Search for vacation rentals in Pittsfield.

Whether it's vacation home rentals, apartments, condos, or cabins/cottages, we have you covered -- search for rental properties in the entire Pittsfield area to find the perfect spot for your vacay.

107 Hungerford St
	107 Hungerford St Pittsfield, MA $2,000 Vacation Rentals, Unknown  NEW! Lovely single family home in a quiet/friendly neighborhood in the "Stearns" or "Reid" or THS School District. Minutes from Downtwn Pittsfield...

Wealthy Ave
	Wealthy Ave Pittsfield, MA $1,875 Vacation Rentals, Unknown 3 Bedroom 1 Bathroom Washer and Dryer Included Available Furnished or Unfurnished New Dishwasher New Carpeting in Living room Contact Agent for Showings and additional photos. Rental Application......

Pinto Dr
	Pinto Dr Pittsfield, MA $3,000 Vacation Rentals, Unknown Wonderful, spacious family home in a prestigious private neighborhood. Split level with curb appeal, lovingly cared for, and maintained. Freshly painted with excellent appliances and new carpet.......

16 Garland Ave
	16 Garland Ave Pittsfield, MA $2,400 Vacation Rentals, Unknown Beautiful open floor plan, large kitchen with an island. Sliders to large deck, enclosed bac yard. Plenty of off street parking. Large master bedroom with En-suite bathroom and walk-in closet.......

37 Anita Dr
	37 Anita Dr Pittsfield, MA $2,500 Vacation Rentals, Unknown Super cute, newly renovated kitchen, granite countertops, new sink, faucet, window and tiled backsplash. Very private, nice size yard completely fenced in, attached garage. No dogs, first, last,......

34 Ashley St
	34 Ashley St Pittsfield, MA $2,500 Vacation Rentals, Unknown Super cute, newly renovated kitchen, granite countertops, new sink, faucet, window and tiled backsplash. Very private, nice size yard completely fenced in, attached garage. No dogs, first, last,......

273 Wahconah St
	273 Wahconah St Pittsfield, MA $1,200 Vacation Rentals, Unknown Apartment for rent at 273 Wahconah st. Pittsfield ,Ma .Corner of Pecks rd and Wahconan st . 2 bedrooms ,kitchen ,dining room ,living room ,bathroom .Second floor .Not de-leaded .Available April 1.......

28 4th St #28
	28 4th St #28 Pittsfield, MA $1,500 Vacation Rentals, Unknown 2-Bedroom/1-bath apartment located right around the corner from Pittsfield High School within walking distance to local restaurants, Dunkin Donuts, Urgent Care Center, RMV, Post Office, and much......

9 Stearns Ave
	9 Stearns Ave Pittsfield, MA $1,950 Vacation Rentals, Unknown Beautiful Piece of Property - Central yet Private Easy commute to Pittsfield, Lenox, Albany or Great Barrington Plenty of privacy with your own yard Includes attached garage with a loft space......

275B Bradford St
	275B Bradford St Pittsfield, MA $1,450 Vacation Rentals, Unknown 3 Bed, 1 Bath apartment located on Bradford St. Section 8 is welcomed. Tenant will pay gas and electric. First month and $1,450 security deposit due at move in. Available March 1. Message me with......

158 Windsor Ave
	158 Windsor Ave Pittsfield, MA $2,700 Vacation Rentals, Unknown Ranch style house for rent with all the amenities, in a beautiful, quiet and family friendly neighborhood, close to schools and shopping. Main level has a renovated kitchen with a sitting area, 2......

526 Pecks Rd
	526 Pecks Rd Pittsfield, MA $2,400 Vacation Rentals, Unknown Berkshire Farmhouse. Freshly painted lovely home, unfurnished. Two bedrooms, office space, and bathroom upstairs, living, dining , kitchen, and bath downstairs. New washer/dryer, nice closets. New......

36 4th St
	36 4th St Pittsfield, MA $1,395 Vacation Rentals, Unknown First floor 2-Bedroom/1-bath apartment located right around the corner from Pittsfield High School within walking distance to local restaurants, Dunkin Donuts, Urgent Care Center, RMV, Post Office,......

32 4th St
	32 4th St Pittsfield, MA $1,425 Vacation Rentals, Unknown 2-Bedroom/1-bath apartment located right around the corner from Pittsfield High School within walking distance to local restaurants, Dunkin Donuts, Urgent Care Center, RMV, Post Office, and much......

31 Buel St
	31 Buel St Pittsfield, MA $1,200 Vacation Rentals, Unknown Available 3/1/2024 Bright studio apartment for rent. South street area, Pittsfield, Ma. Close to downtown. Kitchen, bath, - living and bedroom are combined. Looking for a quiet professional. Must......

44 John St
	44 John St Pittsfield, MA $1,600 Vacation Rentals, Unknown 4 Bedroom Unit right next to Durant Park! Section 8 is welcomed. The unit is freshly painted and spruced up, and ready for move in November 1st. Comes with washer and dryer hook ups, and an......

24 4th St #30
	24 4th St #30 Pittsfield, MA $1,450 Vacation Rentals, Unknown First floor 2-Bedroom/1-bath apartment located right around the corner from Pittsfield High School within walking distance to local restaurants, Dunkin Donuts, Urgent Care Center, RMV, Post Office,......

138 Pine Grove Dr
	138 Pine Grove Dr Pittsfield, MA $2,925 Vacation Rentals, Unknown BEAUTIFUL SINGLE FAMILY HOUSE FOR RENT. This recently remodeled home located on a dead end street in the highly desired South West corner of Pittsfield is move-in ready and perfect for a small......

