Pittsfield Vacation Rentals

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Check prices for these dates

Tonight
Mar 3 - Mar 4
Tomorrow
Mar 4 - Mar 5
This weekend
Mar 7 - Mar 9
Next weekend
Mar 14 - Mar 16

Vacation Rentals in Pittsfield

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Outdoor dining

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

9.8 out of 10, Exceptional, (139)
"We have stayed at this property twice before and have been very pleased with the amount of bedrooms and sleeping available. The property is always very clean and is equipped with everything you need for cooking and dining.the property is a half way point for family members in several directions. "
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Hancock Village Inn at Jiminy Peak
Miscellaneous

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (10)
"Kids will love the fun bunk room setup, millennials will appreciate the big screen TV's and broadband Internet access, while parentals and grandparents enjoy the fully equipped kitchen and space to enjoy dinner together around a table for 12. Hot tub right outside the kitchen door, close proximity to Jiminy Peak makes it a breeze to shuttle the family back and forth . Extremely clean property.. Rent the extra suite if you have difficulty with stairs, and enjoy having the entire inn to...
The price is ￥90,077
￥159,877 total
includes taxes & fees
Mar 5 - Mar 6
Hancock Village Inn at Jiminy Peak
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, (56)
"Perfect location and accommodation for my family. The home was as described. I would recommend it. The property owner was easy to work with. "
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, (1781)
"Awesome place extremely close to the ski mnt. Has an inside / outside pool plus hot tub! Rooms were great"
The price is ￥16,283
￥19,357 total
includes taxes & fees
Mar 16 - Mar 17
Vacation Village in the Berkshires
The Ponds at Foxhollow
Property grounds

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The Ponds at Foxhollow
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (925)
"Staff was exceptionally helpful and friendly."
The price is ￥22,444
￥24,621 total
includes taxes & fees
Apr 1 - Apr 2
Jiminy Peak Mountain Resort
Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (239)
"Property was very nice Kirchen could use some additons -starting with a ladle "
The price is ￥22,409
￥33,374 total
includes taxes & fees
Apr 2 - Apr 3
Berkshire Village Carriage House - Super Private!!
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
Private Estate, Heated Yearround Outdoor Pool
Fridge, microwave, oven, stovetop

Private Estate, Heated Yearround Outdoor Pool

9.8 out of 10, Exceptional, (17)
"The home was beautiful and it was a gorgeous property too. It had all the right amenities in the kitchen. "
Private Estate, Heated Yearround Outdoor Pool
Peace and quiet on the lake
Interior

Peace and quiet on the lake

9.6 out of 10, Exceptional, (210)
"This was a cozy tucked away location that seemed far away from everything which was exactly what we wanted. The host was extremely communicative before and during the stay. The house had fresh linens and towels as well as basic cleaning supplies. It was cozy for a wintery weekend in. We enjoyed snowshoeing on the frozen lake! Pet-friendly was a huge plus! "
Peace and quiet on the lake
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
BEAUTIFUL ESTATE! POOL, POND, ARCADE, GYM, TRAILS, BARN! ASK ABOUT REDUCED RATES
Fridge, microwave, oven, stovetop

BEAUTIFUL ESTATE! POOL, POND, ARCADE, GYM, TRAILS, BARN! ASK ABOUT REDUCED RATES

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!"
BEAUTIFUL ESTATE! POOL, POND, ARCADE, GYM, TRAILS, BARN! ASK ABOUT REDUCED RATES
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Dining

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

10.0 out of 10, Exceptional, (119)
"The property was great for our group of 8. Slept everyone comfortably, with plenty of places to hangout and lounge all together. We had planned to cook in for a couple meals, so it was a hugely pleasant surprise to see that the kitchen was stocked with every cooking utensil, serving dish, and glassware that you could possibly need. We were maybe even more prepared than in my own kitchen at home. Also very well located. Had an excellent stay and would come back!"
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
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 ￥17,927
￥25,337 total
includes taxes & fees
Mar 17 - Mar 18
Cabin in the woods
Vintage BARN Apartment-POOL-HotTub-FirePit-Hiking-Museums-Theater-Pets welcome!
Smart TV, fireplace, DVD player, books

Vintage BARN Apartment-POOL-HotTub-FirePit-Hiking-Museums-Theater-Pets welcome!

9.6 out of 10, Exceptional, (29)
"We had a very peaceful and relaxing stay. The atmosphere was quiet and calming, perfect for unwinding. Everything about our time here was enjoyable, and we truly appreciated the serene environment. Highly recommend it for anyone looking for a restful getaway! "
Vintage BARN Apartment-POOL-HotTub-FirePit-Hiking-Museums-Theater-Pets welcome!
Private Access To Laurel Lake, Enjoy Lake Life
Outdoor dining

Private Access To Laurel Lake, Enjoy Lake Life

10.0 out of 10, Exceptional, (14)
"The property was better than advertised. Everything anyone could need was provided and we could not have hoped for a better experience. Very large home and could easily accomodate 8 people or more. The Berkshires are magical and this home was great for out time there."
Private Access To Laurel Lake, Enjoy Lake Life
Enjoy comfortable elegance in this secluded grand home located in town
Exterior

Enjoy comfortable elegance in this secluded grand home located in town

10.0 out of 10, Exceptional, (65)
"Beautiful home perfect for our multi-generational family. We loved the separate spaces and easy walk to the town center. We can’t wait to come back!"
Enjoy comfortable elegance in this secluded grand home located in town
Quintessential 6-BR Berkshires Lodge
Exterior

Quintessential 6-BR Berkshires Lodge

10.0 out of 10, Exceptional, (11)
"The house was perfect for us. Spacious, clean, comfortable. Beds comfortable. Bathrooms really nice. The road in the development is dirt, a 4wd is needed as stated. It was muddy and rutty on arrival, then snow and ice , but do-able. Great house. Would recommend "
Quintessential 6-BR Berkshires Lodge
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
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Terrace/patio

Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

9.6 out of 10, Exceptional, (7)
"Lots of cozy relaxation by the fire and fun meals at the spacious dinning table. We had plenty of room to spread out and enjoy ourselves. "
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
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 by IHG
Exterior

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (744)
"Ruby is very helpful and friendly. Thank you! "
The price is ￥15,666
￥17,499 total
includes taxes & fees
Mar 8 - Mar 9
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Berkshire Mountain Lodge
Fridge, microwave, stovetop, coffee/tea maker

Berkshire Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (439)
"Great room. Comfortable. Wished we stayed longer! Will definitely recommend to friends and family. "
The price is ￥17,777
￥22,845 total
includes taxes & fees
Mar 16 - Mar 17
Berkshire Mountain Lodge
Hotel On North
Front of property - evening/night

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (686)
"Loved the ambience and the bar was very nice as well. The hotel provides coffee in the room and in the lobby. Wonderful bed and plenty of room. We will be back"
The price is ￥17,172
￥19,181 total
includes taxes & fees
Mar 6 - Mar 7
Hotel On North
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?

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. Our travelers also rate Hancock Village Inn at Jiminy Peak as a favorite home for rent in Pittsfield.

How many vacation rentals are there in Pittsfield?

With 39 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.