A lake surrounded by autumn-colored trees and a rocky shoreline.

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

Selecting then applying a filter from this group will update the results on a new page

Star rating

Our top choices for Pittsfield hotels

Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area
2.5 star property
Rutland
6.8 out of 10, (1,000 reviews)
"The staff was amazing!!! We will book this again in our next travels up!"
United States
Carol
The price is P7,408
P8,149 total
includes taxes & fees
Jul 5 - Jul 6
Days Inn by Wyndham Rutland/Killington Area

Hampton Inn Rutland

Hampton Inn Rutland
2.5 star property
Rutland
9.0 out of 10, Wonderful, (1,001 reviews)
"Nice comfortable bed, nice selection of breakfast items"
United States
Hawley
The price is P8,351
P9,186 total
includes taxes & fees
Jul 15 - Jul 16
Hampton Inn Rutland

Middlebury Sweets Motel

Middlebury Sweets Motel
2.5 star property
Middlebury
8.6 out of 10, Excellent, (400 reviews)
"Clean room, friendly staff,helpful resources listed."
United States
Michael
The price is P8,446
P9,292 total
includes taxes & fees
Jul 7 - Jul 8
Middlebury Sweets Motel

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT
2.0 star property
Randolph Center
9.4 out of 10, Exceptional, (480 reviews)
"Great stay for passing through. It’s super clean and great dog friendly option"
United States
John
The price is P7,663
P8,352 total
includes taxes & fees
Aug 2 - Aug 3
My Place Hotel-Randolph VT

Green Trails Inn

Green Trails Inn
3.0 star property
Brookfield
10.0 out of 10, Exceptional, (6 reviews)
"Historical charm combined with Immaculate style—- killer food hospitality highly recommend this place—- so wonderful"
United States
Christine
The price is P10,379
P11,313 total
includes taxes & fees
Jul 15 - Jul 16
Green Trails Inn

Best Western Inn & Suites Rutland-Killington

Best Western Inn & Suites Rutland-Killington
2.5 star property
Rutland
8.8 out of 10, Excellent, (1,000 reviews)
"Staff very friendly and helpful! Room was very clean and the bed is very comfortable!"
United States
katrina
The price is P9,288
P10,217 total
includes taxes & fees
Jul 6 - Jul 7
Best Western Inn & Suites Rutland-Killington

The Mountain Inn at Killington

The Mountain Inn at Killington
2.5 star property
Killington
9.2 out of 10, Wonderful, (1,000 reviews)
"Clean, comfortable and great location. Plus they have a hotel dog on staff!"
United States
Laura
The price is P8,237
P9,515 total
includes taxes & fees
Jul 5 - Jul 6
The Mountain Inn at Killington

The Vermont Inn

The Vermont Inn
3.0 star property
Rutland
9.2 out of 10, Wonderful, (430 reviews)
"Clean, cozy, nice staff!"
United States
Mary
The price is P11,963
P13,040 total
includes taxes & fees
Jul 5 - Jul 6
The Vermont Inn

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1,000 reviews)
"Beautiful place to stay"
United States
Jeff
The price is P13,760
P16,149 total
includes taxes & fees
Jul 19 - Jul 20
On The River Inn

Courtyard Middlebury

Courtyard Middlebury
3.0 star property
Middlebury
8.8 out of 10, Excellent, (576 reviews)
"Clean room, helpful staff, good restaurants, onsite guest laundry."
United States
Anne
The price is P9,153
P10,068 total
includes taxes & fees
Jul 7 - Jul 8
Courtyard Middlebury

Mountain Sports Inn

Mountain Sports Inn
2.0 star property
Killington
8.8 out of 10, Excellent, (1,000 reviews)
"Great place"
United States
Peter
The price is P6,696
P7,365 total
includes taxes & fees
Jul 5 - Jul 6
Mountain Sports Inn

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington
2.5 star property
Rutland
8.2 out of 10, Very Good, (1,001 reviews)
"very nice stay, very clean, staff very helpful"
United States
Mancione
The price is P7,735
P8,509 total
includes taxes & fees
Aug 2 - Aug 3
Comfort Inn Rutland - Killington

