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Check prices for these dates

Next weekend
1 Aug - 3 Aug
In two weeks
8 Aug - 10 Aug
In one month
22 Aug - 24 Aug
In two months
19 Sept - 21 Sept

Featured Cottages in Healdsburg and around

Chalk Hill Cottage Close to Wineries
Exterior

Chalk Hill Cottage Close to Wineries

9.8 out of 10, Exceptional, (37)
"The Chalk Hill cottage was the perfect getaway for Sonoma wine lovers. Located in Alexander Valley and close to great wineries."
Chalk Hill Cottage Close to Wineries
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)
"Our group had a wonderful time. The property was perfect in every way & would certainly rent again if lucky enough to return to Healdsburg."
Private 1-bedroom Guest House with Great Amenities
Healdsburg Plaza Gem--Complimentary wine tasting at Croix included!
Property grounds

Healdsburg Plaza Gem--Complimentary wine tasting at Croix included!

9.8 out of 10, Exceptional, (42)
"We had a perfect experience. The house is very clean and functional and the location simply cannot be beat. The local management company was very responsive and helpful. We stayed for 2 weeks and really got a feel for living in town given the proximity to restaurants, coffee shops, highways, wineries etc. I would highly recommend this house and we will absolutely be back if they will have us."
The price is €891
includes taxes & fees
29 Jul - 30 Jul
Healdsburg Plaza Gem--Complimentary wine tasting at Croix included!
Mountain Cottage near Russian River, hiking & downtown, family and pet friendly
Terrace/patio

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

9.2 out of 10, Wonderful, (58)
"The cottage is a comfortable house. "
Mountain Cottage near Russian River, hiking & downtown, family and pet friendly
Russian Riverside Cottage in Healdsburg
Fireplace

Russian Riverside Cottage in Healdsburg

8.6 out of 10, Excellent, (9)
"I stayed there with my family, including my 19-month old son and we had the best time. The river is so calming and the outdoor patio was a huge hit. It's also just a quick 10-min drive from downtown."
Russian Riverside Cottage in Healdsburg
Enjoy a Slice Of Country--Two miles to Downtown Healdsburg
Terrace/patio

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

10.0 out of 10, Exceptional, (62)
"Very clean, very beautiful, very quiet! A perfect place to stay while visiting Healdsburg."
Enjoy a Slice Of Country--Two miles to Downtown Healdsburg
Santini Farmhouse | Complimentary tasting at Croix Winery included!
Exterior

Santini Farmhouse | Complimentary tasting at Croix Winery included!

10.0 out of 10, Exceptional, (46)
"Everything was perfect"
Santini Farmhouse | Complimentary tasting at Croix Winery included!
Heron House--Complimentary wine tasting at Croix included!
Outdoor spa tub

Heron House--Complimentary wine tasting at Croix included!

10.0 out of 10, Exceptional, (23)
"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--Complimentary wine tasting at Croix included!
Mill Creek by Avantstay Modern Design, Patio, Hot Tub
House (2 Bedrooms) | Interior

Mill Creek by Avantstay Modern Design, Patio, Hot Tub

3.0 star property
Mill Creek by Avantstay Modern Design, Patio, Hot Tub
Peaceful Windsor Retreat w/ Private Hot Tub!
House (3 Bedrooms) | Interior

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!
Healdsburg Cottage Walk to the Plaza, Workspace
Terrace/patio

Healdsburg Cottage Walk to the Plaza, Workspace

10.0 out of 10, Exceptional, (226)
"Host was great, place is adorable. Great stay. "
Healdsburg Cottage Walk to the Plaza, Workspace
Heart of Healdsburg | Complimentary wine tasting at Croix Estate included!
Outdoor dining

Heart of Healdsburg | Complimentary wine tasting at Croix Estate included!

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 | Complimentary wine tasting at Croix Estate included!
Fitch St Escape | Complimentary wine tasting at Croix Estate included!
Outdoor dining

Fitch St Escape | Complimentary wine tasting at Croix Estate included!

10.0 out of 10, Exceptional, (6)
"We loved everything about our stay on Fitch Street. The house was cute and comfortable and was the perfect jumping off point for our month in Healdsburg. We would definitely stay there again!"
Fitch St Escape | Complimentary wine tasting at Croix Estate included!
Chic wine country cottage and garden
Fridge, microwave, oven, stovetop

Chic wine country cottage and garden

10.0 out of 10, Exceptional, (2)
"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
Pool

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
True Wine Country Living: 2BR Converted Milkbarn on Family Vineyard
Outdoor dining

True Wine Country Living: 2BR Converted Milkbarn on Family Vineyard

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 €436
includes taxes & fees
20 Aug - 21 Aug
True Wine Country Living: 2BR Converted Milkbarn on Family Vineyard
Modern, secluded retreat - Walk to the plaza and to wineries!
Smart TV

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

10.0 out of 10, Exceptional, (15)
"Visited with my wife and another couple. We loved the layout and location of this beautiful home."
Modern, secluded retreat - Walk to the plaza and to wineries!
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)
"The perfect spot for us to relax and refresh for all the Healdsburg and wine country activities! Very quiet and a very short drive to downtown Healdsburg. "
Updated Healdsburg River Cottage: Minutes from Plaza, Tasting Rooms & Vineyards
Cozy cottage tucked away on a private country road
Exterior

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
Wine Country Vacation Home w/ Fireplace!
Property grounds

Wine Country Vacation Home w/ Fireplace!

3.0 star property
Wine Country Vacation Home w/ Fireplace!
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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Top Healdsburg Hotel Reviews

The Lodge at Healdsburg, Tapestry Collection by Hilton

The Lodge at Healdsburg, Tapestry Collection by Hilton

10/10 Excellent
"The spaces to enjoy a chat were many!"
Dena 1-night trip
Posted 2 days ago
The Lodge at Healdsburg, Tapestry Collection by Hilton

Frequently asked questions

How much do cottages in Healdsburg cost?
Prepare to pay between €436 and €891 per night for cottages in Healdsburg. Whatever your budget, an awesome stay is just a click or two away on Expedia. 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?
Lock in your holiday dates and then choose from 24 cottages in Healdsburg. Looking for a place where you can relax and stay in touch with nature? Expedia will help you find your ideal retreat in a few quick clicks.
Are there any family-friendly cottages in Healdsburg?
Check in to Wine Country Getaway Modern Three and make your family holiday to Healdsburg a memorable one. This family-friendly cottage has a 3-star rating and amenities such as WiFi and a firepit. Once you've checked in and unpacked your things, there's no shortage of family-friendly attractions to discover in and around Healdsburg. Healdsburg Museum and Pacific Coast Air Museum are two of our top suggestions.