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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)
"We had a great stay, very clean and the staff was friendly! "
United States
Jordyn
The price is CA $196
CA $216 total
includes taxes & fees
Jun 7 - Jun 8
Hampton Inn Rutland

Lincoln Inn & Gallery

Lincoln Inn & Gallery
3.0 star property
West Woodstock
8.8 out of 10, Excellent, (68 reviews)
"Peaceful, historic property with amiable keepers."
United States
Elisabeth
The price is CA $201
CA $221 total
includes taxes & fees
May 10 - May 11
Lincoln Inn & Gallery

Middlebury Sweets Motel

Middlebury Sweets Motel
2.5 star property
Middlebury
8.6 out of 10, Excellent, (397 reviews)
"The staff was wonderful and communicated well. The connection to the candy shop and uniqueness of the motel was adorable. The outside needs some updating but the rooms were nice. We enjoyed our stay, thank you! "
United States
Sami
The price is CA $163
CA $180 total
includes taxes & fees
May 10 - May 11
Middlebury Sweets Motel

The Mountain Inn at Killington

The Mountain Inn at Killington
2.5 star property
Killington
9.2 out of 10, Wonderful, (1,004 reviews)
"Always love our stay - dog friendly and people friendly!"
United States
Hanna
The price is CA $183
CA $211 total
includes taxes & fees
Jun 4 - Jun 5
The Mountain Inn at Killington

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT
2.0 star property
Randolph Center
9.4 out of 10, Exceptional, (441 reviews)
"Great location for us when visiting VT."
United States
Jeannine
The price is CA $136
CA $148 total
includes taxes & fees
May 26 - May 27
My Place Hotel-Randolph VT

Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area
2.5 star property
Rutland
6.6 out of 10, (1,006 reviews)
"Very nice property. "
United States
Carla
The price is CA $183
CA $202 total
includes taxes & fees
May 10 - May 11
Days Inn by Wyndham Rutland/Killington Area

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1,006 reviews)
"Clean room, friendly staff, family-friendly. "
United States
Suwei
The price is CA $201
CA $272 total
includes taxes & fees
May 10 - May 11
On The River Inn

Green Trails Inn

Green Trails Inn
3.0 star property
Brookfield
10.0 out of 10, Exceptional, (1 review)
"Historical charm combined with Immaculate style—- killer food hospitality highly recommend this place—- so wonderful"
United States
Christine
The price is CA $159
CA $174 total
includes taxes & fees
Jun 7 - Jun 8
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)
"Excellent stay for the price."
United States
Anthony
The price is CA $232
CA $256 total
includes taxes & fees
May 21 - May 22
Best Western Inn & Suites Rutland-Killington

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington
2.5 star property
Rutland
8.0 out of 10, Very good, (1,005 reviews)
"Clean room, comfortable bed Great steakhouse next door"
United States
Mark
The price is CA $202
CA $222 total
includes taxes & fees
May 28 - May 29
Comfort Inn Rutland - Killington

Courtyard Middlebury

Courtyard Middlebury
3.0 star property
Middlebury
8.8 out of 10, Excellent, (565 reviews)
"We were in Middlebury to visit the college. The location of the hotel was convenient. Staff are helpful and friendly. Breakfast is an extra cost, and not very good. Would return "
United States
Karen
The price is CA $220
CA $242 total
includes taxes & fees
May 31 - Jun 1
Courtyard Middlebury

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (576 reviews)
"Quiet, well kept, comfortable, convenient."
United States
Elisabeth
The price is CA $99
CA $187 total
includes taxes & fees
May 14 - May 15
Sleep Woodstock Motel

Brandon Inn

Brandon Inn
3.0 star property
Brandon
8.8 out of 10, Excellent, (624 reviews)
"A great and charming place to stay. "
United States
Kurt
The price is CA $150
CA $165 total
includes taxes & fees
May 17 - May 18
Brandon Inn

