Pittsfield vacation rentals

We found 804 vacation rentals — enter your dates for availability

Discover a selection of 29 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:May 22 - May 29

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

South View Chalet!

Killington

9% off
Price is $2,250
$15,748 for 7 nights
All fees included
South View Chalet!

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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:

  • 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 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)
  • 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)
  • Granville Gulf State Reservation (16.1 mi / 25.9 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

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 focus on the nearby Killington area, which is renowned for its expansive ski terrain and vibrant après-ski scene. In Killington, options range from cozy condominiums to spacious lodges that cater to families and groups. Many of these properties feature ski-in/ski-out access, allowing guests to hit the slopes directly from their accommodations. Expect amenities such as hot tubs, fireplaces, and fully equipped kitchens, which provide a comforting retreat after a day of skiing.

Additionally, the surrounding neighborhoods, including Mendon and Pico, offer a quieter atmosphere with vacation rentals that often boast scenic mountain views and easy access to local dining and shopping. Properties in these areas typically include features like outdoor patios, ski storage, and laundry facilities, enhancing the overall convenience for travelers.

For those looking to explore beyond skiing, the Green Mountain National Forest offers numerous hiking and snowshoeing opportunities, with rentals often providing easy access to these trails.
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 24 available throughout the area. These properties typically provide spacious rooms with multiple bedrooms, fully equipped kitchens, and cozy living areas, making them ideal for families or groups looking to enjoy the natural beauty of Vermont. Additionally, several cottages, cabins, condos, and chalets can be found, offering unique, rustic charm and access to outdoor activities like hiking and skiing.
Are there any family house rentals in Pittsfield?
In Pittsfield, Vermont, families will find a variety of vacation rentals, with around 19 options available. This charming town is located in the Green Mountains, providing a picturesque backdrop for outdoor adventures. Many of the homes offer spacious living areas, fully equipped kitchens for preparing family meals, and cozy spots for relaxation after a day of exploration.

The properties often include amenities such as Wi-Fi and outdoor spaces, making it easy for kids to enjoy the fresh air while parents unwind. Additionally, visitors can easily access nearby attractions like the Green Mountain National Forest, which offers hiking trails and scenic vistas, or head to the local ski resorts for winter fun.
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 some pet-friendly house rentals available, with a total of approximately 12 options to choose from. These vacation homes often feature amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces where pets can enjoy the fresh air. Many rentals may also include cozy fireplaces, making them great for relaxing after a day of exploring the beautiful Vermont countryside.

The surrounding area offers stunning natural beauty, with opportunities for hiking, biking, and enjoying the outdoors, which can be great for pet owners looking to engage in activities with their furry friends.
Are there any remote work vacation rentals in Pittsfield?
In Pittsfield, Vermont, there are numerous options for remote work vacation rentals, with around 28 available to choose from. These properties typically come equipped with essential amenities to support a productive work environment, including free Wi-Fi and reliable internet services. Many rentals feature dedicated workspaces, allowing travelers to set up comfortably while enjoying the serene surroundings of the Green Mountains.

The town itself is a peaceful retreat, providing access to outdoor activities such as hiking and skiing in nearby resorts, which can serve as a refreshing break from work. Additionally, the charming atmosphere of Pittsfield, coupled with the natural beauty of the area, makes it an appealing destination for those looking to combine work with leisure. 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, popular vacation rental amenities cater to the needs of travelers looking for comfort and convenience. Most rentals feature fully equipped kitchens, allowing guests to prepare their own meals. Fireplaces are common, providing a cozy atmosphere during colder months. Many properties also offer decks or patios, superb for enjoying the serene surroundings. Additionally, rentals typically include coffee and tea makers for a refreshing start to the day and onsite parking for straightforward access.
When is the best time to visit Pittsfield for a vacation rental?
The best time to book a vacation rental in Pittsfield is during the vibrant month of September. This period marks the end of the peak season, which runs from July to September, attracting visitors eager to experience the stunning fall foliage and the tranquil beauty of Vermont.

In September, the weather is typically mild, with temperatures ranging from the upper 40s to mid-70s Fahrenheit. This comfortable climate makes it ideal for outdoor activities like hiking, biking, and exploring the picturesque landscapes that Pittsfield has to offer. The surrounding Green Mountains provide a breathtaking backdrop for sightseeing, and the scenic routes are great for leisurely drives.

For travelers looking to save a bit on their vacation, consider visiting in November. While this month falls into the low season, it offers a unique charm with fewer crowds and the opportunity to enjoy the peaceful, snowy landscapes. November in Pittsfield presents a different kind of beauty, where the serene atmosphere allows for cozy evenings by the fireplace and explorations of the local culture.

Ultimately, whether you're drawn to the vibrant colors of September or the quietude of November, Pittsfield has a wealth of experiences waiting for you.
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, Vermont, United States of America?
In Pittsfield, Vermont, visitors can enjoy a range of attractions that highlight the area's natural beauty and outdoor activities. The nearby Green Mountain National Forest offers ample opportunities for hiking, with trails that vary in difficulty and provide stunning views of the surrounding landscape. This area is particularly popular for its fall foliage, attracting nature enthusiasts and photographers alike.

In the winter months, the proximity to ski resorts like Killington and Pico makes Pittsfield an excellent base for skiing and snowboarding enthusiasts. The charming small-town atmosphere is complemented by local shops and eateries that showcase Vermont's culture and cuisine.

Additionally, the scenic and tranquil surroundings make it an ideal location for outdoor activities such as fishing, mountain biking, and snowshoeing, appealing to visitors year-round.
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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