Search Pittsfield hotels

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Pittsfield hotels

Hampton Inn Rutland

Hampton Inn Rutland
2.5 star property
Rutland
9.0 out of 10, Wonderful, (1,002 reviews)
"Clean Hotel, rooms, great hot breakfast with fruits. A lot of restaurants nearby. "
United States
Alisher
The price is AU$212
includes taxes & fees
3 May - 4 May
Hampton Inn Rutland

Green Trails Inn

Green Trails Inn
3.0 star property
Brookfield
The price is AU$173
includes taxes & fees
4 May - 5 May
Green Trails Inn

Lincoln Inn & Gallery

Lincoln Inn & Gallery
3.0 star property
West Woodstock
8.8 out of 10, Excellent, (66 reviews)
"Very pleasant and comfortable stay, about 20 mins drive to Killington nearby. Room was clean and quiet, and bed was very comfortable. Nice coffee/hot chocolate bar in the lobby but unfortunately not offering breakfast anymore."
United States
Andrew
The price is AU$225
includes taxes & fees
3 May - 4 May
Lincoln Inn & Gallery

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT
2.0 star property
Randolph Center
9.4 out of 10, Exceptional, (429 reviews)
"Great place to stay!"
Canada
Chenwei
The price is AU$141
includes taxes & fees
18 May - 19 May
My Place Hotel-Randolph VT

Middlebury Sweets Motel

Middlebury Sweets Motel
2.5 star property
Middlebury
8.6 out of 10, Excellent, (395 reviews)
"Clean spacious room and comfortable beds."
United States
Daria
The price is AU$184
includes taxes & fees
22 Apr - 23 Apr
Middlebury Sweets Motel

The Mountain Inn at Killington

The Mountain Inn at Killington
2.5 star property
Killington
9.2 out of 10, Wonderful, (1,009 reviews)
"Great location and shuttle service. Nice breakfast and friendly staff. "
United States
John
The price is AU$216
includes taxes & fees
4 May - 5 May
The Mountain Inn at Killington

Mountain Sports Inn

Mountain Sports Inn
2.0 star property
Killington
8.8 out of 10, Excellent, (1,002 reviews)
"Clean, great breakfast, room is a little small"
United States
Ziye
The price is AU$152
includes taxes & fees
23 Apr - 24 Apr
Mountain Sports Inn

Courtyard Middlebury

Courtyard Middlebury
3.0 star property
Middlebury
8.8 out of 10, Excellent, (562 reviews)
"Very clean and comfortable room. Helpful staff. "
United States
Elizabeth
The price is AU$228
includes taxes & fees
22 Apr - 23 Apr
Courtyard Middlebury

The Vesper

The Vesper
3.0 star property
Woodstock
9.4 out of 10, Exceptional, (58 reviews)
"Uniqueness of rooms, breakfast options and walking distance to so many great spots!"
United States
Emily
The price is AU$240
includes taxes & fees
21 Apr - 22 Apr
The Vesper

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (573 reviews)
"A great place to stay with pets. Rooms are a little tight, but they are clean and comfortable."
United States
Ron
The price is AU$199
includes taxes & fees
3 May - 4 May
Sleep Woodstock Motel

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington
2.5 star property
Rutland
8.0 out of 10, Very good, (1,003 reviews)
"Clean room, comfortable bed Great steakhouse next door"
United States
Mark
The price is AU$220
includes taxes & fees
12 May - 13 May
Comfort Inn Rutland - Killington

Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area
2.5 star property
Rutland
6.6 out of 10, (1,000 reviews)
"Convenient place to stay for skiing in the area. "
United States
Alice
The price is AU$206
includes taxes & fees
20 Apr - 21 Apr
Days Inn by Wyndham Rutland/Killington Area

The Mountain Top Inn & Resort

The Mountain Top Inn & Resort
3.5 star property
Chittenden
9.0 out of 10, Wonderful, (117 reviews)
"Great resort "
United States
Adam
The price is AU$224
includes taxes & fees
21 Apr - 22 Apr
The Mountain Top Inn & Resort

Brandon Inn

Brandon Inn
3.0 star property
Brandon
8.8 out of 10, Excellent, (611 reviews)
"Loved The Brandon Inn. Kind staff, cozy atmosphere, great location and a warm room. I will be returning here!!!"
United States
David J.
The price is AU$165
includes taxes & fees
17 May - 18 May
Brandon Inn

