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

Pittsfield Hotels

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Aug 18 - Aug 19
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Aug 19 - Aug 20
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Aug 21 - Aug 23
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Aug 28 - Aug 30

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Our top choices for Pittsfield hotels

Reserve now, pay later
Hotel
Breakfast included
Pittsfield
Pet friendly

1. The Trailside Inn

The Trailside Inn
North Sherburne
United States
Niall
P9,789
P10,768 total
includes taxes & fees
Aug 19 - Aug 20
The Trailside Inn

2. The Mountain Inn at Killington

The Mountain Inn at Killington
Killington
United States
Travis
P7,691
P8,884 total
includes taxes & fees
Aug 19 - Aug 20
The Mountain Inn at Killington

3. Mountain Meadows Lodge

Mountain Meadows Lodge
Killington
United States
Barry
P9,982
P12,517 total
includes taxes & fees
Aug 19 - Aug 20
Mountain Meadows Lodge

4. The Mountain Top Inn & Resort

The Mountain Top Inn & Resort
Chittenden
United States
Kristen
P19,971
P21,768 total
includes taxes & fees
Aug 31 - Sep 1
The Mountain Top Inn & Resort

5. Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington
Rutland
United States
Mancione
P7,588
P8,346 total
includes taxes & fees
Aug 30 - Aug 31
Comfort Inn Rutland - Killington

6. Hampton Inn Rutland

Hampton Inn Rutland
Rutland
United States
Tarsha
P8,012
P8,813 total
includes taxes & fees
Aug 30 - Aug 31
Hampton Inn Rutland

7. Best Western Inn & Suites Rutland-Killington

Best Western Inn & Suites Rutland-Killington
Rutland
United States
Alex
P9,347
P10,282 total
includes taxes & fees
Aug 30 - Aug 31
Best Western Inn & Suites Rutland-Killington

8. Mountain Sports Inn

Mountain Sports Inn
Killington
United States
Davis
P6,698
P7,368 total
includes taxes & fees
Aug 20 - Aug 21
Mountain Sports Inn

9. Greenbrier Inn

Greenbrier Inn
Killington
United States
David
P10,361
P11,941 total
includes taxes & fees
Sep 2 - Sep 3
Greenbrier Inn

10. North Star Lodge and Resort

North Star Lodge and Resort
Killington
United States
Jessica
P8,111
P8,922 total
includes taxes & fees
Sep 7 - Sep 8
North Star Lodge and Resort

11. Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area
Rutland
United States
Douglas
P7,260
P7,986 total
includes taxes & fees
Aug 30 - Aug 31
Days Inn by Wyndham Rutland/Killington Area

12. Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton
Killington
United States
Holaiza
P8,516
P9,367 total
includes taxes & fees
Aug 30 - Aug 31
Killington Mountain Lodge, Tapestry Collection by Hilton

13. My Place Hotel-Randolph VT

My Place Hotel-Randolph VT
Randolph Center
United States
Joey
P9,061
P9,877 total
includes taxes & fees
Sep 6 - Sep 7
My Place Hotel-Randolph VT

14. Snowed Inn

Snowed Inn
Killington
United States
Rebecca
P7,808
P9,448 total
includes taxes & fees
Aug 19 - Aug 20
Snowed Inn

15. Brandon Inn

Brandon Inn
Brandon
Canada
Michael
P9,267
P10,193 total
includes taxes & fees
Aug 19 - Aug 20
Brandon Inn

16. Après Inn Killington

Après Inn Killington
Killington
United States
Lei
P8,480
P9,328 total
includes taxes & fees
Aug 31 - Sep 1
Après Inn Killington

17. Emrose Luxury Cabins

Emrose Luxury Cabins
Brandon
United States
Mycheala
P9,955
P11,249 total
includes taxes & fees
Aug 19 - Aug 20
Emrose Luxury Cabins

18. The Lilac Inn

The Lilac Inn
Brandon
United States
Judith M
P14,686
P16,155 total
includes taxes & fees
Aug 19 - Aug 20
The Lilac Inn

19. Inn at Neshobe River

Inn at Neshobe River
Brandon
United States
Keith
P10,754
P11,829 total
includes taxes & fees
Aug 28 - Aug 29
Inn at Neshobe River

20. Courtyard Middlebury

Courtyard Middlebury
Middlebury
United States
Thomas
P9,346
P10,281 total
includes taxes & fees
Aug 30 - Aug 31
Courtyard Middlebury
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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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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.

