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
11 Sept - 12 Sept
Tomorrow
12 Sept - 13 Sept
This weekend
11 Sept - 13 Sept
Next weekend
18 Sept - 20 Sept

Our top choices for Pittsfield hotels with a pool

A multi-story building with a pool and a covered patio area.
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.
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.
₹13,182
₹14,500 total
includes taxes & fees
12 Sept - 13 Sept
North Star Lodge and Resort
A swimming pool surrounded by snow, with a building in the background.
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.
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.
₹13,659
₹15,777 total
includes taxes & fees
13 Sept - 14 Sept
The Mountain Inn at Killington
A pool area with a wooden building, outdoor seating, and umbrellas.
A spacious living room with a stone fireplace, wooden ceiling beams, and a cozy seating area.
A large, two-story log cabin with a stone foundation, multiple windows, and a balcony.
A spacious room with large windows, a stone wall, and a wooden ceiling.

3. The Mountain Top Inn & Resort

The Mountain Top Inn & Resort
Chittenden
  • Lakeside resort oasis offers pool lounging with mountain vistas, after thrilling ski adventures.
₹26,274
₹28,638 total
includes taxes & fees
14 Sept - 15 Sept
The Mountain Top Inn & Resort
A large house with a swimming pool, a fenced yard, and a well-lit entrance.
A paved patio with outdoor furniture, a decorative garden bed, and a white fence.
A long corridor with tables and chairs, large windows, and a ceiling fan.
A garden entrance with a white pergola covered in ivy, a sign indicating the pool is open, and outdoor seating with umbrellas.

4. Brandon Inn

Brandon Inn
Brandon
  • Dive into a refreshing outdoor pool retreat at this historic hotel with loungers for sun-soaked relaxation.
₹10,542
₹11,596 total
includes taxes & fees
13 Sept - 14 Sept
Brandon Inn
An indoor swimming pool with clear blue water, surrounded by white tiles and blue pillars.
A modern bathroom with a large mirror, dual sinks, a glass shower enclosure, and neatly folded towels on shelves.
A brick building with a sign reading 'Southside Steakhouse' and the number '170' above the entrance.
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.
₹14,601
₹16,061 total
includes taxes & fees
15 Sept - 16 Sept
Comfort Inn Rutland - Killington
A swimming pool with a modern design, surrounded by a fenced patio area with outdoor seating.
A cozy living room with a fireplace, a comfortable sofa, a wooden coffee table, and a television mounted on the wall.
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.

6. Mountain Green

Mountain Green
Killington
  • Splash into mountain adventures at this condo resort with indoor pool and cosy firepit area.
₹7,423
₹22,136 total
includes taxes & fees
13 Sept - 14 Sept
Mountain Green
A swimming pool at dusk with surrounding lounge chairs and a covered area with lights.
A modern living room with a sofa, two round tables, a fireplace, and a television.
A campground with several wooden cabins, a central fire pit area, and a well-maintained lawn.
A modern bedroom with a curved wall, a bed, a sofa, a small table with flowers, and a walk-in closet.

7. Emrose Luxury Cabins

Emrose Luxury Cabins
Brandon
  • Soak in Vermont's magic with eight bubbling hot tubs amid natural splendour at Emrose.
₹15,408
₹17,411 total
includes taxes & fees
13 Sept - 14 Sept
Emrose Luxury Cabins
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 kitchen with wooden cabinets, a stainless steel refrigerator, a stove, and two bar stools.
A modern hotel lobby with a dining area, stone wall, and a view of the outside.

8. 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.
₹18,927
₹20,819 total
includes taxes & fees
13 Sept - 14 Sept
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

On The River Inn

On The River Inn

8/10 Good
"We selected and reserved a room with a river view and were assigned 105. The actual river was not visible from our windows or balcony. That was a little disappointing. The room itself was very nice and well maintained. The food in the 506 Bistro was excellent, both the daily breakfasts and the two dinners we had there. The wings with maple were especially tasty. The staff we engaged were nice. We probably will not visit Woodstock again now that we spent a few days there, but if we did I would stay there again but not pay a premium price for a river view."
Russell 5-night trip
Posted 10 hours ago
On The River Inn
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

8/10 Good
"The room was clean & the staff very helpful. We were pleasantly surprised by the substantial breakfast which came with our booking & loved the pool/hot tub. It was older but very clean!"
Susan 1-night trip
Posted 1 day ago
Comfort Inn Rutland - Killington
North Star Lodge and Resort

North Star Lodge and Resort

10/10 Excellent
"We found the staff very friendly. Especially the weekend bar tender/ chef, Dan O. He was also very efficient and his bar bites were great. Plenty of restaurants nearby and people were very friendly throughout the area. We found the room clean but a bit dated. The King size bed was pretty comfortable! We would go back!"
Melinda 3-night trip
Posted 3 days ago
North Star Lodge and Resort
Hampton Inn Rutland

Hampton Inn Rutland

8/10 Good
"Most of the staff at the front desk needs to work on their people skills big time!!"
Kasey 4-night trip
Posted 5 days ago
Hampton Inn Rutland
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

10/10 Excellent
"A great place to stay when you’re visiting Killington!"
Mason 3-night trip
Posted 10 days ago
Killington Mountain Lodge, Tapestry Collection by Hilton
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 13 days ago
Courtyard Middlebury

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. My Place Hotel-Randolph VT: Offers a children's pool, an indoor pool and a sauna. Emrose Luxury Cabins: Features continental, an indoor pool and free self parking.
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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