Pittsfield Hotels

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Feb 16 - Feb 17
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Feb 17 - Feb 18
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Feb 21 - Feb 23
In two weeks
Feb 28 - Mar 2

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Top 10 trending Pittsfield hotels

Stay At Jimmy's
Front of property

Stay At Jimmy's

3.0 star property
10.0 out of 10, Exceptional, (26)
"Good ownership, very helpful"
The price is P14,403
P15,843 total
includes taxes & fees
Feb 18 - Feb 19
Stay At Jimmy's
The Shire Woodstock
Property grounds

The Shire Woodstock

3.0 star property
8.8 out of 10, Excellent, (724)
"Stayed for a family ski weekend. Wonderful, clean accommodations with a great view. "
The price is P8,447
P10,083 total
includes taxes & fees
Feb 25 - Feb 26
The Shire Woodstock
The Vesper
Individually decorated, individually furnished, free WiFi, bed sheets

The Vesper

3.0 star property
9.6 out of 10, Exceptional, (14)
"I loved that this property was within walking distance to all the shops and restaurants in downtown Woodstock "
The price is P8,134
P8,948 total
includes taxes & fees
Feb 20 - Feb 21
The Vesper
Woodstock Inn & Resort
Lobby

Woodstock Inn & Resort

4.5 star property
9.2 out of 10, Wonderful, (501)
"Great resort, beautiful property-only issue was room was cold - aside from that, loved the stay "
The price is P17,295
P21,570 total
includes taxes & fees
Mar 2 - Mar 3
Woodstock Inn & Resort
The Jackson
Fireplace

The Jackson

4.0 star property
10.0 out of 10, Exceptional, (200)
"Great stay clean and comfortable. Staff was very accommodating and friendly. "
The price is P12,911
P14,202 total
includes taxes & fees
Mar 2 - Mar 3
The Jackson
506 On the River Inn
Private kitchen

506 On the River Inn

4.0 star property
9.4 out of 10, Exceptional, (962)
"Great 3 night stay all around! "
The price is P13,246
P14,571 total
includes taxes & fees
Feb 23 - Feb 24
506 On the River Inn
Sleep Woodstock Motel
Individually decorated, desk, blackout drapes, iron/ironing board

Sleep Woodstock Motel

2.0 star property
9.6 out of 10, Exceptional, (458)
"Such a cute room. Convenient and cozy. Easy check in process. "
The price is P5,900
P6,490 total
includes taxes & fees
Feb 24 - Feb 25
Sleep Woodstock Motel
Echo Lake Inn
Exterior

Echo Lake Inn

2.5 star property
8.6 out of 10, Excellent, (94)
"Old fashioned inn with wonderful hosts."
The price is P16,859
P18,376 total
includes taxes & fees
Feb 25 - Feb 26
Echo Lake Inn
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, (130)
"."
The price is P7,462
P8,133 total
includes taxes & fees
Feb 19 - Feb 20
My Place Hotel-Randolph VT
Turn of River Lodge
Interior

Turn of River Lodge

2.5 star property
9.0 out of 10, Wonderful, (243)
"Cute lodge, friendly atmosphere "
The price is P12,725
P13,998 total
includes taxes & fees
Feb 20 - Feb 21
Turn of River Lodge
Fall Line Condo D6 3 Bedroom Condo
Living area

Fall Line Condo D6 3 Bedroom Condo

3.5 star property
The price is P63,772
P102,114 total
includes taxes & fees
Feb 18 - Feb 19
Fall Line Condo D6 3 Bedroom Condo
Fall Line Condos by Killington VR - 3 Bedrooms
Interior

Fall Line Condos by Killington VR - 3 Bedrooms

3.5 star property
The price is P22,396
P50,759 total
includes taxes & fees
Feb 27 - Feb 28
Fall Line Condos by Killington VR - 3 Bedrooms
Beautiful 2br/2ba Fall Line Condo W/ Mountain Views, Pool, Hot Tub, Sauna, Shuttle. G6b 2 Bedroom Condo
Exterior

Beautiful 2br/2ba Fall Line Condo W/ Mountain Views, Pool, Hot Tub, Sauna, Shuttle. G6b 2 Bedroom Condo

