Best Pittsfield Hotels in 2026 from HK$729 - Fully Refundable Options

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

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

Go beyond your typical stay in Pittsfield

Pet friendly

Pool

Apartment

Family friendly

Hot tub

Condo

Waterpark

Chalet

Cottage

Cabin

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Pittsfield hotels

1. The Trailside Inn

North Sherburne

Niall

HK$1,249

HK$1,373 total

includes taxes & fees

31 Aug - 1 Sept

32-inch flat-screen TV with cable channels, TV

2. Greenbrier Inn

Killington

David

HK$1,322

HK$1,523 total

includes taxes & fees

28 Aug - 29 Aug

Blackout curtains, iron/ironing board, bed sheets

Coffee/tea maker, mini-fridge, microwave

3. Best Western Inn & Suites Rutland-Killington

Rutland

Alex

HK$1,403

HK$1,543 total

includes taxes & fees

30 Aug - 31 Aug

4. Mountain Meadows Lodge

Killington

Barry

HK$1,112

HK$1,419 total

includes taxes & fees

13 Sept - 14 Sept

In-room safe, blackout curtains, free WiFi, individually decorated

5. The Mountain Inn at Killington

Killington

Allison

HK$981

HK$1,133 total

includes taxes & fees

30 Aug - 31 Aug

Travel cot, free rollaway beds, free WiFi, individually decorated

6. Mountain Sports Inn

Killington

Davis

HK$894

HK$983 total

includes taxes & fees

30 Aug - 31 Aug

Desk, laptop workspace, blackout curtains, iron/ironing board

7. Comfort Inn Rutland - Killington

Rutland

Tracy

HK$1,067

HK$1,174 total

includes taxes & fees

30 Aug - 31 Aug

Laptop workspace, iron/ironing board, individually decorated

Private beach, sun-loungers, beach towels, kayaking

8. The Mountain Top Inn & Resort

Chittenden

Kristen

HK$2,547

HK$2,777 total

includes taxes & fees

1 Sept - 2 Sept

9. North Star Lodge and Resort

Killington

Corey

HK$931

HK$1,024 total

includes taxes & fees

8 Sept - 9 Sept

10. Hampton Inn Rutland

Rutland

Brent

HK$1,118

HK$1,230 total

includes taxes & fees

6 Sept - 7 Sept

Coffee/tea maker, full-sized fridge, microwave, stovetop

11. My Place Hotel-Randolph VT

Randolph Center

Joey

HK$1,272

HK$1,387 total

includes taxes & fees

9 Sept - 10 Sept

12. Killington Mountain Lodge, Tapestry Collection by Hilton

Killington

Joseph

HK$1,219

HK$1,341 total

includes taxes & fees

30 Aug - 31 Aug

13. Snowed Inn

Killington

James

HK$995

HK$1,204 total

includes taxes & fees

30 Aug - 31 Aug

Desk, blackout curtains, iron/ironing board, free cots/infant beds

14. Days Inn by Wyndham Rutland/Killington Area

Rutland

Charlotte

HK$926

HK$1,019 total

includes taxes & fees

30 Aug - 31 Aug

Memory-foam beds, desk, free WiFi, bed sheets

15. Après Inn Killington

Killington

Margaret

HK$1,082

HK$1,190 total

includes taxes & fees

31 Aug - 1 Sept

16. Brandon Inn

Brandon

Michael

HK$1,182

HK$1,300 total

includes taxes & fees

30 Aug - 31 Aug

Desk, blackout curtains, iron/ironing board, free WiFi

17. Sleep Woodstock Motel

Woodstock

John

HK$663

HK$729 total

includes taxes & fees

31 Aug - 1 Sept

18. Killington Haus

Killington

Samir

HK$881

HK$970 total

includes taxes & fees

2 Sept - 3 Sept

19. Killington Grand Hotel

Base Area

Sheryl

HK$1,820

HK$2,135 total

includes taxes & fees

30 Aug - 31 Aug

20. The Jackson

West Woodstock

Brian

HK$1,403

HK$1,543 total

includes taxes & fees

30 Aug - 31 Aug

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Pittsfield attractions

Roger Clark Memorial Central Library

After visiting Roger Clark Memorial Central Library, make a plan to see the other sights and activities in Pittsfield.

See properties

Pittsfield Town Hall

After visiting Pittsfield Town Hall, make a plan to see the other sights and activities in Pittsfield.

See properties

Learn more about Pittsfield

Nestled in Vermont's Green Mountains, Pittsfield offers excellent hiking on the Long Trail and thrilling mountain biking at Green Mountain Trails. Riverside picnics along the Tweed River provide peaceful breaks between seasonal activities at nearby Killington Resort.

See all hotels in Pittsfield

Top Pittsfield Hotel Reviews

Sleep Woodstock Motel

8/10 Good

"Centrally located to waterfalls we went to Had everything we needed"

Emrose Luxury Cabins

10/10 Excellent

"The Cabins are very nice clean and cozy , love how well they were thought out to fit everything so perfectly in a small space . Full bathroom , full kitchen and nice size refrigerator and microwave . Perfect for a romantic getaway . Plus the outdoor accommodations were great . And can’t wait for the soon to come restaurant and lounge for the guests . A++ stay . Staff were very nice and helpful"

Hampton Inn Rutland

10/10 Excellent

"Excellent location and delicious breakfast! Friendly staff"

The Shire Woodstock

8/10 Good

"It was a nice and cozy place to stay and experience Woodstock VT."

Killington Mountain Lodge, Tapestry Collection by Hilton

8/10 Good

"Food was shocking ....."

Comfort Inn Rutland - Killington

8/10 Good

"Enjoyed my stay. Felt safe."

Brandon Inn

10/10 Excellent

"Beautiful, well-maintained historic inn at the center of Brandon. Room was very quiet and clean. Within walking distance of everything. Great place!"

Woodstock Inn & Resort

10/10 Excellent

"Amazing! Will visit again."

Killington area home - 4-seasons, hot tub and A/C

8/10 Good

"House was very nice overall. Spacious and well laid out. Certain things felt a little dirty - grout in the showers, the bedding, etc. Nothing egregious, just not pristinely clean."