Find hotels in Pittsfield, VT from ￥16,779

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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 ￥66,800
￥151,538 total
includes taxes & fees
Dec 16 - Dec 17
The Getaway 4 Bedroom Home
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 ￥50,638
￥55,195 total
includes taxes & fees
Dec 16 - Dec 17
The Mountain Top Inn & Resort
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, (1003)
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 ￥20,528
￥22,582 total
includes taxes & fees
Dec 16 - Dec 17
Comfort Inn Rutland - Killington
Room, 1 King Bed, Non Smoking | Desk, blackout drapes, iron/ironing board, free cribs/infant beds
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, (1002)
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 ￥18,541
￥20,396 total
includes taxes & fees
Dec 17 - Dec 18
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, (555)
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 ￥52,820
￥64,959 total
includes taxes & fees
Dec 16 - Dec 17
Woodstock Inn & Resort
Property grounds
The Shire Woodstock

The Shire Woodstock

The Shire Woodstock
3.0 star property
Woodstock
8.8 out of 10, Excellent, (893)
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.
"This place was charming!! Enjoyed everything about it and so much to do right there in the inn."
United States
Ross
The price is ￥30,071
￥38,792 total
includes taxes & fees
Dec 22 - Dec 23
On The River Inn
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.
"Beautiful fireplace at the breakfast area in the morning, very helpful staff and quaint hotel."
United States
BETTY
The price is ￥27,907
￥30,698 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Best Western Inn & Suites Rutland-Killington
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, (549)
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 ￥12,060
￥25,575 total
includes taxes & fees
Dec 16 - Dec 17
Sleep Woodstock Motel
Exterior
Courtyard Middlebury

Courtyard Middlebury

Courtyard Middlebury
3.0 star property
Middlebury
8.8 out of 10, Excellent, (544)
Located near the Town Hall Theater, this quiet Middlebury hotel offers American cuisine at Business Bistro. Enjoy a workout in the health club, relax at the bar, and appreciate room conveniences like refrigerators and microwaves.
"Great hotel, fairly centered , great staff!"
United States
Angelo
The price is ￥18,074
￥19,881 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Courtyard Middlebury
Front of property
The Jackson

The Jackson

The Jackson
4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (257)
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
Hampton Inn Rutland

Hampton Inn Rutland

Hampton Inn Rutland
2.5 star property
Rutland
9.0 out of 10, Wonderful, (970)
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 ￥22,935
￥25,228 total
includes taxes & fees
Dec 21 - Dec 22
Hampton Inn Rutland
Interior
Lincoln Inn & Gallery

Lincoln Inn & Gallery

Lincoln Inn & Gallery
2.0 star property
West Woodstock
8.6 out of 10, Excellent, (57)
Escape to this cozy Woodstock inn with complimentary WiFi and parking. Near Ottaquechee River and Union Arena Community Center, you'll appreciate the warm lobby fireplace. Snowmobiling adventures start right on the property for winter thrills.
"A very pleasant VT stay at a reasonable price."
United States
Sean
The price is ￥25,942
￥28,538 total
includes taxes & fees
Dec 16 - Dec 17
Lincoln Inn & Gallery
Front of property
Cortina Inn

Cortina Inn

Cortina Inn
3.0 star property
Rutland
6.6 out of 10, (653)
"Exelent service and everything is clean I feel so good in the cortina hotel "
United States
sagrario
The price is ￥15,272
￥16,798 total
includes taxes & fees
Dec 16 - Dec 17
Cortina Inn
Front of property
Stay At Jimmy's

Stay At Jimmy's

Stay At Jimmy's
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (46)
This cozy Woodstock B&B offers free continental breakfast daily, plus convenient WiFi and parking. Explore nearby attractions like Billings Park and Trail or Red Wagon Toy Company, then return to this welcoming retreat.
"Very cool vibe at this very comfortable B&B. Hosts were very friendly and responsive. Would definitely stay here again!"
United States
Thomas
The price is ￥38,797
￥42,677 total
includes taxes & fees
Dec 16 - Dec 17
Stay At Jimmy's
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 ￥15,254
￥16,779 total
includes taxes & fees
Dec 16 - Dec 17
Middlebury Sweets Motel
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, (47)
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.
"Cute B&B, great location! Easy walk to coffee house and downtown area. We really enjoyed our stay!"
United States
Roger
The price is ￥26,994
￥29,693 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The Vesper
Exterior
Brandon Inn

Brandon Inn

Brandon Inn
3.0 star property
Brandon
8.8 out of 10, Excellent, (566)
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 ￥17,331
￥19,065 total
includes taxes & fees
Dec 23 - Dec 24
Brandon Inn
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 ￥39,965
￥43,563 total
includes taxes & fees
Dec 16 - Dec 17
The Vermont 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, (960)
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 ￥34,917
￥40,330 total
includes taxes & fees
Dec 21 - Dec 22
The Mountain Inn at Killington
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

The Shire Woodstock

The Shire Woodstock

10/10 Excellent
"The staff was super nice and flexible! Location was great "
Frida Nohemi 1-night trip
Posted 2 days ago
The Shire Woodstock

More cheap stays in Pittsfield

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2440 Vermont 66 Randolph Center VT
The price is ￥15,611 per night from Jan 1 to Jan 2
￥15,611
￥17,016 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 The Mountain Inn at 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?
5 BR Duplex with Hot Tub & Firepit 1 minute from Killington Resort!: Located near Pittsfield, this vacation home rental 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?
Woodstock Inn & Resort: Features a seasonal outdoor pool, an indoor pool, and 4 restaurants. The Mountain Inn at Killington and North Star Lodge and 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. 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 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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