Pittsfield vacation rentals

We found 789 vacation rentals — enter your dates for availability

Discover a selection of 30 homes and other vacation rentals in Pittsfield that are perfect for your trip. Whether you’re staying in a vacation home with a group or just with your pet, you'll find the best amenities for hanging out with the people that matter most, which might include cable TV and a washer and dryer. Whatever you're looking for, you'll find a rental for everyone's needs, including a place that is accessible or non-smoking.

Vacation rentals with weekly discounts - Pittsfield

Showing deals for:Mar 27 - Apr 3

Image gallery for 4BR/3BA ★ hot tub, sauna, billiards, A/C, & grill!

Our signature fieldstone fireplace in our huge great room.
9.8 out of 10, Exceptional, (18 reviews)
Exceptional
(18 reviews)

4BR/3BA ★ hot tub, sauna, billiards, A/C, & grill!

Killington

17% off
Price is $795
$5,565 for 7 nights
All fees included
4BR/3BA ★ hot tub, sauna, billiards, A/C, & grill!

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Find out more about Pittsfield

Why visit Pittsfield

  • Outdoor Adventures: Pittsfield is a haven for outdoor enthusiasts, offering skiing, hiking, and beautiful lakes for recreation.
  • Charming Accommodations: Choose from cozy cabins, private homes, and condos that cater to every traveler's needs.
  • Scenic National Parks: Explore nearby national parks that showcase Vermont's stunning natural landscapes.
  • Family-Friendly Activities: Enjoy a variety of activities perfect for families, ensuring fun for all ages.
  • Warm Local Hospitality: Experience the welcoming nature of the community, enhancing your vacation experience.

Popular types of accommodation in Pittsfield

Planning your getaway to Pittsfield? The next step is finding the perfect place to stay. From charming houses and cozy condos to rustic cabins, the options are plentiful. Whether you’re looking for a short-term apartment rental or monthly accommodations, Pittsfield has something to suit every traveler’s needs. Explore various house rentals with essential amenities to ensure a comfortable stay and make the most of your experience in this beautiful destination.

  • Houses: The top choice for visitors to Pittsfield, offering spacious living and a home-like atmosphere for families and groups.
  • Condos: A popular option for those seeking modern amenities and convenient locations, ideal for couples or small families.
  • Cabins: These rustic retreats are perfect for nature enthusiasts looking for a cozy escape in the woods.
  • Apartments: A great choice for travelers wanting a comfortable and budget-friendly stay in the heart of the community.
  • Cottages: These charming accommodations provide a quaint and intimate setting for a relaxing getaway.**

Top attractions near Pittsfield

Pittsfield, Vermont, offers an exciting vacation for those seeking ski, adventure, and sports activities. Visitors can explore popular points of interest such as ski resorts, national parks, and beautiful lakes. The attractions in and around Pittsfield provide a perfect mix of outdoor adventures and cultural experiences, making it an ideal destination for families, groups, or solo travelers looking to embrace the great outdoors.

  • Killington Resort: Experience thrilling skiing and snowboarding at this premier ski resort, renowned for its diverse trails and breathtaking mountain views. Enjoy outdoor adventures year-round, from hiking in the summer to winter sports.
  • Gifford Woods State Park: Discover stunning scenery and abundant wildlife in this beautiful state park. Perfect for hiking and exploring nature, it offers peaceful trails surrounded by lush forests and serene landscapes.
  • Killington Adventure Center: A family-friendly theme park featuring exciting attractions, including zip lines and mini-golf, perfect for entertainment and creating lasting memories with loved ones.

Things to do recommended for couples

For a romantic getaway in Pittsfield, explore the stunning slopes at Killington Resort, only 10 miles away, or enjoy the thrilling rides at Pico Mountain, 8 miles from town. Don't miss the K-1 Express Gondola, 11 miles away, offering breathtaking views and a touch of adventure.

Things to do recommended for families

Families can enjoy tennis at Killington School for Tennis, just 8 miles from Pittsfield, or experience adventure at the Green Mountain Rock Climbing Center, located 13 miles away. Both venues offer fun and engaging activities suitable for all ages.

