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

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Check availability on Pittsfield Hotels with Pool

Tonight
11 Oct - 12 Oct
Tomorrow
12 Oct - 13 Oct
Next weekend
16 Oct - 18 Oct
In two weeks
23 Oct - 25 Oct

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 room with large windows, a stone wall, and a wooden ceiling.
A large, two-story log cabin with a stone foundation, multiple windows, and a balcony.

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.
฿9,891
฿10,782 total
includes taxes & fees
1 Nov - 2 Nov
The Mountain Top Inn & Resort
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.'

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.
฿4,436
฿4,880 total
includes taxes & fees
14 Oct - 15 Oct
North Star Lodge and Resort
A pool area with lounge chairs and umbrellas, surrounded by landscaped gardens and a building with large windows.
A two-story lodge with a stone facade, wooden balconies, and a well-maintained lawn.
A rustic interior with a stone hot tub, wooden furniture, and a mountain mural.
A stone fireplace with a fire, a log, and a person reading a book.

3. Summit Lodge

Summit Lodge
Killington
  • Alpine relaxation awaits at Killington inn with 2 outdoor pools, hot tub, and poolside bar.
฿6,880
฿8,466 total
includes taxes & fees
16 Oct - 17 Oct
Summit Lodge
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 building with a modern design, featuring large windows and a covered outdoor seating area.

4. 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.
฿4,496
฿5,193 total
includes taxes & fees
19 Oct - 20 Oct
The Mountain Inn at Killington
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 hotel lobby with a dining area, stone wall, and a view of the outside.
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.

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.
฿5,402
฿5,942 total
includes taxes & fees
27 Oct - 28 Oct
Best Western Inn & Suites Rutland-Killington
A pool area with lounge chairs and a view of a mountainous landscape.
A reception desk with a stone wall backdrop and wooden accents, a person with a suitcase, and a television screen above the desk.
A sign for the Grand Hotel Spa in Killington, Vermont, with a mountain backdrop.
A spacious lobby with leather seating, a stone fireplace, and a staircase leading to an upper level.

6. 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.
฿7,786
฿9,133 total
includes taxes & fees
13 Oct - 14 Oct
Killington Grand Hotel
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.

7. 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.
฿4,140
฿4,554 total
includes taxes & fees
1 Nov - 2 Nov
Comfort Inn Rutland - Killington
An indoor swimming pool with a wooden ceiling, large windows, and lounge chairs.
A conference room with tables, chairs, and a projector screen.
A hotel room with a large bed, a wooden headboard, two bedside tables with lamps, and a framed picture on the wall.
A modern kitchen with granite countertops, wooden cabinets, and a central island.

8. 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.
฿4,532
฿4,985 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.
A paved patio with outdoor furniture, a decorative garden bed, and a white fence.
Front of property

9. Brandon Inn

Brandon Inn
Brandon
  • Dive into a refreshing outdoor pool retreat at this historic hotel with loungers for sun-soaked relaxation.
฿4,511
฿4,962 total
includes taxes & fees
1 Nov - 2 Nov
Brandon Inn
A large indoor swimming pool with clear blue tiles, sunlit by large windows, and equipped with lounge chairs and a ceiling fan.
A two-story house with a balcony, surrounded by lush greenery and a pond.
A spacious living room with a chandelier, multiple armchairs, a coffee table, and a rug.
A spacious living room with a large American flag, a fireplace, and a chandelier.

10. 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.
฿5,471
฿6,756 total
includes taxes & fees
1 Nov - 2 Nov
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

Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

10/10 Excellent
"Spacious room, parking"
ARACELI 1-night trip
Posted 3 hours ago
Days Inn by Wyndham Rutland/Killington Area
Woodstock Inn & Resort

Woodstock Inn & Resort

10/10 Excellent
"Room was spacious and very clean upon arrival. Staff was also very attentive and took care all our needs."
Marlene 3-night trip
Posted 4 hours ago
Woodstock Inn & Resort
The Mountain Inn at Killington

The Mountain Inn at Killington

10/10 Excellent
"Great hotel!"
Petra 2-night trip
Posted 10 hours ago
The Mountain Inn at Killington
Courtyard Middlebury

Courtyard Middlebury

10/10 Excellent
"All around good experience"
Robert 1-night trip
Posted 1 day ago
Courtyard Middlebury
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

8/10 Good
"Nice stop during our roadtrip. Loved the layout of the room and we really appreciate the staff's help. They are incredibly friendly and accommodating to customers."
Kathryn 1-night trip
Posted 1 day ago
Killington Mountain Lodge, Tapestry Collection by Hilton
North Star Lodge and Resort

North Star Lodge and Resort

8/10 Good
"Room was clean, beds are comfortable, coffee was good. Lodge is comfortable. Parts of it are a bit dated. Overall it is a good value and conveniently located."
Amy 1-night trip
Posted 2 days ago
North Star Lodge and Resort
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

8/10 Good
"Clean room, good staff, good breakfast"
tuhin 3-night trip
Posted 4 days ago
Comfort Inn Rutland - Killington
On The River Inn

On The River Inn

10/10 Excellent
"Karen at the front desk was absolutely delightful. She saw me struggling with my dog and bags, and helped me to my room. Dan on the housekeeping was so nice. We saw him almost every day. The hotel is incredibly pet friendly. It's so convenient to walk out of your room directly onto the rear lawn, and down toward the river. I had a nice chat with the lady who lives across the river. She also has a dog. The drive to downtown was just a few minutes. I highly recommend the farmer's market (you pass it on the way to downtown Woodstock). The room was very clean. The sink and bathroom door could use some updates, but other than that it was lovely. I would definitely return again with my pup."
VS 4-night trip
Posted 5 days ago
On The River Inn

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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