Find hotels in Pittsfield, VT from $108

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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 Getaway 4 Bedroom Home

The Shire Woodstock

The Shire Woodstock
3.0 star property
Woodstock
8.8 out of 10, Excellent, (894)
"Wonderful place to stay!"
United States
Robin
$157 nightly
The price is $172
Jan 12 - Jan 13, 2026
Total with taxes and fees
The Shire Woodstock

The Jackson

The Jackson
4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (258)
"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
$199 nightly
The price is $219
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Jackson

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1002)
"Rearaurant staff was top notch. "
United States
Daniel
$252 nightly
The price is $278
Jan 11 - Jan 12, 2026
Total with taxes and fees
On The River 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
$280 nightly
The price is $308
Jan 7 - Jan 8, 2026
Total with taxes and fees
Kedron Valley Inn

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (549)
"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
$135 nightly
The price is $149
Jan 6 - Jan 7, 2026
Total with taxes and fees
Sleep Woodstock Motel

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
$359 nightly
The price is $395
Jan 19 - Jan 20, 2026
Total with taxes and fees
Woodstock Inn & Resort

Mountain Meadows Lodge

Mountain Meadows Lodge
3.5 star property
Killington
9.4 out of 10, Exceptional, (183)
"Staff was amazing! They made the stay even better with their hospitality and overall service. I recommend this Lodge to anyone looking to go to Killington who wants a fun and relaxing stay. "
United States
Jaden
$242 nightly
The price is $266
Jan 4 - Jan 5, 2026
Total with taxes and fees
Mountain Meadows Lodge

The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (51)
"Charming bed and breakfast"
United States
Nicholas
$169 nightly
The price is $186
Jan 5 - Jan 6, 2026
Total with taxes and fees
The Vesper

Mountain Valley Retreat

Mountain Valley Retreat
2.5 star property
Killington
9.6 out of 10, Exceptional, (191)
"This was my third stay with Mike and Barbara. It's just so lovely in a beautiful rural setting! And sure can't complain about the hearty breakfasts cooked by Chef Mike. It's certain I'll return on another ski adventure to Killington."
United States
Kathy
$110 nightly
The price is $124
Jan 11 - Jan 12, 2026
Total with taxes and fees
Mountain Valley Retreat

Turn of River Lodge

Turn of River Lodge
2.5 star property
Killington
8.8 out of 10, Excellent, (270)
"We enjoyed our stay. Close proximity to a lot of things to see and do. "
United States
Linda
$115 nightly
The price is $127
Jan 7 - Jan 8, 2026
Total with taxes and fees
Turn of River Lodge

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton
3.5 star property
Killington
7.4 out of 10, Good, (1004)
"Good place to stay when you ski"
United States
Josh
$188 nightly
The price is $207
Jan 21 - Jan 22, 2026
Total with taxes and fees
Killington Mountain Lodge, Tapestry Collection by Hilton

Summit Lodge

Summit Lodge
3.0 star property
Killington
8.6 out of 10, Excellent, (400)
"Good location and close to ski area. Good free breakfast makes stay nicer. Staff are nice. "
United States
RAYMOND
$193 nightly
The price is $212
Jan 4 - Jan 5, 2026
Total with taxes and fees
Summit Lodge

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
$249 nightly
The price is $274
Jan 4 - Jan 5, 2026
Total with taxes and fees
Stay At Jimmy's

North Star Lodge and Resort

North Star Lodge and Resort
2.0 star property
Killington
8.6 out of 10, Excellent, (1000)
"Spotless room also very accommodating and friendly! Loved our short stay!"
United States
Candace
$160 nightly
The price is $176
Jan 4 - Jan 5, 2026
Total with taxes and fees
North Star Lodge and Resort

Snowed Inn

Snowed Inn
3.5 star property
Killington
9.8 out of 10, Exceptional, (374)
"A wonderful hotel. The atmosphere is warm and clean."
United States
Fevzi
$260 nightly
The price is $286
Jan 6 - Jan 7, 2026
Total with taxes and fees
Snowed Inn

Greenbrier Inn

Greenbrier Inn
2.0 star property
Killington
9.4 out of 10, Exceptional, (646)
"It was a very quaint inn in a gorgeous location."
United States
ELIZABETH
$166 nightly
The price is $182
Jan 5 - Jan 6, 2026
Total with taxes and fees
Greenbrier Inn

