Enjoy your stay and find the best Holiday homes in Pittsfield at affordable prices
Searching for a holiday home in Pittsfield (Massachusetts)? Explore a great selection of vacation homes in Pittsfield to find the one that best fits to your needs, starting from $101 per night. Holiday homes offer a relaxing escape, providing a cozy retreat for vacationers seeking a home away from home.
Holiday home in Lenox near Pittsfield, Massachusetts
Located in Lenox, within 8.5 km of Tanglewood and 8.8 km of Cranwell Spa & Golf Club, Charming Lenox Home View of October Mountain offers accommodatio...
Holiday home in Lenox near Pittsfield, Massachusetts
Located in Lenox, 5.6 km from Tanglewood and 5.9 km from Cranwell Spa & Golf Club, Beautiful Lenox Home, 3 Mi to Shakespeare and Co! provides accommod...
Holiday home in Lenox near Pittsfield, Massachusetts , 76 East Dugway Road
Located in Lenox, 5.2 km from Tanglewood and 5.5 km from Cranwell Spa & Golf Club, Restored 1881 Farm House provides air-conditioned accommodation wit...
Holiday home in Hancock near Pittsfield, Massachusetts , 37 Corey Road
Within 33 km of Tanglewood and 33 km of Cranwell Spa & Golf Club, Unique Yeti-Theme Ski On Off Suite Jiminy-Sleeps 4 features free WiFi and a fitness ...
Holiday home in Hancock near Pittsfield, Massachusetts , 37 Corey Road
Within 33 km of Tanglewood and 33 km of Cranwell Spa & Golf Club, Deluxe Ski On Off 1BR Suite Sleeps 4 on Jiminy Mtn features free WiFi and a fitness ...
Holiday home in Hancock near Pittsfield, Massachusetts , Corey Road 37
Within 33 km of Tanglewood and 33 km of Cranwell Spa & Golf Club, Gorgeous New Zen Suite Sleeps 4-Ski On Off Jiminy provides free WiFi and a fitness c...
Holiday home in Hancock near Pittsfield, Massachusetts , Corey Road 37
Within 33 km of Tanglewood and 33 km of Cranwell Spa & Golf Club, WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk features free WiFi and a fitness ...
Holiday home in Hinsdale near Pittsfield, Massachusetts
Located 32 km from Cranwell Spa & Golf Club, 32 km from Tanglewood Musical Center and 40 km from Norman Rockwell Museum, Picturesque Cottage with Sunr...
Holiday home in Stockbridge near Pittsfield, Massachusetts
Stockbridge Home - Walk to Lakefront Beach! is situated in Stockbridge, 3.9 km from Tanglewood, 5.7 km from Cranwell Spa & Golf Club, and 6.5 km from ...
Holiday home in Hancock near Pittsfield, Massachusetts
Situated in Hancock, 34 km from Tanglewood and 34 km from Cranwell Spa & Golf Club, Hancock Log Cabin Retreat 2 Miles to Jiminy Peak! provides accommo...
Holiday home in Stockbridge near Pittsfield, Massachusetts
Set in Stockbridge, 4.7 km from Tanglewood Musical Center and 5.1 km from Norman Rockwell Museum, Cozy Stockbridge Cabin - Walk to Beach and Lake! pro...
Holiday home in Stockbridge near Pittsfield, Massachusetts
Tranquil 3BR Stockbridge House with Private Deck! is situated in Stockbridge, 8.5 km from Tanglewood Musical Center, 9.1 km from Tanglewood, and 14 km...
Holiday home in Adams near Pittsfield, Massachusetts
Charming Adams Home Near Dtwn, Trails and More! is situated in Adams, 37 km from Cranwell Spa & Golf Club, 37 km from Tanglewood Musical Center, and 4...
Holiday home in Becket near Pittsfield, Massachusetts
Berkshires Home on 11 Acres with Pond and 2 Fire Pits! is located in Becket, 22 km from Cranwell Spa & Golf Club, and provides a patio, garden, and fr...
Holiday home in Otis near Pittsfield, Massachusetts
Berkshires Cabin 2 Mi to Appalachian Trail! is located in Otis, 21 km from Cranwell Spa & Golf Club, 25 km from Tanglewood, as well as 26 km from Tang...
Holiday home in Great Barrington near Pittsfield, Massachusetts
Offering lake views, Lakefront Berkshires Retreat with Deck, Dock and Boat! is an accommodation set in Great Barrington, 8.3 km from Norman Rockwell M...
Holiday home in Monterey near Pittsfield, Massachusetts
Set 22 km from Norman Rockwell Museum, 24 km from Tanglewood and 25 km from Tanglewood Musical Center, Cozy Monterey Home with Porch Walk to Lake Garf...
Holiday home in Williamstown near Pittsfield, Massachusetts , 111 North Street
North Getaway Cottage is situated in Williamstown, 46 km from Tanglewood, 46 km from Cranwell Spa & Golf Club, as well as 46 km from Tanglewood Musica...
Holiday home in Charlemont near Pittsfield, Massachusetts
Set in Charlemont, within 43 km of The Clark Art Institute, Charlemont Outdoor Retreat on the Chickley River! offers accommodation with free WiFi and ...
Holiday home in Great Barrington near Pittsfield, Massachusetts
Located in Great Barrington, 18 km from Norman Rockwell Museum, 22 km from Cranwell Spa & Golf Club and 23 km from Tanglewood Musical Center, Cozy Gre...
The most popular Holiday-homes in Pittsfield based on average guest rating (Top 10).
Cheapest Holiday-homes in Pittsfield
The cheapest Holiday-homes in Pittsfield based on room rate per night (Top 10).
Most booked Holiday-homes in Pittsfield
The most booked Holiday-homes in Pittsfield based on popularity with guests (Top 10).
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