Pittsfield Holiday Houses

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.

includes taxes & fees

19 Oct - 20 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.

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

Stockbridge

Kevin M.

includes taxes & fees

18 Oct - 19 Oct

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

Stockbridge

Sophie L.

includes taxes & fees

19 Oct - 20 Oct

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

4. 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.

includes taxes & fees

9 Nov - 10 Nov

A bedroom with a large bed, a sofa, a desk, and two windows.

5. The Woods Resort Killington - 2B Townhouse with Spa, Pool & Jacuzzi

The Woods

includes taxes & fees

1 Nov - 2 Nov

A cozy living room with a stone fireplace, a large sectional sofa, and a wooden ceiling.

6. The Tower House | Hot Tub | Firepit | Dog-Friendly

Killington

Patrick B.

includes taxes & fees

21 Oct - 22 Oct

A cozy living room with a fireplace, a television, and a view of a snowy deck.

7. Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.

Killington

Mark B.

includes taxes & fees

18 Oct - 19 Oct

A stone fireplace with a black mantel, framed picture, and decorative items.

8. SnowArts, Wood Burning fireplace, Close to slopes

Killington

Tammy W.

A spacious living area with a fireplace, a television, and a dining area with natural light.

9. Breakaway House: Renovated Killington Duplex, Unit B. Great location! Close to Skiing.

Killington

Ron L.

A cozy living room with a fireplace, a sofa set, and a stone wall.

10. Bearmont- Pool, HotTub, Fireplace

The Woods

Tyler B.

includes taxes & fees

26 Oct - 27 Oct

A modern living room with a flat-screen TV, grey sofas, a dining table with chairs, and a large window with a view of greenery.

11. CozyDen- Location, Ski Off/ Shuttle On

Killington

Berni H.

includes taxes & fees

21 Oct - 22 Oct

A covered porch with a grill, two Adirondack chairs, and a fire pit.

12. Estelle Cottage- Pool, hot tub, Fireplace

The Woods

"Yes!! King beds!! Tall people love king beds and they delivered. This does not diminish the fact that everything was excellent for our stay. From the welcome gifts including some great local coffee and syrup, to the relaxing sauna, the comfortable large living room and bedrooms, and all amenities, we wanted for nothing. Truly a gem on our whole vacation! We looked forward to returning in the late afternoon knowing we had a quiet evening and a good sleep ahead of us. Truly a great place to...

Devin

includes taxes & fees

4 Nov - 5 Nov