Things to do recommended for groups

Group travelers in Pittsfield can enjoy a round of golf at Green Mountain National Golf Course, just 5 miles away. For culture and entertainment, visit the Paramount Theater, 14 miles from town. Don't forget to check out Black Dog Sports, located 10 miles away for some local shopping.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Pittsfield

When you're planning a trip—whether it's with friends, family, your pets, or for an extended stay—be sure to prioritize your filters accordingly. Here are some helpful booking tips for Vrbo.

  • Traveling to Pittsfield with a group: Think about how many bedrooms you require and any additional features you might want, like a full kitchen or outdoor area for group gatherings. The good news is that Vrbo allows you to filter for all of these options and more.
  • Traveling to Pittsfield with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, you might want to think about how close you are to attractions that are fun for the whole family.
  • Taking your pets with you to Pittsfield: For many families, a trip isn’t truly complete without their furry companion. If this resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly properties come equipped with feeding bowls and cozy beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Pittsfield: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features like parking, a well-equipped kitchen, or a private pool in your search.

Where to stay near Pittsfield

Pittsfield, Vermont, offers a unique blend of adventure and tranquility for tourists seeking an unforgettable experience. Whether you’re hitting the slopes, exploring the scenic beauty, or enjoying family-friendly activities, this charming city and its surrounding areas promise unforgettable moments. Nearby towns enhance the romantic and secluded vibes, creating the perfect backdrop for relaxation or exploration. Discover the warm hospitality of the local community as you immerse yourself in this captivating destination.

  • Killington: Located a mere 7 miles from Pittsfield, Killington is a haven for outdoor enthusiasts and adventure seekers. Renowned for its expansive ski resorts, Killington attracts visitors year-round with its thrilling slopes and breathtaking mountain views. In addition to skiing, the area offers a range of activities such as snowboarding and mountain biking in the warmer months. The scenic Killington Peak and surrounding valleys provide perfect backdrops for hiking and nature photography, making it an ideal destination for those looking to immerse themselves in the outdoors.
  • Rutland: Situated 14 miles away from Pittsfield, Rutland is a vibrant city that serves as a gateway to the Green Mountains. Known for its rich history and outdoor recreation, Rutland is perfect for those who love skiing, adventure, and sports. The nearby trails and ski fields invite visitors to explore the winter wonderland, while the charming downtown area offers local dining and shopping experiences. With stunning views of lakes and valleys, Rutland provides an inviting atmosphere for relaxation and adventure alike, making it a must-visit for any traveler.
  • Stockbridge: Just 3 miles from Pittsfield, Stockbridge is a picturesque town that embodies the charm of New England. Visitors flock to Stockbridge for its outdoor experiences, including skiing and hiking among the stunning landscapes of valleys, lakes, and mountains. The town is also known for its art scene and cultural attractions, providing a well-rounded experience for tourists. Whether you're hitting the slopes in winter or exploring the scenic trails in summer, Stockbridge offers a perfect blend of adventure and tranquility.

Best time to go to Pittsfield

If you're planning a trip to Pittsfield, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from July to September, while off-peak times, like May and November to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January18.0°F (-7.8°C)Light RainMostly CloudyAverageModerately High
February20.1°F (-6.6°C)Light RainMostly CloudyAverageModerately High
March28.4°F (-2.0°C)Light RainMostly CloudyAverageAverage
April40.6°F (4.8°C)Light RainMostly CloudyAverageModerately Low
May54.1°F (12.3°C)Light RainMostly SunnySlightly LowModerately Low
June61.5°F (16.4°C)Light RainMostly SunnyAverageAverage
July67.5°F (19.7°C)Light RainMostly SunnySlightly HighAverage
August65.7°F (18.7°C)Light RainMostly SunnySlightly HighAverage
September58.6°F (14.8°C)Light RainMostly SunnySlightly HighModerately Low
October46.9°F (8.3°C)Light RainMostly CloudyAverageAverage
November34.3°F (1.3°C)Light RainMostly CloudySlightly LowAverage
December25.3°F (-3.7°C)Light RainMostly CloudySlightly LowModerately High

