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

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Check availability on Pittsfield Ski Hotels

Tonight
6 Oct - 7 Oct
Tomorrow
7 Oct - 8 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

Our top choices for Pittsfield ski hotels

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.
A kitchen with wooden cabinets, stainless steel appliances, and a marble countertop.
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a large island with bar stools.
A dining area with a wooden table and chairs, large windows, and a ceiling with recessed lighting.

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

NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking
North Sherburne
AED 845
AED 2,507 total
includes taxes & fees
7 Oct - 8 Oct
NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking
A spacious living area with a red sectional sofa, a wooden dining table, and a kitchen in the background.
A spacious living area with a red sectional sofa, a brick fireplace, and a dining table with chairs.
A spacious kitchen with wooden cabinets, a stainless steel refrigerator, and a large island with stools.
A spacious living room with a red leather sofa, a wooden coffee table, and a red wood-burning stove.

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, Vermont
North Sherburne
AED 797
AED 2,442 total
includes taxes & fees
7 Oct - 8 Oct
Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont
A spacious living room with a stone fireplace, wooden furniture, and a large potted plant.
A cozy living room with a stone fireplace, wooden furniture, and a television.
A cozy living room with a fireplace, wooden furniture, and a television.
A cozy living room with a fireplace, a white sofa, a coffee table with candles, and a bag with the text "Love is All Around".

3. The Trailside Inn

The Trailside Inn
North 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
18 Oct - 19 Oct
The Trailside Inn
A table with a checkered placemat, a red vase with greenery and berries, and a clear plastic bag with items.
A spacious loft-style living area with a high ceiling, wooden beams, and a cozy fireplace. A staircase with a wooden railing leads to an upper level.
A sign for Greenbrier Inn and a gift shop, with a snow-covered ground.
A spacious living room with a high ceiling, wooden beams, a staircase, and a large window.

4. Greenbrier Inn

Greenbrier Inn
Killington
  • Experience pure ski bliss at this mountain hotel near Killington Resort, where snowy adventures await right outside your door.
AED 642
AED 740 total
includes taxes & fees
18 Oct - 19 Oct
Greenbrier Inn
A dining area with a wooden table and chairs, a fireplace, and a cozy seating area with a couch and a TV.
A modern kitchen with a granite countertop, a built-in oven, and a bar area with stools.
A kitchen with wooden cabinets, a refrigerator, a stove, a microwave, and a sink.
A wooden cabin with a white door labeled "Outer Limits," a covered porch, and a snow-covered deck.

5. Mountain Sports Inn

Mountain Sports Inn
Killington
  • Alpine retreat steps from Killington Ski Resort with cozy rooms and mountain views.
AED 511
AED 562 total
includes taxes & fees
7 Oct - 8 Oct
Mountain Sports Inn
A cozy living room with a stone fireplace, a round wooden coffee table, and a beige sofa.
A pool area with lounge chairs and umbrellas, surrounded by landscaped gardens and a building with large windows.
An outdoor seating area with tables and chairs, a stone planter with flowers, and a building with a sloped roof and large windows.
A rustic interior with a stone hot tub, wooden furniture, and a mountain mural.

6. Summit Lodge

Summit Lodge
Killington
  • Ski mountain thrills await at Summit Lodge, just minutes from Killington Resort with hot tubs and outdoor pools for post-slope relaxation.
AED 628
AED 785 total
includes taxes & fees
16 Oct - 17 Oct
Summit Lodge
A spacious room with large windows, a stone wall, and a wooden ceiling.
A cozy living room with a stone fireplace, leather sofa, and a patterned rug.
A lodge with a fire pit, outdoor seating, and a covered area with string lights.
A large, two-story log cabin with a stone foundation, multiple windows, and a balcony.

