Healdsburg Vacation Rentals

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Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

Our top choices for Healdsburg vacation rentals

Dining

Cozy Riverfront Cabin - Beach Access & Wood Stove

Cozy Riverfront Cabin - Beach Access & Wood Stove
Guerneville
9.6 out of 10, Exceptional, (17 reviews)
"Great location on the river. Can't wait to come back in the summer."
United States
Gregg B.
The price is ￥22,194
￥79,288 total
includes taxes & fees
May 18 - May 19
Cozy Riverfront Cabin - Beach Access & Wood Stove
Outdoor dining

Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK

Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK
Guerneville
8.0 out of 10, Very Good, (2 reviews)
"Our stay was fantastic! The cabin was everything we needed for a few days; cozy, and quiet. The outdoor spaces were great and the hot tub was perfect at the end of the day. The host was super helpful and responded to my questions almost immediately. "
United States
Rosa N.
The price is ￥61,809
￥119,570 total
includes taxes & fees
May 22 - May 23
Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK
Interior

Creekside Under the Redwoods

Creekside Under the Redwoods
Guerneville
9.8 out of 10, Exceptional, (20 reviews)
"Very cute and comfortable place! We enjoyed our stay!"
United States
Kathy M.
The price is ￥23,947
￥54,061 total
includes taxes & fees
Jun 1 - Jun 2
Creekside Under the Redwoods
Fridge, microwave, oven, stovetop

Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape

Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
Northwest Santa Rosa
9.4 out of 10, Exceptional, (23 reviews)
"enjoyed our stay, no surprises and a good value"
United States
Craig M.
The price is ￥23,017
￥64,416 total
includes taxes & fees
May 17 - May 18
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
Interior

Tranquil Redwood Retreat

Tranquil Redwood Retreat
Guerneville
8.8 out of 10, Excellent, (10 reviews)
"Comfortable place to stay, close to everything. Host was amazing. "
United States
Joelle S.
The price is ￥24,001
￥54,819 total
includes taxes & fees
May 17 - May 18
Tranquil Redwood Retreat
Outdoor dining

Redwood Riverfront - Hot Tub and Tastings Included

Redwood Riverfront - Hot Tub and Tastings Included
Healdsburg
9.2 out of 10, Wonderful, (67 reviews)
"We had a decent stay at Riverfront. Having the house by the river was pleasant. We were a bit disappointed to find that the hot tub was below the deck and we couldnt use it at night since there seem to be no outdoor light. Overall it was nice secluded stay."
United States
Kenneth M.
The price is ￥39,685
￥125,530 total
includes taxes & fees
May 19 - May 20
Redwood Riverfront - Hot Tub and Tastings Included
Pool

Lodge Room for 2-3 people

Lodge Room for 2-3 people
Geyserville
The price is ￥19,162
￥24,629 total
includes taxes & fees
May 24 - May 25
Lodge Room for 2-3 people
Outdoor pool, a heated pool

Top Wine Country Condo - Full Resort Amenity Access - 2 Bedroom/2 Bath - Sleep 6

Top Wine Country Condo - Full Resort Amenity Access - 2 Bedroom/2 Bath - Sleep 6
Windsor
10.0 out of 10, Exceptional, (1 review)
The price is ￥31,748
￥59,191 total
includes taxes & fees
May 18 - May 19
Top Wine Country Condo - Full Resort Amenity Access - 2 Bedroom/2 Bath - Sleep 6
TV, fireplace

Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries

Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries
Northwest Santa Rosa
9.8 out of 10, Exceptional, (73 reviews)
"Loved our stay!!"
United States
kristen s.
The price is ￥36,744
￥84,746 total
includes taxes & fees
May 17 - May 18
Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries
Dining

Russian River Brew-cation Home

Russian River Brew-cation Home
Northwest Santa Rosa
10.0 out of 10, Exceptional, (56 reviews)
"The house was great! We enjoyed our stay"
United States
Warren M.
The price is ￥28,350
￥76,190 total
includes taxes & fees
May 17 - May 18
Russian River Brew-cation Home
Exterior detail

Farm Country Cottage in Downtown Geyserville, Vineyard Views + UNTI Wine

Farm Country Cottage in Downtown Geyserville, Vineyard Views + UNTI Wine
Geyserville
10.0 out of 10, Exceptional, (2 reviews)
"Cozy, rustic, and with all great amenities."
United States
Gina I.
The price is ￥31,748
￥57,781 total
includes taxes & fees
Jun 15 - Jun 16
Farm Country Cottage in Downtown Geyserville, Vineyard Views + UNTI Wine
A heated pool

Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6

Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
Windsor
9.2 out of 10, Wonderful, (45 reviews)
"Check-in was a little difficult, but the condo itself was convenient and a great stay."
United States
SB L.
The price is ￥31,748
￥59,191 total
includes taxes & fees
May 18 - May 19
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
Dining

Wine Country Cottage Escape

Wine Country Cottage Escape
Fulton
The price is ￥26,192
￥58,988 total
includes taxes & fees
May 21 - May 22
Wine Country Cottage Escape
Dining

