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

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4 Sep - 5 Sep
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5 Sep - 6 Sep
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4 Sep - 6 Sep
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11 Sep - 13 Sep

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Our top choices for Pittsfield hotels

1. Stay At Jimmy's

Stay At Jimmy's
Woodstock
United States
Jeanne
AED 1,282
AED 1,410 total
includes taxes & fees
10 Sep - 11 Sep
Stay At Jimmy's

2. The Shire Woodstock

The Shire Woodstock
Woodstock
United States
Paul
AED 783
AED 931 total
includes taxes & fees
9 Sep - 10 Sep
The Shire Woodstock

3. The Vesper

The Vesper
Woodstock
United States
Keith
AED 643
AED 707 total
includes taxes & fees
7 Sep - 8 Sep
The Vesper

4. Kedron Valley Inn

Kedron Valley Inn
South Woodstock
United States
Kathryn
AED 1,355
AED 1,491 total
includes taxes & fees
9 Sep - 10 Sep
Kedron Valley Inn

5. Woodstock Inn & Resort

Woodstock Inn & Resort
Woodstock
United States
Kevin
AED 1,502
AED 1,814 total
includes taxes & fees
7 Sep - 8 Sep
Woodstock Inn & Resort

6. On The River Inn

On The River Inn
West Woodstock
United Kingdom
Laura
AED 929
AED 1,103 total
includes taxes & fees
9 Sep - 10 Sep
On The River Inn

7. The Jackson

The Jackson
West Woodstock
United States
Yanil
AED 661
AED 727 total
includes taxes & fees
7 Sep - 8 Sep
The Jackson

8. Lincoln Inn & Gallery

Lincoln Inn & Gallery
Woodstock
United States
Elisabeth
AED 680
AED 748 total
includes taxes & fees
10 Sep - 11 Sep
Lincoln Inn & Gallery

9. Sleep Woodstock Motel

Sleep Woodstock Motel
Woodstock
United States
John
AED 370
AED 549 total
includes taxes & fees
8 Sep - 9 Sep
Sleep Woodstock Motel

10. Deer Brook Inn

Deer Brook Inn
Woodstock
United States
Laurence
AED 855
AED 940 total
includes taxes & fees
6 Sep - 7 Sep
Deer Brook Inn

11. Woodbridge Inn

Woodbridge Inn
Woodstock
United States
eric
AED 1,818
AED 2,000 total
includes taxes & fees
7 Sep - 8 Sep
Woodbridge Inn

12. Echo Lake Inn

Echo Lake Inn
Plymouth
United States
Michael
AED 804
AED 877 total
includes taxes & fees
7 Sep - 8 Sep
Echo Lake Inn

13. My Place Hotel-Randolph VT

My Place Hotel-Randolph VT
Randolph Center
United States
Holly
AED 657
AED 717 total
includes taxes & fees
6 Sep - 7 Sep
My Place Hotel-Randolph VT

14. Green Trails Inn

Green Trails Inn
Brookfield
United States
Margaret
AED 576
AED 627 total
includes taxes & fees
10 Sep - 11 Sep
Green Trails Inn

15. Turn of River Lodge

Turn of River Lodge
Killington
United States
Anne
AED 364
AED 400 total
includes taxes & fees
10 Sep - 11 Sep
Turn of River Lodge

16. Killington Haus

Killington Haus
Killington
United States
Samir
AED 375
AED 412 total
includes taxes & fees
6 Sep - 7 Sep
Killington Haus

17. Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton
Killington
United States
Mason
AED 509
AED 560 total
includes taxes & fees
10 Sep - 11 Sep
Killington Mountain Lodge, Tapestry Collection by Hilton

18. Killington Grand Hotel

Killington Grand Hotel
Base Area
United States
Amanda
AED 853
AED 1,000 total
includes taxes & fees
7 Sep - 8 Sep
Killington Grand Hotel

19. Snowed Inn

Snowed Inn
Killington
United States
James
AED 466
AED 564 total
includes taxes & fees
9 Sep - 10 Sep
Snowed Inn

20. Après Inn Killington

Après Inn Killington
Killington
United States
Margaret
AED 380
AED 418 total
includes taxes & fees
9 Sep - 10 Sep
Après Inn Killington
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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.
See properties

