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Holiday homes in Pittsfield You’ll Love

Top-Rated Pittsfield Holiday homes for Every Budget and Style!

Looking for a holiday home in Pittsfield (Massachusetts)? Browse a wide range of vacation rentals – from cozy retreats to spacious family homes – starting at just $51.00 per night. Whether you are planning a weekend getaway or a longer stay, you will find the perfect home away from home in the heart of Pittsfield.

We found 12 Holiday-homes in Pittsfield and the surrounding area (within 40 miles)

Restored 1881 Farm House in Lenox, USA

Restored 1881 Farm House

Holiday home in Lenox near Pittsfield, Massachusetts , 76 East Dugway Road
Restored 1881 Farm House offers accommodations in Lenox, 8.6 miles from Norman Rockwell Museum and 26 miles from The Clark Art Institute.
  • Pets allowed
  • Family rooms

Exceptional 5 Reviews 9.8

from $326.15 Show details »

Beautiful Lenox Home, 3 Mi to Shakespeare and Co! in Lenox, USA

Beautiful Lenox Home, 3 Mi to Shakespear...

Holiday home in Lenox near Pittsfield, Massachusetts
Beautiful Lenox Home, 3 Mi to Shakespeare and Co! offers accommodations in Lenox, 3.7 miles from Cranwell Spa & Golf Club and 3.7 miles from Tanglewoo...
  • Parking
  • Spa and wellness centre

Very good 4 Reviews 8.0

from $409.57 Show details »

Lenox House with Screened Patio and Mountain View in Lenox, USA

Lenox House with Screened Patio and Moun...

Holiday home in Lenox near Pittsfield, Massachusetts
Lenox House with Screened Patio and Mountain View offers accommodations in Lenox, 5.3 miles from Tanglewood and 5.5 miles from Cranwell Spa & Golf Clu...
  • Parking
  • Pets allowed
  • Spa and wellness centre
  • Outdoor pool
  • Swimming pool

no reviews

from $236.17 Show details »

Richmond Cottage with Fire Pit and Furnished Deck! in Richmond, USA

Richmond Cottage with Fire Pit and Furni...

Holiday home in Richmond near Pittsfield, Massachusetts
Richmond Cottage with Fire Pit and Furnished Deck! is located in Richmond, just 6.8 miles from Tanglewood and 10 miles from Norman Rockwell Museum.
  • Parking

no reviews

from $82.00 Show details »

Family-Friendly Richmond Cottage with Private Yard in Pittsfield, USA

Family-Friendly Richmond Cottage with Pr...

Holiday home in Pittsfield, Massachusetts
Family-Friendly Richmond Cottage with Private Yard is located in Pittsfield, just 6.7 miles from Tanglewood Musical Center and 7.1 miles from Tanglewo...
  • Parking
  • Pets allowed

Fabulous 1 Reviews 9.0

from $88.00 Show details »

6 Mi to Skiing Pet-Friendly Home in Pittsfield! in Pittsfield, USA

6 Mi to Skiing Pet-Friendly Home in Pitt...

Holiday home in Pittsfield, Massachusetts
6 Mi to Skiing Pet-Friendly Home in Pittsfield! is located in Pittsfield, just 9.3 miles from Tanglewood and 9.4 miles from Cranwell Spa & Golf Club.
  • Parking
  • Pets allowed

no reviews

from $240.16 Show details »

Berkshire Vacation Rentals: Chic Pittsfield Home With A View in Pittsfield, USA

Berkshire Vacation Rentals: Chic Pittsfi...

Holiday home in Pittsfield, Massachusetts , Tamarack Road 35
Berkshire Vacation Rentals: Chic Pittsfield Home With A View is located in Pittsfield, just 7.1 miles from Tanglewood and 7.3 miles from Cranwell Spa ...
  • Parking
  • Pets allowed

Good 2 Reviews 7.5

from $344.78 Show details »

Spacious Historic Home in the Berkshires! in Pittsfield, USA

Spacious Historic Home in the Berkshires...

