Search Hotels with Pool in Pittsfield

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 Pool

Tonight
23 Dec - 24 Dec
Tomorrow
24 Dec - 25 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, (1002)
"Rearaurant staff was top notch. "
United States
Daniel
The price is Rp5.452.525
Rp6.612.990 total
includes taxes & fees
29 Dec - 30 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, (1000)
"Spotless room also very accommodating and friendly! Loved our short stay!"
United States
Candace
North Star Lodge and Resort
Interior entrance
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
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 Rp2.768.205
Rp3.045.027 total
includes taxes & fees
6 Jan - 7 Jan 2026
Hampton Inn Rutland
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, (1009)
"Clean rooms and polite workers. Try to stay there every time we go to Vermont."
United States
Michael
The price is Rp2.410.016
Rp2.651.019 total
includes taxes & fees
4 Jan - 5 Jan 2026
Comfort Inn Rutland - Killington
Outdoor pool, pool loungers
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 Rp2.006.529
Rp2.207.183 total
includes taxes & fees
28 Dec - 29 Dec
Brandon Inn
Indoor pool, seasonal outdoor pool, pool umbrellas, pool loungers
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 Rp5.351.863
Rp6.625.237 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 Rp4.303.300
Rp4.690.597 total
includes taxes & fees
25 Dec - 26 Dec
The Vermont Inn
2 outdoor pools, pool umbrellas, pool loungers
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 Rp2.914.165
Rp3.205.581 total
includes taxes & fees
6 Jan - 7 Jan 2026
Summit Lodge
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

The Mountain Top Inn & Resort

The Mountain Top Inn & Resort

10/10 Excellent
"Absolutely wonderful! The hotel and staff were great. We deeply appreciated the upgrade! No one wanted to leave. "
Wendy 1-night trip
Posted 1 month ago
The Mountain Top Inn & Resort

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: 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.