60+ Private Villas and Holiday Rentals in Pittsfield |
  1. USA
  2. Vermont
  3. Central Vermont- Killington
  4. Pittsfield

Pittsfield Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Pittsfield

Discover more than 60 vacation rentals available in Pittsfield. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Pittsfield.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Pittsfield, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Pittsfield. On average, places to stay near Pittsfield offer 1639.34 ft², with nightly prices averaging US $641.

With Casai, finding and comparing holiday rentals in Pittsfield is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

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Top Accommodation Types in Pittsfield

Type Count
Vacation Homes 52
Holiday Apartments 2

Use these Quick Filters to Find a Holiday Rental in Pittsfield

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Pittsfield.

Weather in Pittsfield, VT

View the weather forecast for Pittsfield before booking your Pittsfield Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Pittsfield, VT

Casai offers a large selection of top attractions around Pittsfield . Research things to do on your vacation before you visit Pittsfield.


Killington Resort
Killington Peak
Pico Mountain at Killington Ski Resort
Green Mountain National Forest
Lake Bomoseen
Pico Peak
Little Pico Mountain
Paramount Theater
Rutland Regional Medical Center
Lake Dunmore
Rutland Country Club
Suicide Six Ski Area
Sugarbush Farm
Killington Golf Course
Woodstock Country Club
Billings Farm and Museum
Middlebury College Snow Bowl Ski Area
Branbury State Park
Silver Lake State Park
Brandon Music

Frequently Asked Questions About Pittsfield?

What are the top holiday rentals in Pittsfield?

With numerous options available in Pittsfield, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Pittsfield:

Which holiday homes in Pittsfield are best for families?

If you're searching for a family-friendly holiday home in Pittsfield, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Pittsfield:

How many Casai.nz holiday rentals are available in Pittsfield?

As of 2025, Casai boasts over 60 properties listed in the Pittsfield area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Pittsfield.


People Also Ask

There are 60 Pittsfield, VT Holiday Rentals

Recently Booked Holiday Rentals in Pittsfield