Inn at Neshobe River

Inn at Neshobe River
3.0 star property
Brandon
9.6 out of 10, Exceptional, (18 reviews)
"Great little BAnd B just outside town. Shares property with a brewery and also offers a small food menu for dinner Fantastic view of the golf course 5 th hole Great hospitality and crazy good breakfast "
United States
Keith
The price is P10,750
P11,825 total
includes taxes & fees
Jul 6 - Jul 7
Inn at Neshobe River

North Star Lodge and Resort

North Star Lodge and Resort
2.0 star property
Killington
8.8 out of 10, Excellent, (1,000 reviews)
"Great pool, bar, & staff!"
United States
Patrick
The price is P8,446
P9,291 total
includes taxes & fees
Jul 5 - Jul 6
North Star Lodge and Resort

Kedron Valley Inn

Kedron Valley Inn
3.5 star property
South Woodstock
9.0 out of 10, Wonderful, (336 reviews)
"Clean very well decorated room with comfortable beds and lots of pillows. Would stay again "
United States
Andrew
The price is P16,199
P17,818 total
includes taxes & fees
Jul 5 - Jul 6
Kedron Valley Inn

Brandon Inn

Brandon Inn
3.0 star property
Brandon
8.8 out of 10, Excellent, (648 reviews)
"Spacious comfortable family suite. Convenient location, clean beautiful inn, great customer service."
United States
Eva
The price is P9,263
P10,190 total
includes taxes & fees
Jul 6 - Jul 7
Brandon Inn

Mountain Meadows Lodge

Mountain Meadows Lodge
3.5 star property
Killington
9.6 out of 10, Exceptional, (236 reviews)
"Beautiful couple for hosts and stunning location. Great breakfast and hot tub to relax after a long drive. Will come back to stay longer"
Canada
Tanuja
The price is P10,217
P12,774 total
includes taxes & fees
Jul 23 - Jul 24
Mountain Meadows Lodge

Lincoln Inn & Gallery

Lincoln Inn & Gallery
3.0 star property
West Woodstock
8.6 out of 10, Excellent, (77 reviews)
"Peaceful, historic property with amiable keepers."
United States
Elisabeth
The price is P11,610
P12,771 total
includes taxes & fees
Jul 5 - Jul 6
Lincoln Inn & Gallery

The Mountain Top Inn & Resort

The Mountain Top Inn & Resort
3.5 star property
Chittenden
9.0 out of 10, Wonderful, (121 reviews)
"Excellent stay "
United States
Kristen
The price is P19,964
P24,774 total
includes taxes & fees
Jul 6 - Jul 7
The Mountain Top Inn & Resort

Woodstock Inn & Resort

Woodstock Inn & Resort
4.5 star property
Woodstock
9.4 out of 10, Exceptional, (589 reviews)
"Perfect staff and excellent accommodations. 30th anniversary celebration at a perfect hotel."
United States
Christopher
The price is P29,424
P35,069 total
includes taxes & fees
Jul 20 - Jul 21
Woodstock Inn & Resort
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

Learn more about Pittsfield

Nestled in Vermont's Green Mountains, Pittsfield offers excellent hiking on the Long Trail and thrilling mountain biking at Green Mountain Trails. Riverside picnics along the Tweed River provide peaceful breaks between seasonal activities at nearby Killington Resort.

A lake surrounded by autumn-colored trees and a rocky shoreline.

Top Pittsfield Hotel Reviews

More cheap stays in Pittsfield

Find out more about Pittsfield

Top reasons to visit Pittsfield

  • Stunning Outdoor Activities: Pittsfield is a haven for skiing, biking, and hiking enthusiasts, offering exhilarating experiences year-round.
  • Charming Local Atmosphere: The town boasts a warm and welcoming vibe, making it perfect for families and couples seeking a relaxing getaway.
  • Proximity to Ski Resorts: Nearby Killington provides exceptional skiing options, catering to both novices and seasoned skiers.
  • Beautiful Natural Scenery: Explore national parks and serene lakes, offering picturesque views and tranquil retreats.
  • Diverse Accommodation Choices: From agritourism to family-friendly hotels, Pittsfield offers lodging options to suit every traveller's needs.

