Search Pittsfield hotels

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Pittsfield hotels

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT
2.0 star property
Randolph Center
9.4 out of 10, Exceptional, (414 reviews)
"Great place to stay!"
Canada
Chenwei
The price is NZ$216
includes taxes & fees
20 Apr - 21 Apr
My Place Hotel-Randolph VT

Courtyard Middlebury

Courtyard Middlebury
3.0 star property
Middlebury
8.8 out of 10, Excellent, (561 reviews)
"Very clean and comfortable room. Helpful staff. "
United States
Elizabeth
The price is NZ$257
includes taxes & fees
15 Apr - 16 Apr
Courtyard Middlebury

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1,001 reviews)
"Had a lovely stay while visiting, enjoyed the breakfast and the staff were all very friendly and accommodating. Would def stay here again"
United States
dylan
The price is NZ$346
includes taxes & fees
6 Apr - 7 Apr
On The River Inn

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (562 reviews)
"A great place to stay with pets. Rooms are a little tight, but they are clean and comfortable."
United States
Ron
The price is NZ$209
includes taxes & fees
2 Apr - 3 Apr
Sleep Woodstock Motel

Green Trails Inn

Green Trails Inn
3.0 star property
Brookfield
The price is NZ$214
includes taxes & fees
12 Apr - 13 Apr
Green Trails Inn

The Mountain Inn at Killington

The Mountain Inn at Killington
2.5 star property
Killington
9.2 out of 10, Wonderful, (1,005 reviews)
"Great location and shuttle service. Nice breakfast and friendly staff. "
United States
John
The price is NZ$306
includes taxes & fees
8 Apr - 9 Apr
The Mountain Inn at Killington

Lincoln Inn & Gallery

Lincoln Inn & Gallery
3.0 star property
West Woodstock
8.6 out of 10, Excellent, (65 reviews)
"Very pleasant and comfortable stay, about 20 mins drive to Killington nearby. Room was clean and quiet, and bed was very comfortable. Nice coffee/hot chocolate bar in the lobby but unfortunately not offering breakfast anymore."
United States
Andrew
The price is NZ$260
includes taxes & fees
3 Apr - 4 Apr
Lincoln Inn & Gallery

Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area
2.5 star property
Rutland
6.6 out of 10, (1,004 reviews)
"Convenient place to stay for skiing in the area. "
United States
Alice
The price is NZ$242
includes taxes & fees
13 Apr - 14 Apr
Days Inn by Wyndham Rutland/Killington Area

Middlebury Sweets Motel

Middlebury Sweets Motel
2.5 star property
Middlebury
8.6 out of 10, Excellent, (394 reviews)
"Friendly staff, clean, comfortable and convenient to downtown. "
United States
Melissa
The price is NZ$230
includes taxes & fees
5 Apr - 6 Apr
Middlebury Sweets Motel

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington
2.5 star property
Rutland
8.0 out of 10, Very good, (1,002 reviews)
"Clean room, comfortable bed Great steakhouse next door"
United States
Mark
The price is NZ$269
includes taxes & fees
28 Apr - 29 Apr
Comfort Inn Rutland - Killington

Hampton Inn Rutland

Hampton Inn Rutland
2.5 star property
Rutland
9.0 out of 10, Wonderful, (1,001 reviews)
"Clean Hotel, rooms, great hot breakfast with fruits. A lot of restaurants nearby. "
United States
Alisher
The price is NZ$265
includes taxes & fees
16 Apr - 17 Apr
Hampton Inn Rutland

Brandon Inn

Brandon Inn
3.0 star property
Brandon
8.8 out of 10, Excellent, (605 reviews)
"Loved The Brandon Inn. Kind staff, cozy atmosphere, great location and a warm room. I will be returning here!!!"
United States
David J.
The price is NZ$217
includes taxes & fees
6 Apr - 7 Apr
Brandon Inn

The Shire Woodstock

The Shire Woodstock
3.0 star property
Woodstock
8.8 out of 10, Excellent, (917 reviews)
"Wonderful place to stay!"
United States
Robin
The price is NZ$284
includes taxes & fees
5 Apr - 6 Apr
The Shire Woodstock

The Mountain Top Inn & Resort

The Mountain Top Inn & Resort
3.5 star property
Chittenden
9.0 out of 10, Wonderful, (114 reviews)
"Great resort "
United States
Adam
The price is NZ$280
includes taxes & fees
4 Apr - 5 Apr
The Mountain Top Inn & Resort

Emrose Luxury Cabins

Emrose Luxury Cabins
2.0 star property
Brandon
9.0 out of 10, Wonderful, (87 reviews)
"Amazing stay"
United States
Kelsey
The price is NZ$319
includes taxes & fees
12 Apr - 13 Apr
Emrose Luxury Cabins

Best Western Inn & Suites Rutland-Killington

Best Western Inn & Suites Rutland-Killington
2.5 star property
Rutland
8.8 out of 10, Excellent, (1,001 reviews)
"Excellent stay for the price."
United States
Anthony
The price is NZ$308
includes taxes & fees
16 Apr - 17 Apr
Best Western Inn & Suites Rutland-Killington

Turn of River Lodge

Turn of River Lodge
2.5 star property
Killington
9.0 out of 10, Wonderful, (294 reviews)
"Great place "
United States
Matthew
Turn of River Lodge

Mountain Sports Inn

Mountain Sports Inn
2.0 star property
Killington
8.8 out of 10, Excellent, (1,000 reviews)
"Clean, great breakfast, room is a little small"
United States
Ziye
The price is NZ$190
includes taxes & fees
9 Apr - 10 Apr
Mountain Sports Inn

The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (57 reviews)
"Uniqueness of rooms, breakfast options and walking distance to so many great spots!"
United States
Emily
The price is NZ$245
includes taxes & fees
2 Apr - 3 Apr
The Vesper

Greenbrier Inn

Greenbrier Inn
2.0 star property
Killington
9.4 out of 10, Exceptional, (676 reviews)
"Great ski hotel. "
United States
Nikolai
The price is NZ$302
includes taxes & fees
6 Apr - 7 Apr
Greenbrier Inn
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.
Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Pittsfield attractions

Top Pittsfield Hotel Reviews

More cheap accommodation in Pittsfield

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 My Place Hotel-Randolph VT and Comfort Inn Rutland - Killington. 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?
Comfort Inn Rutland - Killington: Offers continental, an indoor pool and free self parking. Woodstock Inn & Resort and Best Western Inn & Suites Rutland-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 41 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.

Explore a world of travel with Expedia