Pittsfield Vacation Rentals
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Our top choices for Pittsfield vacation homes
1. NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking
NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat ParkingNorth Sherburne
10.0 out of 10, Exceptional, (2 reviews)
"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.
The price is CA $321
CA $948 total
includes taxes & fees
Oct 31 - Nov 1
2. Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont
Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, VermontNorth Sherburne
10.0 out of 10, Exceptional, (1 review)
"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.
3. Ski Home/Arcade Mountain Views Near Killington/Woodstock
Ski Home/Arcade Mountain Views Near Killington/WoodstockStockbridge
10.0 out of 10, Exceptional, (3 reviews)
"Skied Killington for 2 days and was a 20 min drive. Fun to drive the 100."
Kevin M.
The price is CA $149
CA $764 total
includes taxes & fees
Oct 28 - Oct 29
4. Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/WoodstockStockbridge
10.0 out of 10, Exceptional, (3 reviews)
"Exactly as pictured, specious, clean. Owners were extremely responsive and kind."
Sophie L.
The price is CA $149
CA $764 total
includes taxes & fees
Oct 28 - Oct 29
5. 4BR Killington Home Perfect for Families, Pet-Friendly
4BR Killington Home Perfect for Families, Pet-FriendlyNorth Sherburne
10.0 out of 10, Exceptional, (24 reviews)
"Our group had a wonderful ski weekend at the house! It was well stocked with everything we needed and the fireplace was perfect to relax near after a day on the slopes. "
Christina V.
The price is CA $343
CA $1,031 total
includes taxes & fees
Oct 28 - Oct 29
6. Cozy Killington A-Frame w/ Hot Tub, Modern Kitchen & Forest Views – Near Skiing & Hiking Trails
Cozy Killington A-Frame w/ Hot Tub, Modern Kitchen & Forest Views – Near Skiing & Hiking TrailsNorth Sherburne
10.0 out of 10, Exceptional, (1 review)
"Great property to stay at highly recommend and will hopefully be staying again soon!"
Robert R.
The price is CA $293
CA $1,032 total
includes taxes & fees
Nov 11 - Nov 12
7. Luxury Condo Tucked in the Heart of Killington
Luxury Condo Tucked in the Heart of KillingtonKillington
10.0 out of 10, Exceptional, (1 review)
"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.
The price is CA $113
CA $385 total
includes taxes & fees
Nov 3 - Nov 4
8. The Outpost Double | Modern 2BR Ground Level Duplex | Exclusive Ski Deals
The Outpost Double | Modern 2BR Ground Level Duplex | Exclusive Ski DealsKillington
10.0 out of 10, Exceptional, (1 review)
"Great amenitiesCleanNewAnd easy access to Starship Gondola at KillingtonWent with my two sons - we had a great time"
Gifford F.
The price is CA $263
CA $695 total
includes taxes & fees
Oct 28 - Oct 29
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Pittsfield Hotel Reviews
The Mountain Inn at Killington
8/10 Good
Find out more about Pittsfield
Pittsfield Vacation Homes information
Number of reviews | 183 |
|---|---|
Accommodation | 619 Vacation Homes |
Lowest Price | CA $385 |
Highest Price | CA $1,198 |
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- Colony Club C12 Located in the heart of Killington is a beautiful spacious townhouse with plenty of space for multiple families to vacation together. (please note this unit has NO AIR CONDITIONING) The Killington golf course and Green Mountain Natio
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