Pittsfield Holiday Rentals, Vermont: Private House Rentals

Our top choices for Pittsfield hotels

The Shire Woodstock

Woodstock

Arlene

Rp2.931.805 total

includes taxes & fees

9 Jun - 10 Jun

The Vesper

Woodstock

Melissa

Rp3.410.503 total

includes taxes & fees

8 Jun - 9 Jun

Kedron Valley Inn

South Woodstock

Andrew

Rp4.549.739 total

includes taxes & fees

27 May - 28 May

Woodstock Inn & Resort

Woodstock

Christopher

Rp10.130.050 total

includes taxes & fees

15 Jun - 16 Jun

On The River Inn

West Woodstock

Suwei

Rp4.118.205 total

includes taxes & fees

16 Jun - 17 Jun

The Jackson

West Woodstock

Courtney

Rp2.557.803 total

includes taxes & fees

3 Jun - 4 Jun

Deluxe Suite | Private kitchen | Mini-fridge, microwave, coffee/tea maker, freezer

Sleep Woodstock Motel

Woodstock

Elisabeth

Rp2.434.299 total

includes taxes & fees

3 Jun - 4 Jun

Deer Brook Inn

Woodstock

Sara

Rp4.534.046 total

includes taxes & fees

8 Jun - 9 Jun

Echo Lake Inn

Plymouth

Danielle

Rp4.451.114 total

includes taxes & fees

27 May - 28 May

My Place Hotel-Randolph VT

Randolph Center

Jeannine

Rp2.158.451 total

includes taxes & fees

16 Jun - 17 Jun

Green Trails Inn

Brookfield

Christine

Rp2.423.557 total

includes taxes & fees

8 Jun - 9 Jun

Killington

Kailyn

Rp2.748.368 total

includes taxes & fees

28 May - 29 May

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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.

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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

Cortina Inn

2/10 Terrible

"I’m going to start out saying the room was very clean. It looked as though the staff had ran out to Walmart and bought new sheets, pillows and a blanket along with new towels. The bathroom was clean, no amenities, and the carpet had been freshly vacuumed. This is the first hotel I have ever looked for bedbugs. The lobby appeared to be an easy fifty years old with no updates and the hallways although very wide were dirty. They had not been vacuumed in a very long time. As I left the hotel in early evening a younger couple approached me and said someone had approached them and told them not to go to the far end of the lot because there were gang members in the corner. There were people in several rooms but no cars in the parking lot only mine and the young couples. I was very uncomfortable with the location of my room, it was at the very far end of a hallway and I believe I was the only reservation in that location. The elevator did work but for some reason when I asked to see the room the desk clerk had us walk down several hallways then up the stairs when the elevator would have been around the corner. Needless to say instead of staying for the original five nights I had booked I only stayed one night then moved on to a hotel that better represented itself. I believe I booked the Cortina through Hotels.com and am quite surprised they would recommend a hotel with such poor standards. The Cortina should be removed from the listings. My card has been credited."

Lincoln Inn & Gallery

8/10 Good

"We found our check-in to be accomodating especially since I have mobility issues. Our room was to be on the second floor and we were provided with a first floor upgrade at a nominal fee. It was quiet with a comfortable bed . We did find that our operation of the television was quite difficult. We feel there should have been more explanation on its control. There needs to be a more stringent final check of room readiness for the next visitor. We found the trash container in the kitchen to be half full upon our arrival. The kurig coffee maker had an empty coffee pod left in the machine after its last use by the previous traveller. This was a turnoff for us."

Mountain Meadows Lodge

10/10 Excellent

"I don't usually write reviews, but I have to describe how amazing this place is! The property is beautiful and the amenities are wonderful. It's charming and clean with so many things to enjoy like the sauna (with lake views), hot tub, kayaks and adorable game room with vintage pool table, movie area and foosball table (my favorite). All those things said, the best part was the hospitality. Victoria & Mike were so welcoming and personally made our stay very enjoyable. Victoria waited up for us to check in and made us feel so welcomed. The complimentary breakfast was wonderful (thanks Mike!) and the warm cookies...oh the cookies. We left the hotel wanting to stay longer and felt like we were leaving new friends behind. We will DEFINITELY be back!"

The Mountain Inn at Killington

10/10 Excellent

"We had a fantastic time at the Mountain Inn. I was there for a 100 mile race and the staff went above and beyond to ensure I had everything I needed to be successful. They even went to the trouble to make me my own breakfast to go! We will absolutely be back to see JP and Bodie!"

More cheap stays in Pittsfield

My Place Hotel-Randolph VT

2440 Vermont 66 Randolph Center VT

Rp1.980.230

Rp2.158.451 total

16 Jun - 17 Jun

includes taxes & fees

9.4/10 Exceptional! (456 reviews)

Frequently asked questions

Where is the best place to stay in Pittsfield?

Located 9.5 mi (15.3 km) from the heart of Pittsfield, Killington Mountain Lodge, Tapestry Collection by Hilton is a top choice for your stay, based on our traveller data. Two other choices for your trip to the area are Comfort Inn Rutland - Killington 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 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: Features continental, an indoor pool and free self parking. Woodstock Inn & Resort and The Mountain Inn at Killington are a couple of other choices that feature an on-site pool. View all hotels with pools in Pittsfield.

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 42 hotels and other accommodation options to choose from. Find out more about Pittsfield.

What are the top places to visit in Pittsfield?

Favourite places to visit include Green Mountain National Forest, Roger Clark Memorial Central Library and Pittsfield Town Hall. You'll also find Gifford Woods State Park 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.

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Our top choices for Pittsfield hotels

The Shire Woodstock

The Vesper

Kedron Valley Inn

Woodstock Inn & Resort

On The River Inn

The Jackson

Sleep Woodstock Motel

Deer Brook Inn

Echo Lake Inn

My Place Hotel-Randolph VT

Green Trails Inn

Viewmont Chalet

Killington Haus

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Grand Hotel

Snowed Inn

Après Inn Killington

Mountain Green

North Star Lodge and Resort

The Mountain Inn at Killington

Stay near popular Pittsfield attractions

Roger Clark Memorial Central Library

Learn more about Pittsfield

Top Pittsfield Hotel Reviews

Cortina Inn

More cheap stays in Pittsfield

My Place Hotel-Randolph VT

Frequently asked questions

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