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Our top choices for Pittsfield chalets
Dreamy Artist Chalet in Secluded Historic Village
Dreamy Artist Chalet in Secluded Historic VillageEast Warren
9.4 out of 10, Exceptional, (12 reviews)
"Everything was beautiful. But for sure needs new mattress and pillows. "
Jeanette R.
The price is SAR 1,341
SAR 2,161 total
includes taxes & fees
22 Mar - 23 Mar
Gnome Home Mountain Ski Chalet w/Sauna Killington
Gnome Home Mountain Ski Chalet w/Sauna KillingtonStockbridge
10.0 out of 10, Exceptional, (4 reviews)
"Nice property in a beautiful location. Host was very responsive and informative. Thanks for the stay!"
Gerald S.
The price is SAR 1,407
SAR 2,607 total
includes taxes & fees
22 Mar - 23 Mar
Handcrafted Log Home Near Sugarbush & Mad River Glen • Walk to Blueberry Lake
Handcrafted Log Home Near Sugarbush & Mad River Glen • Walk to Blueberry LakeEast Warren
10.0 out of 10, Exceptional, (3 reviews)
"The house is amazing. The hosts clearly love it, and it shows in how well it is set up and stocked. Highly recommended."
Greg E.
The price is SAR 1,313
SAR 2,508 total
includes taxes & fees
10 Mar - 11 Mar
West Park Chalet at Killington: Great for Groups! Hot tub, games, discounted ski rentals.
West Park Chalet at Killington: Great for Groups! Hot tub, games, discounted ski rentals.Killington
8.8 out of 10, Excellent, (3 reviews)
"Great location and ski house layout. Pool Table Rec Room, TV Rec Room and Hot Tub."
Rob S.
Bigelow Chalet at Killington: 8BR/4.5 BA Pet Friendly Home w/ Hot Tub, Fireplace.
Bigelow Chalet at Killington: 8BR/4.5 BA Pet Friendly Home w/ Hot Tub, Fireplace.Killington
8.8 out of 10, Excellent, (3 reviews)
"Awesome property and very responsive staff! Highly recommended. "
Anthony P.
BearHaus-Fireplace, HUGE indoor Hot Tub, Sleeps 14
BearHaus-Fireplace, HUGE indoor Hot Tub, Sleeps 14Killington
9.6 out of 10, Exceptional, (5 reviews)
"Great property - excellent hosts. Close to mountain and restaurants"
Eric D.
The price is SAR 2,240
SAR 4,836 total
includes taxes & fees
25 Feb - 26 Feb
Kilbourne Lodge ︙ Cozy Mid-Mod ︙ Fireplace ︙ Ski Shuttle
Kilbourne Lodge ︙ Cozy Mid-Mod ︙ Fireplace ︙ Ski ShuttleKillington
9.4 out of 10, Exceptional, (8 reviews)
"Great stay, thanks!"
Bret R.
The price is SAR 3,938
SAR 6,293 total
includes taxes & fees
21 Mar - 22 Mar
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
Brandon Inn
10/10 Excellent
