Hotels with Swimming Pool in Healdsburg, California

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Check availability on Healdsburg Hotels with Swimming Pool

Tonight
Dec 25 - Dec 26
Tomorrow
Dec 26 - Dec 27
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Healdsburg hotels with a pool

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Geyserville Inn

Geyserville Inn

Geyserville Inn
3.5 star property
Geyserville
9.2 out of 10, Wonderful, (1001)
"Friendly staff and clean comfortable rooms. We enjoyed the breakfast at the restaurant next door. "
United States
Jill
The price is P7,471
P9,320 total
includes taxes & fees
Dec 26 - Dec 27
Geyserville Inn
Outdoor pool, open 7:00 AM to 10:00 PM, sun loungers
Dry Creek Inn MOD Collection by Sonesta

Dry Creek Inn MOD Collection by Sonesta

Dry Creek Inn MOD Collection by Sonesta
3.0 star property
Healdsburg
8.0 out of 10, Very Good, (1003)
"Clean room, staff was very friendly and checking in was easy"
United States
Benjamin
The price is P6,989
P8,121 total
includes taxes & fees
Dec 26 - Dec 27
Dry Creek Inn MOD Collection by Sonesta
2 outdoor pools, open 7:00 AM to 10:00 PM, free cabanas, pool umbrellas
Appellation Healdsburg

Appellation Healdsburg

Appellation Healdsburg
4.5 star property
Healdsburg
9.2 out of 10, Wonderful, (35)
"Beautiful resort!! "
United States
Jennifer
The price is P18,222
P25,267 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Appellation Healdsburg
Outdoor pool
Cottages on River Road

Cottages on River Road

Cottages on River Road
2.5 star property
Guerneville
9.6 out of 10, Exceptional, (1000)
"Fantastic, beautiful place at a reasonable price. Great included breakfast and super friendly staff.. Will definitely return here when in the area "
United States
Carlos
Cottages on River Road
Outdoor pool
Hampton Inn & Suites Windsor - Sonoma Wine Country

Hampton Inn & Suites Windsor - Sonoma Wine Country

Hampton Inn & Suites Windsor - Sonoma Wine Country
2.5 star property
Windsor
9.2 out of 10, Wonderful, (1000)
"Breakfast and staff is friendly "
United States
Kimbinh
The price is P5,935
P6,778 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Hampton Inn & Suites Windsor - Sonoma Wine Country
Outdoor pool
Holiday Inn Express® Windsor Sonoma Wine Country by IHG

Holiday Inn Express® Windsor Sonoma Wine Country by IHG

Holiday Inn Express® Windsor Sonoma Wine Country by IHG
2.5 star property
Windsor
9.2 out of 10, Wonderful, (1270)
"Breakfast bar was amazing. Holiday decorations were really planned out and looked amazing at night. "
United States
Joel
The price is P5,580
P6,361 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Holiday Inn Express® Windsor Sonoma Wine Country by IHG
Poolside bar
The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel

The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel

The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel
3.0 star property
Santa Rosa
8.4 out of 10, Very Good, (2124)
"Fast friendly check in, clean comfortable room, good breakfast options, would definitely stay here again "
United States
Narayan
The price is P5,356
P6,224 total
includes taxes & fees
Jan 15 - Jan 16, 2026
The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel
Outdoor pool
Hampton Inn & Suites Santa Rosa Sonoma Wine Country

Hampton Inn & Suites Santa Rosa Sonoma Wine Country

Hampton Inn & Suites Santa Rosa Sonoma Wine Country
2.5 star property
Santa Rosa
9.6 out of 10, Exceptional, (450)
"Loved the hotel and customer service "
United States
Denise And Erik
The price is P5,983
P6,941 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Hampton Inn & Suites Santa Rosa Sonoma Wine Country
Indoor pool
Holiday Inn Windsor Wine Country by IHG

Holiday Inn Windsor Wine Country by IHG

Holiday Inn Windsor Wine Country by IHG
3.0 star property
Windsor
9.0 out of 10, Wonderful, (1027)
"Nice place, helpful staff, clean and quiet, great value"
United States
Brad
The price is P5,580
P6,361 total
includes taxes & fees
Dec 28 - Dec 29
Holiday Inn Windsor Wine Country by IHG
Outdoor pool
Hotel Trio Healdsburg

Hotel Trio Healdsburg

Hotel Trio Healdsburg
3.0 star property
Healdsburg
9.4 out of 10, Exceptional, (871)
"Room was very clean and the breakfast was good "
United States
Ioana
The price is P8,927
P11,602 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Hotel Trio Healdsburg
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

Top Healdsburg Hotel Reviews

Fairview Inn and Suites

Fairview Inn and Suites

10/10 Excellent
"Nice spacious suite. Loved the jet tub. Very peaceful location… Will be back…. "
Napoleon 3-night trip
Posted 9 days ago
Fairview Inn and Suites

Frequently asked questions

What are some accommodations with pools in Healdsburg?
Hotel Trio Healdsburg: Features a snack bar/deli, an outdoor pool, and full. Fairview Inn and Suites: Offers free self parking, a seasonal outdoor pool, and complimentary wireless internet access.
What is there to see and do in Healdsburg?
Spend some time experiencing the great outdoors at Russian River and Healdsburg Ridge Open Space Preserve. During your stay, check out sights such as Healdsburg Plaza, Jordan Vineyard & Winery, and Dry Creek Vineyard. Healdsburg appeals to visitors with its beautiful river views, selection of wineries, and array of dining options.
When is the best time to book a hotel with a pool in Healdsburg?
You may want to consider a place to stay with an outdoor swimming pool if you're planning to visit Healdsburg in the hottest months of July, August, or September when the average temperature is 69°F. Lodging with an indoor pool may be the way to go if you are visiting during the coldest months of December, January, or February when the average temperature is 49°F.

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