100 Cummings Ave
	100 Cummings Ave Pittsfield, MA $2,100 Vacation Rentals, Unknown Great Berkshire entire home with fenced in yard, full deck and screened patio for lease. Pets welcome (w/$250 non-refundable deposit). 2BR/1BA furnished living room, Master Bedroom and Kitchen......

2 Maple Ln
	2 Maple Ln Pittsfield, MA $2,100 Vacation Rentals, Unknown The house is fully furnished (utilized as AirBnB in summer). It is situated on a corner lot of a nice residential neighborhood. You can walk to Brattle Brook Park in 5 mins, which has beautiful......

109 Plumb St
	109 Plumb St Pittsfield, MA $2,200 Vacation Rentals, Unknown Great single family cottage home in south western Pittsfield. This fully furnished home comes with clean, comfortable cottage furnishings and hosts many new features such as refinished hard wood......

50 Cleveland St
	50 Cleveland St Pittsfield, MA $3,000 Vacation Rentals, Unknown Cute single family 3 bedroom 1.5 bath home on large double lot. Quiet dead end street. Freshly painted interior with Washer/Dryer hook-ups. One car detached garage....

341 Tamarack Rd
	341 Tamarack Rd Pittsfield, MA $3,100 Vacation Rentals, Unknown This single-family home is located on a dead-end street in Berkshire County. The private home features hardwood floors throughout with a large open concept for your everyday needs. The custom......

31 Courtland Pl
	31 Courtland Pl Pittsfield, MA $1,800 Vacation Rentals, Unknown This 3 bedroom, 1 bathroom spacious apartment boasts lots of natural light and comes equipped with a washer and dryer. The kitchen comes with a stove and refrigerator. 1 Off street parking spot.......

100 Brown St
	100 Brown St Pittsfield, MA $650 Vacation Rentals, Unknown Private room full furnished with refrigerator in room, sharing bathroom, living room and kitchen. Room has nice new carpet and big closet....

96 Melbourne Rd
	96 Melbourne Rd Pittsfield, MA $1,900 Vacation Rentals, Unknown Welcome to 96 Melbourne. An adorable home, nestled on the outskirts of Pittsfield with easy access to the main roadways. Close proximity to Berkshire Community College and the towns of Lee, Lenox......

273 2nd St
	273 2nd St Pittsfield, MA $650 Vacation Rentals, Unknown Month to Month rental, first and last required to move in, heat hot water & electric included access common bathroom kitchen dinning & living....

256 Wahconah St #1
	256 Wahconah St #1 Pittsfield, MA $1,700 Vacation Rentals, Unknown Just rehabbed! 3 Bedroom-1 Bath, Apartment located in a friendly, quiet neighborhood, with off street parking, and conveniently located near downtown Pittsfield and Berkshire Medical center. This......

47 Fort Hill Ave
	47 Fort Hill Ave Pittsfield, MA $1,735 Vacation Rentals, Unknown Welcome to Fort hill. An adorable home, nestled on the outskirts of Pittsfield with easy access to the main roadways. Close proximity to Berkshire Community College and the towns of Lee, Lenox and......

40 Fort Hill Ave
	40 Fort Hill Ave Pittsfield, MA $2,345 Vacation Rentals, Unknown Welcome to Fort Hill. An adorable home, nestled on the outskirts of Pittsfield with easy access to the main roadways. Close proximity to the towns of Lee, Lenox and Richmond, with views of the......

273 2nd St
	273 2nd St Pittsfield, MA $600 Vacation Rentals, Unknown Month to Month rental, first and last required to move in, heat hot water & electric included access common bathroom kitchen dinning & living....

Berkshire Ave
	Berkshire Ave Pittsfield, MA $1,750 Vacation Rentals, Unknown Beautiful large single family home for rent on a dead end street with lots of land to enjoy. It's 2 bed and 1 bath. Beautiful neighborhood and friendly neighbors. Only few blocks away from......

51 Boylston St
	51 Boylston St Pittsfield, MA $1,200 Vacation Rentals, Unknown Half Duplex, contains 6 rooms ( 3 bedrooms), one bath, pantry, freshly painted, hardwood floors, off street parking. Stove, Refrigerator and Washer, Dryer included. Basement and attic for storage.......

125 Mountain Dr
	125 Mountain Dr Pittsfield, MA $3,300 Vacation Rentals, Unknown **Video tour available on Youtube! Search 125 Mountain Drive, Pittsfield** 8 month lease, available now until June 1 with option to renegotiate going forward. House is partially furnished, option......

36 Flintstone Dr
	36 Flintstone Dr Pittsfield, MA $2,800 Vacation Rentals, Unknown Lovely ranch available for 6 month lease in a quiet, highly sought-after southeast Pittsfield neighborhood. This neat as a pin home features 3 bedrooms, 2 full baths, kitchen, dining room and......

98 Plunkett St
	98 Plunkett St Pittsfield, MA (Contact seller for price) Vacation Rentals, Unknown This fully furnished dream home is available for move-in October 1st. This beautiful property features 3 bedrooms, 1 bathroom along with an attached in-law suite. The in-law suite features 1......

162 Woodlawn Ave #1
	162 Woodlawn Ave #1 Pittsfield, MA $1,150 Vacation Rentals, Unknown Cozy 1 bedroom apartment. Pets considered.Vouchers welcome. Heat and hot water included....