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Vacation rentals in Pittsfield

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Pittsfield

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

Charming Apartment In Berkshire Victorian Home
Entire rental unit · 8 guests · 5 beds · 1.5 baths

Charming Apartment In Berkshire Victorian Home3rd Floor Penthouse Unit. This charming apartment is located in the heart of Pittsfield's Historical District in a beautiful Victorian Home. Enjoy looking out the beautiful stained glass windows original to the home dating back to 1899 or sitting out on the front stone terrace. Whether it is lounging on the rooftop deck, catching up with friends & family in the open kitchen/dining/living area, or reading a book in the office nook; there is a little special spot for everyone's needs!

Lavishly Appointed 2BR Apartment Home with Balcony
SUPERHOST
Entire rental unit · 4 guests · 2 beds · 1 bath

Lavishly Appointed 2BR Apartment Home with BalconyIndulge yourself with this sumptuously decorated and well equipped apartment suite. Cuddle up with a glass of wine for a movie night, whip up a great meal in a first rate kitchen, or curl up with a riveting book on a lush and exquisite vintage brass bed. For a breath of fresh air, go outside and listen to the rush of the river from your balcony or the courtyard garden. Whatever you decide, do it with us, the Ledgewood Team. We look forward to elevating your Airbnb experience.

Berkshires getaway: nature, culture & relaxation
Entire guest suite · 2 guests · 1 bed · 1 bath

Berkshires getaway: nature, culture & relaxationKing bed and birch beams rule this nature inspired space. You have sole access to a large deck where to enjoy the sounds and sights of nature and is perfect for morning coffee or wine at night. Skylights, sliding door, large windows as well as plenty of light fixtures will brighten up your stay. Radiant heat, 3 ceiling fans and A/C will keep you comfortable. We are surrounded by nature yet ten minutes from county’s largest supermarket and centrally located from all Berkshires’ cultural venues.

Vacation rentals for every style

Get the amount of space that is right for you.

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Popular amenities for Pittsfield vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Pittsfield

SUPERHOST
  1. Entire residential home
  2. Stephentown
Pet Friendly Studio
SUPERHOST
  1. Entire cottage
  2. Pittsfield
Berkshire Lakeview Tranquility
  1. Entire residential home
  2. Pittsfield
NEW to Berkshires! Hygge House on Richmond Pond
SUPERHOST
  1. Entire cottage
  2. Pittsfield
The Oliver Wendell Holmes Guesthouse @ Holmesdale
SUPERHOST
  1. Private room
  2. Pittsfield
Queen Room w/Private Bath in Quiet Berkshires Home
SUPERHOST
  1. Private room
  2. Pittsfield
Equestrian retreat
SUPERHOST
  1. Entire rental unit
  2. Pittsfield
One Bedroom in Downtown
SUPERHOST
  1. Entire residential home
  2. Pittsfield
Honeysuckle Rose Cottage
  1. Entire residential home
  2. Pittsfield
Beautiful 4 Bedroom HOME Berkshire getaway
  1. Entire residential home
  2. Lenox
Cheerful 3 bedroom house bordering state forest
  1. Private room
  2. Pittsfield
Cottage Oasis in the Heart of the Berkshires
SUPERHOST
  1. Entire cottage
  2. Lanesborough
The Sail Loft

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