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

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Check availability on Pittsfield Hotels with Pool

Tonight
26 Aug - 27 Aug
Tomorrow
27 Aug - 28 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sept - 6 Sept

Our top choices for Pittsfield hotels with a pool

A multi-story building with a pool and a covered patio area.
A snow-covered road with a sign reading 'Welcome to Killington.'
A bar area with a star sign, bicycles, and a patterned carpet.
A spacious living room with a fireplace, leather sofas, a wooden coffee table, and a view of the outdoors.

1. North Star Lodge and Resort

North Star Lodge and Resort
Killington
  • Refreshing heated outdoor pool at Killington resort with sauna and fitness centre complements ski adventures.
Rp2.105.255
Rp2.315.780 total
includes taxes & fees
8 Sept - 9 Sept
North Star Lodge and Resort
A swimming pool surrounded by snow, with a building in the background.
A hotel room with two beds, a wooden headboard, a desk, and a window with a view of greenery.
A lobby with a stone wall, wooden staircase, and a reception desk.
A modern bathroom with a large bathtub, a glass-enclosed shower, and a toilet.

2. The Mountain Inn at Killington

The Mountain Inn at Killington
Killington
  • Splash into alpine bliss at this mountain inn's heated outdoor pool with scenic resort views.
Rp2.216.897
Rp2.560.685 total
includes taxes & fees
27 Aug - 28 Aug
The Mountain Inn at Killington
A swimming pool with a modern design, surrounded by a fenced patio area with outdoor seating.
A lodge with a snow-covered roof, a ski lift, and a mountainous backdrop.
A spacious living room with a wooden dining area, a fireplace, and a large TV.
A snow-covered residential area with multi-story buildings, a ski slope in the background, and a clear sky.

3. Mountain Green

Mountain Green
Killington
  • Splash into mountain adventures at this condo resort with indoor pool and cosy firepit area.
Rp1.383.124
Rp4.124.482 total
includes taxes & fees
31 Aug - 1 Sept
Mountain Green
A pool area with a wooden building, outdoor seating, and umbrellas.
A lodge with a fire pit, outdoor seating, and a covered area with string lights.
A large, two-story log cabin with a stone foundation, multiple windows, and a balcony.
A spacious living room with a stone fireplace, wooden ceiling beams, and a cozy seating area.

4. The Mountain Top Inn & Resort

The Mountain Top Inn & Resort
Chittenden
  • Lakeside resort oasis offers pool lounging with mountain vistas, after thrilling ski adventures.
Rp5.759.325
Rp6.277.664 total
includes taxes & fees
8 Sept - 9 Sept
The Mountain Top Inn & Resort
An indoor swimming pool with clear blue water, surrounded by white tiles and blue pillars.
A brick building with a sign reading 'Southside Steakhouse' and the number '170' above the entrance.
A modern bathroom with a large mirror, dual sinks, a glass shower enclosure, and neatly folded towels on shelves.
A modern hotel lobby with a blue sofa, a round coffee table, and abstract art on the walls.

5. Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington
Rutland
  • Soak in pure relaxation at this mountain getaway, where the indoor pool beckons after exhilarating ski adventures nearby.
Rp2.362.032
Rp2.598.235 total
includes taxes & fees
30 Aug - 31 Aug
Comfort Inn Rutland - Killington
An indoor swimming pool with clear glass walls, a wooden ceiling, and a tiled floor.
A modern lounge area with orange upholstered chairs, a fireplace, and large windows offering a view of autumn trees.
A covered outdoor area with a wooden ceiling, potted plants, and a bench.
A modern interior with a wooden counter, seating area, and large windows.

6. Hampton Inn Rutland

Hampton Inn Rutland
Rutland
  • Splash into family fun with an indoor pool sanctuary at this hotel where winter adventures meet waterside bliss.
Rp2.528.432
Rp2.781.274 total
includes taxes & fees
7 Sept - 8 Sept
Hampton Inn Rutland
A spacious indoor area with a large dining table, several chairs, and a sofa. There is a glass door leading outside, and the room has a wooden ceiling structure.
A Best Western Inn & Suites with a well-maintained lawn, a parking area, and a building with a porch.
A modern hotel lobby with a dining area, stone wall, and a view of the outside.
A kitchen with wooden cabinets, a stainless steel refrigerator, a stove, and two bar stools.

7. Best Western Inn & Suites Rutland-Killington

Best Western Inn & Suites Rutland-Killington
Rutland
  • Outdoor pool oasis for summer stays near slopes, with year-round adventures waiting just outside your door.
Rp3.172.059
Rp3.489.266 total
includes taxes & fees
27 Aug - 28 Aug
Best Western Inn & Suites Rutland-Killington
A large indoor swimming pool with clear blue tiles, sunlit by large windows, and equipped with lounge chairs and a ceiling fan.
A spacious living room with a chandelier, multiple armchairs, a coffee table, and a rug.
A two-story house with a balcony, surrounded by lush greenery and a pond.
A spacious living room with a large American flag, a fireplace, and a chandelier.

8. On The River Inn

On The River Inn
West Woodstock
  • Splash into bliss with an indoor pool, hot tub, and children's splash area amid scenic views.
Rp4.060.944
Rp4.856.794 total
includes taxes & fees
8 Sept - 9 Sept
On The River Inn
View all properties

Choose what matters most at hotels with a pool in Pittsfield

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Pittsfield Hotel Reviews

Hampton Inn Rutland

Hampton Inn Rutland

10/10 Excellent
"Excellent location and delicious breakfast! Friendly staff"
Hiram 2-night trip
Posted 14 hours ago
Hampton Inn Rutland
The Mountain Inn at Killington

The Mountain Inn at Killington

10/10 Excellent
"Such a great experience and stay. We checked in as guests and left as family. The rooms were clean and comfortable, the location perfect, and the staff beyond friendly and helpful. Will definitely be returning."
Denise 1-night trip
Posted 17 hours ago
The Mountain Inn at Killington
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

8/10 Good
"Food was shocking ....."
DIARMUID 1-night trip
Posted 2 days ago
Killington Mountain Lodge, Tapestry Collection by Hilton
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

8/10 Good
"Enjoyed my stay. Felt safe."
Tracy 3-night trip
Posted 3 days ago
Comfort Inn Rutland - Killington
Woodstock Inn & Resort

Woodstock Inn & Resort

10/10 Excellent
"Amazing! Will visit again."
Leah 4-night trip
Posted 3 weeks ago
Woodstock Inn & Resort

Frequently asked questions

What are some accommodation options with pools in Pittsfield?
Woodstock Inn & Resort: Offers a seasonal outdoor pool, an indoor pool and 4 restaurants. The Mountain Inn at Killington: Hotel, 1-minute walk from Killington Resort. Provides daily, an outdoor pool and free self parking. Killington Mountain Lodge, Tapestry Collection by Hilton: Offers continental, an indoor pool and free self parking. Comfort Inn Rutland - Killington: Features 8 hot tubs, a seasonal outdoor pool and a sauna. Emrose Luxury Cabins: Provides a children's pool, an indoor pool and a sauna.
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.

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