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

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Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sep - 20 Sep
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov
No exact matches found, but these alternatives could be just right

Recommended hotels in Pittsfield

Breakfast and dinner served

The Mountain Inn at Killington

The Mountain Inn at Killington
2.5 star property
Killington
9.2 out of 10, Wonderful, (1,006 reviews)
"Great place to stay with the best staff!"
United States
Travis
The price is ฿4,537
฿5,240 total
includes taxes & fees
30 Jul - 31 Jul
The Mountain Inn at Killington
Lobby

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington
2.5 star property
Rutland
8.2 out of 10, Very good, (1,008 reviews)
"Good breakfast"
United States
Darshil
The price is ฿3,928
฿4,321 total
includes taxes & fees
30 Jul - 31 Jul
Comfort Inn Rutland - Killington
Lounge

Greenbrier Inn

Greenbrier Inn
2.0 star property
Killington
9.4 out of 10, Exceptional, (685 reviews)
The price is ฿5,699
฿6,568 total
includes taxes & fees
4 Aug - 5 Aug
Greenbrier Inn
Fireplace

North Star Lodge and Resort

North Star Lodge and Resort
2.0 star property
Killington
8.8 out of 10, Excellent, (1,001 reviews)
"It was a very nice and comfortable stay Lee at the front desk was extremely"
United States
shaya
The price is ฿4,647
฿5,112 total
includes taxes & fees
16 Aug - 17 Aug
North Star Lodge and Resort
Lobby sitting area

Mountain Sports Inn

Mountain Sports Inn
2.0 star property
Killington
8.8 out of 10, Excellent, (1,000 reviews)
"Breakfast had hard boiled eggs and fruit, room was functional, shower was good, great place for ski vacation"
United States
Davis
The price is ฿3,853
฿4,238 total
includes taxes & fees
5 Aug - 6 Aug
Mountain Sports Inn
Free daily buffet breakfast

Hampton Inn Rutland

Hampton Inn Rutland
2.5 star property
Rutland
9.0 out of 10, Wonderful, (1,001 reviews)
"Great place to stay Very clean and close to a lot of stores breakfast was good clean room staff was great parking was free and great"
United States
Tarsha
The price is ฿5,105
฿5,615 total
includes taxes & fees
23 Aug - 24 Aug
Hampton Inn Rutland
Lobby

Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area
2.5 star property
Rutland
6.8 out of 10, (1,005 reviews)
The price is ฿3,562
฿3,919 total
includes taxes & fees
26 Jul - 27 Jul
Days Inn by Wyndham Rutland/Killington Area
Interior detail

The Trailside Inn

The Trailside Inn
3.0 star property
North Sherburne
9.2 out of 10, Wonderful, (155 reviews)
"Great room - very clean and comfortable. Helpful and welcoming staff - even left out breakfast for our early departure."
United States
Niall
The price is ฿5,384
฿5,923 total
includes taxes & fees
27 Jul - 28 Jul
The Trailside Inn
Front of property

Brandon Inn

Brandon Inn
3.0 star property
Brandon
8.8 out of 10, Excellent, (660 reviews)
"Wonderful hosts, nice historic inn in quaint town"
United States
Katherine
The price is ฿5,097
฿5,607 total
includes taxes & fees
4 Aug - 5 Aug
Brandon Inn
BBQ/picnic Area

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT
2.0 star property
Randolph Center
9.4 out of 10, Exceptional, (495 reviews)
"I love that place"
United States
Tiffany
The price is ฿4,476
฿4,879 total
includes taxes & fees
16 Aug - 17 Aug
My Place Hotel-Randolph VT
Lobby

Best Western Inn & Suites Rutland-Killington

Best Western Inn & Suites Rutland-Killington
2.5 star property
Rutland
8.8 out of 10, Excellent, (1,000 reviews)
"Staff was very nice and went extra miles with finding activities I was interested in doing."
United States
Alex
The price is ฿6,054
฿6,659 total
includes taxes & fees
13 Aug - 14 Aug
Best Western Inn & Suites Rutland-Killington
Exterior

Après Inn Killington

Après Inn Killington
2.0 star property
Killington
9.4 out of 10, Exceptional, (190 reviews)
"Location is great"
United States
Lei
The price is ฿5,014
฿5,515 total
includes taxes & fees
5 Aug - 6 Aug
Après Inn Killington
Exterior

Courtyard Middlebury

Courtyard Middlebury
3.0 star property
Middlebury
9.0 out of 10, Wonderful, (584 reviews)
"Very comfortable, clean room. Good location."
United States
Ann
The price is ฿5,374
฿5,911 total
includes taxes & fees
28 Jul - 29 Jul
Courtyard Middlebury
Lake view

