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

Search Hotels with Swimming Pool in Pittsfield

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Check availability on Pittsfield Hotels with Swimming Pool

Tonight
26 Oct - 27 Oct
Tomorrow
27 Oct - 28 Oct
This weekend
30 Oct - 1 Nov
Next weekend
6 Nov - 8 Nov

Our top choices for Pittsfield hotels with a pool

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 spacious living room with a stone fireplace, wooden ceiling beams, and a cozy seating area.
A spacious room with large windows, a stone wall, and a wooden ceiling.

1. The Mountain Top Inn & Resort

The Mountain Top Inn & Resort
Chittenden
  • Lakeside resort oasis offers pool lounging with mountain vistas, after thrilling ski adventures.
₹24,647
₹31,522 total
includes taxes & fees
9 Nov - 10 Nov
The Mountain Top Inn & Resort
A multi-story building with a pool and a covered patio area.
A bathroom with a large freestanding bathtub, a mirror, and a wooden vanity.
A snow-covered road with a sign reading 'Welcome to Killington.'
A bar area with a star sign, bicycles, and a patterned carpet.

2. 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.
₹11,215
₹12,336 total
includes taxes & fees
2 Nov - 3 Nov
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 building with a modern design, featuring large windows and a covered outdoor seating area.
A modern bathroom with a large bathtub, a glass-enclosed shower, and a toilet.

3. 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.
₹11,762
₹13,584 total
includes taxes & fees
29 Oct - 30 Oct
The Mountain Inn at Killington
A pool area with lounge chairs and a view of a mountainous landscape.
A sign for the Grand Hotel Spa in Killington, Vermont, with a mountain backdrop.
A reception desk with a stone wall backdrop and wooden accents, a person with a suitcase, and a television screen above the desk.
A spacious lobby with leather seating, a stone fireplace, and a staircase leading to an upper level.

4. Killington Grand Hotel

Killington Grand Hotel
Base Area
  • Ski slope to steamy soaks: heated outdoor pool and hot tubs deliver mountain views after your slope adventures.
₹22,046
₹25,860 total
includes taxes & fees
30 Oct - 31 Oct
Killington Grand Hotel
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.

5. 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.
₹15,296
₹16,826 total
includes taxes & fees
2 Nov - 3 Nov
Best Western Inn & Suites Rutland-Killington
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 hotel lobby with a reception desk, seating area, and a coffee table with a fruit basket.
A modern bathroom with a large mirror, dual sinks, a glass shower enclosure, and neatly folded towels on shelves.

6. 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.
₹11,766
₹12,943 total
includes taxes & fees
15 Nov - 16 Nov
Comfort Inn Rutland - Killington
An indoor swimming pool with a wooden ceiling, large windows, and lounge chairs.
A covered outdoor area with a wooden ceiling, potted plants, and a bench.
A hotel room with a bed, a TV, a fireplace, a desk, and a chair.
A modern interior with a wooden reception desk, seating area, and large windows.

7. 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.
₹12,831
₹14,115 total
includes taxes & fees
8 Nov - 9 Nov
Hampton Inn Rutland
A large house with a swimming pool, a fenced yard, and a well-lit entrance.
A long corridor with tables and chairs, large windows, and a ceiling fan.
Front of property
A paved patio with outdoor furniture, a decorative garden bed, and a white fence.

8. Brandon Inn

Brandon Inn
Brandon
  • Dive into a refreshing outdoor pool retreat at this historic hotel with loungers for sun-soaked relaxation.
₹11,879
₹13,067 total
includes taxes & fees
1 Nov - 2 Nov
Brandon Inn
An indoor swimming pool with a high ceiling, multiple ceiling fans, and a seating area with chairs and tables.
A spacious dining area with wooden tables and chairs, large windows offering a view of the outdoors, and a modern interior design with a wooden ceiling.
A spacious living area with a fireplace, leather sofas, and a dining area with wooden furniture.
A hotel room with two beds, a large beach mural on the wall, and a wooden floor.

9. Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area
Rutland
  • Dive into relaxation with a warm indoor pool escape at this cosy ski-friendly hotel.
₹11,217
₹12,339 total
includes taxes & fees
29 Oct - 30 Oct
Days Inn by Wyndham Rutland/Killington Area
A swimming pool with lounge chairs and umbrellas, surrounded by a white fence and tall trees.
A modern kitchen with wooden cabinets, stainless steel appliances, and a central island.
A modern bathroom with a dual sink vanity, a toilet, a glass shower enclosure, and a small shelf with towels.
A modern bedroom with a bed, a sofa, a wooden coffee table, a TV, and a window with a view.

10. The Suites at Killington Center

The Suites at Killington Center
Killington
₹21,576
₹44,621 total
includes taxes & fees
29 Oct - 30 Oct
The Suites at Killington Center
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

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

10/10 Excellent
"Beautiful property. Staff is very friendly and helpful"
Alicia 1-night trip
Posted 22 hours ago
Killington Mountain Lodge, Tapestry Collection by Hilton
On The River Inn

On The River Inn

10/10 Excellent
"Great place would stay again"
Joseph 2-night trip
Posted 23 hours ago
On The River Inn
Woodstock Inn & Resort

Woodstock Inn & Resort

10/10 Excellent
"Amazing venue for our wedding!"
Riley 2-night trip
Posted 23 hours ago
Woodstock Inn & Resort
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

8/10 Good
"This was a good hotel for a decent price."
Leila 1-night trip
Posted 3 days ago
Comfort Inn Rutland - Killington
North Star Lodge and Resort

North Star Lodge and Resort

8/10 Good
"It was a decent place to stay. We were bummed the pool wasn’t working but understood."
Kayla 1-night trip
Posted 3 days ago
North Star Lodge and Resort

Frequently asked questions

What are some accommodation options with pools in Pittsfield?
The Mountain Inn at Killington: Hotel, 1-minute walk from Killington Resort. Offers daily, an outdoor pool and free self parking. Woodstock Inn & Resort: Provides a seasonal outdoor pool, an indoor pool and 4 restaurants. Killington Mountain Lodge, Tapestry Collection by Hilton: Features 8 hot tubs, a seasonal outdoor pool and a sauna. The Jackson: Features a children's pool, an indoor pool and a sauna. Emrose Luxury Cabins: Offers a snack bar/deli, a seasonal outdoor pool and daily.
What is there to see and do in Pittsfield?
Surround yourself with nature at Green Mountain National Forest. Discover sights such as Pittsfield Town Hall and Roger Clark Memorial Central Library 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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