The Best Hotels with a Pool in Pittsfield, VT from ₩219,689 in 2026

Q: What are some accommodations 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.

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Our top choices for Pittsfield hotels with a pool

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

On The River Inn

West Woodstock

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

₩366,459 total

includes taxes & fees

Jun 15 - Jun 16

The Mountain Inn at Killington

Killington

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

₩233,026 total

includes taxes & fees

Jun 8 - Jun 9

Echo Lake Inn

Plymouth

Outdoor tennis court meets poolside paradise at this charming bed and breakfast retreat.

₩377,974 total

includes taxes & fees

Jun 2 - Jun 3

Outdoor pool, a heated pool, open 10:00 AM to 10:00 PM, pool umbrellas

North Star Lodge and Resort

Killington

Refreshing heated outdoor pool at Killington resort with sauna and fitness center complements ski adventures.

₩219,689 total

includes taxes & fees

Jun 3 - Jun 4

Brandon Inn

Brandon

Dive into a refreshing outdoor pool retreat at this historic hotel with loungers for sun-soaked relaxation.

₩232,351 total

includes taxes & fees

Jun 2 - Jun 3

Hampton Inn Rutland

Rutland

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

₩237,736 total

includes taxes & fees

Jun 21 - Jun 22

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Choose what matters most at hotels with a pool in Pittsfield

Breakfast included

4 stars

Top Pittsfield Hotel Reviews

Hampton Inn Rutland

10/10 Excellent

"Breakfast was plentiful and kitchen area was very clean. Pool and fitness room was clean as well as our room."

Days Inn by Wyndham Rutland/Killington Area

4/10 Poor

"Room was clean but the neighbors we had were screaming and fighting the majority of the night making it to where we got absolutely no sleep. It was awful! Otherwise it was a good room and we were in close distance to the police academy where we were headed the next day."

North Star Lodge and Resort

10/10 Excellent

"Amazing hot pool, great staff, another marvelous stay very close to the mountain and plenty of other activities. Laundry room is clutch (coin operated machines, change available at front desk). The wife had an injury and wasn't able to navigate stairs all that well, the front desk was understanding and were kind enough to move our room to the main floor, requiring no stairs, while the elevator was being worked on. New ownership is busy making some upgrades and maintenance and hopefully the vibes will remain the same as we've loved for years!"