The Best Pittsfield, VT Chalets from $360

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

Bundle & Save
Get more, spend less whenever you see Bundle & Save deals
OneKeyCash
Earn OneKeyCash on all your eligible bookings
Upfront pricing
We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Pittsfield chalets

A rustic cabin with a wooden deck, surrounded by dense greenery and a rocky landscape.

1. Gnome Home Mountain Ski Chalet w/Sauna Killington

Stockbridge

Gerald S.

$434 nightly

Nov 8 - Nov 9

Total with taxes and fees

A wooden shed with a cross-braced door in a garden with a house in the background.

2. Fabulous 4-bedroom chalet in tranquil Killington getaway with Hot tub two Kings

North Sherburne

Matthew R.

$325 nightly

Nov 7 - Nov 8

Total with taxes and fees

A wooden deck with a view of a forested hillside.

3. Quintessential Vermont Log Chalet • Fire Pit • Private Deck • Sugarbush

East Warren

Beth Y.

$321 nightly

Dec 1 - Dec 2

Total with taxes and fees

A cabin surrounded by a forest with snow on the ground.

4. Dreamy Artist Chalet in Secluded Historic Village

East Warren

Jonathan B.

$389 nightly

Nov 8 - Nov 9

Total with taxes and fees

View all properties

Find vacation rentals that suit your style

Cabins

Private vacation homes

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

Top Pittsfield Hotel Reviews

On The River Inn

10/10 Excellent

"We loved our spacious room, the sauna, pool/hot tub and game room! We were welcomed with a s’mores pack and spent the evening by the cozy fire pit. Lovely hotel!"

Emrose Luxury Cabins

8/10 Good

"The cabins are new and well maintained. There are pots and pans and spatulas but incredibly no coffee maker. I don’t believe I’ve ever stayed in a room at any price point without a coffee maker. Also, the bed is up against a wall so you have to choose who has to crawl in and out of the bed to go to the bathroom, get a glass of water, etc. Not fun. There was also no contact information for management, so when we couldn’t figure out how to get the heater or fireplace working, we had to chat with Hotels.com who claimed our room did not have heat. Really? Vermont in the fall? Are you kidding me? After I almost lost my mind, they had someone from hotel management call me and instruct me how to turn the heat on. He was very nice and solved the problem, but how about providing contact information of someone on premises if there is an issue? The place is fairly new, and I like the concept, but they have a few things to iron out before they are ready for prime time. Let’s start with an $25 coffee maker in every room. Is that too much to ask? And Hotels.com really needs to get their chat proficiency together…."

Find out more about Pittsfield

Pittsfield Chalets information

Number of reviews	33
Accommodation	30 Chalets
Lowest Price	$360
Highest Price	$455

Room 1

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for Pittsfield chalets

1. Gnome Home Mountain Ski Chalet w/Sauna Killington

2. Fabulous 4-bedroom chalet in tranquil Killington getaway with Hot tub two Kings

3. Quintessential Vermont Log Chalet • Fire Pit • Private Deck • Sugarbush

4. Dreamy Artist Chalet in Secluded Historic Village

Find vacation rentals that suit your style

Top Pittsfield Hotel Reviews

On The River Inn

Turn of River Lodge

Emrose Luxury Cabins

Greenbrier Inn

Woodstock Inn & Resort

Find out more about Pittsfield

Pittsfield Chalets information

Explore a world of travel with Expedia