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

Pittsfield Vacation Rentals

Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

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, (1,086 reviews)
"A nice place to stay in the Berkshires."
United States
Robert
$125 nightly
The price is $139
Aug 31 - Sep 1
Total with taxes and fees
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 clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
$496 nightly
The price is $554
Aug 24 - Aug 25
Total with taxes and fees
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.
$1,060 nightly
The price is $1,149
Sep 9 - Sep 10
Total with taxes and fees
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, (2,553 reviews)
"Place was clean and well equipped, pool and amenities were great too !"
United States
Nyra
$108 nightly
The price is $121
Aug 26 - Aug 27
Total with taxes and fees
Vacation Village in the Berkshires
A bedroom with a wooden bed, a window with a view of trees, and a red chair.

5. Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway

Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway
Sand Lake
$183 nightly
The price is $203
Aug 23 - Aug 24
Total with taxes and fees
Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway
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, (31 reviews)
"This was a wonderful place to stay. We especially loved the easy access to the toys so the kids could start playing while we unloaded the car. It was perfect and just what we needed."
United States
Megan A.
$293 nightly
The price is $327
Aug 31 - Sep 1
Total with taxes and fees
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
A two-story blue house with a porch, surrounded by a garden with orange flowers.

7. Getaway Near Mass MoCA, Great Hiking, Scenic Views

Getaway Near Mass MoCA, Great Hiking, Scenic Views
Stamford
10.0 out of 10, Exceptional, (34 reviews)
"Perfect for our weekend getaway. Close to the activities we wanted in North Adams, Mass, but just across the state line in a lovely rural setting. A very nice apartment... just as described. So happy to have chosen this for our stay!"
United States
Bill
$128 nightly
The price is $143
Aug 24 - Aug 25
Total with taxes and fees
Getaway Near Mass MoCA, Great Hiking, Scenic Views
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

8. 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
$499 nightly
The price is $554
Aug 24 - Aug 25
Total with taxes and fees
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
A rustic wooden interior with various stalls selling items like books, snacks, and wine.

9. 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, (5 reviews)
"We had a great stay! The kids absolutely loved the room. Great location and lots to do. Thanks again!!"
United States
Jen B.
$220 nightly
The price is $245
Aug 25 - Aug 26
Total with taxes and fees
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
A lakeside picnic area with a bench and umbrella, surrounded by autumn-colored trees.

10. 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)
"Gorgeous place.Great stay.Will diff be backG"
United States
Gerard C.
$466 nightly
The price is $521
Aug 24 - Aug 25
Total with taxes and fees
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
A rustic wooden interior with various stalls selling items like books, snacks, and wine.

11. 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, (13 reviews)
"Staying right in the mountain was ideal. The condo was perfect. "
United States
patricia f.
$220 nightly
The price is $245
Aug 25 - Aug 26
Total with taxes and fees
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
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.
$212 nightly
The price is $237
Aug 25 - Aug 26
Total with taxes and fees
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

13. Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Hancock
9.6 out of 10, Exceptional, (35 reviews)
"Great and clean property! Very easy to access and good parking too."
United States
Todd A.
$305 nightly
The price is $341
Aug 23 - Aug 24
Total with taxes and fees
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Cherry Plain State Park with a sandy beach, people relaxing, and a lake.

14. 2 Bed Berkshire Apt minutes to Jiminy Peak Ski

2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Stephentown
8.4 out of 10, Very Good, (12 reviews)
"Great location and property. thank you"
United States
Christine P.
$279 nightly
The price is $297
Aug 23 - Aug 24
Total with taxes and fees
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

15. Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (4 reviews)
"Quiet location"
United States
Alicia S.
$220 nightly
The price is $245
Aug 25 - Aug 26
Total with taxes and fees
Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

16. 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)
"excellent communication with property manager."
United States
Nancy H.
$512 nightly
The price is $568
Aug 24 - Aug 25
Total with taxes and fees
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

17. Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Hancock
9.8 out of 10, Exceptional, (22 reviews)
"Great skiing and proximity to mountain. Great for families"
United States
John F.
$220 nightly
The price is $245
Aug 25 - Aug 26
Total with taxes and fees
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
A room with a sofa, a TV, a wooden floor, and a balcony with a view of trees.

18. Berkshires farm, 30+ guests, 50 acres

Berkshires farm, 30+ guests, 50 acres
New Lebanon
10.0 out of 10, Exceptional, (1 review)
$2,050 nightly
The price is $2,079
Sep 22 - Sep 23
Total with taxes and fees
Berkshires farm, 30+ guests, 50 acres
A two-story house with a front porch, surrounded by a garden with various plants and rocks.

19. Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (39 reviews)
"The house was lovely - my sisters and I had a wonderful time. Everything was warm and welcoming - it felt like home! We hope to make it an annual visit :)"
United States
Anonymous traveler
$846 nightly
The price is $945
Sep 20 - Sep 21
Total with taxes and fees
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
A patio with a wooden table and benches, a grill, and a garden with trees and flowers.

20. 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
$544 nightly
The price is $552
Sep 14 - Sep 15
Total with taxes and fees
NEW RENO Historic Creamery in Berkshires w/hot tub
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

FairBridge Inn Express

FairBridge Inn Express

10/10 Excellent
"It was very nice and everyone was extremely helpful"
ERICIA 1-night trip
Posted 4 hours ago
FairBridge Inn Express

Find out more about Pittsfield

Everything you need to know about Pittsfield vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Pittsfield vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pittsfield vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Pittsfield vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pittsfield. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Pittsfield in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $121 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Pittsfield rentals

At Expedia, we put the best Pittsfield vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Pittsfield rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pittsfield vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pittsfield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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: Visitors like this Pittsfield vacation home rental. It 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 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 Pontoosuc Lake and Housatonic River 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.