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

Search Hotels with Pool in Pittsfield

  • 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

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, (1,008 reviews)
  • cleanliness
    Splash into bliss with an indoor pool, hot tub, and children's splash area amid scenic views.
The price is ฿8,623
฿10,218 total
includes taxes & fees
11 Aug - 12 Aug
On The River Inn
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 ฿4,433
฿4,877 total
includes taxes & fees
26 Jul - 27 Jul
Hampton Inn Rutland
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
Indoor pool

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington
2.5 star property
Rutland
8.2 out of 10, Very good, (1,007 reviews)
  • cleanliness
    Soak in pure relaxation at this mountain getaway, where the indoor pool beckons after exhilarating ski adventures nearby.
The price is ฿3,865
฿4,252 total
includes taxes & fees
26 Jul - 27 Jul
Comfort Inn Rutland - Killington
Seasonal outdoor pool, open 9:00 AM to 9:00 PM, pool umbrellas

The Mountain Top Inn & Resort

The Mountain Top Inn & Resort
3.5 star property
Chittenden
9.0 out of 10, Wonderful, (121 reviews)
  • cleanliness
    Lakeside resort oasis offers pool lounging with mountain vistas, after thrilling ski adventures.
The price is ฿10,820
฿11,794 total
includes taxes & fees
14 Jul - 15 Jul
The Mountain Top Inn & Resort
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
13 Jul - 14 Jul
North Star Lodge and Resort
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
15 Jul - 16 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 ฿4,165
฿4,581 total
includes taxes & fees
13 Jul - 14 Jul
Days Inn by Wyndham Rutland/Killington Area
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.
Woodstock Inn & Resort
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
13 Jul - 14 Jul
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.
View all properties

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 2 hours ago
Hampton Inn Rutland

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.