative and made sure our stay was comfortable. 10/10 highly recommend you to stay here. "
$550 nightly
The price is $614
Aug 13 - Aug 14
Total includes taxes and fees
Hummingbird Haven is a Berkshires retreat surrounded by nature and local charm.
Home in Great Barrington
Enjoy cooking in this well-lit kitchen with a large window offering a view of the outdoors.

Home in Great Barrington

9.8 out of 10, Exceptional, (21)
"Our family had a wonderful experience and stay. "
$373 nightly
The price is $417
Aug 6 - Aug 7
Total includes taxes and fees
Home in Great Barrington
Restored Historic 1850s Barn "Carriage House" Studio @ Hillsdale Town Center
Exterior

Restored Historic 1850s Barn "Carriage House" Studio @ Hillsdale Town Center

$270 nightly
The price is $291
Jul 20 - Jul 21
Total includes taxes and fees
Restored Historic 1850s Barn "Carriage House" Studio @ Hillsdale Town Center
Comfortable Berkshires retreat on mtn resort, SISO
Relax by the pool surrounded by lush views and shaded lounge areas.

Comfortable Berkshires retreat on mtn resort, SISO

9.6 out of 10, Exceptional, (4)
"Hosts were very responsiveHouse was clean and well maintainedExcellent locationOverall great stay"
$501 nightly
The price is $508
Jul 20 - Jul 21
Total includes taxes and fees
Comfortable Berkshires retreat on mtn resort, SISO
New Home - Heart of Williamstown 183
Relax in this inviting living room with a sofa, coffee table, and large window offering a view of the deck and surrounding trees.

New Home - Heart of Williamstown 183

10.0 out of 10, Exceptional, (1)
"Great place to stay. House is brand new with plenty of room. Has 3 bedrooms plus a finished room in basement which is equivalent of a 4th room. Hiking and restaurants are close to the property. Plenty of parking. Highly recommend. Absolutely no complaints."
$1,124 nightly
The price is $1,256
Jul 16 - Jul 17
Total includes taxes and fees
New Home - Heart of Williamstown 183
Treat yourself at the stunning June Farms Wellness Huts!
Escape to a serene cabin surrounded by a lush garden, featuring a spacious entrance and comfortable outdoor seating.

Treat yourself at the stunning June Farms Wellness Huts!

10.0 out of 10, Exceptional, (8)
"Most AMAZING!!!!Going back sooooon!!!"
$340 nightly
The price is $377
Jul 30 - Jul 31
Total includes taxes and fees
Treat yourself at the stunning June Farms Wellness Huts!
Near Tanglewood: Historic Summer Retreat
Enjoy cooking in this well-equipped kitchen with a stove, oven, refrigerator, coffee maker, and knife block.

Near Tanglewood: Historic Summer Retreat

9.4 out of 10, Exceptional, (20)
"Nice home, spacious, clean, close to Jiminy Peak mountain (15mins)"
$482 nightly
The price is $521
Jul 15 - Jul 16
Total includes taxes and fees
Near Tanglewood: Historic Summer Retreat
Experience Timeless Elegance in The Edith Wharton Room!
Cozy retreat with a large bed, dresser, desk, and TV.

Experience Timeless Elegance in The Edith Wharton Room!

$306 nightly
The price is $381
Jul 15 - Jul 16
Total includes taxes and fees
Experience Timeless Elegance in The Edith Wharton Room!
The Lakeshore House
Surrounded by lush greenery, this two-story house offers a serene retreat with a balcony and a small pond in the foreground.

The Lakeshore House

$780 nightly
The price is $842
Jul 15 - Jul 16
Total includes taxes and fees
The Lakeshore House
Hillsdale Escape with Pool, Firepit, Hot Tub, Game Room
Relax in the serene outdoor patio, featuring a fire pit, round table, and comfortable seating.

Hillsdale Escape with Pool, Firepit, Hot Tub, Game Room

$1,479 nightly
The price is $1,597
Aug 4 - Aug 5
Total includes taxes and fees
Hillsdale Escape with Pool, Firepit, Hot Tub, Game Room
Spacious 5-bedroom house in charming Lee with WiFi
5 bedrooms, iron/ironing board, WiFi, bed sheets

Spacious 5-bedroom house in charming Lee with WiFi

$892 nightly
The price is $996
Aug 12 - Aug 13
Total includes taxes and fees
Spacious 5-bedroom house in charming Lee with WiFi
Great Barrington Get Away
Enjoy cooking in this kitchen with stainless steel appliances, a large window offering a view of the outdoors, and a convenient trash can.

Great Barrington Get Away

9.4 out of 10, Exceptional, (23)
"Nice, cozy, clean house with character. Great location as we could walk to town. Would stay again for sure."
$657 nightly
The price is $734
Jul 15 - Jul 16
Total includes taxes and fees
Great Barrington Get Away
Glass Lake Cottage
Outdoor dining

Glass Lake Cottage

10.0 out of 10, Exceptional, (1)
"Glass lake cottage was the perfect relaxing retreat while I was visiting for a wedding at the Old Daley Inn! The place was clean, had a well stocked kitchen and everything I needed. We were lucky to catch a fantastic sunset and enjoyed the view from the large deck. Will definitely be back! "
$708 nightly
The price is $786
Jul 25 - Jul 26
Total includes taxes and fees
Glass Lake Cottage
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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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. Some other top choices in Pittsfield are Hancock Village Inn at Jiminy Peak and Lake Front Home in Heart of the Berkshires Near Jiminy Peak.

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.