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1,001 reviews)
"Had a lovely stay while visiting, enjoyed the breakfast and the staff were all very friendly and accommodating. Would def stay here again"
United States
dylan
The price is AU$298
includes taxes & fees
3 May - 4 May
On The River Inn

Best Western Inn & Suites Rutland-Killington

Best Western Inn & Suites Rutland-Killington
2.5 star property
Rutland
8.8 out of 10, Excellent, (1,002 reviews)
"Excellent stay for the price."
United States
Anthony
The price is AU$261
includes taxes & fees
3 May - 4 May
Best Western Inn & Suites Rutland-Killington

The Shire Woodstock

The Shire Woodstock
3.0 star property
Woodstock
8.8 out of 10, Excellent, (919 reviews)
"Wonderful place to stay!"
United States
Robin
The price is AU$189
includes taxes & fees
6 May - 7 May
The Shire Woodstock

Emrose Luxury Cabins

Emrose Luxury Cabins
2.0 star property
Brandon
9.0 out of 10, Wonderful, (92 reviews)
"Amazing stay"
United States
Kelsey
The price is AU$255
includes taxes & fees
21 Apr - 22 Apr
Emrose Luxury Cabins

North Star Lodge and Resort

North Star Lodge and Resort
2.0 star property
Killington
8.8 out of 10, Excellent, (1,000 reviews)
"Nice place to stay and room had a view of Superstar slope. "
United States
Rick
The price is AU$212
includes taxes & fees
3 May - 4 May
North Star Lodge and Resort

The Vermont Inn

The Vermont Inn
3.0 star property
Rutland
9.2 out of 10, Wonderful, (428 reviews)
"Great location, extremely friendly staff, very quaint B&B with awesome hot tub and sauna right next to Pico and Killington. Will look to stay here every time we ski in the area. "
United States
Dylan
The price is AU$296
includes taxes & fees
3 May - 4 May
The Vermont 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.
Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Pittsfield attractions

Top Pittsfield Hotel Reviews

Recent Reviews in Pittsfield

More cheap accommodation in Pittsfield

Find out more about Pittsfield

Top reasons to visit Pittsfield

  • Thrilling Ski Resorts: Pittsfield is renowned for its fantastic ski fields, perfect for both beginners and seasoned skiers.
  • Scenic Hiking Trails: Explore stunning state parks and mountain valleys, ideal for hiking and appreciating nature.
  • Charming Towns: Nearby towns like Williamstown and Stockbridge offer a romantic atmosphere and friendly locals.
  • Outdoor Adventure: Enjoy activities like mountain biking in warmer months, making it a year-round destination.
  • Comfortable Accommodations: Choose from a range of delightful lodgings, including agritourism properties and family-friendly hotels.

Find great hotels near Pittsfield

Pittsfield, Vermont, offers a delightful selection of accommodation options, perfect for travellers seeking a comfortable stay. From charming agritourism properties to family-friendly hotels, you’ll discover places that cater to your adventure or golf-themed holiday. Enjoy a restful night on a comfy bed and start your day right with hearty breakfast inns. No matter your preference, Pittsfield has the ideal lodging choice for your holiday experience.

  • Killington Mountain Lodge, Tapestry Collection by Hilton: Nestled in the heart of adventure, the Killington Mountain Lodge, Tapestry Collection by Hilton offers a unique blend of comfort and business facilities, perfect for the adventurous traveller. Located 14.5km from Pittsfield, this 3.5-star hotel features versatile meeting spaces and a fully equipped business centre for corporate guests. For those seeking thrills, the lodge provides access to a variety of outdoor activities including skiing, rock climbing, and mountain biking, ensuring an exhilarating stay amidst stunning landscapes.
  • Best Western Inn & Suites Rutland-Killington: Situated 17.7km from Pittsfield, the Best Western Inn & Suites Rutland-Killington is an inviting pet-friendly haven for adventure enthusiasts. This accommodation allows pets, making it ideal for those travelling with furry companions. Guests can enjoy an array of outdoor activities nearby, such as ziplining, snowshoeing, and kayaking. The warm hospitality and family-friendly atmosphere create a welcoming environment for all visitors, ensuring a memorable getaway filled with adventure and comfort.
  • The Mountain Inn at Killington: Just 16.1km from Pittsfield, The Mountain Inn at Killington is an excellent choice for those passionate about skiing and golf. This charming inn offers easy access to ski lifts and shuttles, making it a convenient base for winter sports lovers. Guests can also indulge in golfing experiences, with multiple courses nearby. The inn’s rustic charm and adventure-filled surroundings provide the perfect backdrop for an unforgettable escape into the great outdoors.

