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Check prices for these dates

Next weekend
10 Oct - 12 Oct
In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov

Cottages in Healdsburg

Chalk Hill Cottage Close to Wineries
Exterior

Chalk Hill Cottage Close to Wineries

9.8 out of 10, Exceptional, (41)
"Perfect private location"
Chalk Hill Cottage Close to Wineries
Healdsburg Cottage Walk to the Plaza, Workspace
Property grounds

Healdsburg Cottage Walk to the Plaza, Workspace

9.8 out of 10, Exceptional, (228)
"Host was great, place is adorable. Great stay. "
Healdsburg Cottage Walk to the Plaza, Workspace
True Wine Country Living: 2BR Converted Milkbarn on Family Vineyard
Property grounds

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 AED 915
AED 2,055 total
includes taxes & fees
2 Nov - 3 Nov
True Wine Country Living: 2BR Converted Milkbarn on Family Vineyard
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)
"The property was so cute - the pictures don't do it justice! Roxanne was an excellent and communicative host. I told her we were celebrating my mom's 70th birthday and she very sweetly had a card and balloons for her in the kitchen! The center of town is very close by. I'd highly recommend this place and would be very glad to stay again!"
Enjoy a Slice Of Country--Two miles to Downtown Healdsburg
Heron House | A Wine Country Escape
Outdoor spa tub

Heron House | A Wine Country Escape

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 | A Wine Country Escape
Mountain Cottage near Russian River, hiking & downtown, family and pet friendly
Outdoor dining

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

9.2 out of 10, Wonderful, (62)
"Very adequate lodging for 6 with 2 bathrooms. Nice directions for a short walk down to the river."
Mountain Cottage near Russian River, hiking & downtown, family and pet friendly
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!
Russian Riverside Cottage in Healdsburg
Fireplace

Russian Riverside Cottage in Healdsburg

8.8 out of 10, Excellent, (11)
"We had a wonderful stay. "
Russian Riverside Cottage in Healdsburg
Santini Farmhouse | A Wine Country Escape
Exterior

Santini Farmhouse | A Wine Country Escape

10.0 out of 10, Exceptional, (49)
"Everything was perfect"
Santini Farmhouse | A Wine Country Escape
Fitch St Escape | A Wine Country Escape
Exterior

Fitch St Escape | A Wine Country Escape

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 | A Wine Country Escape
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
Heart of Healdsburg | A Wine Country Escape
Exterior

Heart of Healdsburg | A Wine Country Escape

9.0 out of 10, Wonderful, (2)
"The property was wonderful, would book again in a minute, it was so cute and comfortable ❤️❤️❤️"
Heart of Healdsburg | A Wine Country Escape
Modern, secluded retreat - Walk to the plaza and to wineries!
Exterior

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!
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
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
Downtown Healdsburg Wine Country Retreat
Exterior

Downtown Healdsburg Wine Country Retreat

9.6 out of 10, Exceptional, (4)
"This was a beautiful property with lots of storage space, a lovely well, well-equipped kitchen, and an excellent location just outside the downtown. We truly enjoyed our extended stay and hope to return on our next trip. Thank you again for a great visit."
Downtown Healdsburg Wine Country Retreat
Wine Country Vacation Home w/ Fireplace!
Exterior

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

Hotel Trio Healdsburg

Hotel Trio Healdsburg

10/10 Excellent
"The room was perfect. Two rooms is so nice. Here for a wedding, bed super comfy, soft pillows. Nice decor. Nice little kitchen. LOVE coffee and water all day, needed it. Cute outside area. Great breakfast. All in all a great visit !"
Vicki 4-night trip
Posted 2 days ago
Hotel Trio Healdsburg

Frequently asked questions

How much do cottages in Healdsburg cost?
Prepare to pay between AED 2,055 and AED 2,055 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 vacation dates and then choose from 18 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.
Why book your cottage in Healdsburg with Expedia?
We think that a vacay should be a walk in the park, so if you're on the lookout for cottages in Healdsburg at a competitive rate, Expedia has you covered. Save those pennies and select an economical option far from the rush of the city, or splurge on a 5-star cottage to spoil your favorite people.