A historic building with classical architecture, a traffic light, and a yellow taxi.

Pittsfield Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Pittsfield vacation rentals

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

1. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,160 reviews)
"Absolutely wonderful room with many amenities with short drive to Tanglewood and restaurant options."
United States
Jay
The price is ￥12,519
￥17,497 total
includes taxes & fees
Oct 1 - Oct 2
Berkshire Mountain Lodge
A wooden deck with a table and chairs, surrounded by a white railing.

2. 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!
Pittsfield
8.4 out of 10, Very good, (10 reviews)
"Very comfortable and clean accommodations in a nice neighborhood, and a great deck to appreciate the view."
United States
Stephen L.
The price is ￥47,027
￥78,705 total
includes taxes & fees
Oct 13 - Oct 14
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
A wooden deck with outdoor furniture, including chairs and a table, surrounded by a lush garden and trees.

3. Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (22 reviews)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is ￥90,664
￥159,543 total
includes taxes & fees
Sep 29 - Sep 30
Hancock Village Inn Near Jiminy Peak
A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

4. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,683 reviews)
"Love this place for a weekend getaway."
United States
Jacob
The price is ￥14,964
￥18,440 total
includes taxes & fees
Sep 30 - Oct 1
Vacation Village in the Berkshires
A snow-covered outdoor area with a fire pit, tables, and chairs.

5. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"Loved this spot. Beautiful view of the mountain. Beyond easy checkin and check out process. Everything you need is on the mountain - we didnt have to leave all weekend. Highly recommend! "
United States
Maura D.
The price is ￥15,146
￥34,311 total
includes taxes & fees
Sep 29 - Sep 30
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
A modern kitchen with white cabinetry, a stainless steel dishwasher, and a window with a view.

6. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Dalton
9.8 out of 10, Exceptional, (33 reviews)
"We were on a girls backpacking trip and this was the perfect location right off the trail to clean up, get some great rest and grab dinner. The people are so friendly in Dalton and this place had everything we needed!"
United States
Allie T.
The price is ￥23,356
￥51,563 total
includes taxes & fees
Oct 8 - Oct 9
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
A lakeside picnic area with a bench and umbrella, surrounded by autumn-colored trees.

7. 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, (39 reviews)
"The house was very clean! The hot tub was great! From checking in and checking out the host made everything so easy. We will definitely stay again!"
United States
Kyle R.
The price is ￥26,046
￥62,824 total
includes taxes & fees
Sep 29 - Sep 30
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
A rustic wooden interior with various stalls selling items like books, snacks, and wine.

8. Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"The apartment itself is very clean and perfect for what we needed - a quick 2 night stay. The pool, hot tub and Jiminy Peak right there was great. Howie, the owner, was excellent with communication. Not his fault, the Country Inn itself is a bit outdated yet front desk assistants were so nice and friendly."
United States
Ann
The price is ￥15,146
￥34,311 total
includes taxes & fees
Sep 29 - Sep 30
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
A covered outdoor seating area with two chairs and a view of a grassy landscape.

9. Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center

Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center
Lenox
Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center
A rustic wooden interior with shelves stocked with various products, a 'Tree-Free' sign, and a section with bottled beverages.

10. Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (3 reviews)
"Stayed one night at one of my favorite ski spots. Will be back again!"
United States
Neil J.
The price is ￥15,146
￥34,311 total
includes taxes & fees
Sep 29 - Sep 30
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

11. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
The price is ￥35,231
￥87,159 total
includes taxes & fees
Oct 5 - Oct 6
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

12. Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Hancock
9.4 out of 10, Exceptional, (18 reviews)
"Nice Place"
United States
Tom C.
The price is ￥15,146
￥34,311 total
includes taxes & fees
Sep 29 - Sep 30
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Four people seated at a table with food and drinks, wearing winter sports helmets.

13. Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4

Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
Hancock
9.8 out of 10, Exceptional, (9 reviews)
"A great, comfy suite! We had a great stay! "
United States
Wendy D.
The price is ￥15,146
￥34,311 total
includes taxes & fees
Sep 29 - Sep 30
Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

14. Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Hancock
9.8 out of 10, Exceptional, (25 reviews)
"We stayed here twice this season and it was wonderful. The unit was clean, conveniently located and was fully equipped with all the essentials, making our stay comfortable and seamless from start to finish. We will definitely be back!"
United States
Kristina L.
The price is ￥15,146
￥34,311 total
includes taxes & fees
Sep 29 - Sep 30
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

15. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.8 out of 10, Exceptional, (7 reviews)
"The host was extremely communicative and went above and beyond to ensure guest comfort."
United States
Diego G.
The price is ￥27,681
￥83,275 total
includes taxes & fees
Oct 5 - Oct 6
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
A wooden cabin with a porch, a door, and a window.

16. Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Boulder Pines Cabin in the woods
Sand Lake
10.0 out of 10, Exceptional, (18 reviews)
"This was a dash away and perfect! "
United States
Linda R.
The price is ￥19,660
￥28,806 total
includes taxes & fees
Sep 29 - Sep 30
Taborton Harvest Boulder Pines Cabin in the woods
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

17. 2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Hancock
9.8 out of 10, Exceptional, (6 reviews)
"Excellent communication with our host and property exactly as described. Easy check in/check out."
United States
Jillian G.
The price is ￥28,310
￥52,528 total
includes taxes & fees
Oct 1 - Oct 2
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
A patio with a wooden table and benches, a grill, and a garden with trees and flowers.

18. NEW RENO Historic Creamery in Berkshires w/hot tub

NEW RENO Historic Creamery in Berkshires w/hot tub
New Lebanon
10.0 out of 10, Exceptional, (7 reviews)
"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "
United States
Anonymous traveler
The price is ￥39,005
￥79,067 total
includes taxes & fees
Sep 29 - Sep 30
NEW RENO Historic Creamery in Berkshires w/hot tub
A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

19. NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.6 out of 10, Excellent, (7 reviews)
"Awesome location went for a solo trip w the purpose of spending time alone in nature with myself and god got exactly that calm quiet beautiful scenic area great room and service would book again"
United States
Varun M.
The price is ￥11,010
￥31,834 total
includes taxes & fees
Sep 29 - Sep 30
NEW RENO - Chalet-style farm loft near Tanglewood
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

20. 1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count

1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
Hancock
9.4 out of 10, Exceptional, (6 reviews)
"Convenience to slopes and restaurants really great….,had a nice stay"
United States
Thomas S.
The price is ￥15,146
￥34,311 total
includes taxes & fees
Sep 29 - Sep 30
1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
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

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"One of the most unique establishments in the US. It brings one back to time when life was much simpler. Highly recomended."
Michael 1-night trip
Posted 2 hours ago
The Red Lion 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
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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?

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: You might want to consider this vacation home rental near Pittsfield, which is located near skiing and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals are there in Pittsfield?

With 35 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 Onota Lake 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.