Pittsfield Vacation Rentals

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Check prices for these dates

In two weeks
Nov 21 - Nov 23
In two months
Jan 2 - Jan 4
In three months
Jan 30 - Feb 1
In four months
Feb 27 - Mar 1

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
Pittsfield
7.8 out of 10, Good, (6)
"Very clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
The price is ￥41,285
￥75,421 total
includes taxes & fees
Nov 17 - Nov 18
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Exterior
Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak

Hancock
10.0 out of 10, Exceptional, (15)
"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...
United States
Jim O.
The price is ￥91,899
￥170,459 total
includes taxes & fees
Nov 18 - Nov 19
Hancock Village Inn Near 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
Pittsfield
2.0 out of 10, (1)
"THIS. PLACE. IS. A. DUMP. Do NOT STAY HERE under any circumstances."
United States
Michael
The price is ￥23,013
￥34,276 total
includes taxes & fees
Nov 30 - Dec 1
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
Chatham
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. "
United States
Sue G.
The price is ￥32,985
￥55,189 total
includes taxes & fees
Nov 11 - Nov 12
Sugar Shack - 300 square feet of pure sweetness.
Terrace/patio
BLUSH: Boutique TINY home*private spa*walk to town

BLUSH: Boutique TINY home*private spa*walk to town

Chatham
10.0 out of 10, Exceptional, (6)
"Perfect blend of decore, comfort, and function. We went to Tanglewood which was only a half hour away. Came back to hot tub and fire pit. Beds here are soooo comfy! This is our 2nd time here and won’t be our last."
United States
Melissa D.
The price is ￥32,985
￥55,361 total
includes taxes & fees
Nov 17 - Nov 18
BLUSH: Boutique TINY home*private spa*walk to town
Smart TV, fireplace
HunnyHAUS: Deluxe TINY*private spa*walk to town

HunnyHAUS: Deluxe TINY*private spa*walk to town

Chatham
10.0 out of 10, Exceptional, (9)
"We had the best time here. The house is even cuter and cozier in person (which says a lot because the pictures are great!). The hot tub was a great luxury and the house is literally a 3 minute walk to town. So convenient! We also had a fire in the Viking tent one night which was fun. Heidi was super helpful and quick to respond to any queries during our stay. She even left rose petals on the bed and a bottle of Prosecco chilling in the fridge for us upon our arrival. I would stay here again in a...
United States
Megan H.
The price is ￥34,520
￥63,320 total
includes taxes & fees
Nov 16 - Nov 17
HunnyHAUS: Deluxe TINY*private spa*walk to town
Exterior
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

3.0 star property
Hancock
8.2 out of 10, Very Good, (984)
"It was a fun place to stay. Rooms were clean and dishes well stocked in the kitchenette. "
United States
Sandhya
The price is ￥22,860
￥25,534 total
includes taxes & fees
Nov 10 - Nov 11
Jiminy Peak Mountain Resort
Indoor pool, outdoor pool, pool umbrellas, sun loungers
The Ponds at Foxhollow

The Ponds at Foxhollow

3.0 star property
Lenox
8.6 out of 10, Excellent, (132)
"Perfect location "
United States
krystle
The Ponds at Foxhollow
TV
Florida Mountain Log Cabin

Florida Mountain Log Cabin

2.0 star property
Florida
10.0 out of 10, Exceptional, (4)
"We loved our 1 night stay here - it is a super cute log cabin with comfortable beds and very clean! Our favorite part was the fire pit for smores and the kids especially loved the cozy swings! Host was very accessible. Definitely recommend!"
United States
Kate R.
The price is ￥28,191
￥52,008 total
includes taxes & fees
Nov 11 - Nov 12
Florida Mountain Log Cabin
Lobby
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3.0 star property
Williamstown
8.8 out of 10, Excellent, (2126)
"Clean and great pool and hot tub facilities "
United States
Alyce
The price is ￥14,074
￥17,403 total
includes taxes & fees
Nov 12 - Nov 13
Vacation Village in the Berkshires
Fridge, microwave, oven, stovetop
Cozy Rustic Apt in 18th c Berkshire Farmhouse

