Pittsfield holiday rentals

We found 149 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Pittsfield to find one that's perfect for your trip. Holiday rentals provide the best amenities for you and your friends, family or even pets, such as Wi-Fi and a pool. What you'll find is a property to rent that has what everyone needs, including options that are accessible or non-smoking.

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  • More quality time

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  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Choose a holiday rental for your Pittsfield getaway

Learn about the unique charm of Pittsfield with a stay in a holiday home rental. This city has something for everyone. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in Pittsfield

Are you searching for attractions to see in the city? Venture out of your cosy holiday rental and check out everything that makes Pittsfield a fun spot to go on holiday. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Unadilla Motocross (5.9 mi / 9.5 km)
  • Barnyard Swing Miniature Golf (16 mi / 25.8 km)
  • Cooperstown Brewing Company (17 mi / 27.4 km)
  • Leatherstocking Golf Course (18.3 mi / 29.4 km)
  • Rustic Ridge Winery (9 mi / 14.5 km)
  • Canasawacta Country Club (14.4 mi / 23.2 km)

Exploring the natural features in Pittsfield

Whether you're an adventurous traveller or just want to take in the scenery, you'll be sure to find the perfect setting for your holiday in Pittsfield. Here are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Gilbert Lake State Park (7.7 mi / 12.4 km)
  • Cooperstown Dreams Park (15.8 mi / 25.4 km)
  • Otsego Lake (21.2 mi / 34.2 km)
  • Goodyear Lake (16.4 mi / 26.4 km)
  • Canadarago Lake (18.8 mi / 30.3 km)
  • Rogers Environmental Education Center (13.1 mi / 21.2 km)

Frequently asked questions

What is the best area to stay in Pittsfield when booking a holiday rental?
When considering a holiday rental in Pittsfield, New York, a fantastic area to stay is downtown Pittsfield itself. This vibrant neighbourhood is not only conveniently located but also steeped in history and culture. Here, you can explore the renowned Barrington Stage Company, which offers an array of theatrical performances, and the Berkshire Museum, which features a fascinating collection of art, science, and history exhibits.The downtown area is home to a variety of properties, ranging from charming historic homes to modern apartments, making it an appealing choice for different types of travellers. Additionally, the picturesque parks, such as the nearby Springside Park, provide ample opportunities for outdoor activities and leisurely strolls.
When is the best time to visit Pittsfield for a holiday rental?
The peak season for visiting Pittsfield is from July to September, with August standing out as the most popular month for holiday rentals. During this vibrant period, visitors can engage in a variety of outdoor activities, enjoy local festivals, and explore the stunning landscapes of the Berkshires. The warm summer days, typically ranging from 20 to 30 degrees Celsius, provide an inviting climate for hiking, boating, and sightseeing.August is particularly lively, as families and adventure seekers flock to the area. This month offers a fantastic mix of cultural events, art exhibits, and outdoor concerts, making it an excellent choice for those looking to engage with the local community and enjoy the region's rich heritage.For those seeking a more budget-friendly option, consider planning your visit in February. While this month is quieter, it offers a unique charm with opportunities for winter sports such as skiing and snowshoeing, as well as the chance to experience Pittsfield's peaceful winter landscape.Ultimately, the best time to book a holiday rental in Pittsfield depends on whether you prefer the bustling energy of summer or the tranquil beauty of winter.
What are the top attractions in Pittsfield?
In Pittsfield, visitors can enjoy a blend of cultural and natural attractions. The Berkshire Museum, located in the downtown area, showcases a variety of art, science, and history exhibits, making it a great stop for those interested in local heritage. Nearby, the historic Colonial Theatre often hosts performances and events, providing a taste of the local arts scene.For outdoor enthusiasts, the nearby Pittsfield State Forest offers miles of hiking trails, superb for exploring the area's natural beauty. The forest is ideal for activities such as hiking, birdwatching, and enjoying scenic views, particularly during the autumn foliage season.In the heart of the city, visitors can stroll through the vibrant downtown area, where local shops and restaurants add to the charming atmosphere. The nearby Berkshire Botanical Garden in Stockbridge is also worth a visit, featuring beautifully landscaped gardens and educational programs.
Are all fees included in the Pittsfield holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Pittsfield holiday homes with parking?
Stayz offers a wide selection of holiday homes in Pittsfield with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Pittsfield holiday homes?
You can find great discounts on holiday homes in Pittsfield on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Pittsfield holiday home booking on Stayz?
To find Pittsfield holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Pittsfield?
A long-stay holiday home in Pittsfield is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Pittsfield holiday home?
Book your Pittsfield holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Pittsfield?
Prices for holiday homes in Pittsfield vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Pittsfield to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.