Search Hotels with Pool in Healdsburg

Start date: Check-in selected.
To Date
End date: Check-out

  • 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 Healdsburg Hotels with Pool

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

Our top choices for Healdsburg hotels with a pool

Deluxe Queen Room | View from room
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 Rp2.129.455
Rp2.656.596 total
includes taxes & fees
27 Dec - 28 Dec
Geyserville Inn
Outdoor pool, open 7:00 AM to 10:00 PM, pool 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 Rp1.992.179
Rp2.314.812 total
includes taxes & fees
27 Dec - 28 Dec
Dry Creek Inn MOD Collection by Sonesta
2 outdoor pools, open 7:00 AM to 10:00 PM, free pool cabanas
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 Rp5.193.895
Rp7.202.228 total
includes taxes & fees
11 Jan - 12 Jan 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 Rp1.908.139
Rp2.178.962 total
includes taxes & fees
4 Jan - 5 Jan 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 Rp1.590.395
Rp1.813.050 total
includes taxes & fees
4 Jan - 5 Jan 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, (2127)
"Fast friendly check in, clean comfortable room, good breakfast options, would definitely stay here again "
United States
Narayan
The price is Rp1.526.779
Rp1.774.041 total
includes taxes & fees
15 Jan - 16 Jan 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, (453)
"Loved the hotel and customer service "
United States
Denise And Erik
The price is Rp1.702.225
Rp1.974.581 total
includes taxes & fees
3 Jan - 4 Jan 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, (1028)
"Nice place, helpful staff, clean and quiet, great value"
United States
Brad
The price is Rp1.590.395
Rp1.813.050 total
includes taxes & fees
28 Dec - 29 Dec
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 Rp2.544.632
Rp3.306.958 total
includes taxes & fees
4 Jan - 5 Jan 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

Best Western Dry Creek Inn

Best Western Dry Creek Inn

10/10 Excellent
"conveniently located, room and staff exceeded expectations"
Julianne 2-night trip
Posted 12 days ago
Best Western Dry Creek Inn

Frequently asked questions

What are some accommodation options 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, visit sights such as Healdsburg Plaza, Jordan Vineyard & Winery and Dry Creek Vineyard. Healdsburg appeals to visitors with its stunning 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 plan to visit Healdsburg in the hottest months of July, August or September, when the average temp is 21°C. Accommodation 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 9°C.