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

Pittsfield Hotels with Swimming Pool

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Check availability on Pittsfield Hotels with Swimming Pools

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

Our top choices for Pittsfield hotels with a pool

A multi-story building with a pool and a covered patio area.
A snow-covered road with a sign reading 'Welcome to Killington.'
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.

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.
RM565
RM621 total
includes taxes & fees
27 Sept - 28 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 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.

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.
RM546
RM631 total
includes taxes & fees
18 Oct - 19 Oct
The Mountain Inn at Killington
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.

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.
RM1,126
RM1,227 total
includes taxes & fees
28 Sept - 29 Sept
The Mountain Top Inn & Resort
A swimming pool at dusk with surrounding lounge chairs and a covered area with lights.
A modern gym with a large window, wooden paneling, and illuminated vertical lights.
A modern bedroom with a curved wall, a bed, a sofa, a small table with flowers, and a walk-in closet.
A modern living room with a sofa, two round tables, a fireplace, and a television.

4. Emrose Luxury Cabins

Emrose Luxury Cabins
Brandon
  • Soak in Vermont's magic with eight bubbling hot tubs amid natural splendour at Emrose.
RM660
RM746 total
includes taxes & fees
27 Sept - 28 Sept
Emrose Luxury Cabins
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 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.

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.
RM524
RM577 total
includes taxes & fees
22 Oct - 23 Oct
Comfort Inn 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

Woodstock Inn & Resort

Woodstock Inn & Resort

10/10 Excellent
"Wonderful inn! Everything was wonderful: rooms, food, etc!!"
Ann 2-night trip
Posted 3 hours ago
Woodstock Inn & Resort
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 11 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 1 day 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 1 day 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
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 10 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. Provides daily, an outdoor pool and free self parking. Woodstock Inn & Resort: Features a seasonal outdoor pool, an indoor pool and 4 restaurants. Killington Mountain Lodge, Tapestry Collection by Hilton: Offers 8 hot tubs, a seasonal outdoor pool and a sauna. The Jackson: Offers a children's pool, an indoor pool and a sauna. Emrose Luxury Cabins: Provides 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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