The Best Ski Hotels in Pittsfield, VT from AED 313 in 2026

Check availability on Pittsfield Ski Hotels

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Pittsfield ski hotels

1. Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont

North Sherburne

2. The Shire Woodstock

Woodstock

Alpine bliss awaits at this riverside retreat; slip into ski gear and explore Killington's slopes, then unwind by your cozy fireplace.

AED 992 total

includes taxes & fees

2 Aug - 3 Aug

3. The Vesper

Woodstock

Alpine escape with slopeside perks awaits at The Vesper, a charming bed & breakfast in the shopping district.

AED 707 total

includes taxes & fees

18 Aug - 19 Aug

4. Kedron Valley Inn

South Woodstock

AED 1,491 total

includes taxes & fees

4 Aug - 5 Aug

5. Woodstock Inn & Resort

Woodstock

Experience Woodstock's winter charm with cross-country and downhill skiing, relaxing in hot tubs after snowy adventures.

AED 2,137 total

includes taxes & fees

23 Aug - 24 Aug

6. Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

Sharon

AED 1,279 total

includes taxes & fees

20 Aug - 21 Aug

7. The Jackson

West Woodstock

Unwind in Vermont's winter wonderland with slope-side skiing, snowshoeing, and tubing just minutes from this Victorian bed & breakfast.

AED 651 total

includes taxes & fees

10 Aug - 11 Aug

Elite Room | Blackout drapes, soundproofing, iron/ironing board (on request)

8. Lincoln Inn & Gallery

Woodstock

Ski adventures await at Lincoln Inn, where winter thrills meet gallery views in West Woodstock's snowy landscape.

AED 756 total

includes taxes & fees

3 Aug - 4 Aug

View all properties

Choose what matters most at ski hotels in Pittsfield

Resort

4 stars

Top Pittsfield Hotel Reviews

Best Western Inn & Suites Rutland-Killington

10/10 Excellent

"Interesting Best Western - maybe a ski resort in it's former life? Friendly and fast check in with warm cookies. Easy to find out room, property is very pretty and parking is plentiful. Room was a bit small, and the vestibule was kind of a pain (ski resort holdover!) but the room itself was very clean and the beds were very comfortable. Pool was fine, remotely located at the very back of the property, a little heavy on the chlorine. A hot tub would be a much better use of that space. Breakfast was great. A bit more elevated than a typical BW. They don't make up the rooms automatically, which is kind of a pain. Location is good, downtown is about 10 min away. Lots of great restaurants and bars in Rutland. Cool little town. Definitely the best option for lodging in the area!"

The Mountain Inn at Killington

8/10 Good

"Une super belle place, situé a 2 minutes de killington, le déjeuner est parfait, il y a une salle de jeu avec table de billard et baby foot. Une salle pour ranger et même faire des petits entretien sur le vélo. On était au premier étage et c'était un peu humide, je vous conseille de demander une chambre a l'étage."

Courtyard Middlebury

8/10 Good

"The room was clean, comfortable, and quiet, which made for a pleasant stay. One thing to be aware of is that the property does not offer breakfast, and the pool and hot tub are no longer available. I was told they have been closed for over three years, although the listing photos still show a pool, which was a bit misleading. Updating the photos would help set the right expectations for future guests."

North Star Lodge and Resort

8/10 Good

"The room was nice and so was the pool . We went up to bar that said 5 to 9 3 people were sitting at the bar we sat down and waited for several minutes nobody came out to greet us or ask us what we wanted . So we left plus it was really hot up stairs didnt seem like Ac or anything was on . Not happy about that we had to go out for a drink ."

The Jackson

10/10 Excellent

"This is a gorgeous little inn. The check in/check out is virtual which felt a bit impersonal, but otherwise everything was good. The room is very cozy as were the common areas. There is coffee, tea, and water in the lobby at all times, and there is often a fire going as well. The porch is full of rocking chairs and there is a nice seating area next to a brook in the back yard. Also free wine and cheese each evening for guests!"

Room 1

Change your mind

Treat yourself

Be picky

Check availability on Pittsfield Ski Hotels

Our top choices for Pittsfield ski hotels

1. Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont

2. The Shire Woodstock

3. The Vesper

4. Kedron Valley Inn

5. Woodstock Inn & Resort

6. Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

7. The Jackson

8. Lincoln Inn & Gallery

9. Sleep Woodstock Motel

10. Echo Lake Inn

Choose what matters most at ski hotels in Pittsfield

Top Pittsfield Hotel Reviews

Best Western Inn & Suites Rutland-Killington

The Mountain Inn at Killington

Mountain Meadows Lodge

Comfort Inn Rutland - Killington

Mountain Sports Inn

Courtyard Middlebury

North Star Lodge and Resort

Hampton Inn Rutland

The Jackson

Explore a world of travel with Expedia

Find Ski Hotels in Pittsfield, VT

Change your mind

Treat yourself

Be picky

Check availability on Pittsfield Ski Hotels

Our top choices for Pittsfield ski hotels

1. Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont

2. The Shire Woodstock

3. The Vesper

4. Kedron Valley Inn

5. Woodstock Inn & Resort

6. Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

7. The Jackson

8. Lincoln Inn & Gallery

9. Sleep Woodstock Motel

10. Echo Lake Inn

Choose what matters most at ski hotels in Pittsfield

Top Pittsfield Hotel Reviews

Best Western Inn & Suites Rutland-Killington

Explore a world of travel with Expedia