Pittsfield Vacation Homes

A lake surrounded by autumn-colored trees and a rocky shoreline.

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Our top choices for Pittsfield holiday homes

A modern living room with a red sectional sofa, a round coffee table, wooden ceiling beams, a kitchen area, and a balcony with a view of trees.

1. NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking

North Sherburne

"On our 30th Anniversary trip to Vermont, New Hampshire and Maine we fell in love with Killington, Vermont. So much so we left the coast of Maine and last minute booked our remaining two nights back in Killington at the Poweder Run Lodge. The lodge was a wonderful experience! The location was beautiful, spacious, clean, had a fully stocked kitchen and spectacular views. The hosts were kind and easy to communicate with. We are older and need a continuous running fan and a little softer bed when we...

Heidi P.

A spacious living area with a red sectional sofa, a wooden dining table, and a kitchen in the background.

2. Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont

North Sherburne

"Peak Hill, is a lovely and very clean home, with a fully stocked kitchen and comfy beds. This home is exactly as the pictures that are shown. We had a very small issue with the door lock (battery), called and it was fixed right away, wonderful service. The owner, Geri, we had the opportunity to meet and she is very kind and a pleasure to speak with. We travel alot and l bring pretty much my own kitchen, pillow...... with me where ever l go. However, l would of been fine using all at this...

Essa R.

HK$5,700 total

includes taxes & fees

12 Oct - 13 Oct

A living room with a wooden console table, a potted plant, and two clocks. A staircase and a fireplace with a TV are in the background.

3. Ski Home/Arcade Mountain Views Near Killington/Woodstock

Stockbridge

Kevin M.

4. Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock

Stockbridge

Sophie L.

HK$4,755 total

includes taxes & fees

12 Oct - 13 Oct

A wooden cabin with a snow-covered ground, a wooden fence, and a door with a window above it.

5. Luxury Condo Tucked in the Heart of Killington

Killington

"We were very surprised. The accommodation's well worth the amount we paid. I was surprised how from the start to the close of our Anniversary get away It was such an easygoing experience. The host left fresh towels and bedding linens. The host kept in contact the entire way booking this condo. It was roomy nice Quiet!! I loved the privacy yet close to everything Killington has to offer. Our anniversary was special as we went with the host recommendation for a local resturaunt the Garlic. We have...

Melinda D.

HK$2,284 total

includes taxes & fees

9 Nov - 10 Nov