The Vesper

The Vesper
3.0 star property
Woodstock
9.4 out of 10, Exceptional, (60 reviews)
"This was the cutest little bed and breakfast. The staff was lovely, the check-in was easy, and we had a great time in Woodstock! "
United States
Melissa
The price is CA $213
CA $234 total
includes taxes & fees
May 12 - May 13
The Vesper

Mountain Meadows Lodge

Mountain Meadows Lodge
3.5 star property
Killington
9.6 out of 10, Exceptional, (212 reviews)
"A great place to stay just away from the busier ski area. "
United States
Thomas
The price is CA $193
CA $247 total
includes taxes & fees
May 13 - May 14
Mountain Meadows Lodge

The Shire Woodstock

The Shire Woodstock
3.0 star property
Woodstock
8.8 out of 10, Excellent, (924 reviews)
"Everything was great."
United States
Sue
The price is CA $173
CA $206 total
includes taxes & fees
May 25 - May 26
The Shire Woodstock

The Trailside Inn

The Trailside Inn
3.0 star property
North Sherburne
9.2 out of 10, Wonderful, (154 reviews)
"Everything was great. Super clean, super friendly, it was exactly what we needed."
United States
Michael
The price is CA $217
CA $239 total
includes taxes & fees
May 9 - May 10
The Trailside Inn

North Star Lodge and Resort

North Star Lodge and Resort
2.0 star property
Killington
8.8 out of 10, Excellent, (1,005 reviews)
"Plenty of space, storage, and nice kitchen. Room and bathroom was clean, bed was comfortable, and the heated pool with a view of the mountain was a huge plus after a long day of skiing"
United States
William
The price is CA $163
CA $179 total
includes taxes & fees
May 20 - May 21
North Star Lodge and Resort

Inn at Neshobe River

Inn at Neshobe River
3.0 star property
Brandon
9.4 out of 10, Exceptional, (16 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 CA $239
CA $262 total
includes taxes & fees
May 15 - May 16
Inn at Neshobe River

Emrose Luxury Cabins

Emrose Luxury Cabins
2.0 star property
Brandon
9.0 out of 10, Wonderful, (93 reviews)
"Will definitely be back!! "
United States
Steevyann
The price is CA $221
CA $250 total
includes taxes & fees
May 11 - May 12
Emrose Luxury Cabins
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Stay near popular Pittsfield attractions

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Find out more about Pittsfield

Top reasons to visit Pittsfield

  • Thrilling Ski Adventures: Pittsfield is a paradise for ski enthusiasts, featuring stunning ski resorts and slopes for all skill levels.
  • Scenic Hiking Trails: Explore picturesque hiking trails that showcase the natural beauty of Vermont's landscapes.
  • Cultural Tours: Discover the rich heritage of the area through engaging cultural tours and local attractions.
  • Charming Accommodations: Enjoy a variety of lodging options, from cozy lodges to unique agritourism stays.
  • Vibrant Local Vineyards: Experience the rich flavours of Vermont by visiting nearby vineyards for tastings.

Find great hotels near Pittsfield

Pittsfield, Vermont, offers a variety of lodging options to cater to every traveller's needs, from family-friendly hotels to unique agritourism properties. Whether you're looking for pet-friendly accommodations or an adventurous getaway, you'll find a selection of the best hotels in the area. Explore charming options near Pittsfield and enjoy a memorable stay amidst the stunning natural beauty of Vermont.