See all hotels in Pittsfield
A lake surrounded by autumn-colored trees and a rocky shoreline.

Top Pittsfield Hotel Reviews

Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

10/10 Excellent
"I had a pleasant two-night stay. The hotel was very quiet, the staff were very welcoming, and I really enjoyed the pool."
Mathieu 2-night trip
Posted 10 hours ago
Days Inn by Wyndham Rutland/Killington Area
The Shire Woodstock

The Shire Woodstock

8/10 Good
"We stayed in the River House and had two different rooms as we stayed one night each at the beginning and end of a longer trip to Canada. Both rooms were very clean. One room had a better view of the river than the other. There is construction occurring at the property and we weren’t made aware of it ahead of time so the sawing and drilling made sitting by the river and relaxing a little difficult. The whole property is getting a face lift. The outdoor space was lovely with chairs and fire pits. The location is great. Grocery store across the street and walkable to breakfast and shops. Would recommend but make sure you check about construction and confirm a good view of the river if that is important to you."
Jessica 1-night trip
Posted 18 hours ago
The Shire Woodstock
Brandon Inn

Brandon Inn

10/10 Excellent
"This hotel is beautiful inside and out and located in the heart of town. The guest rooms were very clean and super spacious , the bed was very comfortable, and the continental breakfast was good. Although the staff person who checked us in was noticeably busy as she was also serving at the cafe, it was just a short wait to get us checked in and she was very pleasant. I would absolutely stay here again!"
Emily 1-night trip
Posted 23 hours ago
Brandon Inn
Hampton Inn Rutland

Hampton Inn Rutland

10/10 Excellent
"Very nice hotel"
John 2-night trip
Posted 1 day ago
Hampton Inn Rutland
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

10/10 Excellent
"I spent 2 nights a this beautiful place and loved it. Since the moment we checked in and out we had a great time. The room was very clean, the beds were very comfortable and the view of the mountains at the hot tub was stunning."
Holaiza 2-night trip
Posted 2 days ago
Killington Mountain Lodge, Tapestry Collection by Hilton
Sleep Woodstock Motel

Sleep Woodstock Motel

10/10 Excellent
"Expect easy check in and a clean room in this dog friendly Motel!"
Julie 1-night trip
Posted 2 days ago
Sleep Woodstock Motel
The Mountain Inn at Killington

The Mountain Inn at Killington

8/10 Good
"Everything was good we enjoyed the stay for the weekend."
Trisha 2-night trip
Posted 2 days ago
The Mountain Inn at Killington
Lincoln Inn & Gallery

Lincoln Inn & Gallery

10/10 Excellent
"The room was clean, bed was comfortable, nice amenities, and the coffee, tea and hot chocolate bar in reception was impressive and free. The staff were helpful and professional. The building was clearly very old but extremely well maintained."
Christopher 1-night trip
Posted 4 days ago
Lincoln Inn & Gallery
Mountain Sports Inn

Mountain Sports Inn

8/10 Good
"This is an older building, but clean and well maintained. The AC window units worked very well. The breakfast was tailored to meet our needs and excellent. The staff were friendly, caring and always available, even though summertime has fewer visitors than during the ski season. Highly recommend for the value!"
Neil 2-night trip
Posted 5 days ago
Mountain Sports Inn

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 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.
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: Features a seasonal outdoor pool, an indoor pool, and 4 restaurants. The Mountain Inn at Killington and Comfort Inn Rutland - Killington 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 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 Liberty Hill Farm and Green Mountain National Golf Course 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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