Hotels with Swimming Pool in Healdsburg, California

  • 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 prices for these dates

Tonight
Nov 13 - Nov 14
Tomorrow
Nov 14 - Nov 15
This weekend
Nov 13 - Nov 15
Next weekend
Nov 20 - Nov 22

Our top choices for Healdsburg hotels with a pool

A poolside area with lounge chairs, a table, and a potted plant.

1. Hotel Healdsburg

Hotel Healdsburg
4.0 star property
Healdsburg
9.2 out of 10, Wonderful, (467 reviews)
  • cleanliness
    Splash into a sun-drenched paradise with an attentive poolside service at this Healdsburg retreat.
The price is P31,778
P40,255 total
includes taxes & fees
Nov 16 - Nov 17
Hotel Healdsburg
A poolside area with a tiled deck, a pool with a depth marker, and outdoor seating with chairs and tables.

2. Harmon Guest House

Harmon Guest House
3.0 star property
Healdsburg
9.4 out of 10, Exceptional, (494 reviews)
  • cleanliness
    Splash into poolside paradise with refreshing swims and stylish cabanas at this chic retreat.
The price is P22,913
P29,214 total
includes taxes & fees
Dec 1 - Dec 2
Harmon Guest House
A swimming pool with lounge chairs and umbrellas, surrounded by multi-story buildings with balconies.

3. Hotel Trio Healdsburg

Hotel Trio Healdsburg
3.0 star property
Healdsburg
9.4 out of 10, Exceptional, (1,000 reviews)
  • cleanliness
    Indulge in a refreshing pool escape near Russian River with complimentary area shuttle service.
The price is P9,489
P12,358 total
includes taxes & fees
Nov 19 - Nov 20
Hotel Trio Healdsburg
A modern hotel with a pool, outdoor seating, and a wooden balcony.

4. H2Hotel

H2Hotel
4.0 star property
Healdsburg
9.4 out of 10, Exceptional, (811 reviews)
  • cleanliness
    Sleek outdoor pool sanctuary surrounded by nature offers refreshing escapes after wine country adventures.
The price is P21,723
P27,831 total
includes taxes & fees
Nov 16 - Nov 17
H2Hotel
A pool area with lounge chairs and umbrellas, surrounded by a building with multiple windows and balconies.

5. 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, (1,001 reviews)
  • cleanliness
    Dive into aquatic relaxation at this modern hotel featuring a heated outdoor pool and hot tub surrounded by serene lounging areas.
The price is P7,781
P8,885 total
includes taxes & fees
Nov 20 - Nov 21
Hampton Inn & Suites Windsor - Sonoma Wine Country
An aerial view of a resort with a large swimming pool surrounded by sun loungers and a vineyard.

6. Montage Healdsburg

Montage Healdsburg
5.0 star property
Healdsburg
9.6 out of 10, Exceptional, (143 reviews)
  • cleanliness
    Luxurious poolside retreat featuring two outdoor pools with cabanas, loungers, and refreshing drinks served right to your chair.
The price is P48,718
P61,759 total
includes taxes & fees
Dec 6 - Dec 7
Montage Healdsburg
A swimming pool with a fence, lounge chairs, and a building with columns.

7. 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, (1,298 reviews)
  • cleanliness
    Refresh poolside with panoramic views, hot tub delights, and a sauna that elevates relaxation at this wine country retreat.
The price is P6,305
P7,187 total
includes taxes & fees
Dec 13 - Dec 14
Holiday Inn Express® Windsor Sonoma Wine Country by IHG
A swimming pool with lounge chairs, a pergola, and a gazebo.

8. The Lodge at Healdsburg, Tapestry Collection by Hilton

The Lodge at Healdsburg, Tapestry Collection by Hilton
4.0 star property
Healdsburg
9.0 out of 10, Wonderful, (576 reviews)
  • cleanliness
    Soak in relaxation at this Tuscan-style hotel, where the outdoor pool and 2 hot tubs create a serene retreat in Healdsburg.
The price is P9,234
P10,730 total
includes taxes & fees
Nov 15 - Nov 16
The Lodge at Healdsburg, Tapestry Collection by Hilton
A multi-story hotel with a central archway, balconies, and a parking area.

9. Dry Creek Inn MOD Collection by Sonesta

Dry Creek Inn MOD Collection by Sonesta
3.0 star property
Healdsburg
8.2 out of 10, Very good, (1,003 reviews)
  • cleanliness
    Dive into sun-soaked relaxation with an outdoor pool, bicycles, and vineyard tours nearby.
The price is P7,578
P8,806 total
includes taxes & fees
Nov 15 - Nov 16
Dry Creek Inn MOD Collection by Sonesta
A swimming pool area with lounge chairs and a no diving sign.

10. Holiday Inn Windsor Wine Country by IHG

Holiday Inn Windsor Wine Country by IHG
3.0 star property
Windsor
8.8 out of 10, Excellent, (1,043 reviews)
  • cleanliness
    Dive into a year-round swimming oasis at this hotel with a heated indoor pool and 24-hour fitness center.
The price is P7,260
P8,276 total
includes taxes & fees
Dec 4 - Dec 5
Holiday Inn Windsor Wine Country by IHG
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 Healdsburg

Breakfast included
Hot tub

Hotels with pools and free breakfast in Healdsburg

A hotel with a modern design, featuring a prominent entrance, multiple balconies, and a well-maintained outdoor area with trees and seating.
Hotel Trio Healdsburg

Hotel Trio Healdsburg

Hotel Trio Healdsburg
3.0 star property
Healdsburg
9.4 out of 10, Exceptional, (1000)
The price is P9,489
P12,358 total
includes taxes & fees
Nov 19 - Nov 20
Hotel Trio Healdsburg
View all properties

Hotels with pools and hot tubs in Healdsburg

A spacious balcony with a dining area, featuring a table and chairs, and a decorative light fixture.
The Lodge at Healdsburg, Tapestry Collection by Hilton

The Lodge at Healdsburg, Tapestry Collection by Hilton

The Lodge at Healdsburg, Tapestry Collection by Hilton
4.0 star property
Healdsburg
9.0 out of 10, Wonderful, (576)
The price is P9,234
P10,730 total
includes taxes & fees
Nov 15 - Nov 16
The Lodge at Healdsburg, Tapestry Collection by Hilton
View all properties

4-star hotels with pools in Healdsburg

A spacious balcony with a dining area, featuring a table and chairs, and a decorative light fixture.
The Lodge at Healdsburg, Tapestry Collection by Hilton

The Lodge at Healdsburg, Tapestry Collection by Hilton

The Lodge at Healdsburg, Tapestry Collection by Hilton
4.0 star property
Healdsburg
9.0 out of 10, Wonderful, (576)
The price is P9,234
P10,730 total
includes taxes & fees
Nov 15 - Nov 16
The Lodge at Healdsburg, Tapestry Collection by Hilton
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

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 Mazzocco Winery. 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.