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31 Aug - 1 Sep
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5 Sep - 7 Sep
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Top 10 Pittsfield hotels and places to stay

Mountain Valley Retreat
Exterior

Mountain Valley Retreat

2.5 star property
9.6 out of 10, Exceptional, (182)
"This place is a refuge -- location, facility and hosts!"
The price is ฿3,557
฿4,019 total
includes taxes & fees
1 Sept - 2 Sept
Mountain Valley Retreat
Mountain Sports Inn
Front of property

Mountain Sports Inn

2.0 star property
8.8 out of 10, Excellent, (926)
"Clean, quiet stay."
The price is ฿3,201
฿3,521 total
includes taxes & fees
1 Sept - 2 Sept
Mountain Sports Inn
Lincoln Inn & Gallery
Interior

Lincoln Inn & Gallery

3.0 star property
9.4 out of 10, Exceptional, (35)
"This place was great I cannot say enough about the innkeepers and the staff all in all you'll love it!!"
The price is ฿4,656
฿5,122 total
includes taxes & fees
3 Sept - 4 Sept
Lincoln Inn & Gallery
Sleep Woodstock Motel
Deluxe Suite | 2 bedrooms, individually decorated, desk, blackout curtains

Sleep Woodstock Motel

2.0 star property
9.6 out of 10, Exceptional, (516)
"Rooms are very clean , staff are very friendly , we enjoy our stay here . "
The price is ฿3,347
฿4,215 total
includes taxes & fees
1 Sept - 2 Sept
Sleep Woodstock Motel
The Mountain Inn at Killington
Breakfast and dinner served

The Mountain Inn at Killington

2.5 star property
9.2 out of 10, Wonderful, (879)
"The staff was so welcoming and friendly, the rooms were immaculate and "
The Mountain Inn at Killington
My Place Hotel-Randolph VT
Full-sized fridge, microwave, stovetop, coffee/tea maker

My Place Hotel-Randolph VT

2.0 star property
9.4 out of 10, Exceptional, (260)
"Great place to stay!"
The price is ฿5,348
฿5,829 total
includes taxes & fees
7 Sept - 8 Sept
My Place Hotel-Randolph VT
Comfort Inn Rutland - Killington
Exterior

Comfort Inn Rutland - Killington

2.5 star property
8.0 out of 10, Very good, (1009)
"Staff was very friendly and very helpful we had a pleasant stay."
The price is ฿3,754
฿4,130 total
includes taxes & fees
4 Sept - 5 Sept
Comfort Inn Rutland - Killington
North Star Lodge and Resort
Standard Room, 2 Double Beds | Iron/ironing board, free WiFi, bed sheets

North Star Lodge and Resort

2.0 star property
8.6 out of 10, Excellent, (1006)
"Great place to stay"
North Star Lodge and Resort
Best Western Inn & Suites Rutland-Killington
Lobby

Best Western Inn & Suites Rutland-Killington

2.5 star property
8.8 out of 10, Excellent, (1004)
"I liked it was like staying in a condo. "
The price is ฿5,093
฿5,602 total
includes taxes & fees
7 Sept - 8 Sept
Best Western Inn & Suites Rutland-Killington
Brandon Inn
Exterior

Brandon Inn

3.0 star property
8.6 out of 10, Excellent, (514)
"Great charming stay! "
The price is ฿5,885
฿6,473 total
includes taxes & fees
1 Sept - 2 Sept
Brandon Inn
Hampton Inn Rutland
Exterior

Hampton Inn Rutland

2.5 star property
9.0 out of 10, Wonderful, (934)
"The staff were helpful and morning breakfast very good. "
The price is ฿4,810
฿5,291 total
includes taxes & fees
7 Sept - 8 Sept
Hampton Inn Rutland
Middlebury Sweets Motel
Classic Room, 2 Queen Beds | Desk, iron/ironing board, free WiFi, bed sheets

Middlebury Sweets Motel

2.5 star property
8.6 out of 10, Excellent, (370)
"cute an cozy, and not as tiny as the description makes it out to be"
The price is ฿4,980
฿5,478 total
includes taxes & fees
2 Sept - 3 Sept
Middlebury Sweets Motel
Courtyard Middlebury
Exterior

Courtyard Middlebury

3.0 star property
8.8 out of 10, Excellent, (523)
"Daily or at least every other day housekeeping service would have been appreciated. "
The price is ฿4,627
฿5,090 total
includes taxes & fees
7 Sept - 8 Sept
Courtyard Middlebury
Greenbrier Inn
Lounge

Greenbrier Inn

2.0 star property
9.4 out of 10, Exceptional, (612)
"Convenient spot and priced well."
Greenbrier Inn
On The River Inn
Family Suite, 2 Bedrooms | Private kitchen | Microwave

On The River Inn

4.0 star property
9.4 out of 10, Exceptional, (1003)
"Great location, very quiet with good breakfast choices. "
On The River Inn
Turn of River Lodge
Bicycling

Turn of River Lodge

2.5 star property
9.0 out of 10, Wonderful, (254)
"Rustic, simple, no frills ski lodge. Very friendly staff, solid breakfast and clean rooms. If you’re in town to ski, golf, or get out in the mountains, its a good option to save some dough and still be near everything."
The price is ฿4,090
฿4,500 total
includes taxes & fees
6 Sept - 7 Sept
Turn of River Lodge
The Shire Woodstock
Property grounds

The Shire Woodstock

3.0 star property
8.8 out of 10, Excellent, (812)
"Enjoyed our stay and will return"
The Shire Woodstock
The Jackson
Front of property

The Jackson

4.0 star property
9.8 out of 10, Exceptional, (228)
"Great stay! "
The Jackson
Mountain Meadows Lodge
Lake view

Mountain Meadows Lodge

3.5 star property
9.4 out of 10, Exceptional, (148)
"Lovely grounds, amenities were nice. "
The price is ฿5,059
฿6,373 total
includes taxes & fees
1 Sept - 2 Sept
Mountain Meadows Lodge
Snowed Inn
Front of property

Snowed Inn

3.5 star property
9.8 out of 10, Exceptional, (358)
"Beautiful place to stay! 10/10 would recommend. You're going to love it!"
The price is ฿4,985
฿6,032 total
includes taxes & fees
1 Sept - 2 Sept
Snowed 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.
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Top Pittsfield Hotel Reviews

More cheap stays in Pittsfield

More cheap stays in Pittsfield

The Mountain Inn at Killington

The Mountain Inn at Killington

47 Old Mill Rd, Killington, VT
Get rates

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Explore a world of travel with Expedia

Frequently asked questions

Where is the best place to stay in Pittsfield?

Located 17.9 mi (28.9 km) from the heart of Pittsfield, Woodstock Inn & Resort is a top choice for your stay, based on our traveller data. Two other choices for your trip to the area are The Mountain Inn at Killington and The Shire Woodstock. 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?

Woodstock Inn & Resort: Features a seasonal outdoor pool, an indoor pool and 4 restaurants. The Mountain Inn at Killington and Days Inn by Wyndham Rutland/Killington Area 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.