Search Hotels with Pool in Pittsfield

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Check availability on Pittsfield Hotels with Pool

Tonight
22 Dec - 23 Dec
Tomorrow
23 Dec - 24 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 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, (1001)
"This place was charming!! Enjoyed everything about it and so much to do right there in the inn."
United States
Ross
The price is ฿6,062
฿7,820 total
includes taxes & fees
23 Dec - 24 Dec
On The River 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, (1001)
"Spotless room also very accommodating and friendly! Loved our short stay!"
United States
Candace
North Star Lodge and Resort
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, (646)
"It was a very quaint inn in a gorgeous location."
United States
ELIZABETH
Greenbrier Inn
Outdoor wedding area
Summit Lodge

Summit Lodge

Summit Lodge
3.0 star property
Killington
8.6 out of 10, Excellent, (398)
"The staff was really great and helpful. There are a number of very cool public spaces to enjoy"
United States
George
The price is ฿5,456
฿6,001 total
includes taxes & fees
5 Jan - 6 Jan 2026
Summit Lodge
Indoor pool
Hampton Inn Rutland

Hampton Inn Rutland

Hampton Inn Rutland
2.5 star property
Rutland
9.0 out of 10, Wonderful, (972)
"Very clean, good location, and super helpful staff!"
United States
Sheryl
The price is ฿5,209
฿5,730 total
includes taxes & fees
6 Jan - 7 Jan 2026
Hampton Inn Rutland
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, (965)
"Great place to stay!"
United States
Stephen
The Mountain Inn at Killington
Exterior
Brandon Inn

Brandon Inn

Brandon Inn
3.0 star property
Brandon
8.8 out of 10, Excellent, (566)
"Enjoyed our stay at the Brandon Inn very much!"
United States
Lesley
The price is ฿3,756
฿4,132 total
includes taxes & fees
23 Dec - 24 Dec
Brandon Inn
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, (1007)
"Clean rooms and polite workers. Try to stay there every time we go to Vermont."
United States
Michael
The price is ฿4,512
฿4,963 total
includes taxes & fees
4 Jan - 5 Jan 2026
Comfort Inn Rutland - Killington
Sauna, hot tub, steam room, body treatments, aromatherapy
Woodstock Inn & Resort

Woodstock Inn & Resort

Woodstock Inn & Resort
4.5 star property
Woodstock
9.2 out of 10, Wonderful, (558)
"Luxurious and friendly resort! Loved it"
United States
Elizabeth
The price is ฿10,019
฿12,403 total
includes taxes & fees
19 Jan - 20 Jan 2026
Woodstock Inn & Resort
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)
"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 ฿8,056
฿8,781 total
includes taxes & fees
24 Dec - 25 Dec
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.
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Top Pittsfield Hotel Reviews

North Star Lodge and Resort

North Star Lodge and Resort

10/10 Excellent
"Recommend it nice and clean"
Yuriy 1-night trip
Posted 2 days ago
North Star Lodge and Resort
Greenbrier Inn

Greenbrier Inn

10/10 Excellent
"staff is courteous, friendly and accommodating. Room is clean, no frills but comfortable beds. Would go back! "
Jervin 1-night trip
Posted 3 weeks ago
Greenbrier Inn

Frequently asked questions

What are some accommodation options with pools in Pittsfield?
Killington Mountain Lodge, Tapestry Collection by Hilton: Hotel, 1-minute walk from Killington Resort. Offers daily, an outdoor pool and free self parking. The Mountain Inn at Killington: Provides a seasonal outdoor pool, an indoor pool and 4 restaurants. Woodstock Inn & Resort: Hotel located near Killington Resort. Features a sauna, an outdoor pool and free self parking. North Star Lodge and Resort: Offers continental, an indoor pool and free self parking. Comfort Inn Rutland - Killington: Provides 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.