Pittsfield Hotels

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Check prices for these dates

Tonight
30 Mar - 31 Mar
Tomorrow
31 Mar - 1 Apr
Next weekend
4 Apr - 6 Apr
In two weeks
11 Apr - 13 Apr

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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, (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 €202
includes taxes & fees
31 Mar - 1 Apr
Stay At Jimmy's
The Shire Woodstock
Property grounds

The Shire Woodstock

3.0 star property
8.8 out of 10, Excellent, (733)
"Clean, nice, great value, nice place"
The price is €134
includes taxes & fees
9 Apr - 10 Apr
The Shire Woodstock
The Vesper
Economy Room

The Vesper

3.0 star property
9.6 out of 10, Exceptional, (15)
"Charming inn, great service"
The price is €143
includes taxes & fees
2 Apr - 3 Apr
The Vesper
Woodstock Inn & Resort
Lobby

Woodstock Inn & Resort

4.5 star property
9.2 out of 10, Wonderful, (504)
"All the staff, whether the bartender, wait staff, men at the front door, desk clerk everyone greeting my wife and I with a smile and were very helpful."
The price is €344
includes taxes & fees
6 Apr - 7 Apr
Woodstock Inn & Resort
The Jackson
Fireplace

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 €202
includes taxes & fees
12 Apr - 13 Apr
The Jackson
506 On the River Inn
Family Suite, 2 Bedrooms | Private kitchen

506 On the River Inn

4.0 star property
9.4 out of 10, Exceptional, (982)
"Beautiful pool setting"
The price is €216
includes taxes & fees
31 Mar - 1 Apr
506 On the River Inn
Lincoln Inn & Gallery
Front of property

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 €113
includes taxes & fees
31 Mar - 1 Apr
Lincoln Inn & Gallery
Sleep Woodstock Motel
Deluxe Suite

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 €119
includes taxes & fees
31 Mar - 1 Apr
Sleep Woodstock Motel
Echo Lake Inn
Exterior

Echo Lake Inn

2.5 star property
8.6 out of 10, Excellent, (96)
"Old fashioned inn with wonderful hosts."
The price is €293
includes taxes & fees
31 Mar - 1 Apr
Echo Lake Inn
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, (174)
"The staff were very friendly and accommodating. We were treated with the highest level of professional courtesy. We will definitely return to this location. 5 stars all the way. "
The price is €117
includes taxes & fees
20 Apr - 21 Apr
My Place Hotel-Randolph VT
Turn of River Lodge
Interior

Turn of River Lodge

2.5 star property
9.0 out of 10, Wonderful, (251)
"Everything was perfect except for the small room size. "
The price is €117
includes taxes & fees
1 Apr - 2 Apr
Turn of River Lodge
Killington Mountain Lodge, Tapestry Collection by Hilton
Terrace/patio

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 star property
7.4 out of 10, Good, (1067)
"We loved the staff at the hotel and how smooth the check in and check out was. The property is clean and convenient with a restaurant and a bar. There is a nice common area and a spacious hot tub."
The price is €140
includes taxes & fees
28 Apr - 29 Apr
Killington Mountain Lodge, Tapestry Collection by Hilton
Killington Grand Hotel
Exterior

Killington Grand Hotel

3.5 star property
8.8 out of 10, Excellent, (173)
"Great hotel very child and family friendly"
The price is €370
includes taxes & fees
6 Apr - 7 Apr
Killington Grand Hotel
Snowed Inn
Front of property

Snowed Inn

3.5 star property
9.8 out of 10, Exceptional, (334)
"If you’re looking for a Hallmark movie experience, then this is the spot. Breakfast was made to order every morning, there are boot drying racks, a hot tub with reservations, cozy and quaint decor, an onsite bar, and the property is extremely close to the mountain. I would definitely come back and stay here."
The price is €164
includes taxes & fees
3 Apr - 4 Apr
Snowed Inn
Après Inn Killington
Exterior

Après Inn Killington

2.0 star property
9.4 out of 10, Exceptional, (114)
"We really enjoyed our weekend stay at the Apres Inn. Our room had everything we needed, and was spacious enough to bring our dog. The room was clean and offered space to store our skis. The wifi was also great. It was located in an easy walkable distance from restaurants and bars. "
The price is €138
includes taxes & fees
31 Mar - 1 Apr
Après Inn Killington
Mountain Green
Indoor pool

Mountain Green

2.0 star property
6.4 out of 10, (9)
"We had a great time-- the apartment was clean and cute and the linens fresh. "
The price is €269
includes taxes & fees
7 Apr - 8 Apr
Mountain Green
North Star Lodge and Resort
Kayaking

North Star Lodge and Resort

2.0 star property
8.4 out of 10, Very good, (1067)
"Very clean, Friendly staff, very nice outdoor heated pool, comfortable public spaces, onsite bar, short walk on private walkway to nice restaurant, location on the access road to killington, in room thermostat. A bit of a mixup re the room rate booked was fixed immediately. It didn’t matter much to me but the only negative was the view from my particular room which was only of a stone retaining wall a few feet away but most rooms should have decent views."
The price is €132
includes taxes & fees
1 Apr - 2 Apr
North Star Lodge and Resort
The Mountain Inn at Killington
Outdoor pool, a heated pool

The Mountain Inn at Killington

2.5 star property
9.2 out of 10, Wonderful, (774)
"We love this place! We are repeat customers! Always a great experience!"
The price is €180
includes taxes & fees
31 Mar - 1 Apr
The Mountain Inn at Killington
Breakaway House by Killington Vacation Rentals
Living area

Breakaway House by Killington Vacation Rentals

3.0 star property
The price is €533
includes taxes & fees
1 Apr - 2 Apr
Breakaway House by Killington Vacation Rentals
Mountain Sports Inn
Front of property

Mountain Sports Inn

2.0 star property
8.8 out of 10, Excellent, (875)
"Staff was very helpful"
The price is €101
includes taxes & fees
31 Mar - 1 Apr
Mountain Sports 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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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 traveller data. Two other choices for your trip to 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 are some of the best holiday rentals that Pittsfield has to offer?

Killington Vermont Ski and Snowmobiling House: This highly rated holiday home rental in Pittsfield is located near skiing, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. Make the most of Access to 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, 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 place to stay on a budget in Pittsfield?

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

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 that feature an on-site pool. View all hotels with pools in Pittsfield.

What is the best spa hotel in Pittsfield?

Sweet Life - Vermont Chalet - 6 Person Indoor Hot Tub - 15 min to Killington is a top spa hotel with an arcade/games room, barbecues and billiards/pool table. Kick back and relax in the hot tub. Other popular spa hotels in Pittsfield include Newly Built Killington Vermont Ski House and Sweet Life - GetAway.

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 Appalachian Trail Adventures and Green Mountain National Golf Course 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.