"Oh wow!! I would stay here again tomorrow! Beautiful property, restaurant has amazing food and convenient location. We stayed in the Long View Barn, the 60 mile view was even more spectacular than we imagined!"
"Oh wow!! I would stay here again tomorrow! Beautiful property, restaurant has amazing food and convenient location. We stayed in the Long View Barn, the 60 mile view was even more spectacular than we imagined!"
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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.
I've never wrote a review on any product or hotel until now and that is because the Trailside Inn deserves all the recognition it could get! To start, the owners Josh and Ann are fantastic.
We arrived Friday night after a long drive from Long Island - we were immediately greeted by Josh who welcomed us to the lodge and took the time to show us the best trails at Killington and offered advice on restaurants near by.
It was very cold Saturday so we didn't stay long at the mountain. When we...
I've never wrote a review on any product or hotel until now and that is because the Trailside Inn deserves all the recognition it could get! To start, the owners Josh and Ann are fantastic.
We arrived Friday night after a long drive from Long Island - we were immediately greeted by Josh who welcomed us to the lodge and took the time to show us the best trails at Killington and offered advice on restaurants near by.
It was very cold Saturday so we didn't stay long at the mountain. When we...
Nice place. Close to the mountain. Nice aesthetic quaint and homey feel but also clean new and well kept. Hotel restaurant is a bit mediocre but not too bad. Good service so far on my trip too.
Nice place. Close to the mountain. Nice aesthetic quaint and homey feel but also clean new and well kept. Hotel restaurant is a bit mediocre but not too bad. Good service so far on my trip too.
Timothy
Reviewed February 3, 2024Reviewed February 3, 2024
We got in late because we had an issue charging our electric car. The guy was so friendly and even ran an extension cord so we could charge our car.
The room was clean and so rustic I loved it. The jetted tub was amazing and relaxing.
Lastly the breakfast was delicious and we were told made from scratch! It was so good
Definitely would stay there again!
We got in late because we had an issue charging our electric car. The guy was so friendly and even ran an extension cord so we could charge our car.
The room was clean and so rustic I loved it. The jetted tub was amazing and relaxing.
Lastly the breakfast was delicious and we were told made from scratch! It was so good
Definitely would stay there again!
Enjoyed my late season short stay here. Nice to have a tuning room with a platform. Close to K-1, closer to Ramshead and Snowshed. Right next to Rivershed restaurant which was nice. Late check in was easy. Bed was surprisingly comfortable. Continental breakfast is what you’d expect. All told, will come back if the price is right.
Enjoyed my late season short stay here. Nice to have a tuning room with a platform. Close to K-1, closer to Ramshead and Snowshed. Right next to Rivershed restaurant which was nice. Late check in was easy. Bed was surprisingly comfortable. Continental breakfast is what you’d expect. All told, will come back if the price is right.
We only stayed for two nights but could not have been happier! The staff was extremely helpful and friendly. The views and grounds are beautiful. We loved the beautiful, quiet setting. It rained one of the days we were at the hotel, but the staff was eager to give recommendations of places to go for other indoor activities! We were extremely pleased to visit the Mountain Top Inn and will definitely return for another stay!
We only stayed for two nights but could not have been happier! The staff was extremely helpful and friendly. The views and grounds are beautiful. We loved the beautiful, quiet setting. It rained one of the days we were at the hotel, but the staff was eager to give recommendations of places to go for other indoor activities! We were extremely pleased to visit the Mountain Top Inn and will definitely return for another stay!
I had been following the renovations of this hotel on social media. When I recently came through VT to Drop my child off at summer camp, I decided to give Apres Inn a try. Everything was very clean, very comfortable, check-in was a breeze. Definitely will be back on subsequent trips.
I had been following the renovations of this hotel on social media. When I recently came through VT to Drop my child off at summer camp, I decided to give Apres Inn a try. Everything was very clean, very comfortable, check-in was a breeze. Definitely will be back on subsequent trips.
I stayed in the "Spring Room" this visit. It was spacious, near the coffee station and had a relaxed yet beautiful decor.
A breakfast of fresh fruit, juice, coffee, muffin, omelet, bacon and home fries was served by a lovely hostess.