Find great hotels near Pittsfield

For those seeking a memorable getaway in Pittsfield, Vermont, a variety of accommodation options await. From charming agritourism properties to family-friendly hotels, you’ll discover a range of lodgings perfect for adventure seekers, golf enthusiasts, and families alike. With a focus on comfort and hospitality, Pittsfield's hotels cater to diverse needs, ensuring a delightful stay in this picturesque setting.

  • Best Western Inn & Suites Rutland-Killington: Nestled 17.7km from Pittsfield, the Best Western Inn & Suites Rutland-Killington offers a warm and inviting atmosphere perfect for adventure seekers and pet owners alike. This hotel boasts easy access to ski shuttles and lifts, making it an ideal base for winter sports enthusiasts. Guests can indulge in a variety of adventure activities, including skiing, snowshoeing, and hiking, all conveniently located nearby. The property is pet-friendly, allowing dogs to accompany their owners, with amenities tailored for furry friends. With its focus on outdoor recreation, this hotel is a fantastic choice for those looking to embrace the great outdoors.
  • Happy Bear Motel: Located just 14.5km from Pittsfield, Happy Bear Motel is a charming retreat that offers a laid-back atmosphere, perfect for visitors seeking a budget-friendly stay. The motel features a variety of recreational activities, including access to nearby ski runs and lifts, ensuring that winter sports enthusiasts are well catered for. Guests can unwind in their rooms while enjoying entertainment options like television and cable TV. With its friendly service and convenient location, Happy Bear Motel is a delightful option for families and solo travellers alike.
  • The Mountain Top Inn & Resort: Situated only 11.3km from Pittsfield, The Mountain Top Inn & Resort is a luxurious 3.5-star property that combines breathtaking natural beauty with top-notch amenities. Ideal for those seeking a ski getaway or a relaxing beach experience, this resort provides direct access to the beach along with ski shuttle services. The pet-friendly policy, including amenities for dogs, makes it a welcoming choice for travellers with pets. With its stunning views and range of outdoor activities, this resort promises an unforgettable stay in the heart of nature.

Where to stay near Pittsfield

Pittsfield, Vermont, offers an enchanting getaway for tourists seeking adventure and winter sports. This charming town is perfect for families and couples alike, boasting a warm atmosphere and friendly locals. Nearby Killington provides excellent skiing options, while the surrounding areas are ideal for those seeking picturesque scenery and a secluded retreat. Whether you're looking for a romantic escape or an adventurous holiday, Pittsfield promises an unforgettable experience in the heart of nature.

  • Killington: Situated a mere 11.3km from Pittsfield, Killington is renowned for its exceptional skiing and outdoor adventures, attracting seasonal visitors primarily from November to January. This vibrant city boasts a plethora of activities for sports enthusiasts, with its ski fields and resorts offering thrilling experiences on the slopes. Beyond winter sports, Killington is enveloped by stunning natural landscapes, featuring picturesque mountains, serene lakes, and lush valleys, making it an ideal destination for nature lovers and adventurers alike.
  • Stockbridge: Located just 4.8km from Pittsfield, Stockbridge is a charming city that offers a delightful mix of seasonal attractions. Peak visitor numbers occur in June to July and September, drawing those eager for adventure and sports. Stockbridge is home to excellent skiing facilities, ensuring a thrilling experience for winter sports fans. The area is also enriched by its captivating valleys, tranquil lakes, and the nearby national state park, providing ample opportunities for hiking, sightseeing, and immersing oneself in the beauty of Vermont's natural surroundings.
  • Rutland: Rutland, positioned 22.5km from Pittsfield, welcomes visitors year-round with its diverse offerings. The peak seasons in March, July, and September make it a popular stop for those seeking adventure and sports. The city features excellent skiing venues, including ski fields and resorts that cater to thrill-seekers. Surrounded by scenic lakes, majestic mountains, and the nearby national state park, Rutland presents a perfect blend of outdoor activities and serene landscapes, making it an enticing destination for travellers looking to explore Vermont's rich natural beauty.

