Best Pittsfield Hotels in 2026 from HK$941 - Fully Refundable Options

Our top choices for Pittsfield hotels

1. Green Trails Inn

Brookfield

Christine

HK$1,070 total

includes taxes & fees

17 Jun - 18 Jun

2. My Place Hotel-Randolph VT

Randolph Center

Nicholas

HK$941 total

includes taxes & fees

2 Jul - 3 Jul

3. Sleep Woodstock Motel

Woodstock

Elisabeth

HK$1,128 total

includes taxes & fees

24 Jun - 25 Jun

4. The Jackson

West Woodstock

Courtney

HK$1,358 total

includes taxes & fees

18 Jun - 19 Jun

5. The Mountain Inn at Killington

Killington

Christine

HK$1,214 total

includes taxes & fees

17 Jun - 18 Jun

6. Lincoln Inn & Gallery

West Woodstock

Elisabeth

HK$1,629 total

includes taxes & fees

16 Jun - 17 Jun

7. Mountain Sports Inn

Killington

Peter

HK$940 total

includes taxes & fees

23 Jun - 24 Jun

8. Brandon Inn

Brandon

Eva

HK$1,210 total

includes taxes & fees

14 Jun - 15 Jun

9. Hampton Inn Rutland

Rutland

Elaine

HK$1,261 total

includes taxes & fees

5 Jul - 6 Jul

10. The Vesper

Woodstock

Melissa

HK$1,509 total

includes taxes & fees

14 Jun - 15 Jun

11. Middlebury Sweets Motel

Middlebury

Michael

HK$1,091 total

includes taxes & fees

14 Jun - 15 Jun

12. Comfort Inn Rutland - Killington

Rutland

brian

HK$1,128 total

includes taxes & fees

5 Jul - 6 Jul

13. Inn at Neshobe River

Brandon

Keith

HK$1,433 total

includes taxes & fees

22 Jun - 23 Jun

14. Days Inn by Wyndham Rutland/Killington Area

Rutland

Edita

HK$1,078 total

includes taxes & fees

5 Jul - 6 Jul

15. Stay At Jimmy's

Woodstock

Heather

HK$2,146 total

includes taxes & fees

22 Jun - 23 Jun

16. On The River Inn

West Woodstock

Sophia

17. Emrose Luxury Cabins

Brandon

Tim

HK$1,435 total

includes taxes & fees

6 Jul - 7 Jul

18. The Shire Woodstock

Woodstock

Arlene

HK$1,533 total

includes taxes & fees

1 Jul - 2 Jul

19. Mountain Meadows Lodge

Killington

Tanuja

HK$1,706 total

includes taxes & fees

1 Jul - 2 Jul

20. The Mountain Top Inn & Resort

Chittenden

Kristen

HK$2,360 total

includes taxes & fees

23 Jun - 24 Jun

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Stay near popular Pittsfield attractions

Pittsfield Town Hall

After visiting Pittsfield Town Hall, 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

The Shire Woodstock

10/10 Excellent

"It was a very comfortable and nice place to stay with a lot of things within walking distance and having it next to the river was fun. They also have bonfires that you can sit by at night. It was a wonderful day."

Lincoln Inn & Gallery

6/10 Okay

"My primary complaint was the morning we checked out. Actually we just dropped the key in the basket. You would think with checkout at 10:00 the proprietor would be around to see us off at 9:30. Instead, he was nowhere to be found. The desk had a phone number to call which I did, and the cordless phone rang at the desk but he did not have it with him so we left with the answering machine going off. I just wanted some ice to keep our stuff cold till our next stop. Instead I stopped at a gas station to get ice. Sometimes the devil is in the details."

Mountain Sports Inn

8/10 Good

"This is the 4th or 5th time I have stayed here but in the past it was only for a night or two. This time we were there for 5 nights. There were good things and bad, I’ll start with the bad. My biggest complaints were space for clothing, temperature, and the bed. There are two little drawers in each nightstand, but otherwise all storage areas are open. I prefer to have my underclothes in drawers. That’s a preference thing, but nice to know in advance. The temperature was fine during the day but once you close the blackout drapes, you lose any ability to cool using the window units. The first two nights it was cool enough outside to open a window and that kept it cooler. The last night I was there I slept in top of the cover and blanket (took off comforter first night and never put back on) most of the night to stay cool. If you like to sleep cool (I prefer 67 or 68 degrees), bring a fan. Or maybe ask if they had one, I literally thought of that the last night I was there so didn’t. The bed was harder than I remember it being any other time we stayed and the pillows were flat and hard. It’s also on a spring frame, so every time you move it creaked. We could have asked for more pillows but made do. I would definitely stay again but if it was a longer stay in warmer weather, I would plan ahead and bring a fan. The breakfast was great and had been added to since we last stayed. Ample parking, good WiFi (went down once, but was quickly restored), nice location and friendly people."

More cheap stays in Pittsfield

My Place Hotel-Randolph VT

2440 Vermont 66 Randolph Center VT

HK$863

HK$941 total

2 Jul - 3 Jul

includes taxes & fees

9.4/10 Exceptional! (461 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 Woodstock Inn & Resort and My Place Hotel-Randolph VT. See all available top hotels, or vacation rentals in Pittsfield.

What are some of the best holiday rentals that Pittsfield has to offer?

Killington area home - 4-seasons, hot tub and A/C: This highly rated holiday home rental in Pittsfield is located in the mountains, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday. See all 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?

Woodstock Inn & Resort: Provides a seasonal outdoor pool, an indoor pool and 4 restaurants. The Mountain Inn at Killington and On The River Inn 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 38 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 Green Mountain National Golf Course and Gifford Woods State Park 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.

Pittsfield hotels from HK$941

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Our top choices for Pittsfield hotels

1. Green Trails Inn

2. My Place Hotel-Randolph VT

3. Sleep Woodstock Motel

4. The Jackson

5. The Mountain Inn at Killington

6. Lincoln Inn & Gallery

7. Mountain Sports Inn

8. Brandon Inn

9. Hampton Inn Rutland

10. The Vesper

11. Middlebury Sweets Motel

12. Comfort Inn Rutland - Killington

13. Inn at Neshobe River

14. Days Inn by Wyndham Rutland/Killington Area

15. Stay At Jimmy's

16. On The River Inn

17. Emrose Luxury Cabins

18. The Shire Woodstock

19. Mountain Meadows Lodge

20. The Mountain Top Inn & Resort

Stay near popular Pittsfield attractions

Pittsfield Town Hall

Learn more about Pittsfield

Top Pittsfield Hotel Reviews

The Shire Woodstock

More cheap stays in Pittsfield

My Place Hotel-Randolph VT

Frequently asked questions

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