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

Pittsfield Hotels

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Oct 3 - Oct 4
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Our top choices for Pittsfield hotels

1. The Trailside Inn

The Trailside Inn
North Sherburne
United States
Niall
P10,004
P11,004 total
includes taxes & fees
Oct 18 - Oct 19
The Trailside Inn

2. Mountain Meadows Lodge

Mountain Meadows Lodge
Killington
United States
Matthew
P7,419
P9,731 total
includes taxes & fees
Oct 26 - Oct 27
Mountain Meadows Lodge

3. Greenbrier Inn

Greenbrier Inn
Killington
United States
Hilary
P10,588
P12,203 total
includes taxes & fees
Oct 18 - Oct 19
Greenbrier Inn

4. Mountain Sports Inn

Mountain Sports Inn
Killington
United States
Jacob
P8,729
P9,602 total
includes taxes & fees
Oct 12 - Oct 13
Mountain Sports Inn

5. The Mountain Top Inn & Resort

The Mountain Top Inn & Resort
Chittenden
United States
Patricia
P15,747
P17,165 total
includes taxes & fees
Nov 1 - Nov 2
The Mountain Top Inn & Resort

6. Summit Lodge

Summit Lodge
Killington
United States
Alex
P10,714
P13,392 total
includes taxes & fees
Oct 16 - Oct 17
Summit Lodge

7. North Star Lodge and Resort

North Star Lodge and Resort
Killington
United States
Corey
P8,684
P9,553 total
includes taxes & fees
Oct 20 - Oct 21
North Star Lodge and Resort

8. Snowed Inn

Snowed Inn
Killington
United States
Melissa
P8,792
P10,638 total
includes taxes & fees
Oct 25 - Oct 26
Snowed Inn

9. The Mountain Inn at Killington

The Mountain Inn at Killington
Killington
United States
Christopher
P8,421
P9,727 total
includes taxes & fees
Oct 19 - Oct 20
The Mountain Inn at Killington

10. Best Western Inn & Suites Rutland-Killington

Best Western Inn & Suites Rutland-Killington
Rutland
Canada
Christian
P10,118
P11,129 total
includes taxes & fees
Oct 21 - Oct 22
Best Western Inn & Suites Rutland-Killington

11. Turn of River Lodge

Turn of River Lodge
Killington
United States
Jaime
P7,913
P8,704 total
includes taxes & fees
Oct 14 - Oct 15
Turn of River Lodge

12. Killington Grand Hotel

Killington Grand Hotel
Base Area
United States
Ryan
P14,549
P17,066 total
includes taxes & fees
Oct 12 - Oct 13
Killington Grand Hotel

13. Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton
Killington
United States
Richard
P8,703
P9,573 total
includes taxes & fees
Nov 2 - Nov 3
Killington Mountain Lodge, Tapestry Collection by Hilton

14. Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington
Rutland
United States
Reuben
P6,985
P7,683 total
includes taxes & fees
Oct 25 - Oct 26
Comfort Inn Rutland - Killington

15. Après Inn Killington

Après Inn Killington
Killington
Canada
Christian
P9,677
P10,645 total
includes taxes & fees
Oct 25 - Oct 26
Après Inn Killington

16. Killington Haus

Killington Haus
Killington
United States
Matthew
P6,839
P7,523 total
includes taxes & fees
Oct 19 - Oct 20
Killington Haus

17. Hampton Inn Rutland

Hampton Inn Rutland
Rutland
United States
Brent
P8,720
P9,592 total
includes taxes & fees
Nov 2 - Nov 3
Hampton Inn Rutland

18. Brandon Inn

Brandon Inn
Brandon
Canada
Sharon
P8,449
P9,294 total
includes taxes & fees
Nov 1 - Nov 2
Brandon Inn

19. On The River Inn

On The River Inn
West Woodstock
United Kingdom
Laura
P10,248
P12,654 total
includes taxes & fees
Nov 1 - Nov 2
On The River Inn

20. The Suites at Killington Center

The Suites at Killington Center
Killington
P10,880
P25,784 total
includes taxes & fees
Oct 5 - Oct 6
The Suites at Killington Center
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Stay near popular Pittsfield attractions

Pittsfield Town Hall

After visiting Pittsfield Town Hall, make a plan to see the other sights and activities in Pittsfield.
See properties

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

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

The Mountain Inn at Killington

The Mountain Inn at Killington

10/10 Excellent
"The staff went out of way to help and accommodate us. The chef was great"
Shirlee 3-night trip
Posted less than an hour ago
The Mountain Inn at Killington
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