Après Inn Killington

Après Inn Killington
2.0 star property
Killington
9.4 out of 10, Exceptional, (164)
"Wonderful location, beautiful renovations, friendly staff "
United States
Robyn
$193 nightly
The price is $213
Jan 13 - Jan 14, 2026
Total with taxes and fees
Après Inn Killington

Mountain Sports Inn

Mountain Sports Inn
2.0 star property
The Woods
8.8 out of 10, Excellent, (988)
"Staff was great and breakfast was excellent "
United States
Bruce
$129 nightly
The price is $142
Jan 4 - Jan 5, 2026
Total with taxes and fees
Mountain Sports Inn

Echo Lake Inn

Echo Lake Inn
2.5 star property
Plymouth
8.6 out of 10, Excellent, (98)
"Old fashioned inn with wonderful hosts."
United States
James
$259 nightly
The price is $283
Jan 5 - Jan 6, 2026
Total with taxes and fees
Echo Lake Inn
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Stay near popular Pittsfield attractions

Top Pittsfield Hotel Reviews

More cheap stays in Pittsfield

Hotels in Pittsfield with star-rating

Find out more about Pittsfield

Top reasons to visit Pittsfield

  • Outdoor Adventure: Pittsfield offers thrilling skiing at nearby resorts and scenic biking trails for all adventure seekers.
  • Charming Atmosphere: The town provides a friendly vibe, making it perfect for families and couples looking for a relaxing getaway.
  • Beautiful Nature: Explore stunning lakes and state parks, ideal for outdoor activities and appreciating the area's natural beauty.
  • Diverse Accommodations: Choose from family-friendly hotels, pet-friendly stays, or unique agritourism experiences tailored to your needs.
  • Golfing Opportunities: Enjoy a relaxing day at the local golf course, perfect for unwinding amidst beautiful scenery.

Find great hotels near Pittsfield

Discover a variety of accommodation options in Pittsfield, Vermont, perfect for every type of traveler. Whether you're seeking family-friendly hotels, pet-friendly stays, or unique agritourism experiences, Pittsfield has something to offer. With a focus on adventure and comfort, you'll find the best hotels to suit your needs, along with helpful hotel reviews to guide your choice. Experience the charm of this picturesque town while enjoying quality lodging tailored just for you.

  • Killington Mountain Lodge, Tapestry Collection by Hilton: Experience the essence of adventure at Killington Mountain Lodge, a 3.5-star retreat perfect for outdoor enthusiasts and business travelers alike. Located 9 miles from Pittsfield, this lodge seamlessly blends ski and golf themes with essential business amenities. Guests can take advantage of the nearby ski shuttle or lift, making it easy to hit the slopes. The hotel features a well-equipped business center, multiple meeting rooms, and conference space, catering to corporate needs. With a focus on recreation, the lodge also offers golf experiences for those looking to tee off amidst stunning mountain views.
  • North Star Lodge and Resort: Embrace a family-friendly atmosphere at North Star Lodge and Resort, situated 8 miles from Pittsfield. This welcoming property is particularly LGBTQIA-friendly and offers a plethora of adventure activities both on-site and nearby. Whether you want to go windsurfing, skiing, or horseback riding, there's something for everyone. Families will appreciate the amenities designed for children, including an arcade game room, sledding options, and air hockey tables. North Star Lodge is a great base for creating memorable experiences with loved ones while enjoying the great outdoors.
  • The Mountain Inn at Killington: Nestled 10 miles from Pittsfield, The Mountain Inn at Killington is an inviting hotel that caters to LGBTQIA travelers seeking a blend of ski and golf experiences. With easy access to ski shuttles and lifts, guests can enjoy winter sports at their convenience. The inn also promotes golf-themed activities, making it an excellent choice for golf lovers wishing to enjoy the beautiful Vermont landscape. The warm atmosphere and friendly staff ensure a comfortable and memorable stay for all who visit.

Where to stay near Pittsfield

Experience the charm of Pittsfield, Vermont, where adventure awaits in a friendly atmosphere. This picturesque destination is perfect for ski enthusiasts and families alike. Explore nearby Killington for thrilling outdoor activities or enjoy secluded spots for a romantic getaway. With its warm vibe and stunning scenery, Pittsfield offers the ideal blend of relaxation and excitement for travelers seeking a memorable vacation.

