Find hotels in Pittsfield, VT from ￥17,325

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Our top choices for Pittsfield hotels

House, 4 Bedrooms | Exterior
The Getaway 4 Bedroom Home

The Getaway 4 Bedroom Home

The Getaway 4 Bedroom Home
3.0 star property
Pittsfield
The price is ￥66,663
￥151,227 total
includes taxes & fees
Dec 16 - Dec 17
The Getaway 4 Bedroom Home
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, (1000)
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.
"The staff is wonderful! Friendly, helpful and they work very hard. The room was clean but a little small for our liking so we will make sure to book a larger room next time. You can't beat the location. It's so close to everything!"
United States
Jennifer
The price is ￥27,833
￥30,617 total
includes taxes & fees
Dec 14 - Dec 15
Best Western Inn & Suites Rutland-Killington
Lobby
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, great steak house by the hotel"
United States
Caridad
The price is ￥19,693
￥21,662 total
includes taxes & fees
Dec 14 - Dec 15
Comfort Inn Rutland - Killington
Lobby
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area
2.5 star property
Rutland
6.4 out of 10, (1001)
This Rutland hotel offers convenient access to Spartan Arena with free WiFi and parking for road trippers. Unwind in the indoor pool after exploring Vermont, or relax in the sauna. Clean rooms provide comfort while helpful staff ensure a pleasant stay.
"The food "
United States
Elijah
The price is ￥18,371
￥20,207 total
includes taxes & fees
Dec 14 - Dec 15
Days Inn by Wyndham Rutland/Killington Area
Lobby
Woodstock Inn & Resort

Woodstock Inn & Resort

Woodstock Inn & Resort
4.5 star property
Woodstock
9.2 out of 10, Wonderful, (554)
Surrounded by picturesque Vermont landscapes, this luxury resort offers a tranquil escape with an 18-hole golf course and full-service spa. Enjoy 4 restaurants, indoor and outdoor pools, plus easy access to local covered bridges and theaters.
"Highly recommend stay here"
United States
Margie
The price is ￥52,711
￥64,824 total
includes taxes & fees
Dec 15 - Dec 16
Woodstock Inn & Resort
Exterior
Hampton Inn Rutland

Hampton Inn Rutland

Hampton Inn Rutland
2.5 star property
Rutland
9.0 out of 10, Wonderful, (969)
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 ￥22,888
￥25,177 total
includes taxes & fees
Dec 21 - Dec 22
Hampton Inn Rutland
BBQ/picnic area
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, (342)
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.
"Awesome staff and great room with Kitchenette"
United States
Mary
The price is ￥15,895
￥17,325 total
includes taxes & fees
Jan 1 - Jan 2, 2026
My Place Hotel-Randolph VT
Deluxe Suite | Private kitchen | Mini-fridge, microwave, coffee/tea maker, freezer
Sleep Woodstock Motel

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (548)
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 ￥12,035
￥25,522 total
includes taxes & fees
Dec 14 - Dec 15
Sleep Woodstock Motel
Property grounds
The Shire Woodstock

The Shire Woodstock

The Shire Woodstock
3.0 star property
Woodstock
8.8 out of 10, Excellent, (891)
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
Front of property
The Vermont Inn

The Vermont Inn

The Vermont Inn
3.0 star property
Rutland
9.2 out of 10, Wonderful, (415)
Experience classic New England hospitality at this charming B&B with a seasonal outdoor pool and 24-hour fitness center. Just minutes from Killington Resort, guests enjoy free breakfast, WiFi, and parking, plus relaxing sauna and garden terrace spaces.
"Our room was clean and the bed was very comfortable. The Inn is for sale... which could explain the needed updates. I wish I could buy it! 🤗 We would stay here again. "
United States
Jodie
The price is ￥39,883
￥43,473 total
includes taxes & fees
Dec 14 - Dec 15
The Vermont Inn
Lake view
Mountain Meadows Lodge

Mountain Meadows Lodge

Mountain Meadows Lodge
3.5 star property
Killington
9.4 out of 10, Exceptional, (179)
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.
"All round fantastic place to stay "
United Kingdom
Stephen
The price is ￥27,195
￥33,802 total
includes taxes & fees
Dec 14 - Dec 15
Mountain Meadows Lodge
Front of property
Cortina Inn

Cortina Inn

Cortina Inn
3.0 star property
Rutland
6.6 out of 10, (651)
"Exelent service and everything is clean I feel so good in the cortina hotel "
United States
sagrario
The price is ￥15,394
￥16,933 total
includes taxes & fees
Dec 14 - Dec 15
Cortina Inn
Breakfast and dinner served
The Mountain Inn at Killington

