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.
Home in Canaan
5.0 out of 5 average rating, 132 reviewsCountry 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
Home in Lee
4.89 out of 5 average rating, 234 reviewsCozy 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
Cottage in Lanesborough
4.93 out of 5 average rating, 220 reviewsStone 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
Vacation rentals for every style
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Popular amenities for Pittsfield vacation rentals
Other great vacation rentals in Pittsfield
Apartment in Copake Falls
4.93 out of 5 average rating, 250 reviewsModern Copake Falls Getaway - 8 Mins to Catamount
Sep. 14 – 21
Guesthouse in Becket
4.93 out of 5 average rating, 257 reviewsCountry Cabin
May 5 – 12
Apartment in Pittsfield
4.92 out of 5 average rating, 24 reviewsComfortable Pittsfield Loft
Feb. 1 – 8
Apartment in Pittsfield
5.0 out of 5 average rating, 41 reviewsSimply off North
Sep. 23 – 30
Apartment in Pittsfield
4.81 out of 5 average rating, 16 reviewsCozy Studio Apt in Downtown Victorian
Apr. 17 – 24
Apartment in Pittsfield
4.86 out of 5 average rating, 42 reviewsThe Sunset Sanctuary - King Bed with Kitchen
Mar. 3 – 10
Apartment in Canaan
5.0 out of 5 average rating, 81 reviewsMountain View Getaway
Nov. 17 – 24
Home in Pittsfield
4.98 out of 5 average rating, 41 reviewsLake/Mountain View Getaway
Sep. 9 – 16
Apartment in Lanesborough
4.86 out of 5 average rating, 93 reviewsCozy Rustic Apt. in 18th c. Berkshire Farmhouse
Apr. 29 – May 6
Guesthouse in Pittsfield
4.98 out of 5 average rating, 46 reviewsThe Nest at Birdland
Jun. 3 – 10
Apartment in Pittsfield
4.8 out of 5 average rating, 70 reviewsCharming Apartment inThe Heart of The Berkshires 2
Apr. 26 – May 3
Home in Pittsfield
4.94 out of 5 average rating, 98 reviewsCantabile life in the Berkshires
May 9 – 16
Quick stats about vacation rentals in Pittsfield
Total rentals | 210 properties |
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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 |
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