10/10 Excellent
"Quiet, friendly staff"
Janine 1-night trip
Posted 3 hours ago
Days Inn by Wyndham Rutland/Killington Area
Mountain Sports Inn

Mountain Sports Inn

10/10 Excellent
"Super"
Sandra 1-night trip
Posted 3 hours ago
Mountain Sports Inn
Greenbrier Inn

Greenbrier Inn

10/10 Excellent
"If you are looking for a rustic, vintage, COZY, stay, then this place is for you. It was very comfortable and the owners were very kind and helpful. We thoroughly enjoyed our stay."
Erin 2-night trip
Posted 4 hours ago
Greenbrier Inn
Brandon Inn

Brandon Inn

10/10 Excellent
"It was great to stay in a historic building and see old artefacts exposed. Super interesting and cozy stay!"
Amelia 1-night trip
Posted 5 hours ago
Brandon Inn
The Jackson

The Jackson

10/10 Excellent
"This property is beautiful, peaceful, friendly, welcoming and far enough away from the green for a noiseless stay. The wine, cheese and bites that start your evening are lovely and gives you the opportunity to meet other guests if you choose. Ms. Walton, the host, was friendly, helpful and warm. She made me feel right at home. A magnificent place to stay in Woodstock Vermont"
susan 2-night trip
Posted 20 hours ago
The Jackson
Mountain Meadows Lodge

Mountain Meadows Lodge

10/10 Excellent
"This place is a gem!! The staff is awesome, the breakfast is delicious & homemade, and the views and amenities are great. We will 100% be back and stay longer!"
Lauren 1-night trip
Posted 1 day ago
Mountain Meadows Lodge
On The River Inn

On The River Inn

8/10 Good
"We had a river view suite. Trouble was you couldn’t see the river. There was to much undergrowth and trees, so you couldn’t tell there was a river there. The view from our balcony was beautiful, out onto the large lawn and a small pond. The TVs are old, so you couldn’t stream. Make sure you tell the front desk or put out your door hanger or you won’t get your room refreshed. The bar seemed open only during dinner hours. During our stay, one night the chief was “out” and they only served burgers. Breakfast was around $18, we never went down. Our room was large and bathroom adequate. It’s a 10 minute drive to town. It’a satisfactory hotel, but not worth the price."
Loxley 3-night trip
Posted 1 day ago
On The River Inn
My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

10/10 Excellent
"My family loved how clean was the room and how nice was the staff."
Regis 1-night trip
Posted 2 days ago
My Place Hotel-Randolph VT

More cheap stays in Pittsfield

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2440 Vermont 66 Randolph Center VT
P6,206
P6,764 total
Nov 1 - Nov 2
includes taxes & fees
9.4/10 Exceptional! (569 reviews)
My Place Hotel-Randolph VT
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

19 Allen St Rutland VT
P6,985
P7,683 total
Oct 25 - Oct 26
includes taxes & fees
8/10 Very Good! (1,004 reviews)
Comfort Inn Rutland - Killington
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

401 US-7 Rutland VT
P7,420
P8,162 total
Oct 22 - Oct 23
includes taxes & fees
7/10 Good! (1,016 reviews)
Days Inn by Wyndham Rutland/Killington Area
North Star Lodge and Resort

North Star Lodge and Resort

78 Weathervane Dr Killington VT
P8,684
P9,553 total
Oct 20 - Oct 21
includes taxes & fees
North Star Lodge and Resort
Mountain Sports Inn

Mountain Sports Inn

813 Killington Road Killington VT
P8,729
P9,602 total
Oct 12 - Oct 13
includes taxes & fees
8.8/10 Excellent! (1,005 reviews)
Mountain Sports Inn
The Mountain Inn at Killington

The Mountain Inn at Killington

47 Old Mill Rd Killington VT
P8,421
P9,727 total
Oct 19 - Oct 20
includes taxes & fees
9.2/10 Wonderful! (1,010 reviews)
The Mountain Inn at Killington

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 9.8 mi (15.8 km) from the heart of Pittsfield, The Mountain Inn at Killington is a top choice for your stay based on our traveler data. Other good choices for your stay in the area are Woodstock Inn & Resort 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?
The Mountain Inn at Killington: Hotel, 1-minute walk from Killington Resort. Offers daily, an outdoor pool, and free self parking. Woodstock Inn & Resort and Emrose Luxury Cabins 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 34 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, Pittsfield Town Hall, and Roger Clark Memorial Central Library. You'll also find Green Mountain National Golf Course and Gifford Woods State Park 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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