Pittsfield holiday lettings

We found 781 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:6 Mar - 13 Mar

Image gallery for Killington 4BR-4BA Townhouse Midway on Access Road- 2 Miles from Lifts

Large living room with fireplace, Smart TV, futon and plenty of comfy seating.
10 out of 10, Exceptional, (11 reviews)
Exceptional
(11 reviews)

Killington 4BR-4BA Townhouse Midway on Access Road- 2 Miles from Lifts

Killington, VT

8% off
Price is £7,179
for 7 nights, 1 home
£1,026 per night
includes taxes & fees
Killington 4BR-4BA Townhouse Midway on Access Road- 2 Miles from Lifts

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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)
  • 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 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)
  • Marsh-Billings-Rockefeller National Historical Park (16.6 mi / 26.8 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 area surrounding the village centre is an excellent choice. This quaint neighbourhood offers a charming, rural atmosphere while providing easy access to local attractions. Staying here puts you in close proximity to the picturesque Green Mountain National Forest, which is great for outdoor enthusiasts looking to hike, bike, or simply enjoy the stunning natural scenery.

Another appealing aspect of this area is the proximity to the historic Pittsfield Village Hall, where you can immerse yourself in the local culture and community events. The village centre boasts a selection of holiday rentals, with a variety of properties available to suit different preferences and budgets. The welcoming vibe of the neighbourhood, combined with its access to local attractions, makes it an ideal base for exploring the beauty of Vermont.
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 the best ski resort rentals near Pittsfield, Vermont, travellers should consider the proximity to the nearby Killington Resort, which is renowned for its extensive ski terrain and vibrant après-ski scene. In the town of Killington, you can find a range of accommodations, including spacious chalets and cozy condominiums. Many of these properties come equipped with essential amenities such as fully stocked kitchens, ski storage facilities, and inviting living areas with fireplaces, ideal for relaxing after a day on the slopes.

Additionally, the nearby town of Mendon offers a selection of rustic cabins and lodges, often surrounded by the natural beauty of the Green Mountains. These accommodations typically feature outdoor decks, hot tubs, and access to hiking trails, allowing guests to enjoy both winter sports and the picturesque landscape. Many properties in this area also provide easy access to local dining options and shops, enhancing the overall experience for visitors.
What is the most popular type of holiday rental accomodation in Pittsfield?
In Pittsfield, holiday houses are the most popular type of rental accommodation, with around 34 available throughout the area. These homes are typically spacious and provide a comfortable setting for families or groups, featuring multiple bedrooms, fully equipped kitchens, and often outdoor areas for relaxation. In addition to holiday houses, there are several condos, cabins, and chalets available, which cater to different preferences and group sizes. Many of these properties are situated near outdoor recreational areas, making them ideal for travellers looking to explore the natural beauty of Vermont.
Are there any family house rentals in Pittsfield?
In Pittsfield, Vermont, there are numerous family-friendly house rentals available—specifically, around 23 options throughout the area. Visitors can enjoy the charm of this quaint town, surrounded by stunning natural beauty and outdoor activities. Properties often include spacious living areas, well-equipped kitchens for preparing family meals, and outdoor spaces for children to play. Many homes also feature amenities such as Wi-Fi, laundry facilities, and sometimes even game rooms or fireplaces for cosy evenings after a day of exploring.
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 numerous pet-friendly house rentals available, with about 15 options to choose from. Many of these properties are designed with both comfort and convenience in mind, featuring amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces where pets can roam freely.

The area is located in the beautiful Green Mountains, offering stunning natural scenery and various outdoor activities suitable for pets and their owners. Nearby, the Green Mountain National Forest provides ample opportunities for hiking, with trails that welcome leashed dogs, allowing you to explore the stunning landscapes together.
Are there any remote work holiday rentals in Pittsfield?
In Pittsfield, Vermont, there are numerous remote work-friendly holiday rentals available, with around 31 options to choose from. This picturesque small town is ideal for those seeking a tranquil setting while maintaining productivity. Many of the properties come equipped with essential amenities for remote work, including high-speed Wi-Fi, dedicated desk spaces, and comfortable chairs. Some rentals even feature additional office setups, such as desktop computers or monitors, ensuring that you can work efficiently during your stay. 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 well-equipped kitchens, free Wi-Fi, and essential cookware, dishware, and utensils for travellers looking to prepare their own meals. Many rentals also feature modern conveniences such as microwaves and dishwashers, making it easier for guests to enjoy home-cooked meals after a day of exploring the picturesque surroundings.
When is the best time to visit Pittsfield for a holiday rental?
September is the most popular month to visit Pittsfield, Vermont, as the stunning autumn foliage begins to transform the landscape into a vibrant tapestry of colours. This period, which spans from July to September, attracts many outdoor enthusiasts eager to hike and explore the picturesque trails that the Green Mountain National Forest has to offer. The comfortable temperatures, typically ranging from the mid-teens to low 20s Celsius, create ideal conditions for outdoor activities and sightseeing.

During September, visitors can enjoy the delightful crispness in the air while participating in various activities, including apple picking and local festivals that celebrate the harvest season. This month strikes a superb balance between the busyness of peak season and the serene atmosphere of early autumn, making it an excellent choice for those seeking both adventure and relaxation.

If you're considering a visit at a more budget-friendly time, November presents an opportunity to experience the peaceful beauty of Pittsfield at a lower cost. While the foliage has faded, the quiet charm of the area remains, allowing for tranquil hikes and the chance to explore the local community without the hustle and bustle of summer tourists.
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.
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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