A+ !!!
I stayed in the "Spring Room" this visit. It was spacious, near the coffee station and had a relaxed yet beautiful decor.
A breakfast of fresh fruit, juice, coffee, muffin, omelet, bacon and home fries was served by a lovely hostess.
A+ !!!
Karen
Reviewed September 3, 2017Reviewed September 3, 2017
The pictures do not show how beautiful this property actually is. Looks 100 times better in person. They have a restaurant which is also very good. You don’t need to go anywhere else. The pool is a vibe after a long day of snowboarding. Recommend it 10/10. I will definitely go back again.
The pictures do not show how beautiful this property actually is. Looks 100 times better in person. They have a restaurant which is also very good. You don’t need to go anywhere else. The pool is a vibe after a long day of snowboarding. Recommend it 10/10. I will definitely go back again.
Ayleen
Reviewed February 12, 2024Reviewed February 12, 2024
We were extremely impressed with the Sleep Woodstock Motel! If you get the chance- you need to book this place! Rooms were spacious and super clean, and the bed was extremely comfortable. Room had a fully stocked coffee bar; bathroom had plenty of towels, shampoo, conditioner, and lotion. Each room also has a retro mini fridge with a freezer, microwave, and coffeemaker. There is also a small eating area inside the room, and a table and chairs to sit outside your room on the patio. The room...
We were extremely impressed with the Sleep Woodstock Motel! If you get the chance- you need to book this place! Rooms were spacious and super clean, and the bed was extremely comfortable. Room had a fully stocked coffee bar; bathroom had plenty of towels, shampoo, conditioner, and lotion. Each room also has a retro mini fridge with a freezer, microwave, and coffeemaker. There is also a small eating area inside the room, and a table and chairs to sit outside your room on the patio. The room...
Staying there was like traveling on time and we were avle to learn about the history of the original house and famous bridge in front. The room was extremely clean, comfortable and cozy. The staff very responsive and kind. Breakfast served was delicious and fresh.
Staying there was like traveling on time and we were avle to learn about the history of the original house and famous bridge in front. The room was extremely clean, comfortable and cozy. The staff very responsive and kind. Breakfast served was delicious and fresh.
Jesus
Reviewed October 22, 2026Reviewed October 22, 2026
Mike at the front desk was phenomenal! So helpful, friendly, and funny.
We accidentally left a dress hanging in the closet of our room and he sent it to us with no problem. He was really great!
Mike at the front desk was phenomenal! So helpful, friendly, and funny.
We accidentally left a dress hanging in the closet of our room and he sent it to us with no problem. He was really great!
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.
*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.
Calendar Month
Temperature
Precipitation
Cloudiness
Occupancy
Pricing
January
18.0°F (-7.8°C)
Light Rain
Mostly Cloudy
Average
Average
February
20.1°F (-6.6°C)
Light Rain
Mostly Cloudy
Average
Slightly High
March
28.4°F (-2.0°C)
Light Rain
Mostly Cloudy
Average
Average
April
40.6°F (4.8°C)
Light Rain
Mostly Cloudy
Average
Slightly Low
May
54.1°F (12.3°C)
Light Rain
Mostly Sunny
Slightly Low
Slightly Low
June
61.5°F (16.4°C)
Light Rain
Mostly Sunny
Average
Average
July
67.5°F (19.7°C)
Light Rain
Mostly Sunny
Slightly High
Average
August
65.7°F (18.7°C)
Light Rain
Mostly Sunny
Slightly High
Average
September
58.6°F (14.8°C)
Light Rain
Mostly Sunny
Slightly High
Average
October
46.9°F (8.3°C)
Light Rain
Mostly Cloudy
Average
Slightly High
November
34.3°F (1.3°C)
Light Rain
Mostly Cloudy
Slightly Low
Slightly Low
December
25.3°F (-3.7°C)
Light Rain
Mostly Cloudy
Slightly Low
Slightly 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
What's the top vacation rental in Pittsfield?
PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.: You might like this vacation home rental near Pittsfield. It is located in a rural location and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games. 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?
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.
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.