Vacation rentals in Pittsfield

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Top-rated vacation rentals in Pittsfield

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite

Home in Canaan

5.0 out of 5 average rating, 132 reviews

Country Cottage

Quiet, peaceful cottage nestled on country road w/pond & stream. Located minutes from all season activites; lakes, concerts, theatre, horseracing, VT, MA, skiing, hiking,botanical garden, Tanglewood, Mass Moca, Mt. Greylock & more. Visit local Shaker round barn or simply barbeque on deck & enjoy the woods, flowers, wildlife & nature. Cottage has fully equipped kitchen. Local village has convenience store & Restaurants. Large grocery stores 15-20 mi Vehicle is vital for exploring the area.

Mar. 12 – 19

$209 CAD per night
Guest favourite

Home in Lee

4.89 out of 5 average rating, 234 reviews

Cozy Berkshires Cottage

Stay in a cozy Berkshires 1920's cottage! The bedroom occupies the entire second floor with peaceful views of the surrounding field and yard. The cottage is set back from the main road, easily accessible yet private. - Zoned air conditioning & heating makes every room comfortable year-round. - Close to Tanglewood, Jacob's Pillow, Outlet Mall, Kripalu, Turnpike. - Ideal for couples, solo adventurers, business travelers, and furry friends (pets). (Note: MA requires 11.7% tax added to charges)

Sep. 13 – 20

$210 CAD per night
Guest favourite

Cottage in Lanesborough

4.93 out of 5 average rating, 220 reviews

Stone School Cottage

Romantic getaway or family vacation. Charming stone building served as a one-room schoolhouse from 1832 until 1950. Beautifully situated amidst horse farms on the scenic road to Mt Greylock, centrally located midway between Williamstown and Lenox. We host lots of writers and musicians who love the bright airy space, families that have fun in this big playhouse, and couples seeking a memorable and private retreat. PLEASE NOTE: this truly-unique building has an unusual layout, described below.

Apr. 14 – 21

$274 CAD per night

Popular amenities for Pittsfield vacation rentals

Stay near Pittsfield's top sights

Walmart9 locals recommend
Big Y World Class Market80 locals recommend
Berkshire Roots7 locals recommend
99 Restaurants7 locals recommend
Colonial Theatre56 locals recommend
Berkshire Museum102 locals recommend

Other great vacation rentals in Pittsfield

Guest favourite

Apartment in Copake Falls

4.93 out of 5 average rating, 250 reviews

Modern Copake Falls Getaway - 8 Mins to Catamount

Sep. 14 – 21

$178 CAD per night
Guest favourite

Guesthouse in Becket

4.93 out of 5 average rating, 257 reviews

Country Cabin

May 5 – 12

$187 CAD per night
Guest favourite

Apartment in Pittsfield

4.92 out of 5 average rating, 24 reviews

Comfortable Pittsfield Loft

Feb. 1 – 8

$124 CAD per night
Guest favourite

Apartment in Pittsfield

5.0 out of 5 average rating, 41 reviews

Simply off North

Sep. 23 – 30

$134 CAD per night
Superhost

Apartment in Pittsfield

4.81 out of 5 average rating, 16 reviews

Cozy Studio Apt in Downtown Victorian

Apr. 17 – 24

$134 CAD per night
Superhost

Apartment in Pittsfield

4.86 out of 5 average rating, 42 reviews

The Sunset Sanctuary - King Bed with Kitchen

Mar. 3 – 10

$108 CAD per night
Guest favourite

Apartment in Canaan

5.0 out of 5 average rating, 81 reviews

Mountain View Getaway

Nov. 17 – 24

$157 CAD per night
Guest favourite

Home in Pittsfield

4.98 out of 5 average rating, 41 reviews

Lake/Mountain View Getaway

Sep. 9 – 16

$325 CAD per night
Guest favourite

Apartment in Lanesborough

4.86 out of 5 average rating, 93 reviews

Cozy Rustic Apt. in 18th c. Berkshire Farmhouse

Apr. 29 – May 6

$229 CAD per night
Guest favourite

Guesthouse in Pittsfield

4.98 out of 5 average rating, 46 reviews

The Nest at Birdland

Jun. 3 – 10

$290 CAD per night
Guest favourite

Apartment in Pittsfield

4.8 out of 5 average rating, 70 reviews

Charming Apartment inThe Heart of The Berkshires 2

Apr. 26 – May 3

$195 CAD per night
Guest favourite

Home in Pittsfield

4.94 out of 5 average rating, 98 reviews

Cantabile life in the Berkshires

May 9 – 16

$289 CAD per night

Quick stats about vacation rentals in Pittsfield

Total rentals

210 properties

Rentals with a pool

20 properties have a pool

Pet-friendly rentals

70 properties allow pets

Family-friendly rentals

110 properties are a good fit for families

Total number of reviews

6.9K reviews

Nightly prices starting at

$14 CAD before taxes and fees

Destinations to explore