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

Pittsfield Hotel with Pool

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Check availability on Pittsfield Hotel 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 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.
A lodge with a fire pit, outdoor seating, and a covered area with string lights.

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.
HK$2,315
HK$2,523 total
includes taxes & fees
1 Nov - 2 Nov
The Mountain Top Inn & Resort
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 stone fireplace with a fire, a log, and a person reading a book.
A rustic interior with a stone hot tub, wooden furniture, and a mountain mural.

2. Summit Lodge

Summit Lodge
Killington
  • Alpine relaxation awaits at Killington inn with 2 outdoor pools, hot tub, and poolside bar.
HK$1,610
HK$1,981 total
includes taxes & fees
16 Oct - 17 Oct
Summit Lodge
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 bar area with a star sign, bicycles, and a patterned carpet.
A spacious living room with a fireplace, leather sofas, a wooden coffee table, and a view of the outdoors.

3. 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.
HK$1,038
HK$1,142 total
includes taxes & fees
14 Oct - 15 Oct
North Star Lodge and Resort
A swimming pool surrounded by snow, with a building in the background.
A modern bathroom with a large bathtub, a glass-enclosed shower, and a toilet.
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.

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.
HK$1,052
HK$1,216 total
includes taxes & fees
19 Oct - 20 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 restaurant interior with stone walls, wooden tables and booths, and pendant lighting.
A reception desk with a stone wall backdrop and wooden accents, a person with a suitcase, and a television screen above the desk.

5. 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.
HK$1,822
HK$2,138 total
includes taxes & fees
13 Oct - 14 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 modern hotel lobby with a dining area, stone wall, and a view of the outside.
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.

6. 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.
HK$1,264
HK$1,391 total
includes taxes & fees
27 Oct - 28 Oct
Best Western Inn & Suites Rutland-Killington
A rectangular swimming pool with a blue tile border, surrounded by white lounge chairs and umbrellas.
A modern kitchen with a microwave, stove, and red stools. A living area with a fireplace and a TV is visible in the background.
A modern bathroom with a glass shower enclosure, a marble-tiled floor, and a built-in shelf with a mosaic backsplash.
A modern kitchen with a central island, stainless steel appliances, and wooden cabinets.

7. Skiers Suite: 2RM/2BA Renovated Condo on the Bus Route w/ Pool. Discounted Ski Rentals. #332

Skiers Suite: 2RM/2BA Renovated Condo on the Bus Route w/ Pool. Discounted Ski Rentals. #332
Killington
HK$1,182
HK$3,229 total
includes taxes & fees
12 Oct - 13 Oct
Skiers Suite: 2RM/2BA Renovated Condo on the Bus Route w/ Pool. Discounted Ski Rentals. #332
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 bedroom with a bed, a sofa, a wooden coffee table, a TV, and a window with a view.
A modern bathroom with a dual sink vanity, a toilet, a glass shower enclosure, and a small shelf with towels.

8. The Suites at Killington Center

The Suites at Killington Center
Killington
HK$1,783
HK$3,688 total
includes taxes & fees
19 Oct - 20 Oct
The Suites at Killington Center
An indoor swimming pool with clear lanes, a lifeguard chair, and a windowed wall.
A gym with various exercise machines, a treadmill, and a weight bench.
A modern living room with a fireplace, a grey sofa, a dining table with chairs, and a large 'KILLINGTON' sign on the wall.
A bedroom with a bed, a dresser, a mirror, a window with a view of greenery, and a lamp.

9. CubsCorner - Pool, Sauna, Gym, Close to Mountain!

CubsCorner - Pool, Sauna, Gym, Close to Mountain!
Killington
HK$1,805
HK$3,589 total
includes taxes & fees
13 Oct - 14 Oct
CubsCorner - Pool, Sauna, Gym, Close to Mountain!
An indoor swimming pool with clear lanes, a lifeguard chair, and a windowed wall.
A bed with a checkered blanket, two bedside lamps, and three framed landscape paintings on the wall.
A dining area with a large wooden table and chairs, a potted plant, and a wall with the word "KILLINGTON" in large letters.
A cozy living room with a stone fireplace, leather sofas, and a framed sign on the wall.

10. Robins Nest- FirePlace, Near Pico, Pool

Robins Nest- FirePlace, Near Pico, Pool
Killington
HK$2,405
HK$5,014 total
includes taxes & fees
12 Oct - 13 Oct
Robins Nest- FirePlace, Near Pico, Pool
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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

10/10 Excellent
"Spacious room, parking"
ARACELI 1-night trip
Posted 2 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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