Find hotels in Pittsfield, VT from AED 375

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Compare 1,756 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

The Getaway 4 Bedroom Home

3.0 star property
The price is AED 964
AED 2,846 total
includes taxes & fees
31 Mar - 1 Apr
The Getaway 4 Bedroom Home

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 AED 731
AED 804 total
includes taxes & fees
27 Mar - 28 Mar
Stay At Jimmy's

The Shire Woodstock

3.0 star property
8.8 out of 10, Excellent, (733)
"Clean, nice, great value, nice place"
The price is AED 497
AED 580 total
includes taxes & fees
3 Apr - 4 Apr
The Shire Woodstock

The Vesper

3.0 star property
9.6 out of 10, Exceptional, (15)
"Charming inn, great service"
The price is AED 476
AED 524 total
includes taxes & fees
31 Mar - 1 Apr
The Vesper

Woodstock Inn & Resort

4.5 star property
9.2 out of 10, Wonderful, (504)
"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 AED 1,098
AED 1,370 total
includes taxes & fees
6 Apr - 7 Apr
Woodstock Inn & Resort

The Jackson

4.0 star property
9.8 out of 10, Exceptional, (207)
"Beautiful property with wonderful attention to detail and warm, friendly staff — really enjoyed our stay! Woodstock is a charming town and The Jackson staff offered great local recommendations in addition to providing comfortable lodging with thoughtful amenities, delicious breakfast and pretty views. Thank you to Dave and team — highly recommend!"
The price is AED 774
AED 852 total
includes taxes & fees
27 Mar - 28 Mar
The Jackson

506 On the River Inn

4.0 star property
9.4 out of 10, Exceptional, (982)
"Beautiful building and setting "
The price is AED 658
AED 724 total
includes taxes & fees
27 Mar - 28 Mar
506 On the River Inn

Lincoln Inn & Gallery

3.0 star property
10.0 out of 10, Exceptional, (1)
"We had a wonderful stay at the Lincoln Inn. The property was very cute and historic, and the innkeeper was warm and welcoming."
The price is AED 628
AED 691 total
includes taxes & fees
27 Mar - 28 Mar
Lincoln Inn & Gallery

Sleep Woodstock Motel

2.0 star property
9.6 out of 10, Exceptional, (475)
"Great motel that is much nicer than your typical motel"
The price is AED 375
AED 473 total
includes taxes & fees
30 Mar - 31 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 AED 953
AED 1,039 total
includes taxes & fees
8 Apr - 9 Apr
Echo Lake Inn

Intrepid Angel Farm Cottage In Bridgewater Corners 2 Bedroom Home

3.0 star property
The price is AED 1,244
AED 3,341 total
includes taxes & fees
31 Mar - 1 Apr
Intrepid Angel Farm Cottage In Bridgewater Corners 2 Bedroom Home

My Place Hotel-Randolph VT

2.0 star property
9.4 out of 10, Exceptional, (173)
"It was new, clean, and check in was easy. The room was comfortable and clean. I would stay here again if I was traveling this way again and needed a place to stay."
The price is AED 426
AED 465 total
includes taxes & fees
16 Apr - 17 Apr
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 AED 1,562
AED 4,230 total
includes taxes & fees
31 Mar - 1 Apr
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 AED 1,027
AED 2,754 total
includes taxes & fees
31 Mar - 1 Apr
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, (251)
"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 AED 424
AED 467 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 AED 1,085
AED 2,830 total
includes taxes & fees
31 Mar - 1 Apr
Sunrise West Glade: 3br, 3ba Ski In/ski Out Condo 3 Bedroom Condo

Fall Line Condo D1 1 Bedroom Condo

3.5 star property
The price is AED 559
AED 1,609 total
includes taxes & fees
31 Mar - 1 Apr
Fall Line Condo D1 1 Bedroom Condo

Fall Line Condo E1 1 Bedroom Condo

3.5 star property
The price is AED 636
AED 1,827 total
includes taxes & fees
31 Mar - 1 Apr
Fall Line Condo E1 1 Bedroom Condo

Fall Line Condos by Killington VR - 2 Bedrooms

3.5 star property
The price is AED 564
AED 1,954 total
includes taxes & fees
31 Mar - 1 Apr
Fall Line Condos by Killington VR - 2 Bedrooms

Fall Line Condo B2 3 Bedroom Condo

3.5 star property
4.0 out of 10, (1)
"This property should not be rented and I body ever got back to us and toilet was broken. You shouldn’t market this on Expedia. "
The price is AED 1,205
AED 2,794 total
includes taxes & fees
31 Mar - 1 Apr
Fall Line Condo B2 3 Bedroom Condo
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 Woodstock Inn & Resort and Killington Mountain Lodge, Tapestry Collection by Hilton. See all available top hotels, or vacation rentals in Pittsfield.

What's the top vacation rental in Pittsfield?

Killington Vermont Ski and Snowmobiling House: This highly rated vacation home rental in Pittsfield is located near skiing and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the hot tub in this rental home to help you unwind. 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: Offers 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. 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 Appalachian Trail Adventures and Green Mountain National Golf Course 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.