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

Pittsfield Hotel Guide - Hotels with Pool in Pittsfield, Vermont

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Check availability on Pittsfield Hotels with Pool

Tonight
31 Aug - 1 Sept
Tomorrow
1 Sept - 2 Sept
This weekend
4 Sept - 6 Sept
Next weekend
11 Sept - 13 Sept

Our top choices for Pittsfield hotels with a pool

A multi-story building with a pool and a covered patio area.
A spacious living room with a fireplace, leather sofas, a wooden coffee table, and a view of the outdoors.
A bathroom with a large freestanding bathtub, a mirror, and a wooden vanity.
A snow-covered road with a sign reading 'Welcome to Killington.'

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.
€113
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 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.
A hotel room with two beds, a wooden headboard, a desk, and a window with a view of greenery.

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.
€125
includes taxes & fees
1 Sept - 2 Sept
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 cozy living room with a fireplace, a comfortable sofa, a wooden coffee table, and a television mounted on the wall.

3. Mountain Green

Mountain Green
Killington
  • Splash into mountain adventures at this condo resort with indoor pool and cosy firepit area.
€201
includes taxes & fees
1 Sept - 2 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 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.

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.
€306
includes taxes & fees
1 Sept - 2 Sept
The Mountain Top Inn & Resort
A rectangular swimming pool with a metal ladder, surrounded by a white fence, and a wooden building with a green door in the background.
A room with large windows, a fireplace, and wicker chairs.
A sign for Cedarbrook with a well-maintained garden and trees in the background.
A red building with a bear logo, a stone pathway, and neatly trimmed bushes.

5. Deluxe One bedroom Queen Suite on the 2nd floor with outdoor heated pool 209

Deluxe One bedroom Queen Suite on the 2nd floor with outdoor heated pool 209
Killington
€148
includes taxes & fees
1 Sept - 2 Sept
Deluxe One bedroom Queen Suite on the 2nd floor with outdoor heated pool 209
A rectangular outdoor swimming pool with a clear blue water surface, surrounded by a white fence, and a wooden building with a green door to the right.
A red building with a bear logo, a stone pathway, and neatly trimmed bushes.
A sign for Cedarbrook with a well-maintained garden and trees in the background.
A room with large windows, a fireplace, and wicker chairs.

6. Two Queen Bed Standard Hotel Room w/outdoor heated pool 204

Two Queen Bed Standard Hotel Room w/outdoor heated pool 204
Killington
€125
includes taxes & fees
4 Sept - 5 Sept
Two Queen Bed Standard Hotel Room w/outdoor heated pool 204
An indoor swimming pool with clear glass walls, a wooden ceiling, and a tiled floor.
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 counter, 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.
€128
includes taxes & fees
7 Sept - 8 Sept
Hampton Inn Rutland
A swimming pool with lounge chairs and umbrellas, surrounded by a white fence and trees.
A modern bedroom with a large bed, a ceiling fan, a bedside table, a lamp, and a window with curtains.
A room with a blue wall, a framed picture, a potted plant, a lamp, and a red telephone booth.
An aerial view of a residential area with houses, a swimming pool, and a parking lot.

8. 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.
Killington
Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.
An indoor swimming pool with clear blue water, surrounded by white tiles and blue pillars.
A modern hotel lobby with a blue sofa, a round coffee table, and abstract art on the walls.
A hotel lobby with a reception desk, seating area, and a coffee table with a fruit basket.
A brick building with a sign reading 'Southside Steakhouse' and the number '170' above the entrance.

9. 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.
€130
includes taxes & fees
6 Sept - 7 Sept
Comfort Inn Rutland - Killington
An indoor swimming pool with a high ceiling, multiple ceiling fans, and a seating area with chairs and tables.
A hotel room with two beds, a large beach mural on the wall, and a wooden floor.
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.

10. 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.
€124
includes taxes & fees
7 Sept - 8 Sept
Days Inn by Wyndham Rutland/Killington Area
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Choose what matters most at hotels with a pool in Pittsfield

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Pittsfield Hotel Reviews

Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

8/10 Good
"Room was very spacious"
Shannon 1-night trip
Posted 4 hours ago
Days Inn by Wyndham Rutland/Killington Area
Hampton Inn Rutland

Hampton Inn Rutland

8/10 Good
"Breakfast foods subpar."
Matthew 1-night trip
Posted 5 hours ago
Hampton Inn Rutland
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

10/10 Excellent
"Everything was perfect. The staff was really nice and helpful"
Rosanna 2-night trip
Posted 1 day ago
Comfort Inn Rutland - Killington
Courtyard Middlebury

Courtyard Middlebury

10/10 Excellent
"It was a very convenient location. There is a restaurant/bar, which was nice. The woman at the desk was incredibly friendly and helpful. We were very pleased with our stay and would stay there again."
Nancy 2-night trip
Posted 2 days ago
Courtyard Middlebury
On The River Inn

On The River Inn

10/10 Excellent
"This was one of the nicest hotels I have ever stayed in! We had a river view room with rocking chairs on the balcony, s’mores kits were offered every night (pick up by the front desk) and 2 fire pits to choose from. Game room was cute (although the air hockey table’s fan wasn’t strong on one side), library was absolutely gorgeous. Loved having water refilling stations on 2 of the 3 floors and 24/7 coffee/tea stations, too. Queen beds were very comfy, and the room was so spacious. I’d love another piece of furniture with drawers to keep our stuff though - we lived out of our suitcases because there was only an armoire with 3 half drawers. And maybe another towel bar or hooks in the bathroom to hang the towels to dry, especially if you have 4 people in a room. Breakfast buffet (included with our Expedia stay but extra for others) was always hot & fresh. We had 4 breakfasts: French toast, pancakes, waffles, french toast again. There was always fresh homemade pastries and muffins, yogurt, and oatmeal. I would have loved some fresh fruit like berries to go with the yogurt instead of apples and oranges. Staff was always so nice and helpful, especially at breakfast. Housekeeping forgot twice to give us the 4 fresh towels (gave 3 instead) but we got replacements when we asked at the desk."
Christopher 4-night trip
Posted 2 days ago
On The River Inn
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

10/10 Excellent
"Bathroom was clean with lots of towels, the room was larger than I expected and everything was ok with it."
Daniel 1-night trip
Posted 4 days ago
Killington Mountain Lodge, Tapestry Collection by Hilton

Frequently asked questions

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