Pittsfield Hotel Guide - Hotels with Pool in Pittsfield, Vermont

Q: What are some accommodation options with pools in Pittsfield?

Comfort Inn Rutland - Killington : Offers continental, an indoor pool and free self parking. Killington Mountain Lodge, Tapestry Collection by Hilton : Offers buffet, a seasonal outdoor pool and free self parking. My Place Hotel-Randolph VT : Features a seasonal outdoor pool, an indoor pool and 4 restaurants. Best Western Inn & Suites Rutland-Killington : Hotel located near Killington Resort. Offers a sauna, an outdoor pool and free self parking. Woodstock Inn & Resort : Inn located near Killington Resort. Provides full, 2 outdoor swimming pools and free self parking.

Where to?

Dates

March 2026

April 2026

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check availability on Pittsfield Hotels with Pool

Tonight

Tomorrow

This weekend

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.

Sauna, hot tub, steam room, body treatments, aromatherapy

Woodstock Inn & Resort

Woodstock

Experience year-round aquatic bliss at this alpine retreat with indoor and seasonal outdoor pools.

includes taxes & fees

22 Mar - 23 Mar

The Woodstocker B&B

Woodstock

includes taxes & fees

27 Mar - 28 Mar

The Suites at Killington Center

Killington

includes taxes & fees

4 Mar - 5 Mar

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 centre complements ski adventures.

Comfortable mountain gem with pool, mountain views, & indoor parking space

Killington

includes taxes & fees

3 Mar - 4 Mar

Grey Bonnet Inn

Killington

includes taxes & fees

2 Apr - 3 Apr

Echo Lake Inn

Plymouth

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

includes taxes & fees

1 Apr - 2 Apr

View all properties

Choose what matters most at hotels with a pool in Pittsfield

Breakfast included

4 stars

Top Pittsfield Hotel Reviews

Best Western Inn & Suites Rutland-Killington

10/10 Excellent

"It was a great stay. Clean, spacious, and a great breakfast too. Would definitely stay there again. "

The Mountain Inn at Killington

10/10 Excellent

"We lover our stay at The Mountain Inn at Killington. It's close enough to walk to main Lift Snowshed about 7-10 minutes walk but they have free shuttle service upon calling for any pickups. If you own EV car, they got charging station about 3 minutes walk away on level 2 charger but is not free, 30 cents per kw for tesla but more for other EV at 50 cents I believe. Their continental breakfast is great but no eggs or proteins however it is best with begal and danish and cereal, Oatmeal and COFFEE. Oh free water bottle so you can bring one to the slopes too. I would stay there again and again. They got heated outdoor small pool for relaxing after long day or awesome skiing/boarding. The only negative is their restaurant, not bad but expensive dinning option. pretty costly for good but not great food. Service was super of course"

Frequently asked questions

What are some accommodation options with pools in Pittsfield?

Comfort Inn Rutland - Killington: Offers continental, an indoor pool and free self parking. Killington Mountain Lodge, Tapestry Collection by Hilton: Offers buffet, a seasonal outdoor pool and free self parking. My Place Hotel-Randolph VT: Features a seasonal outdoor pool, an indoor pool and 4 restaurants. Best Western Inn & Suites Rutland-Killington: Hotel located near Killington Resort. Offers a sauna, an outdoor pool and free self parking. Woodstock Inn & Resort: Inn located near Killington Resort. Provides full, 2 outdoor swimming pools and free self parking.

What is there to see and do in Pittsfield?

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

Room 1

Change your mind

Treat yourself

Be picky

Check availability on Pittsfield Hotels with Pool

Our top choices for Pittsfield hotels with a pool