Find hotels in Pittsfield, VT from ￥17,556

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Our top choices for Pittsfield hotels

Deluxe Suite | Individually decorated, desk, blackout drapes, iron/ironing board
Sleep Woodstock Motel

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (550)
Enjoy a peaceful retreat near Killington and Sugarbush ski resorts. This well-maintained motel offers clean rooms and friendly staff in a beautiful Vermont setting. Free WiFi and parking make it easy to explore Ottaquechee River and local hiking trails.
"The staff at this motel are 5 star! Lisa went above and beyond to make my stay easy since I was there for a medical procedure. "
United States
Crystal
The price is ￥12,244
￥23,254 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Sleep Woodstock Motel
Full-size fridge, microwave, stovetop, coffee/tea maker
My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT
2.0 star property
Randolph Center
9.4 out of 10, Exceptional, (349)
Just off I-89 in Randolph Center, this hotel offers convenient amenities including complimentary WiFi and self parking. The 24-hour front desk ensures assistance anytime while Whale Dance Sculpture and Montague Golf Club await nearby.
"Excellent "
United States
Diana
The price is ￥16,106
￥17,556 total
includes taxes & fees
Jan 25 - Jan 26, 2026
My Place Hotel-Randolph VT
Exterior
Mountain Valley Retreat

Mountain Valley Retreat

Mountain Valley Retreat
2.5 star property
Killington
9.6 out of 10, Exceptional, (191)
Experience mountain adventures from this tranquil B&B offering complimentary full breakfast, WiFi, and parking. Outdoor enthusiasts can enjoy nearby hiking, biking, and kayaking, plus easy access to Pico Mountain and Killington ski areas.
"This was my third stay with Mike and Barbara. It's just so lovely in a beautiful rural setting! And sure can't complain about the hearty breakfasts cooked by Chef Mike. It's certain I'll return on another ski adventure to Killington."
United States
Kathy
The price is ￥17,223
￥19,462 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Mountain Valley Retreat
Property grounds
The Shire Woodstock

The Shire Woodstock

The Shire Woodstock
3.0 star property
Woodstock
8.8 out of 10, Excellent, (894)
Tucked in charming Woodstock, this welcoming hotel provides complimentary WiFi, parking, and bicycle rentals for exploring nearby trails. Guests praise the helpful staff and spotless rooms, with Billings Park and Red Wagon Toy Company just moments away.
"Wonderful place to stay!"
United States
Robin
The Shire Woodstock
Terrace/patio
On The River Inn

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1002)
Discover a tranquil retreat near the train station in Woodstock featuring an indoor pool, hot tub, and on-site 506 Bistro and Lounge. Guests love the helpful staff, complimentary breakfast, and convenient access to Union Arena Community Center.
"Rearaurant staff was top notch. "
United States
Daniel
The price is ￥50,885
￥61,715 total
includes taxes & fees
Dec 29 - Dec 30
On The River Inn
Bicycling
Turn of River Lodge

Turn of River Lodge

Turn of River Lodge
2.5 star property
Killington
9.0 out of 10, Wonderful, (271)
Wake to mountain adventures at this cozy Vermont lodge. Just minutes from Killington and Pico Mountain ski resorts, guests enjoy free continental breakfast and parking. Mountain biking trails await nearby, with 24-hour front desk staff ready to assist throughout your stay.
"We enjoyed our stay. Close proximity to a lot of things to see and do. "
United States
Linda
The price is ￥19,806
￥21,788 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Turn of River Lodge
Exterior
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington
2.5 star property
Rutland
8.0 out of 10, Very Good, (1002)
Situated in central Rutland with easy access to restaurants and activities, this hotel offers an indoor pool and fitness center. Enjoy American cuisine at SOUTHSIDE STEAKHOUSE, while rooms provide refrigerators and microwaves for added convenience.
"Clean rooms and polite workers. Try to stay there every time we go to Vermont."
United States
Michael
The price is ￥22,491
￥24,741 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Comfort Inn Rutland - Killington
Front of property
Mountain Sports Inn