Booking with Vrbo is simple

Are you hoping to save on your upcoming travel plans? Being flexible with your travel dates can really help, as prices tend to vary. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We're here to help you make the most of your travel experience.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on the full booking amount. It truly benefits you to take on the planning role. When you enroll in our travel rewards program, One Key, you'll gain access to exclusive member discounts and accumulate OneKeyCash on eligible bookings. Sign up today and begin enjoying your savings.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board is a handy tool designed to help you plan your travels effortlessly. It allows you to create new trips, resume planning from where you last stopped, and keep your travel plans organized. You can easily find the properties you've saved or booked under Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

The friendly city of Pittsfield awaits you

Learn about the unique charm of Pittsfield with a stay in a private vacation home. This welcoming city allures visitors with its bars and restaurants. If you're looking for accommodations with space to entertain friends and family, Vrbo 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 hoping to discover top things to see and do in the city? Venture out of your cozy vacation rental and check out everything that Pittsfield has to offer. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:

  • Killington Resort (10.1 mi / 16.2 km)
  • Pico Mountain at Killington Ski Resort (8.6 mi / 13.8 km)
  • Killington Golf Course (10 mi / 16.1 km)
  • Killington Adventure Center (10.1 mi / 16.3 km)
  • Saskadena Six Ski Area (15.3 mi / 24.6 km)
  • Rikert Nordic Center (15.4 mi / 24.8 km)

Exploring the natural features in Pittsfield

Whether you're an active traveler or just want to take in the scenery, Pittsfield is a great place to spend some time outside. These are some of the area's most stunning natural features, all within 30 miles (48.2 km) of the city center:

  • Pico Peak (9.3 mi / 14.9 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)
  • Marsh-Billings-Rockefeller National Historical Park (16.6 mi / 26.8 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 center. If you're unable to find a flight that fits your schedule, you might consider flying into 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 vacation rental?
When planning a vacation in Pittsfield, Vermont, a fantastic area to consider for your rental is the vicinity around the Pittsfield Village center. This charming neighborhood offers a quaint, picturesque setting with a strong sense of community. Staying here gives you easy access to local attractions such as the stunning Green Mountain National Forest, where you can enjoy hiking, biking, and breathtaking views of the surrounding landscape.

Another appealing option is the area near the Coolidge State Forest, which provides a serene escape into nature with its extensive trails and beautiful scenery. This location is particularly great for outdoor enthusiasts, as it offers various recreational opportunities, including fishing and birdwatching.

In terms of vacation rentals, Pittsfield has a modest selection of properties, ranging from cozy cabins to more spacious homes, allowing visitors to find something that suits their needs and group size.
How much does it cost to rent a vacation home in Pittsfield?
Prices for vacation 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 vacation 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 the best ski resort rentals near Pittsfield, Vermont, travelers should consider accommodations in the nearby Killington area, which is one of the most popular ski destinations in the region. In Killington, visitors can find a variety of options, including cozy lodges and vacation homes that cater to families and groups. Many of these properties come equipped with essential amenities such as fully stocked kitchens, living areas with fireplaces, and sometimes even private hot tubs or saunas, providing a superb way to relax after a day on the slopes.

Additionally, the town of Mendon, located just a short drive from Pittsfield, offers charming rentals with easy access to both Killington Resort and Pico Mountain. Many of these homes feature rustic decor, outdoor spaces for barbecuing, and proximity to local dining options. Travelers can enjoy the scenic beauty of the Green Mountains while having the convenience of nearby ski areas.

For those looking to experience the local culture, the area around Pittsfield also has quaint bed and breakfasts and inns that provide a more intimate atmosphere, often featuring homemade breakfasts and personalized service.
What is the most popular type of vacation rental accomodation in Pittsfield?
In Pittsfield, vacation houses are the most popular type of rental, with about 34 available throughout the area. These homes provide ample space, featuring multiple bedrooms, fully equipped kitchens, and cozy living areas, making them ideal for families or groups looking to enjoy the scenic beauty of Vermont. Many vacation houses also offer outdoor spaces like decks or yards, superb for relaxation after a day of exploring the nearby Green Mountains.