Where to stay near Pittsfield

Pittsfield, Vermont, offers an unforgettable escape for adventure lovers and families alike. Nestled in the picturesque Berkshire Hills, explore the beautiful grounds and serene mountain valleys. Just a short drive away, discover the charming towns of Williamstown and Stockbridge, each boasting a romantic atmosphere and friendly locals. Whether you're skiing or soaking in the scenic views, Pittsfield promises a delightful experience that captures the heart of New England.

  • Killington: Situated a mere 11.3km from Pittsfield, Killington is renowned as a premier ski destination, attracting adventure seekers year-round. With visitor numbers surging during the winter months from November to January, this vibrant city offers an array of outdoor sports experiences. Killington's stunning landscape features majestic mountains, pristine lakes, and lush valleys, making it a picturesque spot for both skiing and summer activities. The ski resorts and fields are easily accessible, providing exhilarating slopes for skiing enthusiasts. Whether you're hitting the trails in winter or hiking in warmer months, Killington is a must-visit for outdoor lovers.
  • Rutland: Located 22.5km from Pittsfield, Rutland is a lively city that draws visitors throughout the year. With peaks in March, July, and September, Rutland promises a diverse range of activities for adventure enthusiasts. The city is surrounded by breathtaking lakes, valleys, and mountains, offering a picturesque backdrop for outdoor sports. Visitors can enjoy skiing in the winter and explore the vibrant local culture during the warmer months. Rutland also boasts various events and festivals, making it an ideal spot for those seeking a blend of adventure and community spirit.
  • Stockbridge: Just 4.8km away from Pittsfield, Stockbridge is a charming city that welcomes visitors all year round. With peak travel times in June to July and September, it’s a hotspot for those seeking outdoor adventures. The city is enveloped by stunning valleys, serene lakes, and impressive mountains, creating a perfect playground for skiing and other outdoor activities. Stockbridge’s proximity to nature ensures that you can enjoy a variety of experiences, from skiing in winter to hiking and exploring the great outdoors in summer. This quaint city offers a delightful escape for all adventure lovers.

Things to do near Pittsfield

Pittsfield, Vermont, offers an exciting getaway for adventure seekers and sports enthusiasts. With its renowned ski fields and resorts, visitors can enjoy a lively atmosphere filled with fun activities, including mountain biking during the warmer months. Guest ratings highlight the area's charm, making it a perfect destination for those looking to embrace the thrill of outdoor adventures while soaking in the stunning mountain scenery.

Shopping

Pittsfield offers shopping at Black Dog Sports, a local store for sports gear. If you're up for a drive, check out Diamond Run Mall and Green Mountain Shopping Plaza, both 24.1km away, featuring a mix of family, business, and entertainment vibes.

Recreation

Enjoy a round at Green Mountain National Golf Course, where you can soak in the beautiful outdoors while playing a challenging game. For a serene experience, unwind at Killington School for Tennis, perfect for relaxation and wellness activities. Montague Golf Club offers another great golfing experience amidst stunning landscapes.

Adventure

Killington Resort, 16.1km from Pittsfield, offers thrilling skiing and outdoor adventures amidst stunning landscapes. Pico Mountain, 12.9km away, is perfect for sports enthusiasts eager to hit the slopes. Experience the excitement at Pico Peak, 14.5km from Pittsfield, where adventure and breathtaking views await.

Nightlife

Experience the vibrant nightlife in Pittsfield by catching a show at the Paramount Theater, just 22.5km away, for a dose of culture and romance. For adventure, visit the Green Mountain Rock Climbing Center, 20.9km away, offering thrilling fun for the whole family.

