Top Hotels with Swimming Pools in Pittsfield | Expedia.com.sg

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Check availability on Pittsfield Hotels with Swimming Pools

Tonight

28 May - 29 May

Tomorrow

29 May - 30 May

This weekend

29 May - 31 May

Next weekend

Our top choices for Pittsfield hotels with a pool

Indoor pool, open 8:00 AM to 10:00 PM, pool loungers

On The River Inn

West Woodstock

Splash into bliss with an indoor pool, hot tub, and children's splash area amid scenic views.

includes taxes & fees

24 Jun - 25 Jun

Outdoor pool, a heated pool

The Mountain Inn at Killington

Killington

Splash into alpine bliss at this mountain inn's heated outdoor pool with scenic resort views.

includes taxes & fees

4 Jun - 5 Jun

Indoor pool

Hampton Inn Rutland

Rutland

Splash into family fun with an indoor pool sanctuary at this hotel where winter adventures meet waterside bliss.

includes taxes & fees

14 Jun - 15 Jun

View all properties

Choose what matters most at hotels with a pool in Pittsfield

Breakfast included

4 stars

Top Pittsfield Hotel Reviews

On The River Inn

On The River Inn

10/10 Excellent

"We had one of the apartments out back and it was really nice. The staff was very responsive and helpful. We had dinner at the restaurant and the food was very good and the waiter, Brian I think, was a very nice deadpan comedian. We enjoyed the hot tub too! The only thing we didn't appreciate was that it took about 10 minutes of running the water to get hot water for the sinks and showers. Not really a problem to wait, but it seems a waste of water."

Cortina Inn

Cortina Inn

2/10 Terrible

"I’m going to start out saying the room was very clean. It looked as though the staff had ran out to Walmart and bought new sheets, pillows and a blanket along with new towels. The bathroom was clean, no amenities, and the carpet had been freshly vacuumed. This is the first hotel I have ever looked for bedbugs. The lobby appeared to be an easy fifty years old with no updates and the hallways although very wide were dirty. They had not been vacuumed in a very long time. As I left the hotel in early evening a younger couple approached me and said someone had approached them and told them not to go to the far end of the lot because there were gang members in the corner. There were people in several rooms but no cars in the parking lot only mine and the young couples. I was very uncomfortable with the location of my room, it was at the very far end of a hallway and I believe I was the only reservation in that location. The elevator did work but for some reason when I asked to see the room the desk clerk had us walk down several hallways then up the stairs when the elevator would have been around the corner. Needless to say instead of staying for the original five nights I had booked I only stayed one night then moved on to a hotel that better represented itself. I believe I booked the Cortina through Hotels.com and am quite surprised they would recommend a hotel with such poor standards. The Cortina should be removed from the listings. My card has been credited."

The Mountain Inn at Killington

The Mountain Inn at Killington

10/10 Excellent

"We had a fantastic time at the Mountain Inn. I was there for a 100 mile race and the staff went above and beyond to ensure I had everything I needed to be successful. They even went to the trouble to make me my own breakfast to go! We will absolutely be back to see JP and Bodie!"

North Star Lodge and Resort

North Star Lodge and Resort

4/10 Poor

"Room wasn’t clean black mold in toilet. Furniture was worn. Beds were clean. Advertised having a restaurant and bar. Both were closed. The lock on the door was Not secure metal enforcement plate missing. Room should not have been rented. Ring an avid skier and frequent Killington I would NOT stay there again. Property needs a lot of work"

Frequently asked questions

What are some accommodation options with pools in Pittsfield?

Killington Mountain Lodge, Tapestry Collection by Hilton: Features continental, an indoor pool and free self parking. Comfort Inn Rutland - Killington: Offers a seasonal outdoor pool, an indoor pool and 4 restaurants. Woodstock Inn & Resort: Hotel located near Killington Resort. Features daily, an outdoor pool and free self parking. The Mountain Inn at Killington: Features a children's pool, an indoor pool and a sauna. The Shire Woodstock: Offers a snack bar/deli, a seasonal outdoor pool and daily.

What is there to see and do in Pittsfield?

Surround yourself with nature at Green Mountain National Forest. Discover sights such as Roger Clark Memorial Central Library and Pittsfield Town Hall during your stay.

When is the best time to book a hotel with a pool in Pittsfield?

Taking the local weather in Pittsfield into account can help you maximise your time at the pool during your trip. The hottest months are usually July and August, with an average temperature of 17°C, while the coldest months are January and February, with an average of -5°C. The snowiest months in Pittsfield are January, March, February and December, with each month seeing an average of 26 cm of snowfall.

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