Book Holiday Homes in Pittsfield

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Pittsfield

Gorgeous 3BR 3BA Sleeps 10  Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Hancock
The price is AU$820 per night from 3 Nov to 4 Nov
AU$820
includes taxes & fees
3 Nov - 4 Nov
With a stay at this vacation home, you'll be centrally located in Hancock, within a 5-minute drive of Jiminy Peak Mountain Resort and Mountain Coaster.
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Amore Estate -  beautiful room with many places to explore and relax in.

Amore Estate - beautiful room with many places to explore and relax in.

Lenox
With a stay at this vacation home in Lenox, you'll be within a 10-minute drive of Tanglewood Music Center and Wyndhurst Golf & Club.
Amore Estate - beautiful room with many places to explore and relax in.
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

Valatie
Located in Valatie, this vacation home is on the waterfront, a 1-minute drive from Kinderhook Lake and 6 minutes from Valatie Family Care.
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!
Save an average of 15% on thousands of hotels when you're signed in
Secluded Family Home in Serene Stockbridge Woods

Secluded Family Home in Serene Stockbridge Woods

Stockbridge
Located in South Lee, this vacation home is in a rural location, within a 5-minute drive of Berkshire Botanical Garden and Housatonic River.
Secluded Family Home in Serene Stockbridge Woods
Spectacular views and close to Great Barrington.

Spectacular views and close to Great Barrington.

Great Barrington
Located in Great Barrington, this vacation home is within a 5-minute drive of Housatonic River and Housatonic River Walk.
Spectacular views and close to Great Barrington.
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

Lanesborough
The price is AU$339 per night from 11 Nov to 12 Nov
AU$339
includes taxes & fees
11 Nov - 12 Nov
Located in Lanesborough, this vacation home is in the mountains, within a 15-minute drive of Crane Museum of Papermaking and Berkshire Athenaeum.
Berkshire Village Carriage House - Super Private!!
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

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

Stockbridge
With a stay at this vacation home in West Stockbridge, you'll be within a 5-minute drive of Tanglewood Music Center and Berkshire Botanical Garden.
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!

Cozy Home In The Berkshires, Pet Friendly with fenced in yard!

Adams
A stay at this vacation home places you in the heart of Adams, steps from Mount Greylock State Reservation and 7 minutes by foot from East Hoosac Quaker ...
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi

4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi

East Otis
With a stay at this vacation home in Otis, you'll be on the waterfront, just steps from Otis Reservoir and a 4-minute drive from County Beach.
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
Don't see what you're looking for?
See all available properties in Pittsfield
View all properties
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.

Pittsfield Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Pittsfield vacation homes are the perfect way for you to wing it.

Holiday houses in Pittsfield let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Pittsfield in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Pittsfield adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Pittsfield with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Pittsfield vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Pittsfield Holiday Homes essential information

Accommodation
335 Holiday Homes
Lowest Price
AU$134
Highest Price
AU$820
Popular accommodation
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con, Amore Estate - beautiful room with many places to explore and relax in., Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!, Secluded Family Home in Serene Stockbridge Woods, Spectacular views and close to Great Barrington., Berkshire Village Carriage House - Super Private!!, Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country, Cozy Home In The Berkshires, Pet Friendly with fenced in yard!, 4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi

Top trending hotels in Pittsfield

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

3 out of 5
One West Street, Pittsfield, MA
Fully refundable
The price is AU$153 per night from 30 Nov to 1 Dec
AU$153
includes taxes & fees
30 Nov - 1 Dec
With a stay at Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel, you'll be centrally located in Pittsfield, within a 15-minute drive of Tanglewood Music ...
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is AU$134 per night from 4 Nov to 5 Nov
AU$134
includes taxes & fees
4 Nov - 5 Nov
Located in Pittsfield, FairBridge Inn Express is in the suburbs, a 4-minute drive from Crane Museum of Papermaking and 6 minutes from Berkshire Athenaeum.
FairBridge Inn Express
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundable
The price is AU$310 per night from 5 Nov to 6 Nov
AU$310
includes taxes & fees
5 Nov - 6 Nov
With a stay at Berkshire Mountain Lodge in Pittsfield, you'll be next to a golf course, within a 10-minute drive of Tanglewood Music Center and Guido's ...
Berkshire Mountain Lodge
Save an average of 15% on thousands of hotels when you're signed in
Hotel On North

Hotel On North

3.5 out of 5
297 North Street, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is AU$247 per night from 3 Nov to 4 Nov
AU$247
includes taxes & fees
3 Nov - 4 Nov
With a stay at Hotel On North in Pittsfield, you'll be within a 15-minute drive of Tanglewood Music Center and Berkshire Athenaeum.
Hotel On North
Don't see what you're looking for?
See all available properties in Pittsfield
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.