Search Hotels with Pool in Pittsfield

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Check availability on Pittsfield Hotels with Pool

Tonight
26 Feb - 27 Feb
Tomorrow
27 Feb - 28 Feb
This weekend
27 Feb - 1 Mar
Next weekend
6 Mar - 8 Mar

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, (1,002 reviews)
  • cleanliness
    Splash into bliss with an indoor pool, hot tub, and children's splash area amid scenic views.
On The River Inn
Sauna, hot tub, steam room, body treatments, aromatherapy

Woodstock Inn & Resort

Woodstock Inn & Resort
4.5 star property
Woodstock
9.2 out of 10, Wonderful, (565 reviews)
  • cleanliness
    Experience year-round aquatic bliss at this alpine retreat with indoor and seasonal outdoor pools.
The price is ฿9,602
฿11,929 total
includes taxes & fees
22 Mar - 23 Mar
Woodstock Inn & Resort
Property entrance

The Woodstocker B&B

The Woodstocker B&B
4.0 star property
Woodstock
10.0 out of 10, Exceptional, (51 reviews)
The price is ฿8,275
฿9,103 total
includes taxes & fees
27 Mar - 28 Mar
The Woodstocker B&B
Reception

Grey Bonnet Inn

Grey Bonnet Inn
2.0 star property
Killington
8.0 out of 10, Very good, (73 reviews)
The price is ฿5,097
฿5,606 total
includes taxes & fees
2 Mar - 3 Mar
Grey Bonnet Inn
Outdoor pool

Echo Lake Inn

Echo Lake Inn
2.5 star property
Plymouth
8.6 out of 10, Excellent, (99 reviews)
  • cleanliness
    Outdoor tennis court meets poolside paradise at this charming bed and breakfast retreat.
The price is ฿9,057
฿9,872 total
includes taxes & fees
2 Mar - 3 Mar
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

The Mountain Inn at Killington

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"
Peng M 2-night trip
Posted 13 hours ago
The Mountain Inn at Killington

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.