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Compare 27 Cottages in Healdsburg with updated reviews, rates, and availability.

Mountain Cottage near Russian River, hiking & downtown, family and pet friendly

9.2 out of 10, Wonderful, (55)
"Cute property! It’s a little rustic, but has everything you need. The location is beautiful and convenient to Healdsburg. "
Mountain Cottage near Russian River, hiking & downtown, family and pet friendly

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

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

9.8 out of 10, Exceptional, (40)
"This adorable house is perfectly situated in downtown Healdsburg close to the square and loads of quality dining and wine tasting. Just right for two couples. Beds were comfortable, and the kitchen was well equipped. Will keep in mind for the future!"
Healdsburg Plaza Gem--Beautifully Restored 1880's Cottage Downtown

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 Cottage Walk to the Plaza, Workspace

10.0 out of 10, Exceptional, (225)
"This is a wonderful place to stay - very homey, clean, comfortable and beautiful with everything we needed. I hope to be able to stay there again sometime. "
Healdsburg Cottage Walk to the Plaza, Workspace

Chalk Hill Cottage Close to Wineries

9.8 out of 10, Exceptional, (34)
"Enjoyed a lovely weekend at this wonderful cottage! Everything was so comfortable and welcoming, and the kitchen was very well stocked with more than just the basics. Bring your bug stuff so that you can enjoy the charming and peaceful outdoor space, and enjoy the great location close to wineries and just a short drive from Windsor & Healdsburg hot spots. We would happily stay again!"
Chalk Hill Cottage Close to Wineries

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

Newly Refurbished! Nest Cottage at ru's Farm.

10.0 out of 10, Exceptional, (162)
"This was a long weekend for my husband and me. We loved Ru's farm and Healdsburg, we will be back!"
Newly Refurbished! Nest Cottage at ru's Farm.

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

10.0 out of 10, Exceptional, (42)
"A wonderful property in a beautiful setting. Would definitely stay here again and would highly recommend "
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, (5)
"We rented the house for 5 nights with friends for a wine tasting trip. House worked great for 2 couples. Kitchen is large and worked well for prepping a few meals when we ate in. Kitchen table worked great for meals or playing cards/ winding down at the end of the day. Plenty of storage in the bedrooms to unpack. AC and heat worked well. Nice backyard to hang out and relax after a day of adventure. Easy walk into the square and surrounding area, which we did daily for coffee, breakfast or...
Fitch St Escape! 2 BDRM Bungalow only blocks from the Plaza!

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

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

Mill Creek by Avantstay Modern Design, Patio, Hot Tub

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

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

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

Modern, secluded retreat - Walk to the plaza and to wineries!

10.0 out of 10, Exceptional, (15)
"This is an architectural dreamhouse! It's only a mile from downtown Healdsburg and wineries but is completely private and sits on a pretty lot. The house is stocked with amenities in the kitchen and bathroom. It's the perfect place to relax and unwind. "
Modern, secluded retreat - Walk to the plaza and to wineries!

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

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 716
AED 1,767 total
includes taxes & fees
22 Apr - 23 Apr
Milk barn Magic: Vineyard Escape with 2 Bedrooms

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

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!
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 ✨

10.0 out of 10, Exceptional, (287)
"Amazing cabin. Great location. We had an amazing 2nd time in this little paradise!"
✨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

10.0 out of 10, Exceptional, (241)
"Our group had a fantastic stay at this property. The location is amazing - minutes from downtown Healdsburg but just far enough to feel a bit secluded. Tons of great wineries nearby (I recommend De La Montanya)."
Healdsburg Wine Country Getaway with Panoramic Valley Views -5 min from downtown

Wooded Restful Retreat, with broad scenic views, outdoor dining

10.0 out of 10, Exceptional, (300)
"The house,view, communications and cleanliness were exactly as promised—excellent. We felt welcomed and at home. With the information Cynthia provided, we did everything we wanted easily. Thank you. "
Wooded Restful Retreat, with broad scenic views, outdoor dining
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.