Pittsfield Hotels from S$142

  • Plan, book, stay with confidence
  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check Pittsfield hotel prices

Tomorrow night
This weekend

Filter by

Guest rating
Guest rating
Property class

Top 10 trending Pittsfield hotels

My Place Hotel-Randolph VT

2.0 star property
9.4 out of 10, Exceptional, (75)
"Clean "
The price is S$188
includes taxes & fees
18 Dec - 19 Dec
My Place Hotel-Randolph VT

Luxe 14-acre Vermont Countryside Lodge!

3.0 star property
Luxe 14-acre Vermont Countryside Lodge!

The Woods Lodge

3.0 star property
8.0 out of 10, Very good, (6)
"I loved this place. It's a rustic cottage with all the amenities. It was near the university so it was easy to go back and forth. It was clean and cozy, tucked away in the foliage. The host and hostess were very accommodating and responsive. I hope to stay here again next year. "
The Woods Lodge

Rustic Roxbury Ski Farmhouse With Trails!

3.0 star property
Rustic Roxbury Ski Farmhouse With Trails!

Clear River Inn

3.0 star property
8.8 out of 10, Excellent, (85)
"Staff was very professional and friendly! River the Inn was beautiful! "
Clear River Inn

Killington Area Escape w/ Deck, Views & Hot Tub!

3.0 star property
Killington Area Escape w/ Deck, Views & Hot Tub!

Eagle Ridge Treehouse

4.0 star property
Eagle Ridge Treehouse

The Getaway 4 Bedroom Home

3.0 star property
The Getaway 4 Bedroom Home

Robinson Cabin 3 Bedroom Cabin by RedAwning

3.0 star property
Robinson Cabin 3 Bedroom Cabin by RedAwning

Sweet Life - Vermont Chalet - 6 Person Indoor Hot Tub - 15 Min To Killington 3 Bedroom Home by RedAwning

3.0 star property
Sweet Life - Vermont Chalet - 6 Person Indoor Hot Tub - 15 Min To Killington 3 Bedroom Home by RedAwning

Historic Vermont Ski House w/ Mountain Views!

3.0 star property
Historic Vermont Ski House w/ Mountain Views!

Pet-friendly Roxbury Farmhouse on 350 Acres!

3.0 star property
Pet-friendly Roxbury Farmhouse on 350 Acres!

Lovely Brookfield Home w/ Private Deck & Views

3.0 star property
10.0 out of 10, Exceptional, (1)
" Lovely home, beautifully furnished "
Lovely Brookfield Home w/ Private Deck & Views

Inviting A-frame Cabin w/ Saltwater Hot Tub!

3.0 star property
Inviting A-frame Cabin w/ Saltwater Hot Tub!

Silver Spring Chalet Large 4 bedroom, Pittsfield VT, 20 min to Killington Slopes 4 Home by RedAwning

3.0 star property
Silver Spring Chalet Large 4 bedroom, Pittsfield VT, 20 min to Killington Slopes 4 Home by RedAwning

Mad Meadows 5 Bedroom Chalet by RedAwning

3.0 star property
Mad Meadows 5 Bedroom Chalet by RedAwning

'blueberry Lake Retreat:' 7 Mi to Sugarbush Resort

3.0 star property
'blueberry Lake Retreat:' 7 Mi to Sugarbush Resort

Remote Escape: Vermont Cabin w/ Mountaintop Views!

2.0 star property
Remote Escape: Vermont Cabin w/ Mountaintop Views!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Don't see what you're looking for?
See all available properties in Pittsfield
Save an average of 15% on thousands of hotels when you're signed in
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Where is the best place to stay in Pittsfield?

Located 14.4 mi (23.2 km) from the heart of Pittsfield, Comfort Inn Rutland - Killington is a top choice for your stay, based on our traveller data. Two other choices for your trip to the area are Killington Mountain Lodge, Tapestry Collection by Hilton and Woodstock Inn & Resort. See all available top hotels, or vacation rentals in Pittsfield.

If I need to cancel my hotel reservation in Pittsfield, will I receive a refund?

Yes, you'll find most hotel reservations are fully refundable provided that you cancel before the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of check in. If your reservation is non-refundable, you might be able to still cancel and be given a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Pittsfield.

What's the best place to stay on a budget in Pittsfield?

Based on reviews, Clear River Inn is a popular inn for our travellers who want a more economical choice, and features free WiFi and free parking. View all budget hotels in Pittsfield.

What's the best dog-friendly accommodation option in Pittsfield?

Clear River Inn is a top dog-friendly inn, and offers a restaurant and a nightclub for its human guests. See more pet-friendly hotel accommodations in Pittsfield.

What are some accommodation options with pools in Pittsfield?

Comfort Inn Rutland - Killington: Provides buffet, an indoor pool and free self parking. Woodstock Inn & Resort and North Star Lodge and Resort are a couple of other choices that feature an on-site pool. View all hotels with pools in Pittsfield.

What is the best spa hotel in Pittsfield?

Sweet Life - Vermont Chalet - 6 Person Indoor Hot Tub - 15 min to Killington is a top spa hotel with an arcade/games room, barbecues and billiards/pool table. Kick back and relax in the hot tub. Other popular spa hotels in Pittsfield include Newly Built Killington Vermont Ski House and Sweet Life - GetAway.

How is it to stay in Pittsfield?

Visitors can enjoy all that Pittsfield has to offer, including the bars and restaurants. This city also attracts tourists with its welcoming locals. In Pittsfield, there are 36 hotels and other accommodation options to choose from. Find out more about Pittsfield.

What are the top places to visit in Pittsfield?

A favourite place to visit is Green Mountain National Forest. You'll also find Appalachian Trail Adventures and Pico Mountain at Killington Ski Resort in the area. Take a look at what more there is to see and do in Expedia's Pittsfield guide.

What's the seasonal weather in Pittsfield?

The hottest months are usually July and August, with an average temperature of 17°C, while the coldest months are January and February, with an average of -5°C. The snowiest months in Pittsfield are January, March, February and December, with each month seeing an average of 26 cm of snowfall.