Mountain Meadows Lodge

Mountain Meadows Lodge
3.5 star property
Killington
9.6 out of 10, Exceptional, (246 reviews)
"Beautiful location, property provides everything to relax your mind and soul with genuinely kinds hosts, true gem!"
United States
MALGORZATA
The price is ฿5,627
฿7,036 total
includes taxes & fees
24 Aug - 25 Aug
Mountain Meadows Lodge
Exterior

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton
3.5 star property
Killington
7.4 out of 10, Good, (1,001 reviews)
"We had a great stay. The staff was nice and the property was awesome. The beds were super comfy and the rooms were clean.Close to everything."
United States
Nicole
The price is ฿5,260
฿5,786 total
includes taxes & fees
2 Aug - 3 Aug
Killington Mountain Lodge, Tapestry Collection by Hilton
Front of property

Snowed Inn

Snowed Inn
3.5 star property
Killington
9.8 out of 10, Exceptional, (400 reviews)
"Very convenient location with warmth and wonderful hosts."
United States
Martin
The price is ฿4,398
฿5,322 total
includes taxes & fees
28 Jul - 29 Jul
Snowed Inn
Hallway

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1,005 reviews)
"convenient location with very comfortable accommodations"
United States
Tonine
The price is ฿9,558
฿11,257 total
includes taxes & fees
4 Aug - 5 Aug
On The River Inn
Deluxe Suite | Private kitchen | Coffee/tea maker, mini-fridge, microwave, freezer

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (594 reviews)
"Love that they catered to my dog. Will be back!"
United States
Mark
The price is ฿2,616
฿2,878 total
includes taxes & fees
28 Jul - 29 Jul
Sleep Woodstock Motel
Elite Cabin, 1 King Bed, Sauna | Laptop workspace, blackout curtains, free WiFi, individually decorated

Emrose Luxury Cabins

Emrose Luxury Cabins
2.0 star property
Brandon
9.0 out of 10, Wonderful, (104 reviews)
"Very nice, clean place to stay in Brandon. Visited family over the years and this was by far the best stay...."
United States
Tim
The price is ฿5,475
฿6,187 total
includes taxes & fees
26 Jul - 27 Jul
Emrose Luxury Cabins
The Jewel | Living area | TV

The Mountain Top Inn & Resort

The Mountain Top Inn & Resort
3.5 star property
Chittenden
9.0 out of 10, Wonderful, (121 reviews)
"Excellent stay "
United States
Kristen
The price is ฿10,985
฿11,973 total
includes taxes & fees
5 Aug - 6 Aug
The Mountain Top Inn & Resort
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.
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Top Pittsfield Hotel Reviews

Sleep Woodstock Motel

Sleep Woodstock Motel

10/10 Excellent
"Nice clean quiet place with reasonable coffee machine, fridge and functional microwave"
Barbara 1-night trip
Posted less than an hour ago
Sleep Woodstock Motel

Find out more about Pittsfield

Pittsfield Apartments information

Number of reviews
8,172
Accommodation
32 Apartments
Lowest Price
฿3,919
Highest Price
฿23,538

Frequently asked questions

What's it like to stay at an apartment in Pittsfield?
You'll find plenty of places to stay in Pittsfield with 42 accommodation options. Though there aren't many apartments, we can help you locate accommodation that is similar. When you search on Expedia, you can filter by amenities such as a kitchen— just one of the conveniences you might find in an apartment. You can even filter by similar properties such as holiday homes, condos or guest houses.
Why consider apartments instead of traditional hotels?
An apartment is often more spacious than a traditional hotel room and includes a kitchen, so you can have some home-cooked meals. Apartments are ideal for families who want the conveniences of home, and also for couples who want to stay in a quieter area.
What can I expect from the weather when I travel to Pittsfield?
Although weather is just one factor, it can really affect your travel plans, especially when you're planning an extended stay 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.
What should I see and do in Pittsfield?
While exploring the area, visit family-friendly sights like Killington Adventure Center, or get outside and enjoy nature at Green Mountain National Forest. Roger Clark Memorial Central Library and Pittsfield Town Hall are other places to visit while you're in town.
What's the best way to get to and around Pittsfield?
Knowing a bit about the transportation options can make your trip smoother when you get to your destination. Fly into Rutland, VT (RUT-Rutland Southern Vermont Regional), which is located 18.1 mi (29.2 km) from the city centre. You can also search for flights into Lebanon, NH (LEB-Lebanon Municipal), which is 27.2 mi (43.7 km) away. If you'd like to explore around the area, you may want a rental car for your journey.