  • Killington Mountain Lodge, Tapestry Collection by Hilton: Experience adventure and inclusivity at the Killington Mountain Lodge. This 3.5-star hotel, located 14.5km from Pittsfield, caters to both business and leisure travellers, with a warm welcome for the LGBTQIA community. The lodge boasts a range of business amenities, including accessible conference spaces and multiple meeting rooms, making it an ideal choice for corporate retreats. For outdoor enthusiasts, nearby adventure sports such as downhill skiing, snowboarding, and rock climbing await, ensuring an exciting stay for those seeking thrills in the great outdoors.
  • North Star Lodge and Resort: Perfect for families and adventurers alike, North Star Lodge and Resort is located 12.9km from Pittsfield and is known for its family-friendly atmosphere and LGBTQIA welcoming environment. Enjoy a variety of recreational activities, from sailing and snowshoeing to hiking and biking. The resort caters to children with amenities like an arcade game room and sledding opportunities, making it a fantastic choice for families looking to create lasting memories while exploring the beautiful Vermont landscape.
  • The Mountain Inn at Killington: Nestled 16.1km from Pittsfield, The Mountain Inn at Killington offers a golf and ski-themed getaway for adventurers. With easy access to ski shuttles and lifts, guests can hit the slopes with ease. The property also features golf experiences for enthusiasts, coupled with a variety of outdoor activities such as fishing, ice skating, and rafting. This inn is the perfect retreat for those looking to indulge in both winter sports and summer adventures, all while enjoying the serene beauty of the Vermont mountains.

Where to stay near Pittsfield

Pittsfield, Vermont, offers an unforgettable vacation experience for adventure seekers and families alike. Nestled in scenic landscapes, this charming town is perfect for skiing and outdoor sports. Nearby, explore local vineyards that showcase Vermont's rich flavours. Enjoy the friendly atmosphere and romantic settings, making it an ideal getaway for couples and families. With its secluded spots and picturesque scenery, Pittsfield promises a delightful blend of adventure and relaxation for every traveller.

  • Killington: Nestled approximately 11.3km from Pittsfield, Killington is a renowned destination for outdoor enthusiasts. Known for its exceptional ski resorts and adventure sports, this vibrant city attracts visitors primarily from November to January, offering a bustling winter atmosphere. In addition to skiing, outdoor activities such as mountain biking and hiking provide year-round excitement. The stunning natural scenery, including picturesque mountains, serene lakes, and expansive valleys, enhances the travel experience, making Killington a must-visit for thrill-seekers and nature lovers alike.
  • Rutland: Located about 22.5km from Pittsfield, Rutland boasts a lively atmosphere with various activities available throughout the year. While visitor numbers peak in March, July, and September, the city remains a charming spot for year-round exploration. Outdoor activities like skiing and hiking are popular, and the nearby mountains and lakes offer stunning landscapes and recreational opportunities. Rutland's rich history, cultural attractions, and welcoming community make it an engaging destination for adventurers and those seeking a taste of local life.
  • Stockbridge: Just 4.8km from Pittsfield, Stockbridge is a quaint city that draws visitors with its picturesque scenery and outdoor adventures. While it experiences a seasonal peak in June to July and September, it remains an appealing destination for those seeking outdoor experiences year-round. The area is known for its ski resorts and beautiful valleys, lakes, and mountains that provide ample opportunities for exploration. With its charming small-town feel and stunning natural beauty, Stockbridge is perfect for tourists looking to immerse themselves in the great outdoors.

Things to do near Pittsfield

Pittsfield, Vermont, is an ideal destination for ski enthusiasts and adventure seekers. Visitors can enjoy a variety of activities, including skiing at local resorts and exploring scenic hiking trails. Cultural tours provide a glimpse into the area's rich heritage, while cozy ski lodges offer a perfect retreat after a day on the slopes. Whether you're hitting the trails or relaxing by the fire, Pittsfield has something for everyone to enjoy.

Shopping

In Pittsfield, visit Black Dog Sports for sports gear and gifts. If you're up for a drive, check out Diamond Run Mall and Green Mountain Shopping Plaza, both 24.1km away, where you can enjoy a variety of shops and family-friendly entertainment options.

Recreation

Green Mountain National Golf Course offers an invigorating outdoor experience with its beautiful fairways and scenic views, perfect for golf enthusiasts. For a more relaxed atmosphere, the Killington School for Tennis provides a tranquil environment focused on wellness and rejuvenation, ideal for tennis lovers seeking relaxation.

Adventure

At Killington Resort, experience exhilarating skiing and outdoor vibes, located 16.1km from Pittsfield. For sports enthusiasts, Pico Mountain offers thrilling ski experiences, only 12.9km away. Enjoy the stunning scenery along the Deer Leap Trail, a scenic hiking trail also 12.9km from Pittsfield, perfect for adventure seekers.

