Pittsfield Vacation Rentals

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Check prices for these dates

Tonight
Feb 1 - Feb 2
Tomorrow
Feb 2 - Feb 3
Next weekend
Feb 7 - Feb 9
In two weeks
Feb 14 - Feb 16

Vacation Rentals in Pittsfield

Spacious Luxury Berkshire's Estate on 21 acres
Smart TV, fireplace

Spacious Luxury Berkshire's Estate on 21 acres

Spacious Luxury Berkshire's Estate on 21 acres
Hancock Village Inn at Jiminy Peak
Miscellaneous

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (9)
"Annual mother/son ski and food fest!Lots of fun with family and friends. Plenty of space for everyone.. Kitchen wascwell"
The price is ￥92,804
￥162,806 total
includes taxes & fees
Feb 4 - Feb 5
Hancock Village Inn at Jiminy Peak
Chic Pittsfield Home With A View!
Property grounds

Chic Pittsfield Home With A View!

8.6 out of 10, Excellent, (10)
"This property was just as shown in the listing and met our needs very well. It was well appointed and had many inviting areas to gather and relax in. The kitchen was well equipped and easy to use. Some very nice touches with closets and bathroom storage areas that made staying there user friendly. "
Chic Pittsfield Home With A View!
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Exterior

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

10.0 out of 10, Exceptional, (55)
"Perfect lake front home to get away for a quick weekend trip with the family over the holidays!! Location, location location, close proximity to downtown Pittsfield, 15 from Jiminy peak & Bousquet Mt. Andrey was extremely helpful throughout the process with suggestions for food and activities for the kids. The house was a perfect fit for our family and friends. Everyone enjoyed their time there and would definitely book again"
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1759)
"Great place "
The price is ￥20,807
￥24,366 total
includes taxes & fees
Mar 1 - Mar 2
Vacation Village in the Berkshires
The Ponds at Foxhollow by Capital Vacations
Property grounds

The Ponds at Foxhollow by Capital Vacations

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The price is ￥37,122
￥41,466 total
includes taxes & fees
Feb 14 - Feb 15
The Ponds at Foxhollow by Capital Vacations
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (924)
"Staff was exceptionally helpful and friendly."
The price is ￥29,131
￥31,956 total
includes taxes & fees
Feb 2 - Feb 3
Jiminy Peak Mountain Resort
Private Estate, Heated Yearround Outdoor Pool
Fridge, microwave, oven, stovetop

Private Estate, Heated Yearround Outdoor Pool

10.0 out of 10, Exceptional, (16)
"The home was beautiful and it was a gorgeous property too. It had all the right amenities in the kitchen. "
The price is ￥282,674
￥471,360 total
includes taxes & fees
Feb 19 - Feb 20
Private Estate, Heated Yearround Outdoor Pool
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
TV, fireplace, DVD player

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

9.6 out of 10, Exceptional, (39)
"A nice cabin in the woods. Only issue was rodents at the property. We had four sighting in three days. Would stay again if they resolved the mouse problem."
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (239)
"Overall, our stay was great! My girlfriend and I made a quick decision to head up to the slopes to start the new year and found this perfect spot! Great area, 15 mins to multiple ski resorts, cleanly, easy access, had everything we needed. Will be back for sure!"
The price is ￥23,120
￥34,949 total
includes taxes & fees
Feb 2 - Feb 3
Berkshire Village Carriage House - Super Private!!
Pristine Home In Becket Woods
Fridge, microwave, oven, stovetop

Pristine Home In Becket Woods

10.0 out of 10, Exceptional, (13)
"Pristine can mean several different things. My interpretation was to be “like new”. This dwelling did not quite live up to that standard, but was clean, sans the “mud room” and what appeared to be mold on the peak of the ceiling above the living room. The original listing stated firewood was provided by the host. Then, the checkin instructions stated guests provided their own. Not huge, just misstated in the listing (since changed). There was a power outage while we were there, thus no...
Pristine Home In Becket Woods
Peace and quiet on the lake
Interior

Peace and quiet on the lake

9.6 out of 10, Exceptional, (204)
"Such a cozy cabin for a perfect weekend stay with friends. Located close to multiple ski spots around the area, coming back to the cabin after to relax with hot cocoa and a fire going on. Right down the street is a shop that sells delicious sandwiches too. Owners of the property were super nice and quick to respond with any questions we had. Hoping to come back soon and check this place out during the summer time to enjoy the lake life!"
Peace and quiet on the lake
Amore Estate - beautiful room with many places to explore and relax in.
Fridge, microwave, oven, stovetop

Amore Estate - beautiful room with many places to explore and relax in.

