Find hotels in Pittsfield, VT from ฿3,382

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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 ฿15,558
฿33,778 total
includes taxes & fees
25 Dec - 26 Dec
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 ฿10,208
฿11,126 total
includes taxes & fees
23 Dec - 24 Dec
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, (1007)
Situated in central Rutland with easy access to restaurants and activities, this hotel offers an indoor pool and fitness centre. 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 ฿4,512
฿4,963 total
includes taxes & fees
4 Jan - 5 Jan 2026
Comfort Inn Rutland - Killington
Room, 1 King Bed, Non Smoking | Desk, blackout curtains, iron/ironing board, free cots/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 ฿4,645
฿5,110 total
includes taxes & fees
4 Jan - 5 Jan 2026
Days Inn by Wyndham Rutland/Killington Area
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, (1003)
Quiet retreat near Pico Mountain offers a seasonal outdoor pool, tennis court, and 24-hour fitness centre. Enjoy the free ski shuttle and morning breakfast before hitting the slopes. Helpful staff and clean rooms consistently earn praise from travellers.
"Great front desk staff. Rooms were very comfortable. "
United States
JERILYN
The price is ฿5,625
฿6,188 total
includes taxes & fees
4 Jan - 5 Jan 2026
Best Western Inn & Suites Rutland-Killington
Lobby
Woodstock Inn & Resort

Woodstock Inn & Resort

Woodstock Inn & Resort
4.5 star property
Woodstock
9.2 out of 10, Wonderful, (558)
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 theatres.
"Luxurious and friendly resort! Loved it"
United States
Elizabeth
The price is ฿10,019
฿12,403 total
includes taxes & fees
19 Jan - 20 Jan 2026
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, (1001)
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 Centre.
"This place was charming!! Enjoyed everything about it and so much to do right there in the inn."
United States
Ross
The price is ฿6,062
฿7,820 total
includes taxes & fees
23 Dec - 24 Dec
On The River Inn
Exterior
Courtyard Middlebury

Courtyard Middlebury

Courtyard Middlebury
3.0 star property
Middlebury
8.8 out of 10, Excellent, (546)
Located near the Town Hall Theatre, 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.
"Laundry service was efficient and parking was easy "
United States
Agnes
The price is ฿3,711
฿4,082 total
includes taxes & fees
4 Jan - 5 Jan 2026
Courtyard Middlebury
Deluxe Suite | Individually decorated, desk, blackout curtains, 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 ฿2,601
฿4,824 total
includes taxes & fees
6 Jan - 7 Jan 2026
Sleep Woodstock Motel
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 travellers 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, (972)
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 centre 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 ฿5,209
฿5,730 total
includes taxes & fees
6 Jan - 7 Jan 2026
Hampton Inn Rutland
Front of property
Cortina Inn

Cortina Inn

Cortina Inn
3.0 star property
Rutland
6.6 out of 10, (656)
"Exelent service and everything is clean I feel so good in the cortina hotel "
United States
sagrario
The price is ฿3,738
฿4,111 total
includes taxes & fees
23 Dec - 24 Dec
Cortina Inn
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 cosy Woodstock inn with complimentary WiFi and parking. Near Ottaquechee River and Union Arena Community Centre, 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 ฿6,643
฿7,307 total
includes taxes & fees
4 Jan - 5 Jan 2026
Lincoln Inn & Gallery
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 centre. 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 ฿8,056
฿8,781 total
includes taxes & fees
23 Dec - 24 Dec
The Vermont 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 cosy 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 ฿7,821
฿8,603 total
includes taxes & fees
23 Dec - 24 Dec
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 Theatre and Emma Willard House, this cosy 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 ฿3,075
฿3,382 total
includes taxes & fees
30 Dec - 31 Dec
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, (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 ฿5,300
฿5,830 total
includes taxes & fees
23 Dec - 24 Dec
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 ฿3,756
฿4,132 total
includes taxes & fees
23 Dec - 24 Dec
Brandon Inn
Room 22 | Free WiFi, bed sheets
Kedron Valley Inn

Kedron Valley Inn

Kedron Valley Inn
3.5 star property
South Woodstock
9.0 out of 10, Wonderful, (329)
Located in South Woodstock, this inn features the Ransom Tavern for dinner and a cosy bar/lounge with terrace. Free WiFi and parking add convenience while Union Arena and VINS Nature Centre provide nearby exploration options.
"Nice place to stay. Would stay there again & recommend it to friends and family "
United States
Deborah
The price is ฿6,910
฿7,601 total
includes taxes & fees
23 Dec - 24 Dec
Kedron Valley 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

North Star Lodge and Resort

North Star Lodge and Resort

10/10 Excellent
"Recommend it nice and clean"
Yuriy 1-night trip
Posted 1 day ago
North Star Lodge and Resort

More cheap stays in Pittsfield

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2440 Vermont 66 Randolph Center VT
The price is ฿3,155 per night from 11 Jan to 12 Jan
฿3,155
฿3,439 total
11 Jan - 12 Jan 2026
includes taxes & fees
9.2/10 Wonderful! (345 reviews)

Frequently asked questions

Where is the best place to stay in Pittsfield?
Located 9.5 mi (15.3 km) from the heart of Pittsfield, Killington Mountain Lodge, Tapestry Collection by Hilton is a top choice for your stay, based on our traveller data. Two other choices for your trip to the area are The Mountain Inn at Killington and Woodstock Inn & Resort. See all available top hotels, or 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 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?
The Mountain Inn at Killington: Hotel, 1-minute walk from Killington Resort. Offers daily, an outdoor pool and free self parking. Woodstock Inn & Resort and North Star Lodge and Resort are a couple of other choices that feature an on-site pool. View all hotels with pools in Pittsfield.
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. A top sight in the area is Killington Resort. In Pittsfield, there are 42 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. Additionally, you'll find Killington Resort 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.