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Compare 29 Condo Rentals in Middletown with updated reviews, rates, and availability.

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

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

9.2 out of 10, Wonderful, (40)
"The property was beautiful with many amenities. We would gladly stay there again. Close to freeway, and short drive to shopping, wineries, and breweries. Less than a 12 minute drive to Healdsburg. "
The price is SAR 864
SAR 2,128 total
includes taxes & fees
2 Jan - 3 January 2025
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
Worldmark Windsor, Beautiful Wine Country 2BR 2Bath Sleep6 Resort Condos

Worldmark Windsor, Beautiful Wine Country 2BR 2Bath Sleep6 Resort Condos

3.0 star property
8.4 out of 10, Very Good, (8)
"Enjoyed location and proximity to Healdsburg."
Worldmark Windsor, Beautiful Wine Country 2BR 2Bath Sleep6 Resort Condos
Stylish Condo Steps from St. Helena Wineries & Downtown
Interior

Stylish Condo Steps from St. Helena Wineries & Downtown

9.6 out of 10, Exceptional, (4)
"I could not have asked for a better location. Quiet neighborhood, clean, comfy beds and linens, and it looks just like the pictures. We walked to Model bakery in the mornings for their wonderful English muffins. Found a hidden gem tasting room called Hayfork right around the corner (behind Clif Family)that does free tastings on Fridays! Excellent wine! And of course we got in a burger at Gotts. The location makes it easy to walk to Main Street with lots of restaurants and shopping. There...
Stylish Condo Steps from St. Helena Wineries & Downtown
Wine Country Beautiful Worldmark 2Bedroom Resort
Pool

Wine Country Beautiful Worldmark 2Bedroom Resort

9.4 out of 10, Exceptional, (65)
"A comfortable, up-to-date alternative to hotels in the area, with plenty of resort-style and family-friendly amenities."
Wine Country Beautiful Worldmark 2Bedroom Resort
León by Avantstay Private Breathtaking Character Cottage w/ Pool & Hot Tub
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
Wellington by Avantstay Secluded Wine Country Estate w/ Gorgeous Mtn Views
Exterior

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

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

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
Worldmark Windsor, Beautiful Wine Country 2BR 2Bath Sleeps6 NICE!

Worldmark Windsor, Beautiful Wine Country 2BR 2Bath Sleeps6 NICE!

9.6 out of 10, Exceptional, (27)
"Very nice and convenient place. Only hiccup was checking in. It was to be available at 4 pm. Did not get our room till 7 pm"
Worldmark Windsor, Beautiful Wine Country 2BR 2Bath Sleeps6 NICE!
Great Wine Country and Golfing Resort Getaway!!
Exterior

Great Wine Country and Golfing Resort Getaway!!

8.0 out of 10, Very Good, (2)
"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 - 1 Bedroom
Windsor_pool_3_S

WorldMark Windsor - 1 Bedroom

2.0 star property
9.0 out of 10, Wonderful, (2)
"The condo was very clean and had everything needed for a relaxing stay. The pool was also wonderful with no overcrowding! "
WorldMark Windsor - 1 Bedroom
Visit Beautiful California Wine Country with Style - River, Coast, Redwoods
Pool

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

Visit Beautiful California Wine Country with Style - River, Coast, Redwoods
WorldMark Windsor - 2 Bedroom Twin
Windsor_pool_S

WorldMark Windsor - 2 Bedroom Twin

2.0 star property
8.0 out of 10, Very Good, (1)
"Very clean, convenient location, good facilities. Comfortable beds. Well equipped kitchen. Pool was a good size, hot tubs and pool open till 10 pm which was nice after a long day. I had only 2 issues, one that there was no free wifi. I was told before I booked that it would be free for my unit but was given no info. on how to access it for free, Apparently I needed some info. that no one was able to give me so I ended up having to pay for it. And the second of course is the pressure...
WorldMark Windsor - 2 Bedroom Twin
WorldMark Windsor - 2 Bedroom
Windsor_pool_3_S

WorldMark Windsor - 2 Bedroom

2.0 star property
9.6 out of 10, Exceptional, (5)
"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
Black Oak by Avantstay Modern & Chic Santa Rosa Hideaway With Pool Table, & Fire Pit
Living area

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
Estrella by Avantstay Secluded Spanish-style Estate on 7 Acres of Vineyards
Pool

Estrella by Avantstay Secluded Spanish-style Estate on 7 Acres of Vineyards

3.5 star property
Estrella by Avantstay Secluded Spanish-style Estate on 7 Acres of Vineyards
Clementine By Avantstay Bright Modern Retreat w/ Pool, Pool Table & Large Patio
Pool

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
Bennett Valley home is a great location to explore Sonoma Valley.
Exterior detail

Bennett Valley home is a great location to explore Sonoma Valley.

Bennett Valley home is a great location to explore Sonoma Valley.
WorldMark Windsor - 2 Bedroom Twin
Windsor_pool_S

WorldMark Windsor - 2 Bedroom Twin

WorldMark Windsor - 2 Bedroom Twin
Charming 2-bedroom condo in enchanting Healdsburg with WiFi, AC
Living area

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

Charming 2-bedroom condo in enchanting Healdsburg with WiFi, AC
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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Other property types in Middletown

Clear Lake Cottages & Marina
Outdoor pool

Clear Lake Cottages & Marina

2.5 star property
9.0 out of 10, Wonderful, (288)
"Very clean"
The price is SAR 485
SAR 540 total
includes taxes & fees
23 Dec - 24 Dec
Clear Lake Cottages & Marina
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
Family / Kitchen

Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021

10.0 out of 10, Exceptional, (220)
"Great place and good location to host 4 couples to celebrate our 50th birthdays. Thank you!"
The price is SAR 6,198
SAR 7,919 total
includes taxes & fees
29 Dec - 30 Dec
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
The St. Helena House - Within Walking Distance To Downtown. Permit # PL23-018
Exterior

The St. Helena House - Within Walking Distance To Downtown. Permit # PL23-018

10.0 out of 10, Exceptional, (223)
"Our family stayed at the St. Helena House while attending a memorial. The house exceeded our expectations. It was beautifully decorated, comfortable, and homey with many wonderful nooks to read, views of the vineyards out of every window, and a beautiful well stocked kitchen. The beds were very comfortable. The bathrooms were fine with fluffy towels and plenty of hot water with good water pressure in the showers. The owner was very welcoming and available for any questions. It rained all...
The St. Helena House - Within Walking Distance To Downtown. Permit # PL23-018
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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