The Mountain Inn at Killington

The Mountain Inn at Killington
2.5 star property
Killington
9.2 out of 10, Wonderful, (956)
Just steps from Killington Resort with a free ski shuttle, this mountain hotel offers outdoor swimming and fitness options. After slopes, unwind at the bar or restaurant. Guests praise the helpful staff and complimentary breakfast, WiFi, and parking.
"Great place to stay!"
United States
Stephen
The price is ￥34,845
￥40,247 total
includes taxes & fees
Dec 22 - Dec 23
The Mountain Inn at Killington
Fireplace
Summit Lodge

Summit Lodge

Summit Lodge
3.0 star property
Killington
8.6 out of 10, Excellent, (396)
Immerse in mountain charm at this Killington inn offering 2 outdoor pools and a hot tub. After skiing at nearby Killington Resort, savor Irish cuisine at O'Dwyer's Public House. Complimentary breakfast, WiFi and parking enhance your alpine getaway.
"When we first arrived it felt really old and I was wondering what I had booked. Then, the place grew on me as I explored the hotel. I could see this as being really fun in the winter and with a group."
United States
Wendy
The price is ￥27,009
￥29,710 total
includes taxes & fees
Dec 17 - Dec 18
Summit Lodge
Exterior
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, (1003)
"Staff was very helpful and room service was great."
United States
Ankita
The price is ￥29,182
￥32,099 total
includes taxes & fees
Dec 14 - Dec 15
Killington Mountain Lodge, Tapestry Collection by Hilton
Garden
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, (1000)
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
Front of property
Brandon Inn

Brandon Inn

Brandon Inn
3.0 star property
Brandon
8.8 out of 10, Excellent, (564)
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 ￥17,510
￥19,261 total
includes taxes & fees
Dec 15 - Dec 16
Brandon Inn
Premium Suite, Multiple Beds | Balcony
Mountain Sports Inn

Mountain Sports Inn

Mountain Sports Inn
2.0 star property
The Woods
8.8 out of 10, Excellent, (981)
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.
"Everything was superb . Staff is very friendly and breakfast is fabulous ."
United States
Bradford
The price is ￥20,058
￥22,064 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Mountain Sports Inn
The Jewel | Living area | TV
The Mountain Top Inn & Resort

The Mountain Top Inn & Resort

The Mountain Top Inn & Resort
3.5 star property
Chittenden
9.0 out of 10, Wonderful, (96)
Tucked away in Chittenden, this mountain retreat offers ski-in/ski-out access and a private beach. Enjoy cross-country skiing, sledding, or tennis, followed by American cuisine at Highlands Dining Room. Lefferts Pond and the resort's outdoor pool await.
"Absolutely wonderful! The hotel and staff were great. We deeply appreciated the upgrade! No one wanted to leave. "
United States
Wendy
The price is ￥50,534
￥55,082 total
includes taxes & fees
Dec 14 - Dec 15
The Mountain Top Inn & Resort
Interior detail
The Trailside Inn

The Trailside Inn

The Trailside Inn
3.0 star property
North Sherburne
9.0 out of 10, Wonderful, (134)
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.
"Such a great, comfortable place to stay with an awesome staff!"
United States
Daniel
The price is ￥23,852
￥26,237 total
includes taxes & fees
Dec 14 - Dec 15
The Trailside 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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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

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

10/10 Excellent
"We stopped at this hotel on our way up to Stowe Mountain traveling from NJ. The room was affordable, modern, & clean. Our hotel room was a pleasant surprise. We had a full size fridge, microwave, oven, & kitchen in there. We stayed in a hearing impaired room that had a very spacious bathroom. We didn’t notice a lot of food options other than a McDonalds and convenience store about half a mile away. The lobby had a lot of amenities like snacks and other items you may have forgot to pack but were on the pricey side (ex. A bottle of Diet Coke was $4). We would definitely stay again."
Ellen M 1-night trip
Posted 5 days ago
My Place Hotel-Randolph VT

More cheap stays in Pittsfield

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2440 Vermont 66 Randolph Center VT
The price is ￥15,895 per night from Jan 1 to Jan 2
￥15,895
￥17,325 total
Jan 1 - Jan 2, 2026
includes taxes & fees
9.2/10 Wonderful! (342 reviews)

Frequently asked questions

Where is the best place to stay in Pittsfield?
Located 17.9 mi (28.9 km) from the heart of Pittsfield, Woodstock Inn & Resort is a top choice for your stay based on our traveler data. Other good choices for your stay in the area are Comfort Inn Rutland - Killington 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?
PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.: You might like this vacation home rental near Pittsfield. It is located in a rural location and has a fireplace, a patio, and a barbecue grill to put you at ease 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. Kick off your shoes and enjoy yourself with a garden and a selection of games. 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?
Woodstock Inn & Resort: Features a seasonal outdoor pool, an indoor pool, and 4 restaurants. Comfort Inn Rutland - Killington and The Mountain Inn at Killington 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 40 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 Gifford Woods State Park and Pico Mountain at Killington Ski 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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