Pittsfield Hotels

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Our top choices for Pittsfield hotels

The Getaway 4 Bedroom Home

The Getaway 4 Bedroom Home
3.0 star property
Pittsfield
The price is P26,715
P62,994 total
includes taxes & fees
Jan 4 - Jan 5
The Getaway 4 Bedroom Home

The Mountain Top Inn & Resort

The Mountain Top Inn & Resort
3.5 star property
Chittenden
9.0 out of 10, Wonderful, (100)
"Room was comfy and clean. The view from the window was gorgeous. The whole resort was so quaint, warm and beautiful. "
United States
Ping
The price is P19,135
P20,857 total
includes taxes & fees
Jan 3 - Jan 4
The Mountain Top Inn & Resort

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington
2.5 star property
Rutland
8.0 out of 10, Very Good, (1009)
"Clean rooms and polite workers. Try to stay there every time we go to Vermont."
United States
Michael
The price is P8,268
P9,095 total
includes taxes & fees
Feb 1 - Feb 2
Comfort Inn Rutland - Killington

Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area
2.5 star property
Rutland
6.4 out of 10, (1001)
"The food "
United States
Elijah
The price is P8,708
P9,579 total
includes taxes & fees
Jan 4 - Jan 5
Days Inn by Wyndham Rutland/Killington Area

Best Western Inn & Suites Rutland-Killington

Best Western Inn & Suites Rutland-Killington
2.5 star property
Rutland
8.8 out of 10, Excellent, (1000)
"Great front desk staff. Rooms were very comfortable. "
United States
JERILYN
The price is P10,545
P11,600 total
includes taxes & fees
Jan 8 - Jan 9
Best Western Inn & Suites Rutland-Killington

Woodstock Inn & Resort

Woodstock Inn & Resort
4.5 star property
Woodstock
9.2 out of 10, Wonderful, (558)
"Luxurious and friendly resort! Loved it"
United States
Elizabeth
The price is P18,781
P23,250 total
includes taxes & fees
Jan 19 - Jan 20
Woodstock Inn & Resort

Courtyard Middlebury

Courtyard Middlebury
3.0 star property
Middlebury
8.8 out of 10, Excellent, (548)
"Laundry service was efficient and parking was easy "
United States
Agnes
The price is P7,360
P8,095 total
includes taxes & fees
Jan 11 - Jan 12
Courtyard Middlebury

The Shire Woodstock

The Shire Woodstock
3.0 star property
Woodstock
8.8 out of 10, Excellent, (895)
"Wonderful place to stay!"
United States
Robin
The Shire Woodstock

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1005)
"Brilliant stay"
United States
Enrico
On The River Inn

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (552)
"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 P4,875
P9,042 total
includes taxes & fees
Jan 6 - Jan 7
Sleep Woodstock Motel

The Jackson

The Jackson
4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (259)
"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

Hampton Inn Rutland

Hampton Inn Rutland
2.5 star property
Rutland
9.0 out of 10, Wonderful, (978)
"Everything was clean and the staff responsive and friendly. I wish the offerings at breakfast were more substantial. "
United States
Lesley
The price is P9,469
P10,415 total
includes taxes & fees
Jan 8 - Jan 9
Hampton Inn Rutland

Lincoln Inn & Gallery

Lincoln Inn & Gallery
2.0 star property
West Woodstock
8.6 out of 10, Excellent, (58)
"A very pleasant VT stay at a reasonable price."
United States
Sean
The price is P11,128
P12,240 total
includes taxes & fees
Jan 4 - Jan 5
Lincoln Inn & Gallery

Cortina Inn

Cortina Inn
3.0 star property
Rutland
6.6 out of 10, (663)
"Very quiet and comfortable stay."
United States
James
The price is P5,829
P6,412 total
includes taxes & fees
Feb 1 - Feb 2
Cortina Inn

The Vermont Inn

The Vermont Inn
3.0 star property
Rutland
9.2 out of 10, Wonderful, (415)
"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 P15,102
P16,461 total
includes taxes & fees
Jan 7 - Jan 8
The Vermont Inn

Stay At Jimmy's

Stay At Jimmy's
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (46)
"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 P14,660
P16,126 total
includes taxes & fees
Jan 4 - Jan 5
Stay At Jimmy's

Middlebury Sweets Motel

Middlebury Sweets Motel
2.5 star property
Middlebury
8.6 out of 10, Excellent, (388)
"Friendly staff, clean, comfortable and convenient to downtown. "
United States
Melissa
The price is P7,059
P7,765 total
includes taxes & fees
Jan 4 - Jan 5
Middlebury Sweets Motel

The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (52)
"Charming bed and breakfast"
United States
Nicholas
The price is P10,929
P12,022 total
includes taxes & fees
Jan 5 - Jan 6
The Vesper

Brandon Inn

Brandon Inn
3.0 star property
Brandon
8.8 out of 10, Excellent, (572)
"Clean room and staff was wonderful upon check in "
United States
Kaitlyn
The price is P7,042
P7,746 total
includes taxes & fees
Jan 4 - Jan 5
Brandon Inn

Kedron Valley Inn

Kedron Valley Inn
3.5 star property
South Woodstock
9.0 out of 10, Wonderful, (329)
"Nice place to stay. Would stay there again & recommend it to friends and family "
United States
Deborah
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

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 14.4 mi (23.2 km) from the heart of Pittsfield, Comfort Inn Rutland - Killington is a top choice for your stay based on our traveler data. Other good choices for your stay in the area are Killington Mountain Lodge, Tapestry Collection by Hilton 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?
Comfort Inn Rutland - Killington: Features continental, an indoor pool, and free self parking. The Mountain Inn at Killington and Woodstock Inn & Resort 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. A top sight in the area is Killington Resort. 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. Additionally, you'll find Killington 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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