A lake surrounded by autumn-colored trees and a rocky shoreline.

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Check availability on Pittsfield Hotels with a Pool

Our top choices for Pittsfield hotels with a pool

Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers

Woodstock Inn & Resort

Woodstock Inn & Resort
4.5 star property
Woodstock
9.4 out of 10, Exceptional, (590 reviews)
  • cleanliness
    Experience year-round aquatic bliss at this alpine retreat with indoor and seasonal outdoor pools.
The price is NT$17,994
NT$21,209 total
includes taxes & fees
Jul 26 - Jul 27
Woodstock Inn & Resort
Indoor pool, open 8:00 AM to 10:00 PM, sun loungers

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1,008 reviews)
  • cleanliness
    Splash into bliss with an indoor pool, hot tub, and children's splash area amid scenic views.
The price is NT$7,920
NT$9,420 total
includes taxes & fees
Jul 26 - Jul 27
On The River 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.
The price is NT$7,419
NT$8,087 total
includes taxes & fees
Jul 13 - Jul 14
Echo Lake Inn
Outdoor pool

Killington Grand Hotel

Killington Grand Hotel
3.5 star property
Base Area
9.0 out of 10, Wonderful, (214 reviews)
  • cleanliness
    Ski slope to steamy soaks: heated outdoor pool and hot tubs deliver mountain views after your slope adventures.
The price is NT$7,474
NT$8,768 total
includes taxes & fees
Jul 14 - Jul 15
Killington Grand Hotel
Indoor pool

Mountain Green

Mountain Green
2.0 star property
Killington
7.2 out of 10, Good, (28 reviews)
  • cleanliness
    Splash into mountain adventures at this condo resort with indoor pool and cozy firepit area.
The price is NT$2,630
NT$7,639 total
includes taxes & fees
Jul 24 - Jul 25
Mountain Green
Exterior

North Star Lodge and Resort

North Star Lodge and Resort
2.0 star property
Killington
8.8 out of 10, Excellent, (1,004 reviews)
  • cleanliness
    Refreshing heated outdoor pool at Killington resort with sauna and fitness center complements ski adventures.
The price is NT$3,983
NT$4,382 total
includes taxes & fees
Jul 13 - Jul 14
North Star Lodge and Resort
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, (1,012 reviews)
  • cleanliness
    Splash into alpine bliss at this mountain inn's heated outdoor pool with scenic resort views.
The price is NT$4,317
NT$4,986 total
includes taxes & fees
Jul 19 - Jul 20
The Mountain Inn at Killington
Lobby

Best Western Inn & Suites Rutland-Killington

Best Western Inn & Suites Rutland-Killington
2.5 star property
Rutland
8.8 out of 10, Excellent, (1,000 reviews)
  • cleanliness
    Outdoor pool oasis for summer stays near slopes, with year-round adventures waiting just outside your door.
The price is NT$4,867
NT$5,354 total
includes taxes & fees
Jul 15 - Jul 16
Best Western Inn & Suites Rutland-Killington
Indoor pool

Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area
2.5 star property
Rutland
6.8 out of 10, (1,003 reviews)
  • cleanliness
    Dive into relaxation with a warm indoor pool escape at this cozy ski-friendly hotel.
The price is NT$4,027
NT$4,430 total
includes taxes & fees
Jul 13 - Jul 14
Days Inn by Wyndham Rutland/Killington Area
Indoor pool

Hampton Inn Rutland

Hampton Inn Rutland
2.5 star property
Rutland
9.0 out of 10, Wonderful, (1,008 reviews)
  • cleanliness
    Splash into family fun with an indoor pool sanctuary at this hotel where winter adventures meet waterside bliss.
The price is NT$4,286
NT$4,715 total
includes taxes & fees
Jul 26 - Jul 27
Hampton Inn Rutland
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

Hampton Inn Rutland

Hampton Inn Rutland

10/10 Excellent
"Staff was very friendly and helpful"
Wendy 1-night trip
Posted 3 hours ago
Hampton Inn Rutland

Frequently asked questions

What are some accommodations with pools in Pittsfield?
Killington Mountain Lodge, Tapestry Collection by Hilton: Provides 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: Offers a children's pool, an indoor pool, and a sauna. On The River Inn: Provides continental, an indoor pool, and free self parking. My Place Hotel-Randolph VT: 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 into account the local weather in Pittsfield can help you maximize your time at the pool during your trip. The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 23°F. The snowiest months in Pittsfield are January, March, February, and December, with each month seeing an average of 10 inches of snowfall.