Photo by Shannon Willitts

Search and Rent Middletown Condos

Start date: Check-in selected.
To Date
End date: Check-out
    bundle and save illustration

    Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
    one key illustration

    OneKeyCash

    Earn OneKeyCash on all your eligible bookings
    ftc illustration

    Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Oct 3 - Oct 5
In two weeks
Oct 10 - Oct 12
In one month
Oct 24 - Oct 26
In two months
Nov 21 - Nov 23

Condo Rentals in Middletown

Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
Exterior

Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6

9.2 out of 10, Wonderful, (43)
"Very well maintained"
$510 nightly
The price is $564
Oct 7 - Oct 8
Total with taxes and fees
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
Vino Blanco by Avantstay Private Wine Country Home w/ Mtn Views & Deck
House (4 Bedrooms) | Interior

Vino Blanco by Avantstay Private Wine Country Home w/ Mtn Views & Deck

3.5 star property
Vino Blanco by Avantstay Private Wine Country Home w/ Mtn Views & Deck
WorldMark Windsor - 2 Bedroom
Exterior

WorldMark Windsor - 2 Bedroom

2.0 star property
8.6 out of 10, Excellent, (8)
"WorldMark Windsor is a perfect location for wine tasting in the Sonoma area and easy access to the Redwoods and Pacific Coast. We appreciate the amenities as well - full, sized kitchen, 2 bedrooms and 2 full baths. We will stay here again!"
WorldMark Windsor - 2 Bedroom
Stylish Condo Steps from St. Helena Wineries & Downtown
Property grounds

Stylish Condo Steps from St. Helena Wineries & Downtown

9.8 out of 10, Exceptional, (7)
"This is a solid value with a great location in St Helena!"
Stylish Condo Steps from St. Helena Wineries & Downtown
León by Avantstay Private Breathtaking Character Cottage w/ Pool & Hot Tub
Outdoor pool

León by Avantstay Private Breathtaking Character Cottage w/ Pool & Hot Tub

3.5 star property
10.0 out of 10, Exceptional, (1)
"Beautiful home with excellent set up. Spacious, comfortable and in a safe private location. We used the hot tub as it was winter when we came and it was wonderful. Everything was very clean and in working condition. "
León by Avantstay Private Breathtaking Character Cottage w/ Pool & Hot Tub
Mataro by Avantstay Large & Elegant Home in Santa Rosa w/ Hot Tub & Games
Terrace/patio

Mataro by Avantstay Large & Elegant Home in Santa Rosa w/ Hot Tub & Games

3.5 star property
2.0 out of 10, (1)
"Property canceled our stay two days before our arrival. Awful communication and still trying to get our money back even though Avantstay canceled our accommodations on us!"
Mataro by Avantstay Large & Elegant Home in Santa Rosa w/ Hot Tub & Games
Great Wine Country and Golfing Resort Getaway!!
Outdoor dining

Great Wine Country and Golfing Resort Getaway!!

8.8 out of 10, Excellent, (3)
"The property was very clean and easy to get around. They offered many amenities and have a very nice outdoor area to hang out. "
Great Wine Country and Golfing Resort Getaway!!
WorldMark Windsor - 2 Bedroom Accessible
Exterior

WorldMark Windsor - 2 Bedroom Accessible

2.0 star property
8.8 out of 10, Excellent, (3)
"The condo was exactly as described and the queen murphy bed was comfortable. The condo was close to Santa Rosa! "
WorldMark Windsor - 2 Bedroom Accessible
WorldMark Windsor - 2 Bedroom Twin
Exterior

WorldMark Windsor - 2 Bedroom Twin

8.0 out of 10, Very Good, (1)
"Great property & comfortable accommodations. Parking was an issue at night, as its a huge complex. Check in was typical timeshare sales funnel, just be prepared to dodge them. Even still, I'd stay here again"
WorldMark Windsor - 2 Bedroom Twin
WorldMark Windsor - 1 Bedroom
Exterior