Booking tips and Expedia advantages for Pittsfield

To save money on your trip to Pittsfield, consider visiting between April to May or in November, when accommodation prices are typically lower. Avoid Fridays for your stay, as Tuesdays are the most affordable. Use Expedia to refine your search based on your budget and preferred location, and look for eco-certified hotels. Combining your hotel, flights, and activities in a package can lead to significant savings. Lastly, take advantage of free activities in the area to stretch your budget further.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Pittsfield are April to May and November, where the prices are slightly lower. This is in comparison to February, October and December, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Pittsfield is Tuesday. The most expensive day to stay in Pittsfield is Friday.
  • Find cheap hotels on Expedia: Utilise Expedia’s search tool to refine your preferences, such as your budget, desired location, and the type of accommodation you’re after. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels currently available. To find the best prices and deals, simply sort the price filter from lowest to highest.
  • Consider bundling your trip: You can save some cash by combining your Pittsfield hotel reservation with your flights and activities through an Expedia package.

Find the best attractions near Pittsfield

Pittsfield is an ideal destination for ski and adventure enthusiasts, offering a range of outdoor activities. Visitors can explore nearby ski resorts, relax at beautiful lakes, and hike through stunning state parks. This charming town caters to those seeking thrilling experiences and a taste of local culture, making it a perfect spot for an adventurous getaway.

  • Killington Resort: Experience the thrill of winter sports at one of the largest ski resorts in the Eastern United States. With its diverse terrain and lively atmosphere, Killington offers not only skiing but also snowboarding and après-ski activities, making it a fantastic destination for adventure seekers.
  • Pico Peak: Just a stone's throw away, Pico Peak is a hidden gem for skiing enthusiasts. Known for its family-friendly slopes and stunning views, it's an ideal spot to carve through fresh powder or enjoy a leisurely day outdoors in a breathtaking setting.
  • Gifford Woods State Park: Immerse yourself in nature at Gifford Woods State Park, where lush forests and scenic trails await. Ideal for hiking and picnicking, this park offers a tranquil escape with beautiful vistas and abundant wildlife, perfect for outdoor adventurers.

Best time to go to Pittsfield

The best time to visit Pittsfield can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Pittsfield falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Pittsfield falls in January, visitor numbers are average and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January18.0°F (-7.8°C)Light RainMostly CloudyAverageAverage
February20.1°F (-6.6°C)Light RainMostly CloudyAverageSlightly High
March28.4°F (-2.0°C)Light RainMostly CloudyAverageAverage
April40.6°F (4.8°C)Light RainMostly CloudyAverageSlightly Low
May54.1°F (12.3°C)Light RainMostly SunnySlightly LowSlightly Low
June61.5°F (16.4°C)Light RainMostly SunnyAverageAverage
July67.5°F (19.7°C)Light RainMostly SunnySlightly HighAverage
August65.7°F (18.7°C)Light RainMostly SunnySlightly HighAverage
September58.6°F (14.8°C)Light RainMostly SunnySlightly HighAverage
October46.9°F (8.3°C)Light RainMostly CloudyAverageSlightly High
November34.3°F (1.3°C)Light RainMostly CloudySlightly LowSlightly Low
December25.3°F (-3.7°C)Light RainMostly CloudySlightly LowSlightly High

The nearest major airports for your trip to Pittsfield

To visit Pittsfield, Vermont, you can fly into three major airports. Burlington International Airport (BTV) is situated 82.1km away, with nearby hotels such as DoubleTree by Hilton Burlington (3.2km), The Essex Resort & Spa (6.4km), and Hotel Champlain Burlington (4.8km), all offering various transportation services. Lebanon Municipal Airport (LEB) is 43.5km from Pittsfield, with options like Hanover Inn Dartmouth (8.0km) and Hotel Coolidge (3.2km). Lastly, Rutland Southern Vermont Regional Airport (RUT) is just 29.0km away, with hotels like Killington Grand Hotel (16.1km) and Snowed Inn (17.7km) available for your convenience.

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 Woodstock Inn & Resort and Comfort Inn Rutland - Killington. See all available top hotels, or vacation rentals in Pittsfield.
What are some of the best holiday rentals that Pittsfield has to offer?
Killington area home - 4-seasons, hot tub and A/C: This highly rated holiday home rental in Pittsfield is located in the mountains, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday. See all 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?
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 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. In Pittsfield, there are 44 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. You'll also find Green Mountain National Golf Course and Gifford Woods State Park 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.

Explore a world of travel with Expedia