Pittsfield Hotels with Swimming Pool

Start date: Check-in selected.
To Date
End date: Check-out

  • 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 Swimming Pools

Tonight
9 Jan - 10 Jan
Tomorrow
10 Jan - 11 Jan
This weekend
9 Jan - 11 Jan
Next weekend
16 Jan - 18 Jan

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

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1,006 reviews)
"Brilliant stay"
United States
Enrico
On The River Inn
Indoor pool
Hampton Inn Rutland

Hampton Inn Rutland

Hampton Inn Rutland
2.5 star property
Rutland
9.0 out of 10, Wonderful, (982 reviews)
"clean, quiet, warm room. Comfortable beds."
United States
Margaret
The price is RM615
RM676 total
includes taxes & fees
8 Feb - 9 Feb
Hampton Inn Rutland
32-inch flat-screen TV with cable channels, TV
Greenbrier Inn

Greenbrier Inn

Greenbrier Inn
2.0 star property
Killington
9.4 out of 10, Exceptional, (652 reviews)
"Great location near the mountain, very cozy."
United States
Raphael
Greenbrier Inn
Outdoor pool, a heated pool, open 10:00 AM to 10:00 PM, pool umbrellas
North Star Lodge and Resort

North Star Lodge and Resort

North Star Lodge and Resort
2.0 star property
Killington
8.6 out of 10, Excellent, (1,001 reviews)
"Warm and cozy hotel."
United States
Tina
North Star Lodge and Resort
Indoor pool
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington
2.5 star property
Rutland
8.0 out of 10, Very good, (1,005 reviews)
"Rooms were clean and comfortable.."
United States
Nimisha
The price is RM571
RM628 total
includes taxes & fees
11 Jan - 12 Jan
Comfort Inn Rutland - Killington
Exterior
Brandon Inn

Brandon Inn

Brandon Inn
3.0 star property
Brandon
8.8 out of 10, Excellent, (575 reviews)
"Clean room and staff was wonderful upon check in "
United States
Kaitlyn
The price is RM487
RM535 total
includes taxes & fees
11 Jan - 12 Jan
Brandon Inn
Outdoor wedding area
Summit Lodge

Summit Lodge

Summit Lodge
3.0 star property
Killington
8.6 out of 10, Excellent, (406 reviews)
"Good location and close to ski area. Good free breakfast makes stay nicer. Staff are nice. "
United States
RAYMOND
The price is RM707
RM778 total
includes taxes & fees
11 Jan - 12 Jan
Summit Lodge
Outdoor pool, a heated pool
The Mountain Inn at Killington

The Mountain Inn at Killington

The Mountain Inn at Killington
2.5 star property
Killington
9.2 out of 10, Wonderful, (978 reviews)
"Great place to stay!"
United States
Stephen
The price is RM802
RM927 total
includes taxes & fees
11 Jan - 12 Jan
The Mountain Inn at Killington
Lobby
Best Western Inn & Suites Rutland-Killington

Best Western Inn & Suites Rutland-Killington

Best Western Inn & Suites Rutland-Killington
2.5 star property
Rutland
8.8 out of 10, Excellent, (1,001 reviews)
"Great front desk staff. Rooms were very comfortable. "
United States
JERILYN
The price is RM729
RM802 total
includes taxes & fees
19 Jan - 20 Jan
Best Western Inn & Suites Rutland-Killington
Seasonal outdoor pool, pool loungers
The Vermont Inn

The Vermont Inn

The Vermont Inn
3.0 star property
Rutland
9.2 out of 10, Wonderful, (415 reviews)
"Our room was clean and the bed was very comfortable. The Inn is for sale... which could explain the needed updates. I wish I could buy it! 🤗 We would stay here again. "
United States
Jodie
The price is RM1,044
RM1,138 total
includes taxes & fees
11 Jan - 12 Jan
The Vermont 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

Top Pittsfield Hotel Reviews

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

10/10 Excellent
"The room was clean and the staff were helpful. The breakfast set up was good with plenty of hot food as well as other options and ample seating for everyone. Would definitely stay here again for a ski trip. Easy 25 min drive to Killington"
Annika 1-night trip
Posted 3 days ago
Comfort Inn Rutland - Killington

Frequently asked questions

What are some accommodation options with pools in Pittsfield?
Comfort Inn Rutland - Killington: Features continental, an indoor pool and free self parking. Killington Mountain Lodge, Tapestry Collection by Hilton: Hotel, 1-minute walk from Killington Resort. Provides daily, an outdoor pool and free self parking. The Mountain Inn at Killington: Features a seasonal outdoor pool, an indoor pool and 4 restaurants. Woodstock Inn & Resort: Hotel located near Killington Resort. Offers a sauna, an outdoor pool and free self parking. North Star Lodge and Resort: Offers buffet, a seasonal outdoor pool and free self parking.
What is there to see and do in Pittsfield?
Explore places such as Killington Resort while you're in the area. The picturesque setting of Green Mountain National Forest showcases the area's natural beauty.
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.

Explore a world of travel with Expedia