Cozy Rustic Apt in 18th c Berkshire Farmhouse

Lanesborough
9.6 out of 10, Exceptional, (67)
"Very cute! Perfect place for a weekend in the Berkshires"
United States
Melissa P.
The price is ￥20,712
￥31,852 total
includes taxes & fees
Nov 10 - Nov 11
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Outdoor dining
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Sherwood Forest
10.0 out of 10, Exceptional, (3)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is ￥22,369
￥57,889 total
includes taxes & fees
Nov 12 - Nov 13
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
Exterior detail
Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Boulder Pines Cabin in the woods

Sand Lake
10.0 out of 10, Exceptional, (13)
"We LOVED our stay! Cabins were spotless and the main building was just great! Waking up to a picture window behind us with all the fall colors in their glory was such a highlight. "
United States
Barb W.
The price is ￥19,178
￥28,099 total
includes taxes & fees
Nov 10 - Nov 11
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

Sherwood Forest
9.6 out of 10, Exceptional, (9)
"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."
United States
James D.
The price is ￥24,578
￥60,185 total
includes taxes & fees
Nov 11 - Nov 12
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Exterior
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Hinsdale
9.8 out of 10, Exceptional, (33)
"Great cottage - well appointed and very clean. No air conditioning so a bit warm when it’s hot out, but all in all a great stay"
United States
Lindsey E.
The price is ￥24,854
￥64,265 total
includes taxes & fees
Nov 10 - Nov 11
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Exterior detail
Bright Boho Apt in 18th c Berkshire Farmhouse

Bright Boho Apt in 18th c Berkshire Farmhouse

Lanesborough
9.0 out of 10, Wonderful, (22)
"Very nice. Attending a wedding in the area and really needed a place to get dressed and return to sleep. This fit the bill perfectly. Clean and comfortable we enjoyed our visit. Need to come back and visit the many sites in the area."
United States
Margaret K.
The price is ￥22,246
￥33,737 total
includes taxes & fees
Nov 10 - Nov 11
Bright Boho Apt in 18th c Berkshire Farmhouse
Exterior
Bear Creek Cabin

Bear Creek Cabin

Charlemont
10.0 out of 10, Exceptional, (41)
"We enjoyed our stay!!"
United States
Hillary S.
The price is ￥61,368
￥91,856 total
includes taxes & fees
Nov 10 - Nov 11
Bear Creek Cabin
1 bedroom, iron/ironing board, bed sheets
Penthouse Apartment on Park Street

Penthouse Apartment on Park Street

2.0 star property
Adams
9.6 out of 10, Exceptional, (13)
"We had a wonderful relaxing stay in this gorgeous place. The listing is just as described, natural light filled, high ceilings, on the top floor, comfortable bedding, and a thoughtful host. Lea left the A/C on, a bottle of water in the fridge, lots of good coffee, and even some hot cocoa packets for our son. The boba shop right downstairs was awesome and had fun gift items. There is a diner next door and some fantastic restaurants 15-20 minutes away. Very convenient to Mass MOCA and...
United States
Teresa M.
The price is ￥17,797
￥37,531 total
includes taxes & fees
Nov 14 - Nov 15
Penthouse Apartment on Park Street
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

Hancock
10.0 out of 10, Exceptional, (8)
"Perfect place to stay for a quick ski trip. Host was super helpful & accommodating. Suite was comfortable & well-equipped. We’ll be back "
United States
Kevin K.
The price is ￥16,109
￥35,988 total
includes taxes & fees
Nov 12 - Nov 13
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Outdoor dining
2-Bdr Apt In Town, By the Water

2-Bdr Apt In Town, By the Water

Williamstown
9.4 out of 10, Exceptional, (10)
"Lovely property, in good shape. Close to many Williamstown attractions."
United States
Scott M.
2-Bdr Apt In Town, By the Water
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

Quality Inn

Quality Inn

10/10 Excellent
"The staff was amazing, so kind and accommodating. The room was clean, the beds were very comfortable. Nice breakfast options. We were in town for a concert at Mahaiwe and we didn’t use our car once we checked in… a great home base for the weekend. Will definitely be back. "
Kelly 1-night trip
Posted 3 days ago
Quality Inn

Find out more about Pittsfield

Search for holiday rentals in Pittsfield on Expedia! You can easily find your home rentals, villas, holiday apartments in Pittsfield using one of the methods below:

  • View our selection of featured holiday rentals in Pittsfield
  • Use the map to find apartments and other holiday homes in the Pittsfield neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Pittsfield while they last

Look no further and take a look at our great range of rental properties in Pittsfield!

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 Near Jiminy Peak 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.