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Featured Cottages in Healdsburg and around

Healdsburg Plaza Gem--Beautifully Restored 1880's Cottage Downtown
Smart TV, books
Healdsburg Plaza Gem--Beautifully Restored 1880's Cottage Downtown
9.8 out of 10, Exceptional, (34)
"What a perfect spot from which to explore Healdsburg! The location couldn't be better for walking to everything downtown, and also to the Seghesio winery. The home is beautiful, well decorated, and stocked with everything you need in the kitchen. Good attention to detail. We thoroughly enjoyed our stay. "
Healdsburg Plaza Gem--Beautifully Restored 1880's Cottage Downtown
Creekside Cottage and Bungalow. Cozy, pet friendly, close to town. Sleeps 6
Terrace/patio
Creekside Cottage and Bungalow. Cozy, pet friendly, close to town. Sleeps 6
10.0 out of 10, Exceptional, (6)
"This house has everything you need. Very well stocked. Amazing property, especially the yard. 5min to town, very convenient location. Will be back for sure "
Creekside Cottage and Bungalow. Cozy, pet friendly, close to town. Sleeps 6
Newly Refurbished! Nest Cottage at ru's Farm.
Property grounds
Newly Refurbished! Nest Cottage at ru's Farm.
10.0 out of 10, Exceptional, (153)
"The cottage at Ru’s farm was an ideal place nestled next Healdsburg. It was quiet and felt like we had the whole farm to ourself. "
Newly Refurbished! Nest Cottage at ru's Farm.
Healdsburg Cottage Walk to the Plaza, Workspace
Terrace/patio
Healdsburg Cottage Walk to the Plaza, Workspace
9.8 out of 10, Exceptional, (219)
"Just an adorable space and so well appointed! Kelly was easy to communicate with and the check in process was cake! We could walk to the Healdsburg plaza and it’s a quick drive to tons of wineries. We will definitely be visiting again!"
Healdsburg Cottage Walk to the Plaza, Workspace
Chalk Hill Cottage Close to Wineries
Exterior
Chalk Hill Cottage Close to Wineries
9.8 out of 10, Exceptional, (25)
"Great cottage for our Napa Valley visit. Cottage was just the right size for my husband and I. We loved the location. Quiet area with a few wineries close by. Very clean and well equipped. We would love to stay again on our next visit. "
Chalk Hill Cottage Close to Wineries
Heron House--The River House in the Redwoods
Outdoor spa tub
Heron House--The River House in the Redwoods
9.8 out of 10, Exceptional, (20)
"We really enjoyed the home and property and having the intertubes to float on was really nice. I was a bit confused by the listing which showed 3 bedrooms but then listed a sofa bed as a "4th" bedroom in the listing. We arrived believing the 4th bedroom would provide some privacy but that was my error. We also weren't able to use the barbeque due to a propane leak at the tank but we made due with the beautiful stove and everything turned out great. I especially loved the gated driveway which...
Heron House--The River House in the Redwoods
Private 1-bedroom Guest House with Great Amenities
Terrace/patio
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
Enjoy a Slice Of Country--Two miles to Downtown Healdsburg
Property grounds
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
Iron/ironing board, Internet, bed sheets
Vineyard view studio by Russian River w/ private balcony, patio, grill, & WiFi
9.4 out of 10, Exceptional, (72)
"Beautiful, wonderfully clean, great location."
Vineyard view studio by Russian River w/ private balcony, patio, grill, & WiFi
Restored country home with private hot tub, amazing garden patio & firepit
Outdoor dining
Restored country home with private hot tub, amazing garden patio & firepit
9.6 out of 10, Exceptional, (28)
"Clean and comfortable"
Restored country home with private hot tub, amazing garden patio & firepit
Russian Riverside Cottage in Healdsburg
Living area
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
Santini Farmhouse -- Beautiful Italian style Villa, Hot Tub, Vineyard Views
Exterior
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
Fitch St Escape! 2 BDRM Bungalow only blocks from the Plaza!
Outdoor dining
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!
Creek-side home close to river/woods with private hot tub & deck - dog-friendly
Terrace/patio
Creek-side home close to river/woods with private hot tub & deck - dog-friendly
9.0 out of 10, Wonderful, (45)
"We had a great time at this adorable cabin. We really enjoyed sitting in the hot tub! Very close to town and the redwoods! Be sure to check out Armstrong Woods!"
Creek-side home close to river/woods with private hot tub & deck - dog-friendly
Cozy cottage tucked away on a private country road
Miscellaneous
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."
The price is €648
includes taxes & fees
7 Nov - 8 Nov
Cozy cottage tucked away on a private country road
Wine Country Cottage sleeps 4, Healdsburg, Spa
Exterior
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
Fridge, microwave, oven, stovetop
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!
House (3 Bedrooms) | Private kitchen
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
Property grounds
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
Outdoor dining
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 €501
includes taxes & fees
6 Nov - 7 Nov
Milk barn Magic: Vineyard Escape with 2 Bedrooms
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

Healdsburg Wine Country Getaway with Panoramic Valley Views -5 min from downtown
Smart TV, fireplace, DVD player, books
Healdsburg Wine Country Getaway with Panoramic Valley Views -5 min from downtown
10.0 out of 10, Exceptional, (225)
"This property was fantastic! The views were incredible (the sunrises! the vineyards!) and the location was awesome as it was less than a 10 minute drive to the square. The house is nicely updated and comfortable. It is well stocked with kitchen/bathroom essentials, books and games. The next time we’re in Healdsburg the Bliss House will be at the top of our list for accommodations!"
Healdsburg Wine Country Getaway with Panoramic Valley Views -5 min from downtown
Modern Wine Country Cottage in Historic Healdsburg, Premiere Location
Property grounds
Modern Wine Country Cottage in Historic Healdsburg, Premiere Location
10.0 out of 10, Exceptional, (153)
"The cottage and the grounds are absolutely gorgeous! We loved the way the cottage was decorated, so cozy! Everything was well appointed. There are multiple places on the grounds to sit and enjoy a glass of wine and the scenery. It is the perfect size for two couples. The location is close to downtown Healdsburg, Dry Creek wineries and a five-minute walk to the Dry Creek General Store! Napa is only a little over an hour away. The owners and property manager responded quickly when we had...
Modern Wine Country Cottage in Historic Healdsburg, Premiere Location
Beautiful Coop Cottage overlooking vineyards. Three minutes from downtown!
Fridge, microwave, oven, stovetop
Beautiful Coop Cottage overlooking vineyards. Three minutes from downtown!
10.0 out of 10, Exceptional, (230)
"Just like the pictures. Grounds were gorgeous & the stay was very relaxing. My family had a wonderful time. "
Beautiful Coop Cottage overlooking vineyards. Three minutes from downtown!
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 26 cottages in Healdsburg. No matter if you’re holidaying 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 holiday 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.
What is there to do in Healdsburg near my cottage?
Healdsburg has enough experiences and sights to keep you entertained for weeks (or months!), beginning with Dry Creek Vineyard. Mazzocco Winery, Matrix Winery and Chalk Hill Estate Vineyard are other terrific attractions. If you’re in town a while, Hanna Winery and Vineyards and Wilson Winery will put the finishing touches on your itinerary.