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

Sleep Woodstock Motel

Sleep Woodstock Motel

10/10 Excellent
"Clean room."
Richard 2-night trip
Posted 7 hours ago
Sleep Woodstock Motel
Mountain Meadows Lodge

Mountain Meadows Lodge

10/10 Excellent
"Terrific beds & amazing views."
Brian 2-night trip
Posted 10 hours ago
Mountain Meadows Lodge
Emrose Luxury Cabins

Emrose Luxury Cabins

10/10 Excellent
"Really enjoyed the stay here friendly staff and loved the hot tub"
Michael 1-night trip
Posted 11 hours ago
Emrose Luxury Cabins
Woodstock Inn & Resort

Woodstock Inn & Resort

10/10 Excellent
"Beautiful as is the town"
Kevin 1-night trip
Posted 17 hours ago
Woodstock Inn & Resort
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

10/10 Excellent
"Very quiet, great ac. Pool was great"
Nathanael 2-night trip
Posted 2 days ago
Days Inn by Wyndham Rutland/Killington Area
Hampton Inn Rutland

Hampton Inn Rutland

10/10 Excellent
"Great hotel, not there long enough to use amenities. Very expensive for area we thought. But definitely nice!"
Raymond 1-night trip
Posted 2 days ago
Hampton Inn Rutland
My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

10/10 Excellent
"Very nice hotel. We would stay there again."
Judith 1-night trip
Posted 3 days ago
My Place Hotel-Randolph VT
North Star Lodge and Resort

North Star Lodge and Resort

8/10 Good
"Room alittle dates. Some updating should be done throughout. But all around nice place."
Tanya 3-night trip
Posted 3 days ago
North Star Lodge and Resort
The Jackson

The Jackson

10/10 Excellent
"Love this B&B - very well located, the food is amazing and the bedrooms are very comfy! Highly recommend!"
Yanil 1-night trip
Posted 3 days ago
The Jackson

More cheap stays in Pittsfield

Mountain Sports Inn

Mountain Sports Inn

813 Killington Road Killington VT
AED 340
AED 374 total
7 Sep - 8 Sep
includes taxes & fees
Mountain Sports Inn
North Star Lodge and Resort

North Star Lodge and Resort

78 Weathervane Dr Killington VT
AED 382
AED 420 total
21 Sep - 22 Sep
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
North Star Lodge and Resort
The Mountain Inn at Killington

The Mountain Inn at Killington

47 Old Mill Rd Killington VT
AED 410
AED 474 total
6 Sep - 7 Sep
includes taxes & fees
The Mountain Inn at Killington
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

401 US-7 Rutland VT
AED 450
AED 495 total
7 Sep - 8 Sep
includes taxes & fees
6.8/10 (1,005 reviews)
Days Inn by Wyndham Rutland/Killington Area
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

19 Allen St Rutland VT
AED 493
AED 542 total
10 Sep - 11 Sep
includes taxes & fees
Comfort Inn Rutland - Killington
My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2440 Vermont 66 Randolph Center VT
AED 657
AED 717 total
6 Sep - 7 Sep
includes taxes & fees
9.4/10 Exceptional! (538 reviews)
My Place Hotel-Randolph VT

Find out more about Pittsfield

Top reasons to visit Pittsfield

  • Thrilling Outdoor Activities: Pittsfield offers skiing at local resorts and scenic biking trails for adventure seekers.
  • Stunning Natural Scenery: Explore beautiful lakes and national parks, perfect for immersing in nature.
  • Family-Friendly Atmosphere: The welcoming environment makes it an ideal destination for families and groups.
  • Diverse Accommodations: Enjoy a range of lodging options from agritourism to cozy hotels catering to various needs.
  • Nearby Attractions: Venture to nearby Killington for additional slopes and exciting activities.

Find great hotels near Pittsfield

Explore the charming accommodations in Pittsfield, Vermont, where you can find a diverse range of lodging options, including agritourism properties and family-friendly hotels. Whether you're seeking adventure, a golf-themed getaway, or a peaceful retreat, Pittsfield offers various hotels that cater to your needs. Discover the best hotels in the area, complete with essential reviews to ensure a memorable vacation experience.