In addition to vacation houses, there are several condos, cabins, and chalets available, each suiting different travel preferences. The condos typically provide a more compact living space with convenient amenities, while cabins and chalets often emphasize a rustic charm, featuring wood interiors and close proximity to nature trails and skiing opportunities.
Are there any family house rentals in Pittsfield?
In Pittsfield, Vermont, there are numerous family-friendly house rentals available, totaling around 22 options throughout the area. This charming town, located in the Green Mountains, offers a friendly space for families looking to explore the great outdoors. Many of these homes provide ample living space, well-equipped kitchens for preparing family meals, and cozy gathering areas for quality time together.

Visitors can enjoy amenities like outdoor decks for barbecues, game rooms for entertainment, and sometimes even access to nearby hiking trails or swimming holes. The location is superb for those wanting to experience the beauty of Vermont, with close proximity to attractions like the scenic Green Mountain National Forest and the various ski resorts just a short drive away.
Can I find long-stay vacation rentals in Pittsfield?
A long-stay vacation rental in Pittsfield is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Pittsfield?
In Pittsfield, Vermont, there are several pet-friendly house rentals available, providing a welcoming environment for travelers with furry companions. Many of these vacation homes are located in picturesque settings, offering stunning views of the surrounding Green Mountains and easy access to outdoor activities. Expect amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces like decks or patios where pets can enjoy fresh air.

The area is known for its proximity to various outdoor recreational opportunities. Nearby, the Green Mountain National Forest offers ample trails for hiking and exploring, making it a great backdrop for nature lovers and their pets. Additionally, the charming town of Pittsfield itself has local shops and eateries that may be pet-friendly, ideal for visitors traveling with their pets.
Are there any remote work vacation rentals in Pittsfield?
In Pittsfield, Vermont, there are numerous options for remote work vacation rentals, with around 30 available in the area. Travelers can expect properties equipped with amenities tailored for productivity, such as high-speed Wi-Fi, dedicated office spaces, and comfortable desks with chairs to facilitate a focused work environment. Many rentals also feature laptop workspaces and additional comforts like cozy living areas for relaxation after a workday.

Pittsfield is surrounded by the picturesque Green Mountains, offering opportunities for outdoor activities during downtime. The charming local landscape, along with proximity to hiking trails and serene lakes, provides a great backdrop for both work and play. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Pittsfield vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Pittsfield with parking available—perfect for families or travelers 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, vacation rentals typically feature a range of popular amenities that cater to travelers' comfort and convenience. Most properties come equipped with WiFi, allowing guests to stay connected during their stay. Kitchens are a standard inclusion, providing the option to prepare meals and enjoy dining in. Additionally, many rentals offer a coffee and tea maker, great for those who enjoy a warm beverage in the morning or after a day of exploring. A fireplace is also a common feature, adding a cozy atmosphere, especially during the colder months. Some rentals may even include a blender, ideal for making smoothies or other blended treats.
How early should I book a Pittsfield vacation rental?
Book your Pittsfield vacation 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 vacation 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 explore several attractions that highlight the area's natural beauty and outdoor activities. The nearby Green Mountain National Forest offers a range of hiking trails and scenic views, superb for those looking to immerse themselves in nature. In the winter months, the area is popular for skiing and snowboarding, with access to resorts like Killington and Pico Mountain not too far away.

Pittsfield is also close to picturesque lakes such as Silver Lake, which is ideal for kayaking and fishing in the warmer months. The charming small-town atmosphere features local shops and eateries, providing a taste of Vermont's hospitality.
Can I change or cancel my Pittsfield home rental booking on Vrbo?
To find Pittsfield vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 vacation 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.Vrbo also offers support via live chat through our Help Center, 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 organizing 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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