Mountain Sports Inn

Mountain Sports Inn
2.0 star property
The Woods
8.8 out of 10, Excellent, (990)
Experience mountain adventures from this welcoming inn, just a 5-minute drive to Killington Resort and Pico Mountain. Enjoy free Wi-Fi, parking, and daily continental breakfast. Hiking trails, cross-country and downhill skiing await outdoor enthusiasts.
"Staff was great and breakfast was excellent "
United States
Bruce
The price is ￥20,198
￥22,218 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Mountain Sports Inn
Exterior
Hampton Inn Rutland

Hampton Inn Rutland

Hampton Inn Rutland
2.5 star property
Rutland
9.0 out of 10, Wonderful, (974)
Located minutes from Green Mountain Shopping Plaza, this welcoming hotel offers free WiFi and parking. The indoor pool provides year-round relaxation, while the fitness center keeps routines on track. Guests consistently praise the helpful staff and hearty breakfast offerings.
"Very clean, good location, and super helpful staff!"
United States
Sheryl
The price is ￥25,566
￥28,122 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Hampton Inn Rutland
Front of property
The Jackson

The Jackson

The Jackson
4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (258)
Victorian charm awaits at this quiet Woodstock B&B where travelers rave about the delicious morning meal. Relax in the garden, enjoy evening drinks at the bar, or explore nearby Union Arena and Five Elm Arches from this peaceful retreat.
"The Jackson Inn is incredibly charming and in a picturesque area. The room was very comfortable and the restaurant and staff was amazing."
United States
Abby
The Jackson
Exterior
Brandon Inn

Brandon Inn

Brandon Inn
3.0 star property
Brandon
8.8 out of 10, Excellent, (568)
Discover Vermont charm at this inviting inn with outdoor swimming and a garden setting. After exploring nearby Stephen A Douglas Birthplace, unwind at the bar or grab a bite at the café. Free breakfast, WiFi, and parking enhance your countryside escape.
"Enjoyed our stay at the Brandon Inn very much!"
United States
Lesley
The price is ￥17,790
￥19,569 total
includes taxes & fees
Dec 30 - Dec 31
Brandon Inn
Lounge
Greenbrier Inn

Greenbrier Inn

Greenbrier Inn
2.0 star property
Killington
9.4 out of 10, Exceptional, (646)
Surrounded by Vermont's mountain beauty, this welcoming hotel offers hiking trails, snowshoeing, and a refreshing outdoor pool. Just a short drive from two premier Killington ski resorts with free breakfast, WiFi, and parking.
"It was a very quaint inn in a gorgeous location."
United States
ELIZABETH
Greenbrier Inn
Terrace/patio
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton
3.5 star property
Killington
7.4 out of 10, Good, (1006)
"Good place to stay when you ski"
United States
Josh
The price is ￥29,939
￥32,932 total
includes taxes & fees
Jan 21 - Jan 22, 2026
Killington Mountain Lodge, Tapestry Collection by Hilton
Lake view
Mountain Meadows Lodge

Mountain Meadows Lodge

Mountain Meadows Lodge
3.5 star property
Killington
9.4 out of 10, Exceptional, (183)
Surrounded by mountain splendor, this family-friendly retreat offers Kent Bistro dining and relaxing amenities including a sauna. Just minutes from Killington Resort and Pico Mountain skiing, guests consistently praise the attentive staff.
"Staff was amazing! They made the stay even better with their hospitality and overall service. I recommend this Lodge to anyone looking to go to Killington who wants a fun and relaxing stay. "
United States
Jaden
The price is ￥34,273
￥41,614 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Mountain Meadows Lodge
Standard Room, 2 Double Beds | Iron/ironing board, free WiFi, bed sheets
North Star Lodge and Resort

North Star Lodge and Resort

North Star Lodge and Resort
2.0 star property
Killington
8.6 out of 10, Excellent, (1005)
Scenic retreat just minutes from Killington Resort, offering quiet surroundings and mountain convenience. Relax in the outdoor pool, rejuvenate in the sauna, or enjoy a meal at the restaurant. Rooms include refrigerators and microwaves for added comfort.
"Spotless room also very accommodating and friendly! Loved our short stay!"
United States
Candace
North Star Lodge and Resort
Property entrance
The Trailside Inn