7. The Mountain Top Inn & Resort

The Mountain Top Inn & Resort
Chittenden
AED 921
AED 1,004 total
includes taxes & fees
1 Nov - 2 Nov
The Mountain Top Inn & Resort
A spacious living room with a fireplace, leather sofas, a wooden coffee table, and a view of the outdoors.
A bathroom with a large freestanding bathtub, a mirror, and a wooden vanity.
A snow-covered road with a sign reading 'Welcome to Killington.'
A multi-story building with a pool and a covered patio area.

8. North Star Lodge and Resort

North Star Lodge and Resort
Killington
  • 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
18 Oct - 19 Oct
North Star Lodge and Resort
A large, stone and wood lodge with a sign reading 'The Snowed Inn,' surrounded by snow-covered trees and a snow-covered driveway.
A golf course with a winding road, surrounded by trees and mountains.
A cozy cabin interior with a stone fireplace, wooden furniture, and a stone wall.
A cozy living room with a fireplace, wooden furniture, and a stone wall.

9. Snowed Inn

Snowed Inn
Killington
  • Alpine wonderland at Killington's cozy bed & breakfast offers ski storage, fireplace lounges, and direct mountain access.
AED 466
AED 564 total
includes taxes & fees
25 Oct - 26 Oct
Snowed Inn
A spacious living room with a fireplace, a television, and a large window.
A spacious living room with a large window, a television, a sofa, a coffee table, and a guitar.
A kitchen with wooden cabinets, a dining table with chairs, and a staircase with wooden steps.
A kitchen with a wooden countertop, a stove, a hanging light fixture, and a brick wall.

10. 4BR Killington Home Perfect for Families, Pet-Friendly

4BR Killington Home Perfect for Families, Pet-Friendly
North Sherburne
AED 898
AED 2,714 total
includes taxes & fees
7 Oct - 8 Oct
4BR Killington Home Perfect for Families, Pet-Friendly
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Choose what matters most at ski hotels in Pittsfield

Resort
4 stars
5 stars
Spa
Family-friendly

Top Pittsfield Hotel Reviews

The Shire Woodstock

The Shire Woodstock

10/10 Excellent
"Such a beautiful location along the river. Makes us wanna come back during the summer to enjoy all of the additional amenities."
Amy 3-night trip
Posted 5 hours ago
The Shire Woodstock
Mountain Sports Inn

Mountain Sports Inn

8/10 Good
"The location and value were good. The made to order breakfast was terrific."
John 1-night trip
Posted 6 hours ago
Mountain Sports Inn
Woodstock Inn & Resort

Woodstock Inn & Resort

10/10 Excellent
"Clean rooms, very friendly staff, noise AC"
Abdolkarim 1-night trip
Posted 7 hours ago
Woodstock Inn & Resort
On The River Inn

On The River Inn

10/10 Excellent
"Everyone was so friendly and the food at breakfast and dinner was excellent! Looking forward to coming back next year!"
Erinn 1-night trip
Posted 9 hours ago
On The River Inn
Killington Grand Hotel

Killington Grand Hotel

10/10 Excellent
"Staff was friendly hotel clean"
Greg 1-night trip
Posted 10 hours ago
Killington Grand Hotel
Greenbrier Inn

Greenbrier Inn

10/10 Excellent
"This place was outstanding and I highly recommend staying there."
Jeffrey 2-night trip
Posted 11 hours ago
Greenbrier Inn
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

10/10 Excellent
"appreciate Ms Tess when we checked in , she was very helpful and kind"
Estrella 1-night trip
Posted 13 hours ago
Days Inn by Wyndham Rutland/Killington Area
Mountain Meadows Lodge

Mountain Meadows Lodge

10/10 Excellent
"This place was above and beyond all my expectations!! Beautiful place with incredible views !! The Breakfast was delicious and the staff member very friendly !!!"
Soraya 1-night trip
Posted 16 hours ago
Mountain Meadows Lodge
The Jackson

The Jackson

10/10 Excellent
"Amazing stay and great restaurant!"
Ava 1-night trip
Posted 16 hours ago
The Jackson

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