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

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Check availability on Pittsfield Hotels with Swimming Pool

This weekend
31 Jul - 2 Aug
Next weekend
7 Aug - 9 Aug

Our top choices for Pittsfield hotels with a pool

Exterior

North Star Lodge and Resort

North Star Lodge and Resort
2.0 star property
Killington
8.8 out of 10, Excellent, (1,004 reviews)
  • cleanliness
    Refreshing heated outdoor pool at Killington resort with sauna and fitness centre complements ski adventures.
The price is ₹10,622
₹11,685 total
includes taxes & fees
3 Aug - 4 Aug
North Star Lodge and Resort
Outdoor pool, a heated pool

The Mountain Inn at Killington

The Mountain Inn at Killington
2.5 star property
Killington
9.2 out of 10, Wonderful, (1,010 reviews)
  • cleanliness
    Splash into alpine bliss at this mountain inn's heated outdoor pool with scenic resort views.
The price is ₹14,585
₹16,846 total
includes taxes & fees
6 Aug - 7 Aug
The Mountain Inn at Killington
Indoor pool

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington
2.5 star property
Rutland
8.2 out of 10, Very good, (1,013 reviews)
  • cleanliness
    Soak in pure relaxation at this mountain getaway, where the indoor pool beckons after exhilarating ski adventures nearby.
The price is ₹12,081
₹13,289 total
includes taxes & fees
9 Aug - 10 Aug
Comfort Inn Rutland - Killington
Seasonal outdoor pool, open 9:00 AM to 9:00 PM, pool umbrellas

The Mountain Top Inn & Resort

The Mountain Top Inn & Resort
3.5 star property
Chittenden
9.0 out of 10, Wonderful, (121 reviews)
  • cleanliness
    Lakeside resort oasis offers pool lounging with mountain vistas, after thrilling ski adventures.
The price is ₹31,384
₹34,209 total
includes taxes & fees
4 Aug - 5 Aug
The Mountain Top Inn & Resort
Lobby

Best Western Inn & Suites Rutland-Killington

Best Western Inn & Suites Rutland-Killington
2.5 star property
Rutland
8.8 out of 10, Excellent, (1,000 reviews)
  • cleanliness
    Outdoor pool oasis for summer stays near slopes, with year-round adventures waiting just outside your door.
The price is ₹17,296
₹19,026 total
includes taxes & fees
9 Aug - 10 Aug
Best Western Inn & Suites Rutland-Killington
Indoor pool

Hampton Inn Rutland

Hampton Inn Rutland
2.5 star property
Rutland
9.0 out of 10, Wonderful, (1,003 reviews)
  • cleanliness
    Splash into family fun with an indoor pool sanctuary at this hotel where winter adventures meet waterside bliss.
The price is ₹14,570
₹16,027 total
includes taxes & fees
9 Aug - 10 Aug
Hampton Inn Rutland
Seasonal outdoor pool, open 6:00 AM to 10:00 PM, pool umbrellas

Emrose Luxury Cabins

Emrose Luxury Cabins
2.0 star property
Brandon
9.0 out of 10, Wonderful, (106 reviews)
  • cleanliness
    Soak in Vermont's magic with eight bubbling hot tubs amid natural splendour at Emrose.
The price is ₹15,644
₹17,678 total
includes taxes & fees
30 Jul - 31 Jul
Emrose Luxury Cabins
Indoor pool

Mountain Green

Mountain Green
2.0 star property
Killington
7.2 out of 10, Good, (28 reviews)
  • cleanliness
    Splash into mountain adventures at this condo resort with indoor pool and cosy firepit area.
The price is ₹7,537
₹22,476 total
includes taxes & fees
30 Jul - 31 Jul
Mountain Green
Outdoor pool

Killington Grand Hotel

Killington Grand Hotel
3.5 star property
Base Area
9.0 out of 10, Wonderful, (217 reviews)
  • cleanliness
    Ski slope to steamy soaks: heated outdoor pool and hot tubs deliver mountain views after your slope adventures.
The price is ₹22,266
₹26,119 total
includes taxes & fees
2 Aug - 3 Aug
Killington Grand Hotel
Indoor pool

Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area
2.5 star property
Rutland
6.8 out of 10, (1,011 reviews)
  • cleanliness
    Dive into relaxation with a warm indoor pool escape at this cosy ski-friendly hotel.
The price is ₹11,409
₹12,550 total
includes taxes & fees
28 Jul - 29 Jul
Days Inn by Wyndham Rutland/Killington Area
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.
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Choose what matters most at hotels with a pool in Pittsfield

Breakfast included
4 stars

Top Pittsfield Hotel Reviews

Woodstock Inn & Resort

Woodstock Inn & Resort

10/10 Excellent
"Quaint New England charm with beautifully maintained grounds. We enjoyed both the spa and the Red Rooster restaurant which were both wonderful. There was a wedding onsite one night while we were there and while beautiful, made it difficult to enjoy the outside fire and smores that evening as it was very loud. It was remarkable that you could not however hear the noise from inside the Inn. Overall I would highly recommend the Woodstock Inn resort & spa to couples, families and friend trips."
Julie 2-night trip
Posted 7 hours ago
Woodstock Inn & Resort

Frequently asked questions

What are some accommodation options with pools in Pittsfield?
Woodstock Inn & Resort: Offers a seasonal outdoor pool, an indoor pool and 4 restaurants. The Mountain Inn at Killington: Hotel, 1-minute walk from Killington Resort. Provides daily, an outdoor pool and free self parking. On The River Inn: Features a children's pool, an indoor pool and a sauna. Killington Mountain Lodge, Tapestry Collection by Hilton: Offers continental, an indoor pool and free self parking. My Place Hotel-Randolph VT: 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 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.