  • Killington: Nestled 7 miles from Pittsfield, Killington is a ski lover's paradise. Known for its seasonal influx of visitors, particularly from November to January, it offers thrilling adventure sports year-round. Whether you're hitting the ski slopes in winter or exploring mountain trails in the warmer months, Killington is a great destination. The area boasts stunning natural landmarks like lakes and valleys, making it perfect for outdoor enthusiasts. Don't miss the renowned ski resorts that attract visitors from all over the country.
  • Rutland: Located 14 miles from Pittsfield, Rutland is a vibrant city that sees a steady flow of visitors throughout the year, peaking in March, July, and September. Known for its outdoor adventure opportunities, Rutland is an excellent spot for skiing and other sports. The surrounding landscape features picturesque lakes and valleys, ideal for hiking and exploring. With a mix of local culture and seasonal activities, Rutland offers a unique experience for travelers seeking both relaxation and adventure.
  • Stockbridge: Just 3 miles from Pittsfield, Stockbridge is a charming city that attracts visitors year-round, particularly in June to July and September. Known for its outdoor activities, the city is popular for its ski fields and beautiful natural scenery, including valleys, lakes, and mountains. This quaint town provides a perfect backdrop for adventure seekers and those looking to unwind in nature. With a rich history and scenic beauty, Stockbridge is a delightful stop on your Vermont journey.

Things to do near Pittsfield

Pittsfield, Vermont, is an ideal destination for outdoor enthusiasts seeking adventure and sports. Visitors can enjoy skiing at local ski resorts and explore scenic biking trails. For those looking for a weekend getaway, the area also features a golf course, perfect for a relaxing day outdoors. Whether you're hitting the slopes or biking through beautiful landscapes, Pittsfield offers a variety of activities to make your vacation memorable.

Shopping

For unique gifts and souvenirs, visit Black Dog Sports, located 10 miles from Pittsfield. If you're up for a drive, explore the Diamond Run Mall and Green Mountain Shopping Plaza, both 15 miles away, offering a variety of shops and family-friendly atmospheres.

Recreation

Experience the scenic Green Mountain National Golf Course, just 5 miles from Pittsfield, where you can enjoy a round of golf amidst beautiful landscapes. For a more relaxed atmosphere, visit the Killington School for Tennis, located 8 miles away, perfect for unwinding and enhancing your tennis skills.

Adventure

Experience winter thrills at Killington Resort, where you can ski on diverse trails and enjoy the vibrant outdoor atmosphere, located 10 miles from Pittsfield. For a unique skiing experience, visit Pico Mountain, 8 miles away, or hike the scenic Deer Leap Trail, also 8 miles distant, for breathtaking views.

Nightlife

Experience a lively nightlife in Pittsfield with a visit to the Paramount Theater, just 14 miles away, for a cultural evening. For some adventure, check out Green Mountain Rock Climbing Center, located 13 miles away. Finish your night with a romantic film at The Big Picture Theater & Cafe, 29 miles away.

*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 on your trip to Pittsfield, consider visiting during the cheaper months of April to May and November, with Tuesdays being the least expensive days to stay. Use Expedia’s search tool to compare hotel prices and filter for eco-friendly options. Additionally, consider booking a package deal that combines flights and activities for extra savings. Joining Expedia’s One Key membership can provide exclusive discounts and allow you to earn OneKeyCash for future bookings. Look for flexible booking options and great last-minute deals to maximize your budget.

  • 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 lets you set your budget and preferred location, among other options. You can organize your results to display hotels from the lowest to the highest price, ensuring you find the most affordable options first. Additionally, you have the ability to narrow down your choices by hotel type; for instance, selecting the Eco-certified filter will show you a selection of sustainable and environmentally friendly hotels available for booking.
  • Consider bundling your trip: You can potentially save money by combining your hotel stay in Pittsfield with your flights and activities through an Expedia package deal.
  • Become a One Key member: Join Expedia's One Key membership program for exclusive discounts and deals on hotel bookings. You can also earn OneKeyCash to use on future selected hotels.

Find the best attractions near Pittsfield

Pittsfield, Vermont, is an ideal destination for ski enthusiasts and adventure seekers alike. This charming town offers a variety of attractions, including ski resorts, state parks, and serene lakes, perfect for outdoor activities and cultural experiences. Whether you're looking to hit the slopes or explore the natural beauty of the area, Pittsfield provides a memorable vacation filled with excitement and exploration.

