Pittsfield holiday lettings

We found 805 holiday rentals — enter your dates for availability

Discover a selection of 29 homes and other holiday rentals in Pittsfield that are perfect for your trip. Whether you’re staying in a holiday home with friends, family or just with your pet, you'll find the amenities that you need and want, which might include parking and a fireplace. Whatever you're looking for, you're sure to find a property to rent for everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts - Pittsfield

Showing deals for:22 May - 29 May

Image gallery for South View Chalet!

Exterior
9.4 out of 10, Exceptional, (28 reviews)
Exceptional
(28 reviews)

South View Chalet!

Killington

8% off
Price is £13,310
for 7 nights, 1 chalet
£1,901 per night
includes taxes & fees
South View Chalet!

Find spaces that suit your style

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  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

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The friendly city of Pittsfield awaits you

Learn about the unique charm of Pittsfield with a stay in a holiday home rental. This welcoming city attracts visitors thanks to its bars and restaurants. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities and attractions in and around Pittsfield

Are you looking for top things to see and do in the area? Venture out of your holiday home and check out everything that makes Pittsfield a one-of-a-kind holiday spot. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Pico Mountain at Killington Ski Resort (8.6 mi / 13.8 km)
  • Killington Golf Course (10 mi / 16.1 km)
  • Killington Resort (10.1 mi / 16.2 km)
  • Saskadena Six Ski Area (15.3 mi / 24.6 km)
  • Rikert Nordic Center (15.4 mi / 24.8 km)
  • Green Mountain National Golf Course (5.4 mi / 8.7 km)

Exploring the natural features in Pittsfield

Whether you're an outdoor enthusiast or just want to take in the scenery, Pittsfield is a great spot to appreciate mother nature. Here are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Pico Peak (9.3 mi / 14.9 km)
  • Lakota Lake (10.2 mi / 16.5 km)
  • Silver Lake State Park (10.3 mi / 16.6 km)
  • Killington Peak (11.6 mi / 18.6 km)
  • Lake Dunmore (15.9 mi / 25.5 km)
  • Moss Glen Falls (17.1 mi / 27.5 km)

How to get to and around Pittsfield

The nearest airport is in Rutland, VT (RUT-Rutland Southern Vermont Regional), located 18.1 mi (29.2 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could book a flight to Lebanon, NH (LEB-Lebanon Municipal), which is 27.2 mi (43.7 km) away.

Frequently asked questions

What is the best area to stay in Pittsfield when booking a holiday rental?
When considering a holiday rental in Pittsfield, Vermont, the charming neighbourhood of the village centre is an excellent choice. This area offers a delightful blend of scenic beauty and local charm, making it an ideal base for your stay. You'll find a range of properties that cater to various preferences, from cosy cabins to more spacious homes, ensuring there's something for everyone.

One of the top attractions nearby is the Green Mountain National Forest, where outdoor enthusiasts can revel in activities like hiking, biking, and even skiing during the winter months. The forest's stunning landscapes and abundant wildlife provide a great backdrop for both relaxation and adventure. Additionally, the charming local shops and eateries in the village centre offer a taste of the region's warm hospitality and unique flavours.

Another point of interest is the nearby Killington Resort, which boasts excellent skiing and snowboarding opportunities in the winter, as well as mountain biking and hiking trails in the warmer months. Staying in Pittsfield allows easy access to these exciting activities while providing a peaceful retreat away from the more tourist-heavy areas.
How much does it cost to rent a holiday home in Pittsfield?
Prices for holiday rentals 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Pittsfield to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Pittsfield holiday house rentals?
You can find great discounts on house rentals in Pittsfield on Vrbo, 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.
Where are the best Pittsfield ski resort rentals?
For ski resort rentals near Pittsfield, Vermont, visitors should look towards the nearby Killington area, which is renowned for its extensive ski terrain and vibrant après-ski scene. Killington offers a variety of rental options, from cozy chalets to modern condos, many of which are conveniently located close to the slopes. These properties typically feature amenities such as fireplaces, private balconies, and full kitchens, allowing guests to unwind and prepare meals after a day on the mountain.

In addition to Killington, the town of Pittsfield itself provides a more tranquil setting, with charming cabins and rustic lodges available for rent. Many of these accommodations boast scenic views of the surrounding Green Mountains and may include features like outdoor fire pits, hot tubs, and access to hiking trails. The local community is welcoming and often hosts events during the winter season, adding to the overall experience.

