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

Find Ski Hotels in Pittsfield, VT

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Pittsfield Ski Hotels

Tonight
8 Oct - 9 Oct
Tomorrow
9 Oct - 10 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 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.

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 965
AED 2,663 total
includes taxes & fees
12 Oct - 13 Oct
NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking
A spacious living room with a stone fireplace, wooden furniture, and a large potted plant.
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 fireplace, a white sofa, a coffee table with candles, and a bag with the text "Love is All Around".
A cozy living room with a fireplace, wooden furniture, and a television.

2. 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 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 spacious living room with a high ceiling, wooden beams, a staircase, and a large window.

3. 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 wooden cabin with a white door labeled "Outer Limits," a covered porch, and a snow-covered deck.
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 modern kitchen with a granite countertop, a built-in oven, and a bar area with stools.

4. 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
Winter Wonderland
A modern kitchen with a central island, wooden cabinets, and a window with a snowy view.
A room with two leather chairs with antler pillows, a wooden table with a bowl of fruit, and a window overlooking a snowy mountain landscape.
A room with a large window overlooking a snowy landscape.

5. Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock

Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
Stockbridge
AED 615
AED 2,299 total
includes taxes & fees
12 Oct - 13 Oct
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
A living room with a wooden console table, a potted plant, and two clocks. A staircase and a fireplace with a TV are in the background.
A spacious living room with a staircase, a wooden coffee table, a sofa, and a fireplace.
A house with a dark roof, multiple windows, and a wooden deck, surrounded by dense green forest.
A spacious living area with a wooden floor, a staircase, a dining table with chairs, and a sofa.

6. Ski Home/Arcade Mountain Views Near Killington/Woodstock

Ski Home/Arcade Mountain Views Near Killington/Woodstock
Stockbridge
AED 612
AED 2,295 total
includes taxes & fees
13 Oct - 14 Oct
Ski Home/Arcade Mountain Views Near Killington/Woodstock
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.
A rustic interior with a stone hot tub, wooden furniture, and a mountain mural.
A two-story lodge with a stone facade, wooden balconies, and a well-maintained lawn.

7. 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 spacious living room with a stone fireplace, wooden ceiling beams, and a cozy seating area.
A large, two-story log cabin with a stone foundation, multiple windows, and a balcony.
A cozy living room with a stone fireplace, leather sofa, and a patterned rug.

8. 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 multi-story building with a pool and a covered patio area.
A snow-covered road with a sign reading 'Welcome to Killington.'
A bathroom with a large freestanding bathtub, a mirror, and a wooden vanity.

9. 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 golf course with a winding road, surrounded by trees and mountains.
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.

10. 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
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

10/10 Excellent
"Included breakfast was great!"
Bryan 1-night trip
Posted 7 hours ago
Mountain Sports Inn
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

8/10 Good
"Clean room, good staff, good breakfast"
tuhin 3-night trip
Posted 20 hours ago
Comfort Inn Rutland - Killington
Woodstock Inn & Resort

Woodstock Inn & Resort

10/10 Excellent
"Lovely feel to the hotel with friendly staff. Room was comfortable and location is excellent. Love Woodstock as a destination. I am never the biggest fan of breakfast, but really enjoyed it for once"
patrick 3-night trip
Posted 23 hours ago
Woodstock Inn & Resort
Greenbrier Inn

Greenbrier Inn

10/10 Excellent
"Very friendly staff with easy check in and out. Breakfast was fast and convenient and great location!"
Jeff 1-night trip
Posted 1 day ago
Greenbrier Inn
The Shire Woodstock

The Shire Woodstock

8/10 Good
"No heater or couldn't find it. Front door needs adjusted in the jamb area, couldn't push it hard enough to get it into a locked position but other than that it was good"
Tim 1-night trip
Posted 1 day ago
The Shire Woodstock
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

10/10 Excellent
"It may not look like much from the outside, but the newly refurbished rooms, friendly staff, convienient location and the cleanest pool we have used, made for a pleasant stay."
JOHN 1-night trip
Posted 1 day ago
Days Inn by Wyndham Rutland/Killington Area
North Star Lodge and Resort

North Star Lodge and Resort

10/10 Excellent
"The hotel is located in killington so the views are just amazing if you are specially visiting in Fall The Staff was very friendly,our room was big and clean, the hotel was kinda cozy with yellow lights Indeed a good experience ."
Muhammad Armughan 1-night trip
Posted 2 days ago
North Star Lodge and Resort
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 2 days ago
On The River Inn
Killington Grand Hotel

Killington Grand Hotel

10/10 Excellent
"Everything was great about this place!!"
robert 1-night trip
Posted 3 days ago
Killington Grand Hotel

Explore a world of travel with Expedia