- Bundle & SaveGet more, spend less whenever you see Bundle & Save deals
- OneKeyCashEarn OneKeyCash on all your eligible bookings
- Upfront pricingWe are not like the others - we include taxes and fees
Find vacation rentals that suit your style

Cabins

Aparthotels
Our top choices for Pittsfield apartments

1. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone DecorHancock
10.0 out of 10, Exceptional, (6 reviews)
$185 nightly
The price is $207
Nov 10 - Nov 11
Total with taxes and fees

2. 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 UpdatedHancock
10.0 out of 10, Exceptional, (6 reviews)
$185 nightly
The price is $207
Nov 10 - Nov 11
Total with taxes and fees

3. 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 DaltonDalton
9.8 out of 10, Exceptional, (35 reviews)
$262 nightly
The price is $292
Nov 10 - Nov 11
Total with taxes and fees

4. Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone DecorHancock
10.0 out of 10, Exceptional, (3 reviews)
$185 nightly
The price is $207
Nov 10 - Nov 11
Total with taxes and fees

5. Berkshires Apartment at the Stephentown Hotel
Berkshires Apartment at the Stephentown HotelStephentown
10.0 out of 10, Exceptional, (5 reviews)
$193 nightly
The price is $205
Nov 10 - Nov 11
Total with taxes and fees

6. 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 RedoneHancock
10.0 out of 10, Exceptional, (13 reviews)
$185 nightly
The price is $207
Nov 10 - Nov 11
Total with taxes and fees

7. 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 MtnHancock
9.4 out of 10, Exceptional, (19 reviews)
$185 nightly
The price is $207
Nov 10 - Nov 11
Total with taxes and fees

8. Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center
Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga CenterLenox
$264 nightly
The price is $295
Nov 10 - Nov 11
Total with taxes and fees

9. 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 InnHancock
9.8 out of 10, Exceptional, (25 reviews)
$185 nightly
The price is $207
Nov 10 - Nov 11
Total with taxes and fees

10. Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor
Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone DecorHancock
10.0 out of 10, Exceptional, (2 reviews)
$185 nightly
The price is $207
Nov 10 - Nov 11
Total with taxes and fees

11. Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views
Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn ViewsHancock
8.0 out of 10, Very good, (1 review)
$247 nightly
The price is $276
Nov 11 - Nov 12
Total with taxes and fees

12. 2 Bed Berkshire Apt minutes to Jiminy Peak Ski
2 Bed Berkshire Apt minutes to Jiminy Peak SkiStephentown
8.4 out of 10, Very good, (12 reviews)
$220 nightly
The price is $234
Nov 10 - Nov 11
Total with taxes and fees

13. Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain BaseHancock
9.6 out of 10, Exceptional, (33 reviews)
$185 nightly
The price is $207
Nov 10 - Nov 11
Total with taxes and fees

14. Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - GorgeousHancock
9.6 out of 10, Exceptional, (35 reviews)
$258 nightly
The price is $288
Nov 10 - Nov 11
Total with taxes and fees

15. Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4Hancock
9.8 out of 10, Exceptional, (9 reviews)
$185 nightly
The price is $207
Nov 10 - Nov 11
Total with taxes and fees

16. 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 CountHancock
9.4 out of 10, Exceptional, (6 reviews)
$185 nightly
The price is $207
Nov 10 - Nov 11
Total with taxes and fees

17. Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat
Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain RetreatHancock
9.8 out of 10, Exceptional, (21 reviews)
$185 nightly
The price is $207
Nov 10 - Nov 11
Total with taxes and fees

18. Ski On/Off Winter Mountain Suite Jiminy Peak-- Sleeps4- Home Away From Home
Ski On/Off Winter Mountain Suite Jiminy Peak-- Sleeps4- Home Away From HomeHancock
10.0 out of 10, Exceptional, (2 reviews)
$185 nightly
The price is $207
Nov 10 - Nov 11
Total with taxes and fees

19. Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and DowntownNorth Adams
8.0 out of 10, Very good, (2 reviews)
$190 nightly
The price is $212
Nov 15 - Nov 16
Total with taxes and fees

20. 1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone DecorHancock
8.8 out of 10, Excellent, (8 reviews)
$185 nightly
The price is $207
Nov 10 - Nov 11
Total with taxes and fees
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.
Learn more about Pittsfield
Nestled in the heart of the Berkshires, this cultural hub boasts the renowned Berkshire Museum and historic Colonial Theatre. Outdoor enthusiasts can hike nearby Pittsfield State Forest trails before exploring the vibrant downtown's farm-to-table restaurants and local art galleries.


































































































