  • Killington Mountain Lodge, Tapestry Collection by Hilton: Nestled in the heart of adventure, the Killington Mountain Lodge is perfect for thrill-seekers and ski enthusiasts alike. Located 14.5km from Pittsfield, this 3.5-star hotel offers easy access to ski shuttles and lifts, making it a premier destination for winter sports. The lodge features a variety of adventure sports options including rock climbing, ziplining, snowboarding, and downhill skiing nearby. After a day on the slopes, unwind in the cozy lodge atmosphere, complete with modern amenities and a welcoming ambiance.
  • The Mountain Inn at Killington: Situated 16.1km away from Pittsfield, The Mountain Inn at Killington creates an inviting and inclusive atmosphere for all guests. This hotel is particularly welcoming to LGBTQIA travelers and pet owners, offering a golf-themed experience that caters to enthusiasts. Enjoy golfing on-site or partake in the local golfing community. The hotel’s pet policy allows dogs, ensuring your furry friends can join in on the fun, while service animal fees are waived. The Mountain Inn combines comfort with a sense of community, making it a distinctive choice for your stay.
  • North Star Lodge and Resort: Just 12.9km from Pittsfield, North Star Lodge and Resort is designed for those seeking adventure and inclusivity. This LGBTQIA-friendly property offers a variety of recreational activities, including skiing lessons, sailing, windsurfing, and cave exploring. Guests can immerse themselves in the outdoor experience while enjoying the lodge's comfortable accommodations. With its focus on adventure and community, North Star Lodge is an ideal retreat for travelers looking to explore the beauty of Vermont.

Where to stay near Pittsfield

Pittsfield, Vermont, is an ideal getaway for adventure seekers and families alike. With its friendly atmosphere and stunning scenery, visitors can indulge in skiing and various outdoor sports. Explore nearby Killington for additional slopes and activities, or enjoy the romantic, secluded vibes of the region. Whether you're seeking a cozy retreat or an action-packed vacation, Pittsfield offers a warm, inviting experience for everyone.

  • Killington: Nestled just 11.3km from Pittsfield, Killington is a premier destination for outdoor enthusiasts, especially during the winter months. Known for its world-class ski resorts, this city attracts travelers eager to hit the slopes from November to January, offering thrilling skiing, snowboarding, and a vibrant après-ski scene. Killington's stunning landscape features majestic mountains and serene lakes, making it a year-round playground for adventure seekers. Whether you’re skiing down the slopes in winter or hiking scenic trails in summer, Killington promises unforgettable outdoor experiences.
  • Stockbridge: A charming city located a mere 4.8km from Pittsfield, Stockbridge is a delightful getaway that blends natural beauty with cultural richness. Visitors flock here from June to July and September to experience its picturesque valleys, serene lakes, and the nearby national state park. The city is known for its ski facilities, perfect for winter sports enthusiasts, while also offering a host of outdoor activities year-round. Stockbridge’s quaint atmosphere and engaging community events make it a lovely spot for relaxation or adventure.
  • Rutland: Situated 22.5km from Pittsfield, Rutland is a vibrant city that welcomes travelers throughout the year, with peak visits in March, July, and September. Known for its ski fields and resorts, Rutland is ideal for those seeking an adrenaline rush in the winter months. The city is surrounded by beautiful mountains and lakes, providing ample opportunities for outdoor adventures like hiking, fishing, and skiing. With its blend of natural beauty and recreational activities, Rutland offers a dynamic experience for every kind of traveler.

Things to do near Pittsfield

Pittsfield, Vermont, is perfect for an adventurous getaway, offering a variety of outdoor activities such as skiing at local resorts and exploring scenic biking trails. For sports enthusiasts, there are excellent golf courses and opportunities for weekend retreats. Whether you're hitting the slopes or enjoying a leisurely bike ride through the picturesque landscape, Pittsfield promises an exciting vacation experience filled with adventure.

Shopping

Pittsfield offers a charming shopping experience with local favorites like Black Dog Sports, located 16.1km away. If you're up for a drive, visit Diamond Run Mall and Green Mountain Shopping Plaza, both 24.1km away, where you'll find a variety of shops and family-friendly vibes.

Recreation

Green Mountain National Golf Course offers stunning outdoor vibes just 8.0km from Pittsfield, perfect for golf enthusiasts seeking fresh air and beautiful landscapes. For relaxation, the Killington School for Tennis, located 12.9km away, provides a tranquil environment ideal for unwinding while enjoying tennis lessons.

