Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
Top Pittsfield Hotel Reviews
The Trailside Inn
The Trailside InnNorth Sherburne
10/10 Excellent
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...
Alyssa
Mountain Meadows Lodge
Mountain Meadows LodgeKillington
10/10 Excellent
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
Greenbrier Inn
Greenbrier InnKillington
10/10 Excellent
The breakfast was very nice with a large assortment of fruit, breads, muffins, cereal, cheese, yogurts.
The breakfast was very nice with a large assortment of fruit, breads, muffins, cereal, cheese, yogurts.
KEVIN
Après Inn Killington
Après Inn KillingtonKillington
10/10 Excellent
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.
Anonymous traveler
Mountain Sports Inn
Mountain Sports InnKillington
10/10 Excellent
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.
Julianne
Snowed Inn
Snowed InnKillington
10/10 Excellent
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!
Tammy
The Mountain Top Inn & Resort
The Mountain Top Inn & ResortChittenden
10/10 Excellent
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!
Anonymous traveler
The Mountain Inn at Killington
The Mountain Inn at KillingtonKillington
10/10 Excellent
ski trip, great location
ski trip, great location
Donna
North Star Lodge and Resort
North Star Lodge and ResortKillington
10/10 Excellent
The staff made check in a breeze. The king room is large, clean and comfortable. The extra convenience is the restaurant right next door!
The staff made check in a breeze. The king room is large, clean and comfortable. The extra convenience is the restaurant right next door!
Thayer
The Jackson
The JacksonWest Woodstock
10/10 Excellent
Fantastic bed and breakfast tucked away from all the hustle.
Fantastic bed and breakfast tucked away from all the hustle.
Tiffany
Sleep Woodstock Motel
Sleep Woodstock MotelWoodstock
10/10 Excellent
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...
John
On The River Inn
On The River InnWest Woodstock
10/10 Excellent
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
Green Trails Inn
Green Trails InnBrookfield
10/10 Excellent
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
Best Western Inn & Suites Rutland-Killington
Best Western Inn & Suites Rutland-KillingtonRutland
10/10 Excellent
Friendly,accommodating
Friendly,accommodating
Judie
Hampton Inn Rutland
Hampton Inn RutlandRutland
10/10 Excellent
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!
Anonymous traveler
Brandon Inn
Brandon InnBrandon
10/10 Excellent
Nice and clean place.
Staff were very friendly.
Nice and clean place.
Staff were very friendly.
Shahram
Inn at Neshobe River
Inn at Neshobe RiverBrandon
10/10 Excellent
Owners were very nice. The room and bathroom were very clean. Beautiful area of Vermont. Felt very safe staying here. Would recommend.
Owners were very nice. The room and bathroom were very clean. Beautiful area of Vermont. Felt very safe staying here. Would recommend.
Anonymous traveler
Lincoln Inn & Gallery
Lincoln Inn & GalleryWoodstock
10/10 Excellent
We had a wonderful stay at the Lincoln Inn. The property was very cute and historic, and the innkeeper was warm and welcoming.
We had a wonderful stay at the Lincoln Inn. The property was very cute and historic, and the innkeeper was warm and welcoming.
Jennifer
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?
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?
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 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 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.
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.