Hotels with Pool & Resorts in Pittsfield from NZ$209

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Our top choices for Pittsfield hotels with a pool

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1004)
"Brilliant stay"
United States
Enrico
On The River Inn

Greenbrier Inn

Greenbrier Inn
2.0 star property
Killington
9.4 out of 10, Exceptional, (649)
"The staff were very welcoming, and helpful. Wonderful place to stay. "
United States
KRISTA
Greenbrier Inn

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington
2.5 star property
Rutland
8.0 out of 10, Very good, (1005)
"Clean rooms and polite workers. Try to stay there every time we go to Vermont."
United States
Michael
The price is NZ$273
includes taxes & fees
4 Jan - 5 Jan 2026
Comfort Inn Rutland - Killington

Hampton Inn Rutland

Hampton Inn Rutland
2.5 star property
Rutland
9.0 out of 10, Wonderful, (976)
"Everything was clean and the staff responsive and friendly. I wish the offerings at breakfast were more substantial. "
United States
Lesley
The price is NZ$299
includes taxes & fees
7 Jan - 8 Jan 2026
Hampton Inn Rutland

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

Brandon Inn

Brandon Inn
3.0 star property
Brandon
8.8 out of 10, Excellent, (569)
"Enjoyed our stay at the Brandon Inn very much!"
United States
Lesley
The price is NZ$209
includes taxes & fees
5 Jan - 6 Jan 2026
Brandon Inn

Summit Lodge

Summit Lodge
3.0 star property
Killington
8.6 out of 10, Excellent, (402)
"Good location and close to ski area. Good free breakfast makes stay nicer. Staff are nice. "
United States
RAYMOND
The price is NZ$329
includes taxes & fees
27 Jan - 28 Jan 2026
Summit Lodge

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 NZ$682
includes taxes & fees
19 Jan - 20 Jan 2026
Woodstock Inn & Resort

Best Western Inn & Suites Rutland-Killington

Best Western Inn & Suites Rutland-Killington
2.5 star property
Rutland
8.8 out of 10, Excellent, (1000)
"Great front desk staff. Rooms were very comfortable. "
United States
JERILYN
The price is NZ$339
includes taxes & fees
27 Jan - 28 Jan 2026
Best Western Inn & Suites Rutland-Killington

Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.

Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.
2.0 star property
Killington
10.0 out of 10, Exceptional, (1)
"8 mins drive from ski lodge"
United States
YUXIANG
Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.
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.

Top Pittsfield Hotel Reviews

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.