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Find Hotels with a Pool in Middletown, CA

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Check availability on Middletown Hotels with a Pool

Tonight
Dec 20 - Dec 21
Tomorrow
Dec 21 - Dec 22
Next weekend
Dec 26 - Dec 28
In two weeks
Jan 2 - Jan 4

Our top choices for Middletown hotels with a pool

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, (1263)
"Breakfast bar was amazing. Holiday decorations were really planned out and looked amazing at night. "
United States
Joel
The price is ￥14,986
￥17,084 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Holiday Inn Express® Windsor Sonoma Wine Country by IHG
Exterior
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, (1001)
"Breakfast and staff is friendly "
United States
Kimbinh
The price is ￥15,911
￥18,170 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Hampton Inn & Suites Windsor - Sonoma Wine Country
Exterior
Geyserville Inn

Geyserville Inn

Geyserville Inn
3.5 star property
Geyserville
9.2 out of 10, Wonderful, (1000)
"Friendly staff and clean comfortable rooms. We enjoyed the breakfast at the restaurant next door. "
United States
Jill
The price is ￥19,792
￥24,690 total
includes taxes & fees
Dec 22 - Dec 23
Geyserville Inn
Seasonal outdoor pool
Skylark Shores Resort

Skylark Shores Resort

Skylark Shores Resort
2.5 star property
Lakeport
8.2 out of 10, Very Good, (865)
"Great place to stay!"
United States
Russell
The price is ￥15,124
￥18,571 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Skylark Shores Resort
Sauna
El Bonita Motel

El Bonita Motel

El Bonita Motel
3.0 star property
St. Helena
9.2 out of 10, Wonderful, (1001)
"Great location, clean room, quiet and perfect for our stay!"
United States
Michele
The price is ￥18,219
￥20,951 total
includes taxes & fees
Jan 6 - Jan 7, 2026
El Bonita Motel
Indoor pool, sun loungers
Golden Haven Hot Springs

Golden Haven Hot Springs

Golden Haven Hot Springs
2.5 star property
Calistoga
9.4 out of 10, Exceptional, (945)
"great stay"
United States
Ilya
The price is ￥21,154
￥24,326 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Golden Haven Hot Springs
Courtyard
Flamingo Resort & Spa Santa Rosa Sonoma, Tapestry by Hilton

Flamingo Resort & Spa Santa Rosa Sonoma, Tapestry by Hilton

Flamingo Resort & Spa Santa Rosa Sonoma, Tapestry by Hilton
4.0 star property
Santa Rosa
8.4 out of 10, Very Good, (1001)
"Great rooms!"
United States
silvana
The price is ￥16,687
￥26,473 total
includes taxes & fees
Dec 29 - Dec 30
Flamingo Resort & Spa Santa Rosa Sonoma, Tapestry by Hilton
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, (2114)
"Fast friendly check in, clean comfortable room, good breakfast options, would definitely stay here again "
United States
Narayan
The price is ￥14,191
￥16,489 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, (447)
"Great stay easy in and out.... "
United States
Craig
The price is ￥16,040
￥18,606 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Hampton Inn & Suites Santa Rosa Sonoma Wine Country
Outdoor pool
Vineyard Country Inn

Vineyard Country Inn

Vineyard Country Inn
3.5 star property
St. Helena
9.2 out of 10, Wonderful, (729)
"Breakfast was ok and parking was good. Bed was comfortable and room was clean "
United States
Darlene
The price is ￥24,984
￥28,732 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Vineyard Country Inn
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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Top Middletown Hotel Reviews

Frequently asked questions

What are some accommodations with pools in Middletown?
The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel: Features full, an outdoor pool, and free self parking. El Bonita Motel: Offers a sauna, an outdoor pool, and daily. Solage, Auberge Collection: Hotel located near Calistoga Hot Springs. Provides a full-service spa, 6 outdoor pools, and 5 hot tubs. Flamingo Resort & Spa Santa Rosa Sonoma, Tapestry by Hilton: Features a full-service spa, 2 outdoor pools, and 2 bars. La Quinta Inn & Suites Santa Rosa Sonoma: Offers a snack bar/deli, an outdoor pool, and buffet.
What is there to see and do in Middletown?
Take in the natural beauty with a stop at Boggs Mountain Demonstration State Forest. Discover sights such as Twin Pine Casino, Robert Louis Stevenson State Park, and Rabbit Hill Preserve during your stay.
When is the best time to book a hotel with a pool in Middletown?
You may want to consider a place to stay with an outdoor swimming pool if you plan to visit Middletown in the hottest months of July, August, or September when the average temp is 70°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 temp is 48°F.