A calm river with clear water, surrounded by dense greenery and trees.

Search Hotels with Pool in Middletown

  • 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 Middletown Hotels with Pool

Our top choices for Middletown hotels with a pool

Outdoor pool, open 9:00 AM to 9:00 PM, pool loungers

Geyserville Inn

Geyserville Inn
3.5 star property
Geyserville
9.2 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Lounge poolside at this vineyard-view hotel, where the outdoor pool and hot tub offer a serene retreat amid wine country splendour.
The price is ฿4,495
฿5,583 total
includes taxes & fees
27 Jul - 28 Jul
Geyserville Inn
Sauna

El Bonita Motel

El Bonita Motel
3.0 star property
Thoman
9.2 out of 10, Wonderful, (1,011 reviews)
  • cleanliness
    Savour summer bliss with a sparkling pool sanctuary where holiday vibes meet wine country comfort.
The price is ฿5,406
฿6,217 total
includes taxes & fees
29 Jul - 30 Jul
El Bonita Motel
Outdoor pool

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, (1,336 reviews)
  • cleanliness
    Refresh poolside with panoramic views, hot tub delights, and a sauna that elevates relaxation at this wine country retreat.
The price is ฿3,479
฿3,966 total
includes taxes & fees
16 Aug - 17 Aug
Holiday Inn Express® Windsor Sonoma Wine Country by IHG
Outdoor pool, open 9:00 AM to 10 PM, pool umbrellas, pool loungers

The Inn on Pine

The Inn on Pine
3.0 star property
Calistoga
9.6 out of 10, Exceptional, (1,001 reviews)
  • cleanliness
    Escape to a heated outdoor pool retreat with a hot tub sanctuary in Calistoga's wine country.
The price is ฿5,095
฿5,859 total
includes taxes & fees
21 Jul - 22 Jul
The Inn on Pine
Exterior

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, (1,000 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 ฿4,503
฿5,142 total
includes taxes & fees
9 Aug - 10 Aug
Hampton Inn & Suites Windsor - Sonoma Wine Country
Outdoor pool

Hampton Inn & Suites Santa Rosa Sonoma Wine Country

Hampton Inn & Suites Santa Rosa Sonoma Wine Country
2.5 star property
Santa Rosa
9.4 out of 10, Exceptional, (549 reviews)
  • cleanliness
    Float in tranquil waters at this wine country hotel, boasting a sun-drenched outdoor pool and a state-of-the-art gym.
The price is ฿4,654
฿5,399 total
includes taxes & fees
2 Aug - 3 Aug
Hampton Inn & Suites Santa Rosa Sonoma Wine Country
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
3.0 star property
Healdsburg
8.2 out of 10, Very good, (1,001 reviews)
  • cleanliness
    Dive into sun-soaked relaxation with an outdoor pool, bicycles, and vineyard tours nearby.
The price is ฿4,232
฿4,917 total
includes taxes & fees
5 Aug - 6 Aug
Dry Creek Inn MOD Collection by Sonesta
Outdoor pool, pool loungers

Best Western Plus Wine Country Inn & Suites

Best Western Plus Wine Country Inn & Suites
2.5 star property
Santa Rosa
8.0 out of 10, Very good, (1,001 reviews)
  • cleanliness
    Sparkling outdoor pool retreat with comfortable loungers offers refreshing relaxation in the heart of wine country.
The price is ฿4,387
฿5,097 total
includes taxes & fees
28 Jul - 29 Jul
Best Western Plus Wine Country Inn & Suites
Seasonal outdoor pool

Hillside Inn

Hillside Inn
2.5 star property
Santa Rosa
7.4 out of 10, Good, (411 reviews)
  • cleanliness
    Seasonal outdoor pool creates refreshing summer escapes at this charming motel.
The price is ฿3,436
฿3,985 total
includes taxes & fees
19 Jul - 20 Jul
Hillside Inn
Outdoor spa tub

La Quinta Inn & Suites Santa Rosa Sonoma

La Quinta Inn & Suites Santa Rosa Sonoma
3.0 star property
Santa Rosa
9.0 out of 10, Wonderful, (1,129 reviews)
  • cleanliness
    Splash into sunshine at this modern hotel with a refreshing outdoor pool area for leisurely dips.
The price is ฿4,806
฿5,584 total
includes taxes & fees
19 Jul - 20 Jul
La Quinta Inn & Suites Santa Rosa Sonoma
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 Middletown

Breakfast included
4 stars

Top Middletown Hotel Reviews

Dry Creek Inn MOD Collection by Sonesta

Dry Creek Inn MOD Collection by Sonesta

10/10 Excellent
"Great property and location near the hwy and 1 mile from the square. Nice pool but didn’t bring my trunks but next time. The room was very spacious and big bed and bathroom. Great Suite overall !"
Alex 1-night trip
Posted 6 hours ago
Dry Creek Inn MOD Collection by Sonesta

Frequently asked questions

What are some accommodation options with pools in Middletown?
The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel: Hotel located near Charles M. Schulz Museum. Features full, an outdoor pool and complimentary wireless Internet access. Hotel La Rose: Hotel located near Calistoga Hot Springs. Provides a full-service spa, 6 outdoor swimming pools and 5 hot tubs. Solage, Auberge Collection: Hotel located near Healdsburg Plaza. Features complimentary wireless Internet access, an outdoor pool and flat-screen televisions. Dry Creek Inn MOD Collection by Sonesta: Hotel located near Sonoma County Fairgrounds. Offers a full-service spa, 2 outdoor swimming pools and 2 bars. Flamingo Resort & Spa Santa Rosa Sonoma, Tapestry by Hilton: Hotel located near Sonoma County Fairgrounds. Features 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, Rabbit Hill Preserve and Beaver Creek Vineyards 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 that offers an outdoor pool if you'll be visiting Middletown in the hottest months of July, August or September, when the average temperature is 21°C. Accommodation with an indoor pool may be the way to go if you visit during the coldest months of December, January or February, when the average temp is 9°C.