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Aug 24 - Aug 25
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Compare 1,734 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Mountain Sports Inn
Front of property

Mountain Sports Inn

2.0 star property
8.8 out of 10, Excellent, (923)
"Clean, quiet stay."
The price is ₩130,057
₩143,063 total
includes taxes & fees
Aug 25 - Aug 26
Mountain Sports Inn
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 ₩152,194
₩171,979 total
includes taxes & fees
Aug 25 - Aug 26
Mountain Valley Retreat
Comfort Inn Rutland - Killington
Exterior

Comfort Inn Rutland - Killington

2.5 star property
8.0 out of 10, Very Good, (1004)
"Staff was very friendly and very helpful we had a pleasant stay."
The price is ₩185,538
₩204,091 total
includes taxes & fees
Aug 27 - Aug 28
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, (1003)
"Great place to stay"
The price is ₩145,691
₩160,260 total
includes taxes & fees
Aug 26 - Aug 27
North Star Lodge and Resort
Lincoln Inn & Gallery
Interior

Lincoln Inn & Gallery

3.0 star property
9.4 out of 10, Exceptional, (33)
"This place was great I cannot say enough about the innkeepers and the staff all in all you'll love it!!"
The price is ₩199,236
₩219,160 total
includes taxes & fees
Aug 28 - Aug 29
Lincoln Inn & Gallery
Greenbrier Inn
Lounge

Greenbrier Inn

2.0 star property
9.6 out of 10, Exceptional, (611)
"Convenient spot and priced well."
The price is ₩235,696
₩271,639 total
includes taxes & fees
Aug 25 - Aug 26
Greenbrier Inn
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, (369)
"cute an cozy, and not as tiny as the description makes it out to be"
The price is ₩213,071
₩234,378 total
includes taxes & fees
Aug 25 - Aug 26
Middlebury Sweets Motel
My Place Hotel-Randolph VT
Full-size fridge, microwave, stovetop, coffee/tea maker

My Place Hotel-Randolph VT

2.0 star property
9.4 out of 10, Exceptional, (257)
"Great place to stay!"
The price is ₩201,564
₩219,704 total
includes taxes & fees
Sep 7 - Sep 8
My Place Hotel-Randolph VT
The Mountain Inn at Killington
Breakfast and dinner served

The Mountain Inn at Killington

2.5 star property
9.2 out of 10, Wonderful, (874)
"Clean and very friendly, capable staff. 👍"
The price is ₩173,086
₩199,928 total
includes taxes & fees
Aug 25 - Aug 26
The Mountain Inn at Killington
Sleep Woodstock Motel
Deluxe Suite | 2 bedrooms, individually decorated, desk, blackout drapes

Sleep Woodstock Motel

2.0 star property
9.6 out of 10, Exceptional, (512)
"Rooms are very clean , staff are very friendly , we enjoy our stay here . "
The price is ₩143,201
₩180,364 total
includes taxes & fees
Aug 25 - Aug 26
Sleep Woodstock Motel
Brandon Inn
Exterior

Brandon Inn

3.0 star property
8.6 out of 10, Excellent, (509)
"Great stay"
The price is ₩208,644
₩229,509 total
includes taxes & fees
Aug 25 - Aug 26
Brandon Inn
The Jackson
Front of property

The Jackson

4.0 star property
9.8 out of 10, Exceptional, (228)
"Great stay! "
The price is ₩291,659
₩320,825 total
includes taxes & fees
Aug 26 - Aug 27
The Jackson
Best Western Inn & Suites Rutland-Killington
Lobby

Best Western Inn & Suites Rutland-Killington

2.5 star property
8.8 out of 10, Excellent, (1001)
"I liked it was like staying in a condo. "
The price is ₩217,928
₩239,720 total
includes taxes & fees
Sep 1 - Sep 2
Best Western Inn & Suites Rutland-Killington
The Shire Woodstock
Property grounds

