Find Ski Hotels in Pittsfield, VT
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20 Sep - 21 SepTomorrow
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25 Sep - 27 SepIn two weeks
2 Oct - 4 OctOur top choices for Pittsfield ski hotels
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
AED 699
AED 2,329 total
includes taxes & fees
21 Sep - 22 Sep
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
AED 726
AED 2,364 total
includes taxes & fees
21 Sep - 22 Sep
3. The Trailside Inn
The Trailside InnNorth Sherburne
- Cozy guesthouse retreat near Killington Resort offers skiing, sledding, and snowshoeing adventures with a warming lobby fireplace.
AED 585
AED 644 total
includes taxes & fees
21 Sep - 22 Sep
4. North Star Lodge and Resort
North Star Lodge and ResortKillington
- Ski into mountain adventure with a heated pool, sauna, and cozy fireplace at this welcoming Killington retreat near premier slopes.
AED 509
AED 560 total
includes taxes & fees
21 Sep - 22 Sep
5. Mountain Sports Inn
Mountain Sports InnKillington
- Alpine retreat steps from Killington Ski Resort with cozy rooms and mountain views.
AED 511
AED 562 total
includes taxes & fees
21 Sep - 22 Sep
6. Greenbrier Inn
Greenbrier InnKillington
- Experience pure ski bliss at this mountain hotel near Killington Resort, where snowy adventures await right outside your door.
AED 619
AED 714 total
includes taxes & fees
21 Sep - 22 Sep
7. Ski Home/Arcade Mountain Views Near Killington/Woodstock
Ski Home/Arcade Mountain Views Near Killington/WoodstockStockbridge
AED 521
AED 2,182 total
includes taxes & fees
22 Sep - 23 Sep
8. Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/WoodstockStockbridge
AED 704
AED 2,411 total
includes taxes & fees
30 Sep - 1 Oct
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Top Pittsfield Hotel Reviews
Sleep Woodstock Motel
10/10 Excellent
"Clean, cozy, and comfortable. I stayed here for a quick work trip and loved the cozy room. The hand drawn paintings on the wall were super cute. The room was clean and I could easily control the temperature. Although it’s on a busy road, the road noise was minimal at night and they provided ear plugs just in case. I would happily stay here again."
On The River Inn
8/10 Good
"Extremely quaint and love the rooms and balcony… Dining room gorgeous Wish there were Apps on the Tv for streaming… that’s all"
Mountain Meadows Lodge
10/10 Excellent
"Was pleasantly surprised! We definitely stay there again."
The Jackson
10/10 Excellent
"Love staying in this beautiful hotel had very comfy beds and made us feel like we were in the heart of New England"
Woodstock Inn & Resort
8/10 Good
"Woodstock itself is absolutely beautiful and has a wonderful atmosphere. However, we had a few issues in both common areas, and our room that significantly impacted our experience. First, the cleanliness of the lobby was disappointing. I noticed that it was noticeably dusty and had visible spiderwebs in several areas, which did not create a welcoming first impression. Second, the bathroom and bed did not live up to the luxurious standard expected. Both the bathroom sink and bathtub drained incredibly slowly. This resulted in an unpleasant backflow of water whenever I tried to use them, which felt very unhygienic. Lastly, the bed was lopsided and very uncomfortable. The boxspring on both sides of the bed was covered in stains, which took away from the charm and comfort of the room. Everything else was great, and with a little more attention to room cleanliness, this place would be flawless."
The Shire Woodstock
10/10 Excellent
"Na"
North Star Lodge and Resort
8/10 Good
"We loved the heated pool! Front desk staff were very helpful. Our room was clean and very basic. Our room was quiet. Would stay here again."
Killington Mountain Lodge, Tapestry Collection by Hilton
8/10 Good
"Stayed here because of the hot tub!!! Love that it was open until 11pm but wished it was open by like 8 am so we could have used it before we started our day !!"
Courtyard Middlebury
10/10 Excellent
"Very good staff"
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