The Trailside Inn

The Trailside Inn
3.0 star property
North Sherburne
9.0 out of 10, Wonderful, (136)
Surrounded by world-class skiing at Killington and Pico Mountain resorts, this inviting guesthouse offers complimentary continental breakfast, WiFi and parking. Enjoy winter activities right on the property or relax in the garden and terrace after a day outdoors.
"Great choice for ski trip. The room is cozy and warm. "
United States
Dian
The price is ￥25,865
￥28,452 total
includes taxes & fees
Jan 5 - Jan 6, 2026
The Trailside Inn
Economy Room | Individually decorated, individually furnished, free WiFi, bed sheets
The Vesper

The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (51)
Surrounded by seasonal adventure, this charming 3-star B&B offers complimentary continental breakfast, WiFi, and parking. Winter enthusiasts will love the cross-country skiing and snowboarding options, with Billings Park and Dana House Museum just minutes away.
"Charming bed and breakfast"
United States
Nicholas
The price is ￥25,835
￥28,418 total
includes taxes & fees
Jan 12 - Jan 13, 2026
The Vesper
Lobby
Best Western Inn & Suites Rutland-Killington

Best Western Inn & Suites Rutland-Killington

Best Western Inn & Suites Rutland-Killington
2.5 star property
Rutland
8.8 out of 10, Excellent, (1001)
Quiet retreat near Pico Mountain offers a seasonal outdoor pool, tennis court, and 24-hour fitness center. Enjoy the free ski shuttle and morning breakfast before hitting the slopes. Helpful staff and clean rooms consistently earn praise from travelers.
"Great front desk staff. Rooms were very comfortable. "
United States
JERILYN
The price is ￥28,043
￥30,847 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Best Western Inn & Suites Rutland-Killington
Front of property
Cortina Inn

Cortina Inn

Cortina Inn
3.0 star property
Rutland
6.6 out of 10, (660)
"Exelent service and everything is clean I feel so good in the cortina hotel "
United States
sagrario
The price is ￥18,260
￥20,086 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Cortina Inn
Classic Room, 2 Queen Beds | Desk, iron/ironing board, free WiFi, bed sheets
Middlebury Sweets Motel

Middlebury Sweets Motel

Middlebury Sweets Motel
2.5 star property
Middlebury
8.6 out of 10, Excellent, (388)
Located near Town Hall Theater and Emma Willard House, this cozy Middlebury motel offers free WiFi and parking. Guests praise the helpful staff and clean rooms. Daily housekeeping ensures a comfortable visit.
"Friendly staff, clean, comfortable and convenient to downtown. "
United States
Melissa
The price is ￥15,328
￥16,861 total
includes taxes & fees
Dec 30 - Dec 31
Middlebury Sweets Motel
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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Stay near popular Pittsfield attractions

Roger Clark Memorial Central Library

After visiting Roger Clark Memorial Central Library, make a plan to see the other sights and activities in Pittsfield.
See properties

Pittsfield Town Hall

After visiting Pittsfield Town Hall, make a plan to see the other sights and activities in Pittsfield.
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Top Pittsfield Hotel Reviews

On The River Inn

On The River Inn

10/10 Excellent
"The Inn was quite nice. We enjoyed the 2nd floor library area to sit and relax. The restaurant on site 506 Bistro was fabulous. "
Roy 3-night trip
Posted 11 hours ago
On The River Inn

More cheap stays in Pittsfield

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2440 Vermont 66 Randolph Center VT
The price is ￥16,106 per night from Jan 25 to Jan 26
￥16,106
￥17,556 total
Jan 25 - Jan 26, 2026
includes taxes & fees
9.2/10 Wonderful! (346 reviews)

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 The Mountain Inn at Killington. See all available top hotels, or vacation rentals in Pittsfield.
What's the top vacation rental in Pittsfield?
5 BR Duplex with Hot Tub & Firepit 1 minute from Killington Resort!: This vacation home near Pittsfield is located near skiing and has a patio, a selection of games, and laundry facilities 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. You and your friends and family can relax into your vacation with amenities like 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 continental, an indoor pool, and free self parking. The Mountain Inn at Killington 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 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. 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.

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