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

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Check availability on Pittsfield Ski Hotels

Tonight
10 Oct - 11 Oct
Tomorrow
11 Oct - 12 Oct
Next weekend
16 Oct - 18 Oct
In two weeks
23 Oct - 25 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 building with a red exterior, a white door, and a wooden porch with steps leading to it.
A dining area with a wooden table and chairs, large windows, and a ceiling with recessed lighting.
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a large island with bar stools.

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 960
AED 2,678 total
includes taxes & fees
14 Oct - 15 Oct
NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking
A wooden bridge over a rocky stream with lush greenery on both sides.
A spacious living area with a red sectional sofa, a brick fireplace, and a dining table with chairs.
A spacious living area with a red sectional sofa, a wooden dining table, and a kitchen in the background.
A spacious kitchen with wooden cabinets, a stainless steel refrigerator, and a large island with stools.

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 974
AED 2,673 total
includes taxes & fees
12 Oct - 13 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 fireplace, wooden furniture, and a television.
A large building with a covered entrance and multiple windows, surrounded by a grassy area and trees with autumn foliage.
A cozy living room with a stone fireplace, wooden furniture, and a television.

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 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.
A wooden interior with a staircase, a dining area, and a living room with a sofa and a lamp.

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 spacious living room with a wooden dining table, a sofa, and a coffee table. There is a large rug on the floor and a fireplace in the background.
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
12 Oct - 13 Oct
Mountain Sports Inn
A cozy living room with a stone fireplace, a round wooden coffee table, and a beige sofa.
A two-story lodge with a stone facade, wooden balconies, and a well-maintained lawn.
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 754
AED 927 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 large, two-story log cabin with a stone foundation, multiple windows, and a balcony.
A spacious living room with a stone fireplace, wooden ceiling beams, and a cozy seating area.

7. The Mountain Top Inn & Resort

The Mountain Top Inn & Resort
Chittenden
AED 1,084
AED 1,181 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 bar area with a star sign, bicycles, and a patterned carpet.
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 486
AED 535 total
includes taxes & fees
14 Oct - 15 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 wooden interior with a dining area featuring a round table and benches, large windows with a view of greenery, and a sign that reads "Grateful."
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
26 Oct - 27 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 wooden porch with a welcome sign, a door, and a small outdoor seating area.
A kitchen with wooden cabinets, a dining table with chairs, and a staircase with wooden steps.

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

4BR Killington Home Perfect for Families, Pet-Friendly
North Sherburne
AED 898
AED 2,735 total
includes taxes & fees
14 Oct - 15 Oct
4BR Killington Home Perfect for Families, Pet-Friendly
View all properties

Choose what matters most at ski hotels in Pittsfield

Resort
4 stars
5 stars
Spa
Family-friendly

Top Pittsfield Hotel Reviews

Mountain Sports Inn

Mountain Sports Inn

8/10 Good
"It was very nice and comfortable beds. Older but clean."
victoria 1-night trip
Posted 1 hour ago
Mountain Sports Inn
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

8/10 Good
"Great hotel experience—looking forward to returning!"
Matthew 1-night trip
Posted 1 hour ago
Days Inn by Wyndham Rutland/Killington Area
Greenbrier Inn

Greenbrier Inn

10/10 Excellent
"I would highly recommend this inn. Its small"
Vincent 3-night trip
Posted 2 hours ago
Greenbrier Inn
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

8/10 Good
"Nice stop during our roadtrip. Loved the layout of the room and we really appreciate the staff's help. They are incredibly friendly and accommodating to customers."
Kathryn 1-night trip
Posted 3 hours ago
Killington Mountain Lodge, Tapestry Collection by Hilton
Killington Grand Hotel

Killington Grand Hotel

10/10 Excellent
"We were there at peak leaf season… First weekend in October! The view was beautiful. Loved the warm pool and hot tub connected. Hiked and mountain biked on the mountain. Overall, a lovely long weekend. If you were going to Killington, I highly recommend staying at the grand resort."
Frances 3-night trip
Posted 5 hours ago
Killington Grand Hotel
The Mountain Inn at Killington

The Mountain Inn at Killington

10/10 Excellent
"perfect!"
Kim 1-night trip
Posted 1 day ago
The Mountain Inn at Killington
North Star Lodge and Resort

North Star Lodge and Resort

8/10 Good
"Room was clean, beds are comfortable, coffee was good. Lodge is comfortable. Parts of it are a bit dated. Overall it is a good value and conveniently located."
Amy 1-night trip
Posted 1 day ago
North Star Lodge and Resort
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

8/10 Good
"Clean room, good staff, good breakfast"
tuhin 3-night trip
Posted 3 days ago
Comfort Inn Rutland - Killington
On The River Inn

On The River Inn

10/10 Excellent
"Karen at the front desk was absolutely delightful. She saw me struggling with my dog and bags, and helped me to my room. Dan on the housekeeping was so nice. We saw him almost every day. The hotel is incredibly pet friendly. It's so convenient to walk out of your room directly onto the rear lawn, and down toward the river. I had a nice chat with the lady who lives across the river. She also has a dog. The drive to downtown was just a few minutes. I highly recommend the farmer's market (you pass it on the way to downtown Woodstock). The room was very clean. The sink and bathroom door could use some updates, but other than that it was lovely. I would definitely return again with my pup."
VS 4-night trip
Posted 4 days ago
On The River Inn

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