  • Killington Resort: Located 10 miles from Pittsfield, Killington Resort is a premier ski destination offering thrilling winter sports and breathtaking mountain views. Experience a variety of outdoor activities, including skiing, snowboarding, and snowshoeing, as well as scenic hiking trails in warmer months.
  • Gifford Woods State Park: Just 7 miles away, Gifford Woods State Park is a beautiful natural retreat, perfect for hiking and exploring lush forests. The park features stunning scenery, including vibrant fall foliage and serene lakes, making it an ideal spot for nature enthusiasts.
  • Killington Adventure Center: Also 10 miles from Pittsfield, the Killington Adventure Center is a family-friendly theme park offering exciting activities such as mountain coasters and zip lines. Enjoy a day filled with entertainment, adventure, and unforgettable memories with loved ones.

Best time to go to Pittsfield

The best time to visit Pittsfield is dependent 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

Traveling to Pittsfield, Vermont, can be conveniently done via three major airports. Burlington International Airport (BTV) is 51 miles away, with nearby hotels such as the 4-star DoubleTree by Hilton Burlington, just 2 miles from the airport, and the 3.5-star Hotel Champlain Burlington, 3 miles away. Lebanon Municipal Airport (LEB) is 27 miles away, offering options like the 4-star Hanover Inn Dartmouth, located 5 miles from the airport, and the 3-star Hotel Coolidge, 2 miles away. Rutland Southern Vermont Regional Airport (RUT) is 18 miles away, with the 3.5-star Killington Grand Hotel situated 10 miles from the airport. All hotels provide accessible transportation services to their respective airports.

Frequently asked questions

What are the best hotels in Pittsfield that travelers recommend?
Clear River Inn is a charming choice for travelers, earning an excellent review score of 8.8. Nestled in the picturesque setting of Pittsfield, Vermont, this hotel offers stunning river and mountain views that create a serene backdrop for your stay. Guests rave about the premium bedding, ensuring restful nights after days of adventure, and the friendly space that makes it feel like a home away from home.
What are the top pet-friendly hotels in Pittsfield?
Clear River Inn is a charming pet-friendly hotel situated in Pittsfield, Vermont, with a delightful review score of 8.8 from guests who have appreciated its warm atmosphere and attentive service. This inviting property is great for families and travelers with furry companions, allowing dogs and providing amenities like food and water bowls, ensuring a comfortable stay for all. See more pet-friendly hotels in Pittsfield.
What are the best budget hotels in Pittsfield?
Clear River Inn is an inviting choice for budget-conscious travelers seeking a delightful stay in Pittsfield, Vermont. Nestled amidst stunning mountain views, this hotel offers a cozy atmosphere with convenient amenities like complimentary WiFi and free self-parking. Families will appreciate the fully equipped kitchen and premium bedding, great for those looking to prepare meals while enjoying a home-like experience. View all budget hotels in Pittsfield.
When is the best time to go to Pittsfield?
The best time to visit Pittsfield is during the vibrant summer months, particularly in July. This season is marked by warm temperatures averaging around 75°F, superb for enjoying outdoor activities and exploring the natural beauty of the Berkshires. With the lush greenery and blooming flowers, July offers an inviting backdrop for hiking, biking, and leisurely strolls through the scenic parks.

During the peak tourist season, which stretches from late June through August, you'll find a range of events and festivals showcasing local culture and arts. This lively atmosphere is ideal for travelers who appreciate attentive service and want to immerse themselves in the community. You can easily access outdoor concerts, farmers' markets, and art exhibitions, making it an enriching experience.

For those who prefer a quieter visit, September is also a fantastic time to explore Pittsfield. The summer crowds begin to dissipate, and you can still enjoy pleasant temperatures, often in the low 70s Fahrenheit. This month offers a wonderful opportunity to connect with the local scene without the hustle and bustle, allowing for a more relaxed experience in the charming downtown area or at nearby attractions like the Berkshire Museum.

If you're considering a budget-friendly trip, November could be an appealing option, with fewer tourists and lower accommodation rates. While the weather starts to cool down, it's an excellent time for indoor activities, like visiting art galleries and enjoying local cuisine at cozy restaurants.
Can I cancel my hotel reservation on Expedia?
Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline – this is often within 24-48 hours of your scheduled arrival. If you have a non-refundable booking, it might still be possible to receive a refund if you cancel it within 24 hours of booking. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use our "Fully refundable property" filter during your search to find the right Pittsfield hotel for you.
How can I save on a Pittsfield hotel booking with Expedia?
One Key™ - Expedia's free travel rewards program - gives you instant access to perks and Member Prices on Pittsfield hotels. Plus, you'll earn OneKeyCash™* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings.

*OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
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 $108 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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