Nightlife

Pittsfield offers a charming nightlife with the Paramount Theater for a romantic evening, just 22.5km away. For adventure, visit the Green Mountain Rock Climbing Center, located 20.9km away. Alternatively, catch a film at The Big Picture Theater & Cafe, about 46.7km from town, perfect for entertainment and a cozy vibe.

*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 or November, with Tuesdays being the least expensive day for accommodation. Utilize Expedia's search tool to find budget-friendly hotels by adjusting filters and sorting low to high prices. Look for eco-certified options for sustainable stays and consider bundling your hotel, flights, and activities for additional savings. Enjoy free local activities and take advantage of affordable public transport to explore the area without breaking the bank.

  • 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: Expedia's search tool enables you to specify your budget, desired location, and additional preferences. You can easily arrange your results to display prices from lowest to highest, ensuring that you discover the most affordable hotels right away. Additionally, you have the option to refine your choices by hotel type; for instance, selecting the Eco-certified filter will showcase sustainable and environmentally-friendly accommodations available for booking.
  • Consider bundling your trip: You can save money by combining your Pittsfield hotel reservation with your flights and activities through an Expedia package.

Find the best attractions near Pittsfield

Pittsfield, Vermont, is a haven for tourists seeking thrilling ski adventures and outdoor activities. With its stunning ski resorts, beautiful state parks, and serene lakes, visitors can immerse themselves in nature and enjoy a variety of sports. The local attractions cater to those looking for both adventure and cultural experiences, making it an ideal destination for an unforgettable vacation.

  • Killington Resort: Located 16.1km from Pittsfield, this renowned ski resort offers thrilling adventures year-round. Experience the exhilarating slopes in winter and enjoy hiking and mountain biking in warmer months amidst stunning mountain scenery.
  • Gifford Woods State Park: Just 11.3km away, this national park is a nature lover's paradise. Explore its enchanting trails surrounded by lush forests and scenic vistas, perfect for hiking, birdwatching, and picnicking.
  • Killington Adventure Center: Also 16.1km from Pittsfield, this family-friendly theme park is brimming with entertainment. Enjoy a variety of activities, from mini-golf to an alpine slide, making it an ideal destination for fun-filled family outings.

Best time to go to Pittsfield

The best time to visit Pittsfield is dependant on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, 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

If you're planning to visit Pittsfield, Vermont, you have a few major airports to consider. Burlington International Airport (BTV) is 82.1km away, with nearby hotels like the DoubleTree by Hilton Burlington (3.2km) and the Essex Resort & Spa (6.4km), both offering shuttle services. Lebanon Municipal Airport (LEB) is located 43.5km away, with options such as the Hanover Inn Dartmouth (8.0km) and Hotel Coolidge (3.2km). Lastly, Rutland Southern Vermont Regional Airport (RUT) is just 29.0km from Pittsfield, with hotels like Killington Grand Hotel (16.1km) and Snowed Inn (17.7km) nearby. Each airport provides convenient access to the charming town of Pittsfield.

Frequently asked questions

What is the best area to stay in Pittsfield?
The best area to stay in Pittsfield is right in the village centre, particularly around Main Street, as it offers the most convenient access to local amenities and the region's natural beauty.

Pittsfield's village centre is a small, picturesque area typical of rural Vermont. Main Street runs through the heart of the village, where you'll find the general store, a few local eateries, and the town hall. It's a compact and easily navigable area, providing a cosy base for exploring the surrounding Green Mountains.

Couples looking for a relaxing escape will find the village centre ideal. It offers a peaceful setting with immediate access to hiking trails and scenic drives. You can enjoy quiet evenings at local dining spots and spend your days exploring the outdoors, perhaps visiting nearby Gifford Woods State Park or taking a drive along Route 100 for stunning views.