Things to do near Pittsfield

Pittsfield, Vermont, is an ideal destination for skiing and adventure sports enthusiasts. Enjoy a variety of activities, including skiing at local resorts and exploring biking trails. For a leisurely weekend getaway, visit the nearby golf course. Whether you're hitting the slopes or exploring the scenic outdoors, Pittsfield promises a memorable vacation experience.

Shopping

In Pittsfield, visit Black Dog Sports for outdoor gear and gifts. If you're up for a drive, Diamond Run Mall and Green Mountain Shopping Plaza, both 24.1km away, offer a variety of stores, entertainment options, and a family-friendly atmosphere for a delightful shopping experience.

Recreation

Experience the tranquil atmosphere at Killington School for Tennis, where you can unwind while honing your tennis skills. For a more active day, visit Green Mountain National Golf Course, perfect for golf enthusiasts seeking stunning views and outdoor fun, just a short drive from Pittsfield.

Adventure

Embark on the Deer Leap Trail, an 12.9km hike offering stunning views and a true sense of adventure. For winter sports enthusiasts, Killington Resort, located 16.1km away, provides thrilling skiing experiences. Alternatively, enjoy the slopes at Pico Mountain, also 12.9km from Pittsfield, perfect for ski aficionados.

Nightlife

Pittsfield offers a charming nightlife with venues like the Playhouse Movie Theatre and Chandler Music Hall, both 20.9km away, perfect for romance and culture. The Big Picture Theater & Cafe, 46.7km distant, is ideal for family-friendly entertainment and a relaxed atmosphere, ensuring delightful evenings.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Pittsfield

To save money during your visit to Pittsfield, consider travelling in the cheaper months of April to May and November, with Tuesday being the least expensive day to stay. Avoid Fridays for better rates. Utilise Expedia’s search tool to refine your accommodation choices and sort by price from lowest to highest. Look for package deals that combine flights and hotel bookings for added savings. Explore free local attractions and consider public transport options for cost-effective travel around the area.

  • 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 preferred type of accommodation. To find the most affordable prices and offers, sort the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your hotel booking in Pittsfield with your flights and activities through an Expedia package.

Find the best attractions near Pittsfield

Pittsfield, Vermont, is an ideal destination for ski enthusiasts and adventure seekers alike. Visitors can explore the nearby ski resorts, enjoy the natural beauty of national state parks, and relax by the serene lakes. The area offers a range of outdoor activities, cultural experiences, and thrilling adventures, ensuring a memorable holiday for travellers eager to embrace the great outdoors.

  • Liberty Hill Farm: Located a mere 6.4km from Pittsfield, Liberty Hill Farm offers a charming experience of rural life. Visitors can engage in farm activities, learn about sustainable agriculture, and enjoy fresh produce straight from the farm.
  • Wilson Castle: Situated 24.1km away, this historic castle exudes cultural significance with its stunning architecture and beautiful grounds. Explore the intricate interiors and soak in the rich history that permeates the atmosphere.
  • Whale Dance Sculpture: Also 24.1km from Pittsfield, this captivating monument showcases artistic prowess and cultural vibes. The sculpture, inspired by marine life, invites contemplation and appreciation of the natural world.

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 reach Pittsfield, Vermont, you can fly into several major airports. Rutland Southern Vermont Regional Airport (RUT) is located 29.0km away, with nearby hotels such as the 3-star Cortina Inn and Days Inn by Wyndham Rutland/Killington Area, both offering free airport shuttle services. Burlington International Airport (BTV) is 82.1km away, featuring the 4-star Essex Resort & Spa and the 3.5-star Delta Hotels by Marriott Burlington, which provide paid shuttle options. Lastly, Lebanon Municipal Airport (LEB) is situated 43.5km from Pittsfield, with the Windsor Mansion Inn and The Quechee Inn at Marshland Farm nearby, offering convenient access to the airport.

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 traveler data. Other good choices for your stay in the area are Woodstock Inn & Resort and The Mountain Inn at Killington. 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, 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.
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: Provides a seasonal outdoor pool, an indoor pool, and 4 restaurants. The Mountain Inn at Killington and On The River Inn are a couple of other choices with an onsite pool. View all hotels with pools in Pittsfield.
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 42 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 Green Mountain National Golf Course and Gifford Woods State Park 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.

Explore a world of travel with Expedia