Find Hotels with a Pool in Pittsfield, VT

Q: What are some accommodations with pools in Pittsfield?

Killington area home - 4-seasons, hot tub and A/C : Offers a seasonal outdoor pool, an indoor pool, and 4 restaurants. Killington Mountain Lodge, Tapestry Collection by Hilton : Features continental, an indoor pool, and free self parking. My Place Hotel-Randolph VT : Offers buffet, a seasonal outdoor pool, and free self parking. Woodstock Inn & Resort : Hotel located near Killington Resort. Provides a sauna, an outdoor pool, and free self parking. Comfort Inn Rutland - Killington : Inn located near Killington Resort. Features full, 2 outdoor pools, and free self parking.

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April 2026

May 2026

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Our top choices for Pittsfield hotels with a pool

Indoor pool, open 8:00 AM to 10:00 PM, sun loungers

On The River Inn

West Woodstock

Splash into bliss with an indoor pool, hot tub, and children's splash area amid scenic views.

$173 nightly

Apr 27 - Apr 28

Total with taxes and fees

The Suites at Killington Center

Killington

$297 nightly

Apr 8 - Apr 9

Total with taxes and fees

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

Killington

$284 nightly

Apr 9 - Apr 10

Total with taxes and fees

The Suites: Next Door - Studio at Killington Resort on the Bus Route. Discounted Ski Rentals. 531

Killington

$214 nightly

Apr 8 - Apr 9

Total with taxes and fees

Deluxe One bedroom Queen Suite on the 2nd floor with outdoor heated pool 209

Killington

$145 nightly

May 1 - May 2

Total with taxes and fees

Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington

Killington

Mountain studio offers poolside relaxation with access to hiking trails, skiing, and outdoor adventure at Killington Resort.

$221 nightly

Apr 8 - Apr 9

Total with taxes and fees

The Cozy Cubbie: Charming Studio in Killington. Pool. Bus. Discounted Ski Rentals.

Killington

$229 nightly

Apr 7 - Apr 8

Total with taxes and fees

Seasonal outdoor pool, open 9:00 AM to 9:00 PM, pool umbrellas

The Mountain Top Inn & Resort

Chittenden

Lakeside resort oasis offers pool lounging with mountain vistas, after thrilling ski adventures.

$148 nightly

Apr 19 - Apr 20

Total with taxes and fees

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Choose what matters most at hotels with a pool in Pittsfield

Breakfast included

4 stars

Top Pittsfield Hotel Reviews

Hampton Inn Rutland

10/10 Excellent

"We had a great stay, very clean and the staff was friendly! "

The Mountain Inn at Killington

8/10 Good

"Nice place close to the mountain with an attentive and friendly staff. Very clean and well run. It’s not a resort or a place where you stay to enjoy the hotel. You are here to ski / board and this is your place to return to for drinks and a good night sleep. The AC wasn’t working well when we were there but it was still late Winter so not unexpected (was unseasonably warm). The furniture in the sitting areas upstairs needs to be upgraded since that’s really the only place to hangout in morning or afternoons other than the restaurant. Overall very pleased with the place for the price."

Killington Mountain Lodge, Tapestry Collection by Hilton

2/10 Terrible

"was put in a room next to elevator, elevator was rubbing squeeling reported to front desk, they refused to move us, noise kept us up all night long. terrible experience. she said they didn't have any other rooms and refused to move us the hotel was clearly NOT full capacity. Elevator certificate was out of date expired."

Frequently asked questions

What are some accommodations with pools in Pittsfield?

Killington area home - 4-seasons, hot tub and A/C: Offers a seasonal outdoor pool, an indoor pool, and 4 restaurants. Killington Mountain Lodge, Tapestry Collection by Hilton: Features continental, an indoor pool, and free self parking. My Place Hotel-Randolph VT: Offers buffet, a seasonal outdoor pool, and free self parking. Woodstock Inn & Resort: Hotel located near Killington Resort. Provides a sauna, an outdoor pool, and free self parking. Comfort Inn Rutland - Killington: Inn located near Killington Resort. Features full, 2 outdoor pools, 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 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.

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