3.5 star property
The price is P15,412
P39,326 total
includes taxes & fees
Feb 27 - Feb 28
Beautiful 2br/2ba Fall Line Condo W/ Mountain Views, Pool, Hot Tub, Sauna, Shuttle. G6b 2 Bedroom Condo
Fall Line Small Studio - Perfect For Two - On Shuttle Route W/ Amenities G6a 1 Bedroom Condo
Exterior

Fall Line Small Studio - Perfect For Two - On Shuttle Route W/ Amenities G6a 1 Bedroom Condo

2.0 star property
The price is P6,377
P18,337 total
includes taxes & fees
Feb 27 - Feb 28
Fall Line Small Studio - Perfect For Two - On Shuttle Route W/ Amenities G6a 1 Bedroom Condo
Killington Mountain Lodge, Tapestry Collection by Hilton
Terrace/patio

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 star property
7.2 out of 10, Good, (1001)
"It was great other than the hot tub not working correctly "
The price is P11,720
P12,892 total
includes taxes & fees
Mar 17 - Mar 18
Killington Mountain Lodge, Tapestry Collection by Hilton
Whitetail Chalet 4 Bedroom Home
Outdoor spa tub

Whitetail Chalet 4 Bedroom Home

3.0 star property
The price is P40,845
P75,672 total
includes taxes & fees
Feb 26 - Feb 27
Whitetail Chalet 4 Bedroom Home
The Birch Ridge: Blue Velvet Room #10 - Queen Suite In Killington, Vermont. Hot Tub. Lounge. 1 Bedroom Home
Interior

The Birch Ridge: Blue Velvet Room #10 - Queen Suite In Killington, Vermont. Hot Tub. Lounge. 1 Bedroom Home

4.0 star property
The price is P15,184
P27,193 total
includes taxes & fees
Feb 18 - Feb 19
The Birch Ridge: Blue Velvet Room #10 - Queen Suite In Killington, Vermont. Hot Tub. Lounge. 1 Bedroom Home
The Birch Ridge: Family Room #11 - Queen/bunkbed Suite In Killington, Vermont 1 Bedroom Home
Interior

The Birch Ridge: Family Room #11 - Queen/bunkbed Suite In Killington, Vermont 1 Bedroom Home

4.0 star property
The price is P26,572
P45,536 total
includes taxes & fees
Feb 18 - Feb 19
The Birch Ridge: Family Room #11 - Queen/bunkbed Suite In Killington, Vermont 1 Bedroom Home
The Birch Ridge: American Classic Room #7 - King Suite In Killington. Hot Tub. 1 Bedroom Home
Interior

The Birch Ridge: American Classic Room #7 - King Suite In Killington. Hot Tub. 1 Bedroom Home

4.0 star property
The price is P26,572
P42,100 total
includes taxes & fees
Feb 18 - Feb 19
The Birch Ridge: American Classic Room #7 - King Suite In Killington. Hot Tub. 1 Bedroom Home
The Birch Ridge: Mission Room #4 - Queen Suite In Killington, Vermont 1 Bedroom Home
Interior

The Birch Ridge: Mission Room #4 - Queen Suite In Killington, Vermont 1 Bedroom Home

4.0 star property
The price is P15,184
P27,193 total
includes taxes & fees
Feb 18 - Feb 19
The Birch Ridge: Mission Room #4 - Queen Suite In Killington, Vermont 1 Bedroom Home
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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Frequently asked questions

Where is the best place to stay in Pittsfield?

Located 14.4 mi (23.2 km) from the heart of Pittsfield, Comfort Inn Rutland - Killington is a top choice for your stay based on our traveler data. Other good choices for your stay in the area are Killington Mountain Lodge, Tapestry Collection by Hilton and Woodstock Inn & Resort. 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 budget-friendly hotel in Pittsfield?

Based on reviews, Clear River Inn is a popular inn for our travelers who want a more economical choice, and features free WiFi and free parking. View all budget hotels in Pittsfield.

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?

Comfort Inn Rutland - Killington: Features buffet, an indoor pool, and free self parking. Woodstock Inn & Resort and Summit Lodge 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. A top sight in the area is Killington Resort. In Pittsfield, there are 40 hotels and other accommodations to choose from. Find out more about Pittsfield.

What should I see while I'm in Pittsfield?

A favorite place to visit is Green Mountain National Forest. Additionally, you'll find Killington Resort 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.