Top Inns in Pittsfield in 2026

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

Check prices for these dates

Next weekend

In two weeks

In one month

In two months

Our top choices for Pittsfield inns

1. Green Trails Inn

Brookfield

Margaret

฿5,657 total

includes taxes & fees

10 Sept - 11 Sept

2. Kedron Valley Inn

South Woodstock

Kathryn

฿11,899 total

includes taxes & fees

31 Aug - 1 Sept

View all properties

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

Top Pittsfield Hotel Reviews

The Mountain Inn at Killington

10/10 Excellent

"We loved this hotel. We were here in the summer, so we enjoyed the outdoor seating and the outdoor heated pool, plus very close distance to Killington Adventure Center (could have walked but we chose to drive). The game room was great for our teenagers, with a full pool table and board games. The staff was extremely friendly and knowledgable of the area, and gave suggestions for nearby restauarants and hikes. The upstairs has a large indoor lounge area to relax outside your hotel room with friends, which I can see being awesome after a day of skiing."

On The River Inn

10/10 Excellent

"This was one of the nicest hotels I have ever stayed in! We had a river view room with rocking chairs on the balcony, s’mores kits were offered every night (pick up by the front desk) and 2 fire pits to choose from. Game room was cute (although the air hockey table’s fan wasn’t strong on one side), library was absolutely gorgeous. Loved having water refilling stations on 2 of the 3 floors and 24/7 coffee/tea stations, too. Queen beds were very comfy, and the room was so spacious. I’d love another piece of furniture with drawers to keep our stuff though - we lived out of our suitcases because there was only an armoire with 3 half drawers. And maybe another towel bar or hooks in the bathroom to hang the towels to dry, especially if you have 4 people in a room. Breakfast buffet (included with our Expedia stay but extra for others) was always hot & fresh. We had 4 breakfasts: French toast, pancakes, waffles, french toast again. There was always fresh homemade pastries and muffins, yogurt, and oatmeal. I would have loved some fresh fruit like berries to go with the yogurt instead of apples and oranges. Staff was always so nice and helpful, especially at breakfast. Housekeeping forgot twice to give us the 4 fresh towels (gave 3 instead) but we got replacements when we asked at the desk."

The Shire Woodstock

8/10 Good

"We enjoyed our stay very much. We found our stay to very quiet. The back of the property was so peaceful and relaxing sitting by the river, listening to the birds and the gurgling of the river as it moves along. The room was comfortable with a fridge and freezer for snacks/fruit etc. I'd like to see another chair in the room so that 2 people can sit by the window and experience the view although this wasn't a game changer."

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"

Find out more about Pittsfield

Pittsfield Inns information

Number of reviews	357
Accommodation	4 Inns
Lowest Price	฿5,657
Highest Price	฿11,899

Explore a world of travel with Expedia

More ways to book

Book Inns in Pittsfield on Expedia.com

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Pittsfield inns

1. Green Trails Inn

2. Kedron Valley Inn

Top Pittsfield Hotel Reviews

The Mountain Inn at Killington

Courtyard Middlebury

On The River Inn

Killington Mountain Lodge, Tapestry Collection by Hilton

The Shire Woodstock

Hampton Inn Rutland

Sleep Woodstock Motel

Emrose Luxury Cabins

Lincoln Inn & Gallery

Find out more about Pittsfield

Pittsfield Inns information

Explore a world of travel with Expedia

Search Inns in Pittsfield

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Pittsfield inns

1. Green Trails Inn

2. Kedron Valley Inn

Top Pittsfield Hotel Reviews

The Mountain Inn at Killington

Find out more about Pittsfield

Pittsfield Inns information

Explore a world of travel with Expedia