Find hotels in Pittsfield, VT from SAR 383

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Compare 1,699 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Stay At Jimmy's

3.0 star property
10.0 out of 10, Exceptional, (28)
"We spent a wonderful week at Stay at Jimmy’s, with our dog Sofia (they are super dog friendly) and it was the perfect escape. From the moment we arrived, the hospitality was top-notch. The Relax Room was absolutely amazing—the whirlpool tub was the best we’ve ever used, making it the ideal place to unwind. Every morning, we were treated to fresh-baked goods, a great selection of teas, coffee, and soft drinks, which made us feel right at home. The attention to detail in the interior design was...
The price is SAR 746
SAR 821 total
includes taxes & fees
5 Mar - 6 Mar
Stay At Jimmy's

The Shire Woodstock

3.0 star property
8.8 out of 10, Excellent, (729)
"Great hotel, room was cute and with a nice view. 5 min walk to downtown. If we needed anything we just texted the front desk and they got us what we needed. Would stay again!"
The price is SAR 737
SAR 859 total
includes taxes & fees
5 Mar - 6 Mar
The Shire Woodstock

The Vesper

3.0 star property
9.6 out of 10, Exceptional, (15)
"Charming inn, great service"
The price is SAR 650
SAR 715 total
includes taxes & fees
10 Mar - 11 Mar
The Vesper

Woodstock Inn & Resort

4.5 star property
9.2 out of 10, Wonderful, (503)
"The Woodstock Inn & Resort is the quintessential New England inn. Walk in the lobby and you are greeted by a large warm fire. The staff at all levels were gracious and helpful. The room was large, well decorated and extremely comfortable. Great location to walk downtown even with single digit temperatures. The shops were expensive but worth browsing & buying. "
The price is SAR 1,121
SAR 1,399 total
includes taxes & fees
16 Mar - 17 Mar
Woodstock Inn & Resort

The Jackson

4.0 star property
10.0 out of 10, Exceptional, (204)
"Very comfortable accommodations, and incredibly friendly and helpful staff. It was great to have coffee/tea available anytime and we spent lots of time by the cozy fire. "
The price is SAR 791
SAR 870 total
includes taxes & fees
12 Mar - 13 Mar
The Jackson

506 On the River Inn

4.0 star property
9.4 out of 10, Exceptional, (969)
"Beautiful views of the river. Nice restaurant. Rooms well appointed for skiing guests. Pool and library with games and pool table a plus! "
The price is SAR 784
SAR 862 total
includes taxes & fees
5 Mar - 6 Mar
506 On the River Inn

Sleep Woodstock Motel

2.0 star property
9.6 out of 10, Exceptional, (471)
"This place was adorable, and it was a very lucky find on the eve of a storm on a holiday weekend with 2 dogs in tow. Seems to be an old motel renovated. Cute decor. There were lots of cute helpful extras packed into a small space. Coffee, tea and Cider for the Keurig, retro mini fridge, garbage can with recyclables and compost sections, dog quilts. Self check in. Lot was frequently plowed during 24 hours of snow. Close to Killington and downtown Woodstock. Loved the 3pm check in and 11am...
The price is SAR 383
SAR 421 total
includes taxes & fees
5 Mar - 6 Mar
Sleep Woodstock Motel

Echo Lake Inn

2.5 star property
8.6 out of 10, Excellent, (96)
"Old fashioned inn with wonderful hosts."
The price is SAR 984
SAR 1,072 total
includes taxes & fees
10 Mar - 11 Mar
Echo Lake Inn

My Place Hotel-Randolph VT

2.0 star property
9.4 out of 10, Exceptional, (152)
"The accommodations were wonderful. We only wish that a softer pillow was available (all four on our bed where firm.)'"
The price is SAR 435
SAR 475 total
includes taxes & fees
25 Mar - 26 Mar
My Place Hotel-Randolph VT

The Queens Croft V2 - Luxury Killington Ski Home. Newer. Better. Ski-ier. 3 Bedroom Home

3.0 star property
The price is SAR 2,934
SAR 6,072 total
includes taxes & fees
9 Mar - 10 Mar
The Queens Croft V2 - Luxury Killington Ski Home. Newer. Better. Ski-ier. 3 Bedroom Home

Sunrise Timberline: 3br, 2ba Ski In/ski Out Condo 3 Bedroom Condo

3.0 star property
The price is SAR 1,241
SAR 3,064 total
includes taxes & fees
5 Mar - 6 Mar
Sunrise Timberline: 3br, 2ba Ski In/ski Out Condo 3 Bedroom Condo

Turn of River Lodge

2.5 star property
9.0 out of 10, Wonderful, (247)
"Perfect for what i wanted - a bed to sleep"
The price is SAR 433
SAR 477 total
includes taxes & fees
1 Apr - 2 Apr
Turn of River Lodge

Sunrise West Glade: 3br, 3ba Ski In/ski Out Condo 3 Bedroom Condo

3.0 star property
The price is SAR 1,324
SAR 3,173 total
includes taxes & fees
18 Mar - 19 Mar
Sunrise West Glade: 3br, 3ba Ski In/ski Out Condo 3 Bedroom Condo

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 star property
7.2 out of 10, Good, (1000)
"Great place, helpful staff! However, miscommunication with the bus schedule… make sure to stand on correct side of road when using bus* "
The price is SAR 584
SAR 642 total
includes taxes & fees
2 Apr - 3 Apr
Killington Mountain Lodge, Tapestry Collection by Hilton

Whitetail Chalet 4 Bedroom Home

3.0 star property
The price is SAR 1,624
SAR 3,566 total
includes taxes & fees
12 Mar - 13 Mar
Whitetail Chalet 4 Bedroom Home

The Tanglewood Lodge: Amazing Ski Home For Groups. Hot Tub. Close To Killington Resort! 4 Bedroom Home

3.0 star property
The price is SAR 1,890
SAR 4,112 total
includes taxes & fees
6 Mar - 7 Mar
The Tanglewood Lodge: Amazing Ski Home For Groups. Hot Tub. Close To Killington Resort! 4 Bedroom Home

Killington Grand Hotel

3.5 star property
8.8 out of 10, Excellent, (172)
"Great hotel very child and family friendly"
The price is SAR 1,778
SAR 2,085 total
includes taxes & fees
11 Mar - 12 Mar
Killington Grand Hotel

Mountain Green Condo 1B9 1 Condo

3.5 star property
The price is SAR 823
SAR 2,085 total
includes taxes & fees
9 Mar - 10 Mar
Mountain Green Condo 1B9 1 Condo

Snowed Inn

3.5 star property
9.8 out of 10, Exceptional, (330)
"Great location, beautiful property! "
The price is SAR 641
SAR 776 total
includes taxes & fees
3 Apr - 4 Apr
Snowed Inn

Après Inn Killington

2.0 star property
9.4 out of 10, Exceptional, (109)
"Perfect spot and place for a skiers getaway. Clean newly renovated. everything you need for your stay is 5 minutes away form the Inn. The room itself has all you need would 100% recommend"
The price is SAR 553
SAR 609 total
includes taxes & fees
31 Mar - 1 Apr
Après Inn Killington
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 My Place Hotel-Randolph VT. See all available top hotels, or vacation rentals in Pittsfield.

What's the top vacation rental in Pittsfield?

Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi: This vacation home rental near Pittsfield offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub. See all 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?

Comfort Inn Rutland - Killington: Features buffet, an indoor pool, and free self parking. Woodstock Inn & Resort and Days Inn by Wyndham Rutland/Killington Area 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 39 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. 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.