For those interested in skiing, the nearby Pico Mountain is also easily accessible, offering a more family-friendly atmosphere with its manageable slopes and ski school options. Rentals in this area often cater to families, providing additional amenities such as game rooms and ski storage, ensuring a comfortable stay for all.
What is the most popular type of holiday rental accomodation in Pittsfield?
In Pittsfield, holiday houses are the most popular type of holiday rental, with about 96 options available in the area. These properties often feature spacious layouts, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups seeking a comfortable stay. Many holiday houses also include outdoor areas for relaxation and enjoying the picturesque Vermont landscape. Additionally, there are several cottages, cabins, condos, and chalets scattered throughout the area, each providing a unique charm and amenities that cater to various preferences.
Are there any family house rentals in Pittsfield?
In Pittsfield, Vermont, there are numerous family-friendly house rentals available, with about 19 options to choose from. This charming town is located in the picturesque Green Mountains, making it a wonderful destination for families seeking outdoor adventures. Many of these homes feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where children can play or relax after a day of exploring.

Visitors will appreciate the proximity to local attractions such as the scenic Pico Mountain for skiing, hiking trails, and the beautiful lakes nearby, superb for summer activities. Additionally, amenities like Wi-Fi and laundry facilities are commonly found in these properties, ensuring a comfortable stay for families.
Can I find long-stay holiday rentals in Pittsfield?
A long-stay holiday rental 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Pittsfield?
In Pittsfield, Vermont, there are pet-friendly house rentals available, with a total of twelve options for travellers to choose from. Many of these homes come equipped with amenities such as fully stocked kitchens, spacious living areas, and outdoor spaces where pets can enjoy the fresh air.

The area is surrounded by beautiful natural landscapes, making it ideal for outdoor enthusiasts and their furry companions. Nearby, you can explore the Green Mountain National Forest, which offers a variety of trails great for hiking and enjoying nature with your pets. Additionally, the charming small-town atmosphere of Pittsfield allows for leisurely strolls and opportunities to discover local shops and eateries that welcome pets.
Are there any remote work holiday rentals in Pittsfield?
In Pittsfield, Vermont, there are numerous options for remote work holiday rentals, with around 112 properties available to accommodate working travellers. Many of these rentals offer essential amenities such as high-speed Wi-Fi, dedicated laptop workspaces, and free internet services, ensuring a productive environment.

The picturesque surroundings of Pittsfield provide a serene backdrop, great for balancing work and leisure. Travellers can find cosy cabins and homes equipped with comfortable living spaces, allowing for a relaxed atmosphere after a day of remote work. Additionally, the area is known for its beautiful landscapes, making it an ideal location for enjoying outdoor activities during breaks. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Pittsfield holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals 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 on Vrbo 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.
What are popular rental amenities in Pittsfield?
In Pittsfield, popular holiday rental amenities include fully equipped kitchens, allowing guests to prepare their own meals during their stay. Many rentals feature cosy fireplaces, superb for warming up after a day of exploring the outdoors. Decks or patios are also common, offering a nice space to relax and enjoy the natural surroundings. Additionally, most accommodations provide coffee and tea makers for a convenient start to the day, and onsite parking is available, making it easy for travellers with vehicles to access the area.
When is the best time to visit Pittsfield for a holiday rental?
The best time to visit Pittsfield for a holiday rental is during the peak season from July to September, with September being particularly popular. This period attracts outdoor enthusiasts and nature lovers eager to explore the stunning landscapes of Vermont, including the vibrant autumn colours that begin to emerge in late September.

In July and August, you can enjoy warm temperatures averaging around 20 to 25 degrees Celsius, superb for hiking, biking, and taking in the breathtaking views of the Green Mountains. The summer months also offer numerous local events and activities, creating a vibrant setting that's ideal for family trips or adventurous getaways.

For those seeking a more budget-friendly option, November presents a wonderful opportunity to enjoy Pittsfield's serene beauty without the crowds. While the weather may be cooler at around 0 to 10 degrees Celsius, the crisp air and peaceful surroundings are superb for a quiet retreat, allowing you to appreciate the stunning natural scenery and perhaps even some early snowfall.
How early should I book a Pittsfield holiday rental?
Book your Pittsfield holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Pittsfield?
In Pittsfield, Vermont, visitors can discover a range of attractions that highlight the area's natural beauty and outdoor activities. The Green Mountain National Forest is a prominent feature, providing numerous hiking trails and stunning vistas for nature enthusiasts. The nearby Killington Resort offers opportunities for skiing and snowboarding in the winter months, making it a popular destination for winter sports lovers.

For those interested in local culture, the town itself has a charming, small-town atmosphere with quaint shops and eateries that reflect the region's New England heritage. The Pittsfield Historical Society provides insight into the local history, while the surrounding landscape is superb for activities such as fishing and mountain biking during the warmer seasons.
Can I change or cancel my Pittsfield home rental booking on Vrbo?
To find Pittsfield holiday rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo 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 Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Pittsfield holiday rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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