Search Healdsburg Cottages

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    one key icon
    Treat yourself
    Save instantly and earn perks with One Key
    today icon
    Change your mind
    Book hotels with free cancellation

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

Vineyard view studio by Russian River w/ private balcony, patio, grill, & WiFi
9.6 out of 10, Exceptional, (67)
"The property was just as described. This was a little further of a drive to the wineries we were visiting. Easy to check-in and communication was great. The only drawback is the bed is not comfortable."
Vineyard view studio by Russian River w/ private balcony, patio, grill, & WiFi
Newly Refurbished! Nest Cottage at ru's Farm.
10.0 out of 10, Exceptional, (148)
"We thoroughly loved staying here!!!"
Newly Refurbished! Nest Cottage at ru's Farm.
Chalk Hill Cottage Close to Wineries
9.8 out of 10, Exceptional, (15)
"Lovely place for a couple to stay. Convenient location - close to many vineyards and the great town of Healdsburg!"
Chalk Hill Cottage Close to Wineries
Save an average of 15% on thousands of hotels when you're signed in
Healdsburg Cottage Walk to the Plaza, Workspace
9.8 out of 10, Exceptional, (206)
"Overall great. Only comment is that ice and grill had to be shared with home owner. So they had to be there when we wanted them."
Healdsburg Cottage Walk to the Plaza, Workspace
Dry Creek Cottage - Healdsburg
9.8 out of 10, Exceptional, (131)
"Second time at this property- it’s quiet and relaxing. The pool and hot tub felt amazing after a long day of exploring."
Dry Creek Cottage - Healdsburg
Creek-side home close to river/woods with private hot tub & deck - dog-friendly
9.0 out of 10, Wonderful, (43)
"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
Healdsburg Plaza Gem--Beautifully Restored 1880's Cottage Downtown
9.8 out of 10, Exceptional, (31)
"Super charming, very comfortable home - just a short stroll away from the main square. Made a great base for our family visit."
Healdsburg Plaza Gem--Beautifully Restored 1880's Cottage Downtown
Restored country home with private hot tub, amazing garden patio & firepit
9.6 out of 10, Exceptional, (26)
"Clean and comfortable"
Restored country home with private hot tub, amazing garden patio & firepit
Heron House--The River House in the Redwoods
9.8 out of 10, Exceptional, (17)
"Loved this house for a weekend getaway. We loved taking advantage of the deck, grill, and river access. Short drive to the town square and wineries."
Heron House--The River House in the Redwoods
Santini Farmhouse -- Beautiful Italian style Villa, Hot Tub, Vineyard Views
10.0 out of 10, Exceptional, (30)
"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."
Santini Farmhouse -- Beautiful Italian style Villa, Hot Tub, Vineyard Views
Private 1-bedroom Guest House with Great Amenities
10.0 out of 10, Exceptional, (7)
"We really enjoyed our stay at this small but very comfortable cottage. So many pros- hard to name them all: Great location just a few mins to downtown. Very peaceful and quiet, beautiful landscaping and almost rural setting with vineyards and very large lots- no neighbors close by except for the owner's house. The 3 car owner's garage blocks views of the owner's house so you have a lot of privacy. Very comfortable mattresses and bedding, comfy sofa and living room furniture, convenient washer...
Private 1-bedroom Guest House with Great Amenities
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 $349
$693 total
includes taxes & fees
Jun 11 - Jun 12
Cozy cottage tucked away on a private country road
Downtown Healdsburg Wine Country Retreat
10.0 out of 10, Exceptional, (3)
"Spacious and comfortable home. Very clean and everything you need is provided. Responsive host. Safe and quiet neighborhood a short walk (1/4 mile) from the square."
Downtown Healdsburg Wine Country Retreat
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
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!
Quiet Cottage w/ Redwood Forest Views & Deck!
3.5 star property
10.0 out of 10, Exceptional, (1)
"I would recommend this quaint little cottage to anyone who loves being in nature. It was easy to find, quick to access and the communication was fantastic prior to our visit. The cottage is the perfect size for a couple. The dog friendly home is located on a quiet street in the middle of the forest. They even supplied dog bags which was a great touch. The one "complaint" I have would be I wish there were more rugs throughout the cottage. It was rather chilly, but they do have space heaters,...
Quiet Cottage w/ Redwood Forest Views & Deck!
Downtown Healdsburg Cottage
Downtown Healdsburg Cottage
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
Modern Santa Rosa Retreat - Close to Wineries!
3.0 star property
Modern Santa Rosa Retreat - Close to Wineries!
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
Don't see what you're looking for?
See all available properties in Healdsburg
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.

Other property types in Healdsburg

Wooded Restful Retreat, with broad scenic views, outdoor dining
10.0 out of 10, Exceptional, (279)
"Comfy and clean place to stay and relax"
Wooded Restful Retreat, with broad scenic views, outdoor dining
Healdsburg Cottage Walk to the Plaza, Workspace
9.8 out of 10, Exceptional, (206)
"Overall great. Only comment is that ice and grill had to be shared with home owner. So they had to be there when we wanted them."
Healdsburg Cottage Walk to the Plaza, Workspace
✨Rustic Cabin in Dry Creek Valley with beautiful views // 5 miles to Plaza ✨
10.0 out of 10, Exceptional, (264)
"Beautiful cabin literally surrounded.by the Rogers Zinfandel Vineyard. Perfectly appointed and generously supplied. Gracious hosts and excellant communication. Secluded location makes this a true slice of heaven in the Dry Creek Wine Country. Highly recommended!"
✨Rustic Cabin in Dry Creek Valley with beautiful views // 5 miles to Plaza ✨
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.

Healdsburg Cottages information

Number of reviews
663
Accommodation
27 Cottages
Lowest Price
$349
Highest Price
$349

Frequently asked questions

How much do cottages in Healdsburg cost?
Prices for cottages in Healdsburg range between $349 and $349 per night. No matter your budget, you’ll find a perfect place to relax and reconnect with nature. This price was 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?
Pack your suitcase and choose from 27 cottages in Healdsburg. Thinking about a place where you can get reacquainted with nature? Expedia can help you find the ideal property in just a few clicks.
Are there any family-friendly cottages in Healdsburg?
If you want to slow the pace down a notch in Healdsburg, check the crew in to Wine Country Getaway Modern Three. With a 3.5-star rating and handy amenities like free WiFi and a barbecue grill, you’ll find it easy to get comfortable at this family-friendly cottage. After checking in and chilling out in your new digs, it’s time to head out and explore some of the local sights. Pacific Coast Air Museum and Healdsburg Museum are popular family-friendly attractions in Healdsburg.
Why book your cottage in Healdsburg with Expedia?
Expedia has some wonderful cottages in Healdsburg, so start packing for a memorable vacation close to nature. If you need to stick to a budget, select how much you’re willing to spend and the star rating of your property. Or, try out our filters to search for cottages with a pool or a hot tub. We’ll help you find a suitable place whatever your plans or bank balance.
How can I find cheap cottages in Healdsburg?
The easiest way to compare cheap cottages in Healdsburg is with Expedia’s useful filter tool. Tailor your search results by budget, amenities and star rating to take advantage of awesome bargains in just a few clicks.
What is there to do in Healdsburg near my cottage?
You’ll find tons of terrific things to fill your days in Healdsburg. Explore well-known attractions like Francis Ford Coppola Winery, Armstrong Redwoods State Park and Dry Creek Vineyard. Kendall-Jackson Wine Estate and Gardens, Trentadue Winery and Mazzocco Winery are also visitor favorites.

Recent reviews of Healdsburg hotels
Expedia verified reviews