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Compare 23 Cottages in Healdsburg with updated reviews, rates, and availability.

Vineyard view studio by Russian River w/ private balcony, patio, grill, & WiFi

9.4 out of 10, Exceptional, (75)
"Overall I would say our stay was quite pleasant and the property was located near all of the needed amenities. Only negatives were the lighting in the kitchen was basically nonexistent. I know this is a known issue but it really needs to be fixed. Also kitchen equipment was a bit lacking "
Vineyard view studio by Russian River w/ private balcony, patio, grill, & WiFi

Healdsburg Cottage Walk to the Plaza, Workspace

10.0 out of 10, Exceptional, (222)
"Great location just as advertised. The cottage had everything we needed and was very clean. We both thought the bed was really comfortable. "
Healdsburg Cottage Walk to the Plaza, Workspace

Chalk Hill Cottage Close to Wineries

9.8 out of 10, Exceptional, (31)
"We spent 3 nights at Beaux Maison Sonoma Cottage and my wife and I loved it. Very comfy, well equipped and loved the fire pit it the evenings. And the location was great too - on Chalk Hill Road, so in the country but only 15 minutes from Healdsburg and close to many wineries. And only 35 minutes to Calistoga. For future trips for just the two of us, would definitely try to stay again!"
Chalk Hill Cottage Close to Wineries

Newly Refurbished! Nest Cottage at ru's Farm.

9.8 out of 10, Exceptional, (159)
"We had a wonderful experience in the cozy cottage. Kristen went out of her way to make it a lovely stay. Our Bella Winery tour with Mike was a great addition. "
Newly Refurbished! Nest Cottage at ru's Farm.

Enjoy a Slice Of Country--Two miles to Downtown Healdsburg

10.0 out of 10, Exceptional, (60)
"What a lovely little property! The location was great and a very short drive into town and close to many wineries. We spent every morning sitting out on the cute patio drinking coffee and listening to the birds under the beautiful trees. And it was the best stocked house we have ever stayed in! Great selection of spices for cooking and all the other essentials. Fantastic!"
Enjoy a Slice Of Country--Two miles to Downtown Healdsburg

Healdsburg Plaza Gem--Beautifully Restored 1880's Cottage Downtown

9.8 out of 10, Exceptional, (37)
"My husband and I had a wonderful week at the Carma Cottage. The location just off Healdsburg Square makes it so easy to dine, shop, and visit wineries ā€” no car needed! The house itself is very comfortable and there is an ample kitchen and dining area for nights you would rather stay in and cook. Would recommend with enthusiasm!"
Healdsburg Plaza Gem--Beautifully Restored 1880's Cottage Downtown

Heron House--The River House in the Redwoods

10.0 out of 10, Exceptional, (22)
"Home is situated in a very quiet and scenic location on the river, with a nice deck with outside dining and hot tub. Property had kayaks and other river equipment available, too. Home was clean, with a lovely kitchen and rooms. We would stay here again. "
Heron House--The River House in the Redwoods

Santini Farmhouse -- Beautiful Italian style Villa, Hot Tub, Vineyard Views

10.0 out of 10, Exceptional, (40)
"We four have traveled together for many, many years. By now, we know exactly what we are looking for in our home away from home: a open floor plan, wellequipped kitchen, cozy group seating area. Santini had all of that plus comfortables beds, outdoor grilland hot tub, and amazing outdoor space. The guest manual was the best Iā€™ve ever seen! And it was obvious our comfort and safety was important to our hosts! The location was peaceful yet close to everything- we will be back!!"
Santini Farmhouse -- Beautiful Italian style Villa, Hot Tub, Vineyard Views

Fitch St Escape! 2 BDRM Bungalow only blocks from the Plaza!

10.0 out of 10, Exceptional, (4)
"The house is deceiving...it looks like a small bungalow but has a beautiful addition that includes a high end kitchen. The window wall at the back of the addition opens up the entire house to light and a lovely back patio and yard. The location was perfect! We walked to the plaza daily. I highly recommend this property for a visit to Healdsburg."
Fitch St Escape! 2 BDRM Bungalow only blocks from the Plaza!

Cozy cottage tucked away on a private country road

10.0 out of 10, Exceptional, (1)
"Property was exactly as described. It was fun watching sunset and sunrise from the bed at the top of the tower."
Cozy cottage tucked away on a private country road

Private 1-bedroom Guest House with Great Amenities

10.0 out of 10, Exceptional, (11)
"We just stayed at this magnificent property for a week and it was pure bliss. I can't overstate what a special place this is. Fredric and his wonderful wife were amazing hosts. They could not have been more thoughtful, or generous! The property is in a really beautiful location. It offered the perfect mix of peace and quiet, whilst still being just a short distance from all the many fabulous amenities the area has to offer. We loved the outdoor patio and the beautiful gardens! We had such a...
Private 1-bedroom Guest House with Great Amenities

Wine Country Cottage sleeps 4, Healdsburg, Spa

8.6 out of 10, Excellent, (19)
"Everything about this property was great, except the road noise. I loved the location, space, little vineyard out back. Easy walking to downtown. But the busy road was very loud all day and night, especially when asked to turn off air and open windows at night. Maybe it was harvest related."
Wine Country Cottage sleeps 4, Healdsburg, Spa

Heart of Healdsburg Cottage: Prime Location - Tuscan Cottage Near Healdsburg Sq.

