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

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Check availability on Pittsfield Hotels with Pool

Tonight
22 Sep - 23 Sep
Tomorrow
23 Sep - 24 Sep
This weekend
25 Sep - 27 Sep
Next weekend
2 Oct - 4 Oct

Our top choices for Pittsfield hotels with a pool

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 hotel room with two beds, a wooden headboard, a desk, and a window with a view of greenery.
A modern bathroom with a large bathtub, a glass-enclosed shower, and a toilet.

1. 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.
3.489.282 ₫
4.030.238 ₫ total
includes taxes & fees
18 Oct - 19 Oct
The Mountain Inn at 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 large American flag, a fireplace, and a chandelier.
Two Adirondack chairs by a river with a forested hillside in the background.
A spacious living room with a chandelier, multiple armchairs, a coffee table, and a rug.

2. 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.
9.341.180 ₫
10.847.738 ₫ total
includes taxes & fees
23 Sept - 24 Sept
On The River Inn
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 hotel lobby with a blue sofa, a round coffee table, and abstract art on the walls.

3. 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.
3.338.626 ₫
3.672.488 ₫ total
includes taxes & fees
22 Oct - 23 Oct
Comfort Inn Rutland - Killington
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 modern lounge area with orange upholstered chairs, a fireplace, and large windows offering a view of autumn trees.
A modern interior with a wooden counter, seating area, and large windows.

4. 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.
4.245.944 ₫
4.670.538 ₫ total
includes taxes & fees
18 Oct - 19 Oct
Hampton Inn Rutland
A pool area with lounge chairs and umbrellas, surrounded by landscaped gardens and a building with large windows.
An outdoor seating area with tables and chairs, a stone planter with flowers, and a building with a sloped roof and large windows.
A rustic interior with a stone hot tub, wooden furniture, and a mountain mural.
A two-story lodge with a stone facade, wooden balconies, and a well-maintained lawn.

5. Summit Lodge

Summit Lodge
Killington
  • Alpine relaxation awaits at Killington inn with 2 outdoor pools, hot tub, and poolside bar.
19.495.485 ₫
22.608.909 ₫ total
includes taxes & fees
11 Oct - 12 Oct
Summit Lodge
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 bar area with a star sign, bicycles, and a patterned carpet.
A bathroom with a large freestanding bathtub, a mirror, and a wooden vanity.

6. 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.
3.606.372 ₫
3.967.008 ₫ total
includes taxes & fees
27 Sept - 28 Sept
North Star Lodge and Resort
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.
A paved patio with outdoor furniture, a decorative garden bed, and a white fence.

7. Brandon Inn

Brandon Inn
Brandon
  • Dive into a refreshing outdoor pool retreat at this historic hotel with loungers for sun-soaked relaxation.
3.551.730 ₫
3.906.903 ₫ total
includes taxes & fees
22 Oct - 23 Oct
Brandon Inn
An indoor swimming pool with a high ceiling, multiple ceiling fans, and a seating area with chairs and tables.
A reception desk with a wooden finish, a black textured wall, and a blue mat with 'Days Inn' text.
A spacious living area with a fireplace, leather sofas, and a dining area with wooden furniture.
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.

8. 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.
3.074.263 ₫
3.381.690 ₫ total
includes taxes & fees
22 Oct - 23 Oct
Days Inn by Wyndham Rutland/Killington Area
A pool area with a wooden building, outdoor seating, and umbrellas.
A spacious room with large windows, a stone wall, and a wooden ceiling.
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.

9. The Mountain Top Inn & Resort

The Mountain Top Inn & Resort
Chittenden
  • Lakeside resort oasis offers pool lounging with mountain vistas, after thrilling ski adventures.
7.188.025 ₫
7.834.947 ₫ total
includes taxes & fees
23 Sept - 24 Sept
The Mountain Top Inn & Resort
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 modern kitchen with white cabinets, a stainless steel dishwasher, and a microwave.
A Best Western Inn & Suites with a well-maintained lawn, a parking area, and a building with a porch.
A kitchen with wooden cabinets, a stainless steel refrigerator, a stove, and two bar stools.

10. 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.
4.192.082 ₫
4.611.290 ₫ total
includes taxes & fees
21 Oct - 22 Oct
Best Western Inn & Suites Rutland-Killington
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

The Mountain Inn at Killington

The Mountain Inn at Killington

10/10 Excellent
"Beautiful property with unique blend of modern and rustic design"
Nicholas 1-night trip
Posted 3 hours ago
The Mountain Inn at Killington
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

10/10 Excellent
"You can tell that the manager, Pavan, takes pride in this property. He was everywhere checking that things were comfortable and clean for the guests. We will definitely stay there again when we are in Vermont visiting family."
Mary 1-night trip
Posted 19 hours ago
Days Inn by Wyndham Rutland/Killington Area
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

10/10 Excellent
"N/A"
Robert 1-night trip
Posted 23 hours ago
Killington Mountain Lodge, Tapestry Collection by Hilton
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

10/10 Excellent
"Nice hotel !"
Reuben 2-night trip
Posted 2 days ago
Comfort Inn Rutland - Killington
On The River Inn

On The River Inn

8/10 Good
"Extremely quaint and love the rooms and balcony… Dining room gorgeous Wish there were Apps on the Tv for streaming… that’s all"
Marcia 2-night trip
Posted 4 days ago
On The River Inn
Woodstock Inn & Resort

Woodstock Inn & Resort

8/10 Good
"Woodstock itself is absolutely beautiful and has a wonderful atmosphere. However, we had a few issues in both common areas, and our room that significantly impacted our experience. First, the cleanliness of the lobby was disappointing. I noticed that it was noticeably dusty and had visible spiderwebs in several areas, which did not create a welcoming first impression. Second, the bathroom and bed did not live up to the luxurious standard expected. Both the bathroom sink and bathtub drained incredibly slowly. This resulted in an unpleasant backflow of water whenever I tried to use them, which felt very unhygienic. Lastly, the bed was lopsided and very uncomfortable. The boxspring on both sides of the bed was covered in stains, which took away from the charm and comfort of the room. Everything else was great, and with a little more attention to room cleanliness, this place would be flawless."
Erin 3-night trip
Posted 5 days ago
Woodstock Inn & Resort
North Star Lodge and Resort

North Star Lodge and Resort

8/10 Good
"We loved the heated pool! Front desk staff were very helpful. Our room was clean and very basic. Our room was quiet. Would stay here again."
Lorraine 1-night trip
Posted 8 days ago
North Star Lodge and Resort
Courtyard Middlebury

Courtyard Middlebury

10/10 Excellent
"Very good staff"
Nikhil 1-night trip
Posted 9 days ago
Courtyard Middlebury

Frequently asked questions

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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