Search Middletown Cottage Rentals from CA $264

"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!"

"We went to Healdsburg to visit friends and enjoy the sunny weather. We were delighted with the beautiful vineyard views and comfortable cottage, spacious deck, and many other amenities that the host provided. Being in nature was so relaxing that we spent most of our time at the cottage."

"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."

"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."

"We have stayed in Healdsburg before but this is our first time at this property. It won’t be our last. Great location- easy walk to the center of Healdsburg. Cottage is perfect size and amenities. Great hosts. Thank you!"

"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."

"Highly recommend. This was my first time booking in Calistoga and I was very impressed. Beautiful and quiet cottage that makes you feel very comfortable. Easy access to downtown by foot or by car. Beautiful fountain and many beautiful flowers surrounding the property make it even more inviting."

"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."

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

"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."

"3 sisters get together annually to catch up. This is the perfect location with plenty of things to do, places to go and restaurants."

"The Backyard Garden Oasis was quiet and secluded. We enjoyed walking along the quiet street in the morning. The owner is a helpful host. "

"Clean and comfortable"

"When you walked in, the house is very open and welcoming. They have everything that you need, no need to run to store for shampoo/conditional. Kitchen has all the appliances. Beds are comfortable and clean. A great getaway for girls or family trips. We would definitely come back."

"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!"