Holiday home in Pittsfield, Massachusetts
Spacious Historic Home in the Berkshires! is located in Pittsfield, just 7.6 miles from Tanglewood and 7.8 miles from Cranwell Spa & Golf Club.
  • Parking
  • Pets allowed

Fabulous 1 Reviews 9.0

from $399.14 Show details »

Pittsfield Home with Deck - 12 Mi to Jiminy Peak! in Pittsfield, USA

Pittsfield Home with Deck - 12 Mi to Jim...

Holiday home in Pittsfield, Massachusetts
Pittsfield Home with Deck - 12 Mi to Jiminy Peak! is located in Pittsfield, just 12 miles from Tanglewood and 12 miles from Cranwell Spa & Golf Club.
  • Parking

Fabulous 1 Reviews 9.0

from $299.83 Show details »

Lake Views and Dock Access - Pittsfield Cottage! in Pittsfield, USA

Lake Views and Dock Access - Pittsfield...

Holiday home in Pittsfield, Massachusetts
Lake Views and Dock Access - Pittsfield Cottage! is located in Pittsfield, just 12 miles from Cranwell Spa & Golf Club and 12 miles from Tanglewood Mu...
  • Parking

no reviews

from $358.18 Show details »

Lakeside Berkshires Home Near Hiking and Skiing! in Lanesborough, USA

Lakeside Berkshires Home Near Hiking and...

Holiday home in Lanesborough near Pittsfield, Massachusetts
Lakeside Berkshires Home Near Hiking and Skiing! is located in Lanesborough, just 12 miles from Tanglewood and 12 miles from Cranwell Spa & Golf Club.
  • Parking
  • Spa and wellness centre

no reviews

from $51.00 Show details »

Berkshire Mountain Lodge in Pittsfield, USA

Berkshire Mountain Lodge

Lodge in Pittsfield, Massachusetts , 8 Dan Fox Drive
Featuring an indoor swimming pool and a fitness center, Berkshire Mountain Lodge is located in Pittsfield.
  • Parking
  • Sauna
  • Fitness centre
  • Family rooms
  • Indoor pool

Very good 668 Reviews 8.5

from $95.40 Show details »

Number of Holiday homes in Pittsfield 12
Number of guest ratings 2,445
Average price per night $364.00
Lowest price per night $51,00
Highest price per night $4.626,94

Top 10 Cheapest Holiday-homes in Pittsfield

Discover the Cheapest Holiday-homes in Pittsfield – Ranked by Lowest Nightly Rates.

Top 10 Most Booked Holiday-homes in Pittsfield

Check out the Most Booked Holiday-homes in Pittsfield – Based on Guest Popularity.

Holiday homes in Pittsfield (Massachusetts), comfortable and familiar

Staying in a holiday or vacation home in Pittsfield can be a great alternative to a hotel or resort. They can range from small cottages to luxurious villas, and are often located in popular tourist destinations such as beaches or mountains. One of the main benefits is the privacy and flexibility that comes with having your own space. Unlike a hotel room, a holiday home provides you with a living area, kitchen, and sometimes even outdoor space, allowing you to cook your own meals, relax in comfort, and enjoy the company of your friends or family without the interruptions of other guests.

Holiday homes often offer more space than a hotel room. This can be particularly useful for families or groups of friends traveling together, who may need more than one room or want to avoid the cramped feeling of a single hotel room. They can also provide a more authentic travel experience, allowing guests to immerse themselves in the local culture and lifestyle. This can be particularly appealing for those who prefer to stay in quieter, residential areas away from the hustle and bustle of tourist hotspots.

Find the best Holiday home in Pittsfield for your needs

Holiday homes should offer a comfortable and enjoyable stay, providing all the necessary amenities and conveniences to make your vacation experience memorable. At a minimum, your holiday home in Pittsfield should offer a clean and well-maintained living space with comfortable furnishings, adequate lighting, and climate control.

In addition to basic amenities such as a fully equipped kitchen, comfortable bedding, and clean linens and towels, holiday homes should also offer modern conveniences such as Wi-Fi, cable or streaming TV, and laundry facilities. A private outdoor space, such as a balcony or terrace, can also add to the overall enjoyment. They can also offer additional features such as a swimming pool, hot tub, or outdoor grill. Location is also important, for example, close to popular tourist attractions, restaurants and shopping areas.

Accommodation data and pictures provided by Booking.com