Find hotels in Pittsfield, VT from AED 362

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Check prices for these dates

Tonight
22 Feb - 23 Feb
Tomorrow
23 Feb - 24 Feb
Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar

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Compare 1,668 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

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 AED 915
AED 1,006 total
includes taxes & fees
23 Feb - 24 Feb
Stay At Jimmy's
The Shire Woodstock
Property grounds

The Shire Woodstock

3.0 star property
8.8 out of 10, Excellent, (727)
"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 AED 560
AED 653 total
includes taxes & fees
24 Feb - 25 Feb
The Shire Woodstock
The Vesper
Room

The Vesper

3.0 star property
9.6 out of 10, Exceptional, (15)
"Charming inn, great service"
The price is AED 517
AED 568 total
includes taxes & fees
25 Feb - 26 Feb
The Vesper
Woodstock Inn & Resort
Exterior

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 AED 1,098
AED 1,370 total
includes taxes & fees
16 Mar - 17 Mar
Woodstock Inn & Resort
The Jackson
Exterior

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 AED 820
AED 902 total
includes taxes & fees
2 Mar - 3 Mar
The Jackson
506 On the River Inn
Aerial view

506 On the River Inn

4.0 star property
9.4 out of 10, Exceptional, (964)
"It’s been our second time going to On the River Inn VT and we’ve been amazed both times we went there! The view of the lake/courtyard is beautiful and the hotel in general is very clean. My daughter loved the pool and the game room. The staff were very helpful with everything we asked for and the breakfast was top notch. Definitely worth the trip!"
The price is AED 768
AED 844 total
includes taxes & fees
23 Feb - 24 Feb
506 On the River Inn
Sleep Woodstock Motel
Exterior

Sleep Woodstock Motel

2.0 star property
9.6 out of 10, Exceptional, (463)
"Sleep Woodstock is a great economic option to stay when visiting the Killington Ski Mountain. It’s only 15 minutes away and convenient to get to. Sleep Woodstock is also very close to Woodstock with its great option for dinning no shopping. The room was also clean and new. The Sleep Woodstock team also kept the parking area plowed and easy to access even during a huge snow storm. Kudos to everyone."
The price is AED 375
AED 412 total
includes taxes & fees
3 Mar - 4 Mar
Sleep Woodstock Motel
Echo Lake Inn
Front of property

Echo Lake Inn

2.5 star property
8.6 out of 10, Excellent, (94)
"Old fashioned inn with wonderful hosts."
The price is AED 942
AED 1,027 total
includes taxes & fees
25 Mar - 26 Mar
Echo Lake Inn
My Place Hotel-Randolph VT
Exterior

My Place Hotel-Randolph VT

2.0 star property
9.4 out of 10, Exceptional, (137)
"Dillon was exceptional during the check in and immediately addressed our concerns. He was very informative and pleasant. The room is clean & modernly updated. "
The price is AED 511
AED 557 total
includes taxes & fees
28 Feb - 1 Mar
My Place Hotel-Randolph VT
Turn of River Lodge
Interior detail

Turn of River Lodge

2.5 star property
9.0 out of 10, Wonderful, (244)
"This was such a cozy lodge! They provided a complimentary breakfast with plenty of pastries, bread, coffee, water, orange juice & cereal. It was super convenient that breakfast was ready by 6:30am, which was perfect timing for us to eat before hitting the slopes by 8am! This is a shared lodge, so there is a main room on the first floor with large tables & couches in front of a fireplace where you can lounge & mingle with others. Just a heads up, if you don't want to share a bathroom, make sure...
The price is AED 485
AED 533 total
includes taxes & fees
23 Feb - 24 Feb
Turn of River Lodge
Fall Line Condo D1 1 Bedroom Condo
Living area

Fall Line Condo D1 1 Bedroom Condo

3.5 star property
The price is AED 757
AED 1,867 total
includes taxes & fees
2 Mar - 3 Mar
Fall Line Condo D1 1 Bedroom Condo
Fall Line Condos by Killington VR - 3 Bedrooms
Living area

Fall Line Condos by Killington VR - 3 Bedrooms

3.5 star property
The price is AED 1,196
AED 2,927 total
includes taxes & fees
27 Feb - 28 Feb
Fall Line Condos by Killington VR - 3 Bedrooms
Fall Line Small Studio - Perfect For Two - On Shuttle Route W/ Amenities G6a 1 Bedroom Condo
Room

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

2.0 star property
The price is AED 362
AED 1,108 total
includes taxes & fees
27 Feb - 28 Feb
Fall Line Small Studio - Perfect For Two - On Shuttle Route W/ Amenities G6a 1 Bedroom Condo
Beautiful 2br/2ba Fall Line Condo W/ Mountain Views, Pool, Hot Tub, Sauna, Shuttle. G6b 2 Bedroom Condo
Living area

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 AED 824
AED 2,295 total
includes taxes & fees
27 Feb - 28 Feb
Beautiful 2br/2ba Fall Line Condo W/ Mountain Views, Pool, Hot Tub, Sauna, Shuttle. G6b 2 Bedroom Condo
Fall Line Condos by Killington VR - 1 Bedrooms
Dining

Fall Line Condos by Killington VR - 1 Bedrooms

3.5 star property
Fall Line Condos by Killington VR - 1 Bedrooms
Killington Mountain Lodge, Tapestry Collection by Hilton
Exterior

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 star property
7.2 out of 10, Good, (1002)
"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 AED 725
AED 798 total
includes taxes & fees
25 Mar - 26 Mar
Killington Mountain Lodge, Tapestry Collection by Hilton
Whitetail Chalet 4 Bedroom Home
Living area

Whitetail Chalet 4 Bedroom Home

3.0 star property
The price is AED 2,107
AED 4,168 total
includes taxes & fees
24 Feb - 25 Feb
Whitetail Chalet 4 Bedroom Home
The Tanglewood Lodge: Amazing Ski Home For Groups. Hot Tub. Close To Killington Resort! 4 Bedroom Home
Dining

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

3.0 star property
The price is AED 2,203
AED 4,488 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
Outdoor pool

Killington Grand Hotel

3.5 star property
8.8 out of 10, Excellent, (172)
"Great hotel very child and family friendly"
The price is AED 1,741
AED 2,042 total
includes taxes & fees
4 Mar - 5 Mar
Killington Grand Hotel
Mountain Green Condo 1B9 1 Condo
Living area

Mountain Green Condo 1B9 1 Condo

3.5 star property
The price is AED 603
AED 1,785 total
includes taxes & fees
9 Mar - 10 Mar
Mountain Green Condo 1B9 1 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 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. Days Inn by Wyndham Rutland/Killington Area and Woodstock Inn & 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. 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.