9.4 out of 10, Exceptional, (21)
"Fantastic, large house with tons of places to explore in the house and on the property. We came for a long weekend with 3 families and both the adults and kids felt quickly at home and really enjoyed our stay. We cannot wait to some back!"
Amore Estate - beautiful room with many places to explore and relax in.
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Exterior

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

9.6 out of 10, Exceptional, (210)
"The cabin is quiet, tidy, and comfortable. It is within driving distance of several hiking trails and was a great place to spend a long weekend. The host was friendly and communicative, and made sure that we had everything we needed for a nice stay. "
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Amazing Estate w/pool, gym, pond, trails, arcade! Chef dinner w/week long stay!
Fridge, microwave, oven, stovetop

Amazing Estate w/pool, gym, pond, trails, arcade! Chef dinner w/week long stay!

9.6 out of 10, Exceptional, (85)
"We had fun! Game room great! Spacious and comfortable. Never got to enjoy outdoors, so maybe another trip in the future!"
Amazing Estate w/pool, gym, pond, trails, arcade! Chef dinner w/week long stay!
Peaceful Retreat Compound 10 Minutes to Great Barrington!
Interior

Peaceful Retreat Compound 10 Minutes to Great Barrington!

10.0 out of 10, Exceptional, (21)
"This home is located in a beautiful area with plenty of nature surrounding. The amenities included are incredible. A large group of us visited and had so much fun on the pickle ball courts, hanging around the bonfire, and relaxing with the sauna and hot tub. This place can’t be beat!!"
Peaceful Retreat Compound 10 Minutes to Great Barrington!
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
Property grounds

1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor

10.0 out of 10, Exceptional, (5)
"Condo was conveniently located at the base of the mountain. Had everything you would need for a quick weekend getaway. Owner was available for any questions."
The price is ￥24,198
￥45,252 total
includes taxes & fees
Feb 3 - Feb 4
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
Laurel Lake Luxury 4BR, 4.5 Bath, Ranch on Fox Hollow Estate
Fridge, microwave, oven, stovetop

Laurel Lake Luxury 4BR, 4.5 Bath, Ranch on Fox Hollow Estate

Laurel Lake Luxury 4BR, 4.5 Bath, Ranch on Fox Hollow Estate
Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna
Fridge, microwave, oven, stovetop

Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna

10.0 out of 10, Exceptional, (23)
"We stayed at the house with extended family for a ski trip weekend at Catamount. The drive was 30mins away and the house a wonderful place to relax together after a long day on the mountain. The house is spacious, bright, clean and tastefully decorated. The layout is comfortable and practical. The lovely, open-kitchen was well-equipped and allowed us all to gather and chat pre and post dinner. The sauna is a great perk with gorgeous views! Highly recommend! Would love to come back in the summer...
Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna
Cabin in the woods
Exterior

Cabin in the woods

10.0 out of 10, Exceptional, (9)
"This place was awesome... I was 15 minutes away working late... and I was too tired to drive home... I actually scheduled the wrong night and realized it after I got confirmation. But I messaged the renters and they just happened to have a cabin vacancy... they gave me the directions.. the key code and we worked everything out afterwards. The set-up is genius... the common area building has all the plumbing in it. Bathroom and showers with an open very well built living room with a kitchen. My...
The price is ￥18,496
￥26,141 total
includes taxes & fees
Feb 3 - Feb 4
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.
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Other types of properties in Pittsfield you may be interested in

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Exterior

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

3.0 star property
8.0 out of 10, Very Good, (729)
"We stay here often because it is close to our daughter’s school in New York. We love staying here and choose this hotel every time. "
The price is ￥16,338
￥18,250 total
includes taxes & fees
Feb 7 - Feb 8
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Hotel On North
Front of property - evening/night

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (680)
"Had a great stay - such a gem of a hotel. "
The price is ￥17,263
￥19,282 total
includes taxes & fees
Feb 9 - Feb 10
Hotel On North
Berkshire Mountain Lodge
Fridge, microwave, stovetop, coffee/tea maker

Berkshire Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (426)
"It is a 3 day family trip. Our stay was excellent. Room is big and tidy. The staff was very nice and accomodating.. the place is close to all.. restaurant, grocery, gas station etc.. "
The price is ￥16,800
￥21,848 total
includes taxes & fees
Feb 3 - Feb 4
Berkshire Mountain Lodge
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.

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 Canoe Meadows Wildlife Sanctuary 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.