WorldMark Windsor - 1 Bedroom

2.0 star property
9.0 out of 10, Wonderful, (4)
"Very well maintained and responsive staff"
WorldMark Windsor - 1 Bedroom
WorldMark Windsor - 1 Bedroom Accessible
Exterior

WorldMark Windsor - 1 Bedroom Accessible

2.0 star property
10.0 out of 10, Exceptional, (1)
"We were celebrating our 20th wedding anniversary and enjoyed our stay. We were gifted a nice bottle of wine for our anniversary which was a pleasant surprise!"
WorldMark Windsor - 1 Bedroom Accessible
WorldMark Windsor - 2 Bedroom Twin
Exterior

WorldMark Windsor - 2 Bedroom Twin

10.0 out of 10, Exceptional, (1)
"Exactly as described. Comfortable, clean and quiet"
WorldMark Windsor - 2 Bedroom Twin
Black Oak by Avantstay Modern & Chic Santa Rosa Hideaway With Pool Table, & Fire Pit
Interior

Black Oak by Avantstay Modern & Chic Santa Rosa Hideaway With Pool Table, & Fire Pit

3.5 star property
Black Oak by Avantstay Modern & Chic Santa Rosa Hideaway With Pool Table, & Fire Pit
Wellington by Avantstay Secluded Wine Country Estate w/ Gorgeous Mtn Views
Interior

Wellington by Avantstay Secluded Wine Country Estate w/ Gorgeous Mtn Views

3.5 star property
Wellington by Avantstay Secluded Wine Country Estate w/ Gorgeous Mtn Views
WorldMark Windsor - 2 Bedroom Twin
Exterior

WorldMark Windsor - 2 Bedroom Twin

2.0 star property
8.8 out of 10, Excellent, (3)
"Great location in proximity to many wineries. Very clean and comfortable for 4 adults. "
WorldMark Windsor - 2 Bedroom Twin
Wine Country Beautiful Worldmark 2Bedroom Resort
2 bedrooms, iron/ironing board, WiFi, bed sheets

Wine Country Beautiful Worldmark 2Bedroom Resort

9.4 out of 10, Exceptional, (65)
"Great location, very clean, great amenities, perfect for a family vacation"
Wine Country Beautiful Worldmark 2Bedroom Resort
Tranquil 2-bedroom condo in Healdsburg with AC, WiFi
Property grounds

Tranquil 2-bedroom condo in Healdsburg with AC, WiFi

Tranquil 2-bedroom condo in Healdsburg with AC, WiFi
Charming 2-bedroom condo in enchanting Healdsburg with WiFi, AC
Dining

Charming 2-bedroom condo in enchanting Healdsburg with WiFi, AC

2.0 star property
Charming 2-bedroom condo in enchanting Healdsburg with WiFi, AC
Visit Beautiful California Wine Country with Style - River, Coast, Redwoods
Exterior

Visit Beautiful California Wine Country with Style - River, Coast, Redwoods

Visit Beautiful California Wine Country with Style - River, Coast, Redwoods
Clementine By Avantstay Bright Modern Retreat w/ Pool, Pool Table & Large Patio
House (4 Bedrooms) | Interior

Clementine By Avantstay Bright Modern Retreat w/ Pool, Pool Table & Large Patio

3.5 star property
Clementine By Avantstay Bright Modern Retreat w/ Pool, Pool Table & Large Patio
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middletown Hotel Reviews

Hotel La Rose

Hotel La Rose

10/10 Excellent
"Such a beautiful vintage esthetic. So glad they still have one room that has been kept original including the beautiful 4 poster bed. The staff was wonderful and I look forward to my next stay."
Suzanne 2-night trip
Posted 1 day ago
Hotel La Rose

Find out more about Middletown

Find out more about Middletown

Middletown Condo Rentals information

Number of reviews
72
Accommodation
39 Condo Rentals
Lowest Price
$564
Highest Price
$564

Explore a world of travel with Expedia

Explore a world of travel with Expedia