For those planning an active holiday, staying in the village centre puts you in the superb spot for outdoor pursuits. Many accommodations offer direct access to trailheads for hiking, mountain biking, and in winter, cross-country skiing or snowshoeing.
What are the best hotels in Pittsfield that travellers recommend?
For a highly recommended hotel in Pittsfield, consider the Clear River Inn.

The 3-star Clear River Inn, with an 8.8 rating, is a popular choice among travellers. Guests frequently praise the incredible breakfast and appreciate the premium bedding provided. This inn is also ideally located for those interested in outdoor activities, with nearby options for cross-country and downhill skiing, and it offers rooms with delightful river and mountain views.
What are the top pet-friendly hotels in Pittsfield?
For a top pet-friendly hotel in Pittsfield, the Clear River Inn is an excellent choice.

This 3-star hotel, with an 8.8 rating, is praised by guests for its pet-friendly policies, welcoming dogs and providing food and water bowls. It is also a great base for outdoor enthusiasts, with cross-country and downhill skiing areas nearby. The Roger Clark Memorial Central Library is also conveniently located just under 2 kilometres away. Guests particularly appreciate the incredible breakfast. See more pet-friendly hotels in Pittsfield
What are the best budget hotels in Pittsfield?
For a highly-rated budget hotel in Pittsfield, consider the Clear River Inn.

The 3-star Clear River Inn, with an 8.8 rating, is an excellent choice for budget-conscious travellers. Guests frequently highlight the incredible breakfast offered. The hotel provides amenities such as free WiFi and complimentary toiletries. It also offers free self-parking, which is very convenient. For those interested in winter sports, the inn is located near areas for cross-country skiing, downhill skiing, and a general ski area. Additionally, it is close to the Roger Clark Memorial Central Library, just 1.9 km away. View all budget hotels in Pittsfield
What are the most romantic hotels in Pittsfield for couples?
For a romantic hotel in Pittsfield, Vermont, the Clear River Inn is an excellent recommendation for couples.

This 3-star hotel, with an 8.8 rating, offers a lovely setting with many rooms featuring mountain views, and some even include balconies or river views for a truly picturesque experience. Guests appreciate the convenience of a kitchen in their accommodation and the complimentary toiletries. It is also well-located for outdoor activities, with cross-country and downhill skiing areas nearby. Additionally, guests have frequently praised the incredible breakfast provided.
What are the best hotels in Pittsfield near Roger Clark Memorial Central Library?
For hotels in Pittsfield near Roger Clark Memorial Central Library, the Clear River Inn is a great option.

The 3-star Clear River Inn, with an 8.8 rating, is located approximately 1.9 kilometres from Roger Clark Memorial Central Library. This hotel is particularly well-suited for families who enjoy winter sports, as it is conveniently located near cross-country and downhill skiing areas. Guests appreciate the inclusion of kitchens in the accommodations, along with complimentary Wi-Fi and free toiletries. Many rooms offer pleasant mountain views, and free self-parking is available. Previous guests have often described the breakfast as incredible.
When is the best time to go to Pittsfield?
The best time to go to Pittsfield, Vermont, is during the summer (June to August) for outdoor activities or in autumn (September to October) for the stunning foliage.

Summer in Pittsfield offers warm, pleasant weather, ideal for exploring the surrounding Green Mountain National Forest. You'll find numerous hiking trails, such as those leading to the summit of Pico Peak or along the Long Trail. The White River also provides opportunities for fishing and swimming. This season is great for active travellers or couples who enjoy nature and outdoor adventures.

Autumn transforms Pittsfield into a spectacular display of reds, oranges, and yellows as the leaves change colour. The crisp air and picturesque scenery make it an excellent time for scenic drives along Route 100 or exploring local farms and craft shops. This period is particularly popular with couples seeking a romantic getaway or anyone looking for a visually stunning and relaxing escape.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Pittsfield.
How can I save on a Pittsfield hotel booking with Expedia?
Members always get our best prices. Find our best Pittsfield hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.
How much is the nightly rate at a Pittsfield hotel?
Prices for hotels in Pittsfield often vary, but you can find a great deal from CA $148 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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