Search Hotels with Pool in Pittsfield

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Check availability on Pittsfield Hotels with Pool

This weekend
29 May - 31 May
Next weekend
5 Jun - 7 Jun

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

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1,003 reviews)
  • cleanliness
    Splash into bliss with an indoor pool, hot tub, and children's splash area amid scenic views.
"game room, pool, smores at the firepit were all great."
United States
Brendan
The price is Rp3.152.222
Rp4.118.205 total
includes taxes & fees
21 Jun - 22 Jun
On The River Inn
Outdoor pool, a heated pool

The Mountain Inn at Killington

The Mountain Inn at Killington
2.5 star property
Killington
9.2 out of 10, Wonderful, (1,002 reviews)
  • cleanliness
    Splash into alpine bliss at this mountain inn's heated outdoor pool with scenic resort views.
"Loved the outside heated pool!"
United States
Gergana
The price is Rp2.379.470
Rp2.748.368 total
includes taxes & fees
28 May - 29 May
The Mountain Inn at Killington
Outdoor pool, a heated pool, open 10:00 AM to 10:00 PM, pool umbrellas

North Star Lodge and Resort

North Star Lodge and Resort
2.0 star property
Killington
8.8 out of 10, Excellent, (1,000 reviews)
  • cleanliness
    Refreshing heated outdoor pool at Killington resort with sauna and fitness centre complements ski adventures.
"Room and bathroom was clean, bed was comfortable, and the heated pool with a view of the mountain was a huge plus after a long day of skiing"
United States
William
The price is Rp2.355.516
Rp2.591.156 total
includes taxes & fees
28 May - 29 May
North Star Lodge and Resort
Indoor pool

Hampton Inn Rutland

Hampton Inn Rutland
2.5 star property
Rutland
9.0 out of 10, Wonderful, (1,005 reviews)
  • cleanliness
    Splash into family fun with an indoor pool sanctuary at this hotel where winter adventures meet waterside bliss.
"Has a pool the kids enjoy"
United States
eric
The price is Rp2.548.926
Rp2.803.907 total
includes taxes & fees
14 Jun - 15 Jun
Hampton Inn Rutland
Exterior

Brandon Inn

Brandon Inn
3.0 star property
Brandon
8.8 out of 10, Excellent, (636 reviews)
  • cleanliness
    Dive into a refreshing outdoor pool retreat at this historic hotel with loungers for sun-soaked relaxation.
"The pool and the patio is one of the very best I have ever swim in"
United States
Joan
The price is Rp2.487.467
Rp2.736.213 total
includes taxes & fees
8 Jun - 9 Jun
Brandon Inn
Outdoor pool

Echo Lake Inn

Echo Lake Inn
2.5 star property
Plymouth
8.6 out of 10, Excellent, (100 reviews)
  • cleanliness
    Outdoor tennis court meets poolside paradise at this charming bed and breakfast retreat.
"Charming place, the food was great, rooms clean, and service was excellent"
United States
Erik
The price is Rp4.083.591
Rp4.451.114 total
includes taxes & fees
27 May - 28 May
Echo Lake Inn
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.
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Choose what matters most at hotels with a pool in Pittsfield

Breakfast included
4 stars

Top Pittsfield Hotel Reviews

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."
Tracy 5-night trip
Posted 20 hours ago
Cortina Inn

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.