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

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
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, (39)
"The location is very convenient to Kendall-Jackson and many other vineyards. The condo was clean and comfortable for a one night stay. We weren’t there long enough to speak to other details aside from comfortable beds. We weren’t aware that this was a vacation club condo complex and the very hard sell we would be met with. We had flown cross country all day then a drive up from San Francisco. All we wanted was to settle in and grab some dinner. The town of Windsor was fabulous and we enjoyed...
The price is AED 1,377
AED 2,780 total
includes taxes & fees
30 Nov - 1 Dec
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
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
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!!
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
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, (4)
"We needed to stay close to family and were able to spend time with them. Also getting to the airport lead so convenient. "
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
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
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.
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
WorldMark Windsor - 3 Bedroom Deluxe
Windsor_pool_S
WorldMark Windsor - 3 Bedroom Deluxe
2.0 star property
WorldMark Windsor - 3 Bedroom Deluxe
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 comfy setting. Nice, quite location. Exceptional view and amenities. The dock area was wonderful but the bbq/picnic area was amazing! Loved the cottages and the atmosphere. Bob was an amazing host who very forth coming with information and his kindness was top notch. The cleaning ladies made sure the place was spectacular and stocked up. "
The price is AED 511
AED 569 total
includes taxes & fees
23 Nov - 24 Nov
Clear Lake Cottages & Marina
The St. Helena House - Within Walking Distance To Downtown. Permit # PL23-018
View from Vineyard
The St. Helena House - Within Walking Distance To Downtown. Permit # PL23-018
10.0 out of 10, Exceptional, (222)
"We wanted to introduce friends from East Coast to the Napa Valley- history to modern day. This rare restored farmhouse with views of vineyards was ideal. Authentic, comfortable (with just the right amount of modern amenities but not too much to destroy the charm), spacious, wonderfully furnished, with superb kitchen (fully stocked), and screened porches, etc. The hosts were easy to communicate with and would stay again in a heartbeat. We have stayed at 60+ rentals around the world... this unique...
The St. Helena House - Within Walking Distance To Downtown. Permit # PL23-018
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, (219)
"The house was great and the location is super! The sound system in the house was a little challenging for us "old folks", but we made it work!! Would go back again for sure!"
The price is AED 6,060
AED 7,680 total
includes taxes & fees
23 Nov - 24 Nov
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
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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