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Condo Rentals in Middletown

WorldMark Windsor - 2 Bedroom Accessible
Stunning hotel with a classic facade, featuring a central courtyard and elegant balconies.

WorldMark Windsor - 2 Bedroom Accessible

2.0 star property
10.0 out of 10, Exceptional, (2)
"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
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
Stunning hotel with a traditional facade, surrounded by lush lawns and mature trees.

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

9.2 out of 10, Wonderful, (43)
"Very well maintained"
$507 nightly
The price is $561
Aug 17 - Aug 18
Total includes 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
Experience the classic charm of this hotel, surrounded by serene lawns and a central courtyard.

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
WorldMark Windsor - 2 Bedroom Twin
Stunning hotel with a classic facade, featuring a central courtyard and elegant balconies.

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
León by Avantstay Private Breathtaking Character Cottage w/ Pool & Hot Tub
Enjoy a serene poolside retreat surrounded by lush greenery and a well-maintained lawn.

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
WorldMark Windsor - 2 Bedroom Twin
Experience the classic charm of this hotel, featuring a central courtyard and beautifully manicured lawns.

WorldMark Windsor - 2 Bedroom Twin

2.0 star property
8.0 out of 10, Very Good, (2)
"Nice. "
WorldMark Windsor - 2 Bedroom Twin
Great Wine Country and Golfing Resort Getaway!!
Enjoy al fresco dining and relaxation in this outdoor patio area, featuring a barbecue grill and comfortable seating.

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 Twin
Experience the classic charm of this hotel, featuring a central courtyard and beautifully maintained grounds.

WorldMark Windsor - 2 Bedroom Twin

10.0 out of 10, Exceptional, (1)
"Exactly as described. Comfortable, clean and quiet"
WorldMark Windsor - 2 Bedroom Twin
Mataro by Avantstay Large & Elegant Home in Santa Rosa w/ Hot Tub & Games
Relax by the fire pit surrounded by comfortable seating under a charming pergola.

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
Stylish Condo Steps from St. Helena Wineries & Downtown
Property grounds

Stylish Condo Steps from St. Helena Wineries & Downtown

9.6 out of 10, Exceptional, (5)
"This is a solid value with a great location in St Helena!"
Stylish Condo Steps from St. Helena Wineries & Downtown
Tranquil 2-bedroom condo in Healdsburg with AC, WiFi
Relax in a serene patio surrounded by lush greenery and a beautifully manicured lawn.

Tranquil 2-bedroom condo in Healdsburg with AC, WiFi

Tranquil 2-bedroom condo in Healdsburg with AC, WiFi
Black Oak by Avantstay Modern & Chic Santa Rosa Hideaway With Pool Table, & Fire Pit
Relax in a serene backyard with a hot tub, barbecue grill, and comfortable lounge chairs.

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
WorldMark Windsor - 1 Bedroom Accessible
Guests can enjoy balconies with outdoor space on each floor.

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
Charming 2-bedroom condo in enchanting Healdsburg with WiFi, AC
Enjoy meals in the dining area with a round table and four chairs.

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

Charming 2-bedroom condo in enchanting Healdsburg with WiFi, AC
Wine Country Beautiful Worldmark 2Bedroom Resort
Enjoy a restful stay in this cozy room with a comfortable bed, bedside table, and window offering a view of lush surroundings.

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
WorldMark Windsor - 1 Bedroom
Experience the charm of this classic hotel, featuring a central courtyard and elegant balconies on each floor.

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
Charming 1 bedroom Cabin with King bed, Queen Sofa Sleeper, WIFI, Kitchen, Deck
Kitchen features a sink, microwave, stove, and dishwasher, with a window for natural light.

Charming 1 bedroom Cabin with King bed, Queen Sofa Sleeper, WIFI, Kitchen, Deck

Charming 1 bedroom Cabin with King bed, Queen Sofa Sleeper, WIFI, Kitchen, Deck
Visit Beautiful California Wine Country with Style - River, Coast, Redwoods
Stunning hotel with a classic facade, featuring a central courtyard and beautifully manicured gardens.

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

Visit Beautiful California Wine Country with Style - River, Coast, Redwoods
Wellington by Avantstay Secluded Wine Country Estate w/ Gorgeous Mtn Views
Stunning entrance with a stone archway and gravel pathway, surrounded by beautifully landscaped gardens and large windows.

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
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

Holiday Inn Express® Windsor Sonoma Wine Country by IHG

Holiday Inn Express® Windsor Sonoma Wine Country by IHG

10/10 Excellent
"The front desk attendant Matt was very helpful and nice! "
Tanya 1-night trip
Posted 16 hours ago
Holiday Inn Express® Windsor Sonoma Wine Country by IHG