Search Cottages in Middletown

"We thoroughly loved staying here!!!"

"We recently stayed at Chalk Hill Cottage with our two little Yorkies. The property was the perfect size and had first class amenities. The location is awesome, too! The Hosts are quick to respond to questions and are very kind and considerate. We recommend highly!"

"The property had a fully stocked kitchen and close to downtown Santa Rosa but not a walkable distance. My family was very comfortable there and even enjoyed the game room/garage."

"Sunny View Cottage is comfortable, well-equipped, and charming. The location is quiet and rural but very close to great wineries, restaurants (we loved Walter Hansel’s Bistro, just around the corner), and hiking/biking trails. We would definitely stay here again next time we are in the area."

"This is a sweet cottage in a great location-easy access to downtown and other area destinations."

"We liked the house. Everything is very convenient. The views are nice. The birds songs are impressing."

"Charming clean and super well located."

"It’s a small and humble home in a historic neighborhood. A lot of love has been poured into it, and it was such a charming place to stay while we explored the Santa Rosa area! The appliances are modern and pro grade, the bathroom and shower are perfect size, and the hot tub is even placed to provide good privacy during the evening. Definitely a place we will refer our friends and family to!"

"This cottage was by far one of best we have stayed in. Immaculate, charming, everything we needed. Lovely!"

"We loved everything about our stay at WCR! Check in was easy, the apartment was so clean and perfectly appointed, the neighborhood was safe, and check out was a breeze. The location was perfect for splitting our time between Sonoma and Napa. Thank you, Jacqui, for having us as guests!"

"A PERFECT 2 bdrm home in the heart of Dry Creek Valley. The home was wonderfully appointed and the outdoor space terrific! Better even the the online pictures. Minutes from both Healdsburg and Geyserville, the location couldn't be better. We will definitely stay here again."

"Nestled among the trees, with a lovely backyard and pool. You really feel away from it all and you can enjoy the beauty of the wine country! The house was very comfortable and well stocked with pans etc. that you'd need to cook. I would definitely recommend it! The only thing that wasn't clear was how to get into the house."

"Such a wonderful stay! Property is meticulously maintained and communication with the owner outstanding. Very private and rural feel but you still benefit from central location to downtown Healdsburg. We definitely recommend!"

"We loved everything about our stay on Fitch Street. The house was cute and comfortable and was the perfect jumping off point for our month in Healdsburg. We would definitely stay there again!"

"Great cottage within walking distance to downtown Calistoga."

"The cottage was our base for a few days of touring wine country. The cottage is a lovely hide-away in a quiet neighborhood. Due to the weather, we didn't take advantage of the outside amenities. The kitchen is well equipped. There were a few minor maintenance issues that have been reported to the property manager. Note: The upper parking spot is quite steep and your car may bottom out when entering or leaving."

"Second time at this property- it’s quiet and relaxing. The pool and hot tub felt amazing after a long day of exploring."

"Super charming, very comfortable home - just a short stroll away from the main square. Made a great base for our family visit."

"Loved this house for a weekend getaway. We loved taking advantage of the deck, grill, and river access. Short drive to the town square and wineries."

"Fished a tournament this week on clear lake it was a perfect spot for a group of guys to stay and be close to the lake"

"12 of us traveled to Napa for my 40th birthday and we had THE BEST trip ever. The accommodations were lovely, spacious, clean and luxurious. The concierge was so responsive and helpful. The chefs were fantastic. I'd highly recommend this property. As a frequent traveler, I've stayed in many luxury rentals and this was by far my favorite."

"Beautiful home - extremely clean- the kitchen was well equipped and beautiful! Comfortable beds beds- nice sheets. Very private backyard- nice to sit out and visit and enjoy a bottle of wine. There were 4 of us- two couples. Close walking distance to restaurants and shops. Really enjoyed it. The only thing we would have liked was if there were TV’s in all the bedrooms- not just the Main bedroom. Perfect place to stay in St Helena! ❤️"

"Incredible experience!"