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

Chalk Hill Cottage Close to Wineries

Chalk Hill Cottage Close to Wineries

9.8 out of 10, Exceptional, (30)
"Location is excellent, property is clean and quiet, and hosts were very responsive. This is our second time at this cottage and look forward to staying here again. "
Chalk Hill Cottage Close to Wineries
Santini Farmhouse -- Beautiful Italian style Villa, Hot Tub, Vineyard Views

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

10.0 out of 10, Exceptional, (39)
"The Santini Farmhouse was perfect for our girls-weekend-getaway! The house was spotless and had everything we needed (including instructions how to work everything and a great info book for all local amenities). After a hard day touring wineries the hot tub was a perfect place to unwind. ;) It's a peaceful location in beautiful wine country. Highly recommend!"
Santini Farmhouse -- Beautiful Italian style Villa, Hot Tub, Vineyard Views
Newly Refurbished! Nest Cottage at ru's Farm.
Exterior

Newly Refurbished! Nest Cottage at ru's Farm.

9.8 out of 10, Exceptional, (158)
"And well managed...."
Newly Refurbished! Nest Cottage at ru's Farm.
Heron House--The River House in the Redwoods

Heron House--The River House in the Redwoods

10.0 out of 10, Exceptional, (21)
"We had a fabulous stay. Great house with a great location. It was lovely waking up and going outside to enjoy the river and woods around us. 5 min drive from Healdsburg main streets with great stores and restaurants. Enjoyed our drive to the coast, redwoods, and vineyards! Would stay again!"
Heron House--The River House in the Redwoods
Mill Creek by Avantstay Modern Design, Patio, Hot Tub
Terrace/patio

Mill Creek by Avantstay Modern Design, Patio, Hot Tub

3.0 star property
Mill Creek by Avantstay Modern Design, Patio, Hot Tub
Enjoy a Slice Of Country--Two miles to Downtown Healdsburg
Deck seating area

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

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

9.4 out of 10, Exceptional, (74)
"Cute, cozy studio for a quick getaway on the Russian River. Short 5 min drive into town."
Vineyard view studio by Russian River w/ private balcony, patio, grill, & WiFi
Healdsburg Cottage Walk to the Plaza, Workspace
Healdsburg Cottage entrance

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

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 — 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
Russian Riverside Cottage in Healdsburg
Outside main level deck

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
Private 1-bedroom Guest House with Great Amenities
Outdoor dining

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

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
Chalet entrance

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
Downtown Healdsburg Wine Country Retreat

Downtown Healdsburg Wine Country Retreat

9.6 out of 10, Exceptional, (4)
"Nice large one bedroom home in good location. I would stay there again."
Downtown Healdsburg Wine Country Retreat
Wine Country Cottage sleeps 4, Healdsburg, Spa
Outdoor dining

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
Chic wine country cottage and garden
Enjoy the bright and airy kitchen with quartz countertops. Fully stocked.

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
Peaceful Windsor Retreat w/ Private Hot Tub!
Property grounds

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
Beautiful cottage on Fitch Mountain. Star Jasmine covered front porch.

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
Milk barn Magic: Vineyard Escape with 2 Bedrooms
Cozy bedroom featuring a comfortable queen bed, abundant natural sunlight.

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 AED 867
AED 1,951 total
includes taxes & fees
2 Jan - 3 Jan
Milk barn Magic: Vineyard Escape with 2 Bedrooms
Cozy Wooded Cottage of Guerneville

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
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

✨Rustic Cabin in Dry Creek Valley with beautiful views // 5 miles to Plaza ✨
✨Enjoy cooking together in the kitchen ✨

✨Rustic Cabin in Dry Creek Valley with beautiful views // 5 miles to Plaza ✨

10.0 out of 10, Exceptional, (280)
"Charming cabin among the vineyard. Very comfortable, host is very informative. Love the location close to Healdsburg. This was our second visit, we hope to return again."
✨Rustic Cabin in Dry Creek Valley with beautiful views // 5 miles to Plaza ✨
Healdsburg Wine Country Getaway with Panoramic Valley Views -5 min from downtown
Bliss House Panorama View 1

Healdsburg Wine Country Getaway with Panoramic Valley Views -5 min from downtown

10.0 out of 10, Exceptional, (231)
"I highly recommend to stay here and eat at the recommended restaurants. We are 3 out of 7 of the recommendations in the house binder. The house is cozy, updated, immaculate and beautiful."
Healdsburg Wine Country Getaway with Panoramic Valley Views -5 min from downtown
Chalk Hill Cottage Close to Wineries

Chalk Hill Cottage Close to Wineries

9.8 out of 10, Exceptional, (30)
"Location is excellent, property is clean and quiet, and hosts were very responsive. This is our second time at this cottage and look forward to staying here again. "
Chalk Hill Cottage Close to Wineries
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 — 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?
You’ll find 23 cottages in Healdsburg. No matter if you’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 you’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 Expedia’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.