Montague Golf Club, situated 20.9km from Pittsfield, combines outdoor beauty with sports excitement, making it a great spot for golf lovers to enjoy a day on the links amidst picturesque scenery.

Adventure

At Killington Resort, 16.1km from Pittsfield, experience thrilling skiing and snowboarding on diverse slopes. Pico Mountain, 12.9km away, offers fantastic ski opportunities for all levels. For hiking enthusiasts, Deer Leap Trail, also 12.9km from Pittsfield, presents stunning scenery and a chance to connect with nature.

Nightlife

Pittsfield offers a charming nightlife with venues like the Paramount Theater, just 22.5km away, for a romantic evening of culture. For adventure and family fun, visit the Green Mountain Rock Climbing Center, 20.9km away. The Big Picture Theater & Cafe, 46.7km away, combines cinema with a cozy dining experience.

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

Booking tips and Expedia advantages for Pittsfield

For a budget-friendly trip to Pittsfield, plan your visit during the cheaper months of April to May or November, and aim for a Tuesday stay to save the most on accommodations. Utilize Expedia to find great deals by filtering prices and combining hotel, flight, and activity bookings. Take advantage of free outdoor activities like hiking in the Green Mountains, and consider public transport or carpooling to explore the area affordably. Look for flexible booking options and last-minute deals to ensure you get the best rates for your stay.

  • 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: Utilize Expedia’s search tool to narrow down your options based on your budget, desired location, and preferred hotel type. To find the best prices and offers, simply arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your Pittsfield hotel reservations with your flights and activities through an Expedia package.

Find the best attractions near Pittsfield

Pittsfield, Vermont, is a fantastic destination for ski and adventure enthusiasts. Visitors can enjoy a variety of attractions, including ski resorts, national parks, and beautiful lakes. The area caters to those seeking outdoor activities, cultural experiences, and thrilling adventures, making it an ideal vacation spot for travelers looking to immerse themselves in nature and sports.

  • Killington Resort: Experience the thrill of skiing at one of the largest ski resorts in the Eastern United States. Located 16.1km from Pittsfield, Killington Resort offers a wide range of slopes for all skill levels, along with stunning mountain views and lively après-ski activities for a complete outdoor adventure.
  • Gifford Woods State Park: Just 11.3km from Pittsfield, Gifford Woods State Park is a nature lover's paradise, featuring beautiful scenery and extensive hiking trails. Explore lush forests and serene lakes, perfect for a day of outdoor exploration and adventure.
  • Liberty Hill Farm: Situated 6.4km from Pittsfield, Liberty Hill Farm offers a charming glimpse into farm life. Enjoy hands-on experiences with animals, learn about sustainable farming practices, and savor fresh, local produce straight from the farm.

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

Pittsfield, Vermont, is easily accessible via several nearby airports. Burlington International Airport (BTV) is located 82.1km away, with notable hotels like the DoubleTree by Hilton Burlington (3.2km away) and The Essex Resort & Spa (6.4km away), offering shuttle services. Lebanon Municipal Airport (LEB) is 43.5km distant, with good options such as Hanover Inn Dartmouth (8.0km away) and Hotel Coolidge (3.2km away). The closest is Rutland Southern Vermont Regional Airport (RUT), situated 29.0km away, where you can find Killington Mountain Lodge (17.7km away) and Mountain Meadows Lodge (13.2km away). Each airport provides various transportation options for smooth travel.

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 The Mountain Inn at Killington and Woodstock Inn & Resort. See all available top hotels, or vacation rentals in Pittsfield.
What's the top vacation rental in Pittsfield?
Killington area home - 4-seasons, hot tub and A/C: This highly rated vacation home rental in Pittsfield is located in the mountains and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation. See all 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.
Where can I learn more about changing or cancelling my trip to Pittsfield?
To find more details about changing or cancelling your trip to Pittsfield, go to https://www.expedia.com/service/.
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: Offers 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 the best accommodation near Rutland Southern Vermont Regional Airport (RUT)?
Comfort Inn Trolley Square is one of the top choices for your stay and is a popular hotel, featuring free breakfast and an indoor pool. It's located 4.9 mi (7.8 km) from Rutland Southern Vermont Regional Airport. Other choices near the airport include Holiday Inn Rutland-Killington Area and Quality Inn Rutland.
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.