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

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Check availability on Pittsfield Hotels with Pool

Our top choices for Pittsfield hotels with a pool

Indoor pool, seasonal outdoor pool, pool umbrellas, pool 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 ฿18,611
฿21,937 total
includes taxes & fees
26 Jul - 27 Jul
Woodstock Inn & Resort
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, (1,009 reviews)
  • cleanliness
    Splash into bliss with an indoor pool, hot tub, and children's splash area amid scenic views.
The price is ฿8,204
฿9,574 total
includes taxes & fees
20 Jul - 21 Jul
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 ฿7,674
฿8,364 total
includes taxes & fees
14 Jul - 15 Jul
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 ฿7,731
฿9,068 total
includes taxes & fees
14 Jul - 15 Jul
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 cosy firepit area.
The price is ฿2,599
฿7,749 total
includes taxes & fees
19 Jul - 20 Jul
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 centre complements ski adventures.
The price is ฿4,120
฿4,532 total
includes taxes & fees
16 Jul - 17 Jul
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 ฿4,465
฿5,157 total
includes taxes & fees
19 Jul - 20 Jul
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 ฿5,034
฿5,537 total
includes taxes & fees
14 Jul - 15 Jul
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 cosy ski-friendly hotel.
The price is ฿4,219
฿4,641 total
includes taxes & fees
21 Jul - 22 Jul
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, (1,009 reviews)
  • cleanliness
    Splash into family fun with an indoor pool sanctuary at this hotel where winter adventures meet waterside bliss.
The price is ฿4,861
฿5,348 total
includes taxes & fees
11 Aug - 12 Aug
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

Courtyard Middlebury

Courtyard Middlebury

10/10 Excellent
"Great convenient property. Clean and staff was pleasant."
Richard 1-night trip
Posted 2 hours ago
Courtyard Middlebury

Frequently asked questions

What are some accommodation options 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 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.