The Shire Woodstock

3.0 star property
8.8 out of 10, Excellent, (809)
"Enjoyed our stay and will return"
The price is ₩207,896
₩242,411 total
includes taxes & fees
Aug 28 - Aug 29
The Shire Woodstock
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 ₩206,984
₩227,683 total
includes taxes & fees
Sep 7 - Sep 8
Hampton Inn Rutland
Emrose Luxury Cabins
Family Cabin, 2 Queen Beds | Blackout drapes, free WiFi, bed sheets

Emrose Luxury Cabins

2.0 star property
9.2 out of 10, Wonderful, (41)
"The customer service was excellent!"
The price is ₩262,881
₩297,054 total
includes taxes & fees
Aug 25 - Aug 26
Emrose Luxury Cabins
Cortina Inn
Front of property

Cortina Inn

3.0 star property
6.8 out of 10, (595)
"Staff were extremely helpful all during my stay."
The price is ₩123,277
₩135,605 total
includes taxes & fees
Aug 25 - Aug 26
Cortina 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, (1001)
"Great location, very quiet with good breakfast choices. "
The price is ₩272,302
₩350,267 total
includes taxes & fees
Aug 26 - Aug 27
On The River Inn
The Vesper
Economy Room | 1 bedroom, individually decorated, individually furnished, free WiFi

The Vesper

3.0 star property
9.4 out of 10, Exceptional, (28)
"Easy check in. Friendly staff. Bed was comfortable. Walkable to downtown Woodstock. Breakfast was limited but good!"
The price is ₩233,479
₩256,827 total
includes taxes & fees
Aug 26 - Aug 27
The Vesper
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 ₩175,023
₩192,539 total
includes taxes & fees
Sep 6 - Sep 7
Turn of River Lodge
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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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

Lincoln Inn & Gallery

Lincoln Inn & Gallery

10/10 Excellent
"Loved our stay at the Lincoln Inn. Great location, beautiful views, friendly family owned staff, delicious breakfast. Although watch your head in the bathroom. Even with the sign posted on the wall my girlfriend and I both managed to bump our heads on the low ceiling using the restroom. Definitely worth the stay though! "
Matthew 1-night trip
Posted 2 days ago
Lincoln Inn & Gallery

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 traveler data. Other good choices for your stay in the area are The Shire Woodstock and Days Inn by Wyndham Rutland/Killington Area. 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, the majority of hotel reservations are fully refundable if cancelled before the hotel’s cancellation deadline, which is often 24 or 48 hours before your check-in date. If you booked a non-refundable reservation, you may still be able to cancel and get a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Pittsfield.

Where can I learn more about changing or cancelling my trip to Pittsfield?

To find more details about changing or cancelling your trip to Pittsfield, go to https://www.expedia.com/service/.

What's the best pet-friendly place to stay 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 accommodations with pools in Pittsfield?

Woodstock Inn & Resort: Features a seasonal outdoor pool, an indoor pool, and 4 restaurants. Days Inn by Wyndham Rutland/Killington Area and North Star Lodge and Resort are a couple of other choices with an onsite pool. View all hotels with pools in Pittsfield.

What's the best accommodation near Rutland Southern Vermont Regional Airport (RUT)?

Comfort Inn Trolley Square is one of the top choices for your stay and is a popular hotel, featuring free breakfast and an indoor pool. It's located 4.9 mi (7.8 km) from Rutland Southern Vermont Regional Airport. Other choices near the airport include Holiday Inn Rutland-Killington Area and Quality Inn Rutland.

What's it like 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 accommodations to choose from. Find out more about Pittsfield.

What should I see while I'm in Pittsfield?

Favorite 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. Check out what more to see and do in Expedia's Pittsfield guide.

What's the seasonal weather like in Pittsfield?

The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 23°F. The snowiest months in Pittsfield are January, March, February, and December, with each month seeing an average of 10 inches of snowfall.