10.0 out of 10, Exceptional, (1)
"The property was wonderful, would book again in a minute, it was so cute and comfortable ā¤ļøā¤ļøā¤ļø"
Heart of Healdsburg Cottage: Prime Location - Tuscan Cottage Near Healdsburg Sq.

Russian Riverside Cottage in Healdsburg

8.4 out of 10, Very Good, (8)
"We really enjoyed our stay. The communication with owner was great and we will come back again. The beach is just right there and our young adult grandchildren love it."
Russian Riverside Cottage in Healdsburg

Chic wine country cottage and garden

10.0 out of 10, Exceptional, (1)
"We absolutely loved our stay at Harold House! The house is recently renovated, beautifully decorated and well stocked with kitchen equipment and everything else you need for a great stay. There is a huge backyard with plenty of furniture, as well as a fire pit and BBQ. There is also a big garden with lots of fresh fruit, vegetables and herbs. The house is located about a 15 minute walk to the plaza, which is a walk we took almost daily. There are also walking paths nearby on Fitch mountain and...
Chic wine country cottage and garden

Mill Creek by Avantstay Modern Design, Patio, Hot Tub

3.0 star property
Mill Creek by Avantstay Modern Design, Patio, Hot Tub

Milk barn Magic: Vineyard Escape with 2 Bedrooms

10.0 out of 10, Exceptional, (11)
"Ideal for a relaxing time in wine country! The winery on property is fantastic and highly recommend it!"
The price is AEDĀ 643
AEDĀ 1,674 total
includes taxes & fees
4 Feb - 5 Feb
Milk barn Magic: Vineyard Escape with 2 Bedrooms

Cozy Wooded Cottage of Guerneville

8.0 out of 10, Very Good, (1)
"My family of 4 stayed here and it was a perfect nature retreat! Close enough to walk or drive to town, the river, and the market. The space was very open with little privacy, but that was okay for us. The back yard had privacy and the hot tub was hot! Enjoyed the space and location. Would stay again!"
Cozy Wooded Cottage of Guerneville

Peaceful Windsor Retreat w/ Private Hot Tub!

3.0 star property
9.0 out of 10, Wonderful, (2)
"We had a wonderful family stay for Easter. The landscaping is absolutely beautiful. What was particularly helpful was that kitchen cabinets were labeled with where everything was stored making it easier for cooking! One recommendation would be to have a grill on-site. The location was quiet and peaceful and easily accessible to wineries and the town of Windsor."
Peaceful Windsor Retreat w/ Private Hot Tub!

Updated Healdsburg River Cottage: Minutes from Plaza, Tasting Rooms & Vineyards

9.4 out of 10, Exceptional, (52)
"Quiet and clean! John was easy-going and helpful."
Updated Healdsburg River Cottage: Minutes from Plaza, Tasting Rooms & Vineyards
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 Healdsburg

4 BR/4 BA Vineyard Retreat - Solar Heated Pool, Spa, Views

10.0 out of 10, Exceptional, (144)
"Beautiful setting with a wonderful home. Loved the location near Healdsburg. Everything was convenient. The property manager was fantastic!"
4 BR/4 BA Vineyard Retreat - Solar Heated Pool, Spa, Views

Incredibly Beautiful, Private, Unique Home Perched On The Bluff At Ocean's Edge!

10.0 out of 10, Exceptional, (347)
"Beautiful Pacific views, a very comfortable room and a meadow with deer and other wildlife; this is The Sea Ranch!"
Incredibly Beautiful, Private, Unique Home Perched On The Bluff At Ocean's Edge!

Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard

9.8 out of 10, Exceptional, (414)
"This is the second time we have brought friends to the property. It is very clean and homey. We love sitting and watching the ocean, the fireplace was wonderful since it was cold outside. Walked on the beach and ate a few meals out. Looking forward to going back again, it is the perfect getaway!!"
Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard
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.

Frequently asked questions

How much do cottages in Healdsburg cost?
Cottages in Healdsburg range between and per night. These stays offer a chance to reconnect with nature ā€” at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Healdsburg?
Youā€™ll find 23 cottages in Healdsburg. No matter if youā€™re vacationing with the kids or planning a retreat with your best buds, Expedia can help you find the ideal place to get back to nature.
Why book your cottage in Healdsburg with Expedia?
We think that a vacay should be a walk in the park, so if youā€™re seeking cottages in Healdsburg at an affordable rate, Expedia delivers. Save cash and stay in a cheap option far from the rush of the city, or book an upscale cottage to spoil the ones you love most.
How can I find cheap cottages in Healdsburg?
With Expediaā€™s filter tool, booking cheap cottages in Healdsburg is a snap. To discover properties that are friendly on the wallet, narrow your search results by star rating, budget and amenities.