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

Find Hotels with a Pool in Pittsfield, VT

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Pittsfield Hotels with a Pool

This weekend
30 Oct - 1 Nov
Next weekend
6 Nov - 8 Nov

Our top choices for Pittsfield hotels with a pool

A pool area with a wooden building, outdoor seating, and umbrellas.

1. The Mountain Top Inn & Resort

The Mountain Top Inn & Resort
3.5 star property
Chittenden
9.2 out of 10, Wonderful, (131 reviews)
  • cleanliness
    Lakeside resort oasis offers pool lounging with mountain vistas, after thrilling ski adventures.
The price is AED 943
AED 1,208 total
includes taxes & fees
9 Nov - 10 Nov
The Mountain Top Inn & Resort
A multi-story building with a pool and a covered patio area.

2. North Star Lodge and Resort

North Star Lodge and Resort
2.0 star property
Killington
8.6 out of 10, Excellent, (1,004 reviews)
  • cleanliness
    Refreshing heated outdoor pool at Killington resort with sauna and fitness center complements ski adventures.
The price is AED 434
AED 477 total
includes taxes & fees
3 Nov - 4 Nov
North Star Lodge and Resort
A swimming pool surrounded by snow, with a building in the background.

3. The Mountain Inn at Killington

The Mountain Inn at Killington
2.5 star property
Killington
9.2 out of 10, Wonderful, (1,026 reviews)
  • cleanliness
    Splash into alpine bliss at this mountain inn's heated outdoor pool with scenic resort views.
The price is AED 493
AED 569 total
includes taxes & fees
28 Oct - 29 Oct
The Mountain Inn at Killington
A bench with snow accumulation, a fire pit with visible flames, and a wooden fence in the background.

4. Killington Grand Hotel

Killington Grand Hotel
3.5 star property
Base Area
8.8 out of 10, Excellent, (250 reviews)
  • cleanliness
    Ski slope to steamy soaks: heated outdoor pool and hot tubs deliver mountain views after your slope adventures.
The price is AED 853
AED 1,000 total
includes taxes & fees
30 Oct - 31 Oct
Killington Grand Hotel
A swimming pool with lounge chairs and umbrellas, surrounded by a white fence and tall trees.

5. The Suites at Killington Center

The Suites at Killington Center
3.5 star property
Killington
The price is AED 835
AED 1,726 total
includes taxes & fees
29 Oct - 30 Oct
The Suites at Killington Center
A modern living room with a fireplace, a large sectional sofa, and a television mounted above the fireplace.

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

CubsCorner - Pool, Sauna, Gym, Close to Mountain!
Killington
10.0 out of 10, Exceptional, (6 reviews)
The price is AED 877
AED 1,733 total
includes taxes & fees
28 Oct - 29 Oct
CubsCorner - Pool, Sauna, Gym, Close to Mountain!
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.

7. Best Western Inn & Suites Rutland-Killington

Best Western Inn & Suites Rutland-Killington
2.5 star property
Rutland
8.8 out of 10, Excellent, (1,004 reviews)
  • cleanliness
    Outdoor pool oasis for summer stays near slopes, with year-round adventures waiting just outside your door.
The price is AED 592
AED 651 total
includes taxes & fees
2 Nov - 3 Nov
Best Western Inn & Suites Rutland-Killington
A cozy living room with a stone fireplace, leather sofas, and a framed sign on the wall.

8. Robins Nest- FirePlace, Near Pico, Pool

Robins Nest- FirePlace, Near Pico, Pool
Killington
10.0 out of 10, Exceptional, (4 reviews)
The price is AED 1,173
AED 2,429 total
includes taxes & fees
28 Oct - 29 Oct
Robins Nest- FirePlace, Near Pico, Pool
A rectangular swimming pool with a blue tile border, surrounded by white lounge chairs and umbrellas.

9. 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
9.4 out of 10, Exceptional, (12 reviews)
The price is AED 553
AED 1,520 total
includes taxes & fees
28 Oct - 29 Oct
Skiers Suite: 2RM/2BA Renovated Condo on the Bus Route w/ Pool. Discounted Ski Rentals. #332
A rectangular swimming pool with a metal ladder, surrounded by white and brown lounge chairs, and a white fence.

10. Killington Center 632: a spacious 2RM/2BA condo in the heart of Killington. Discounted ski rentals.

Killington Center 632: a spacious 2RM/2BA condo in the heart of Killington. Discounted ski rentals.
Killington
9.6 out of 10, Exceptional, (7 reviews)
The price is AED 443
AED 1,355 total
includes taxes & fees
28 Oct - 29 Oct
Killington Center 632: a spacious 2RM/2BA condo in the heart of Killington. Discounted ski rentals.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Choose what matters most at hotels with a pool in Pittsfield

Breakfast included
4 stars

Top Pittsfield Hotel Reviews

The Mountain Inn at Killington

The Mountain Inn at Killington

8/10 Good
"Good stay"
Allie 2-night trip
Posted 2 hours ago
The Mountain Inn at Killington

Frequently asked questions

What are some accommodations 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 into account the local weather in Pittsfield can help you maximize your time at the pool during your trip. The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 23°F. The snowiest months in Pittsfield are January, March, February, and December, with each month seeing an average of 10 inches of snowfall.