Sonoma Wine Country Getaway | Winemaker’s Home with Modern Comforts

Sonoma Wine Country Getaway | Winemaker’s Home with Modern Comforts
Northwest Santa Rosa
10.0 out of 10, Exceptional, (82 reviews)
"We completely enjoyed our stay. We will be back next time we are in the area."
United States
Robert M.
The price is ￥33,735
￥82,852 total
includes taxes & fees
May 18 - May 19
Sonoma Wine Country Getaway | Winemaker’s Home with Modern Comforts
Interior

Windsor Home with Sauna & Outdoor Fire Pit

Windsor Home with Sauna & Outdoor Fire Pit
Windsor
Windsor Home with Sauna & Outdoor Fire Pit
A heated pool

Farpoint: Heated Infinity Pool, Mountain Views

Farpoint: Heated Infinity Pool, Mountain Views
Santa Rosa
10.0 out of 10, Exceptional, (14 reviews)
"We had excellent communication and customer service from our host. The property had amazing views and a nice home comfortable feel."
United States
Padrick G.
The price is ￥72,679
￥147,277 total
includes taxes & fees
May 20 - May 21
Farpoint: Heated Infinity Pool, Mountain Views
Property grounds

Alexander Valley Lodge w/ Pool, Hot tub, Waterfall, Pool table and Tiki Bar

Alexander Valley Lodge w/ Pool, Hot tub, Waterfall, Pool table and Tiki Bar
Geyserville
9.2 out of 10, Wonderful, (16 reviews)
"We were having a girlfriend’s birthday getaway and this place was just perfect. Comfortable, lots of room, well equipped, & beautiful views. Would definitely return! Host was really great too!"
United States
Sherry W.
The price is ￥70,719
￥147,051 total
includes taxes & fees
May 18 - May 19
Alexander Valley Lodge w/ Pool, Hot tub, Waterfall, Pool table and Tiki Bar
Exterior

Healdsburg Plaza Charmer with Hot Tub!

Healdsburg Plaza Charmer with Hot Tub!
Healdsburg
10.0 out of 10, Exceptional, (18 reviews)
"great location! the cottage was perfect for our trip with pets."
United States
Sue P.
The price is ￥60,670
￥122,539 total
includes taxes & fees
Jun 2 - Jun 3
Healdsburg Plaza Charmer with Hot Tub!
Outdoor dining

Lux Wine Country Oasis with Hot Tub - Wine Tastings Included

Lux Wine Country Oasis with Hot Tub - Wine Tastings Included
Healdsburg
10.0 out of 10, Exceptional, (26 reviews)
"Awesome place and a great location!"
United States
Matt S.
The price is ￥106,038
￥245,967 total
includes taxes & fees
May 21 - May 22
Lux Wine Country Oasis with Hot Tub - Wine Tastings Included
Exterior detail

Luxury Private Estate at Zoella Vineyards in the heart of Wine Country

Luxury Private Estate at Zoella Vineyards in the heart of Wine Country
Healdsburg
9.6 out of 10, Exceptional, (66 reviews)
"Better than expected!! We loved this properly and would most definitely stay again!! It was perfect and magical in every way!!! "
United States
Elaine G.
The price is ￥227,871
￥357,762 total
includes taxes & fees
May 17 - May 18
Luxury Private Estate at Zoella Vineyards in the heart of Wine Country
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

Dry Creek Inn MOD Collection by Sonesta

Dry Creek Inn MOD Collection by Sonesta

10/10 Excellent
"Clean. Cozy bed. Comfortable pillows."
Allison 1-night trip
Posted 3 hours ago
Dry Creek Inn MOD Collection by Sonesta

Find out more about Healdsburg

Search for holiday rentals in Healdsburg on Expedia! You can easily find your home rentals, villas, holiday apartments in Healdsburg using one of the methods below:

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Frequently asked questions

Are there vacation rentals in Healdsburg?

Yes, there are vacation rentals in Healdsburg near SingleThread Farm at Dry Creek, or you can choose a secluded option if you want a relaxing stay. Visitors like the array of shops and scenic riverfront in Healdsburg. While you're here, grab a bite or have a drink at the wineries and top-notch restaurants.

What's the top vacation rental that Healdsburg has to offer?

DOG-FRIENDLY, COZY—PERFECT 4 COUPLES—BOOK 3 NIGHTS—4th FREE! Close to EVERYTHING: This vacation home rental outside of Healdsburg is located on the waterfront and has a balcony, a selection of books, and a Smart TV to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Healdsburg?

Expedia has 144 vacation rentals for your stay in Healdsburg.

What can I see and do in Healdsburg?

Russian River and Healdsburg Ridge Open Space Preserve are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include SingleThread Farm at Dry Creek. Healdsburg Plaza and Jordan Vineyard & Winery are other places to visit while you're in town.

What are vacation rentals like in Healdsburg?

Vacation rentals are privately owned properties you can book for several days or more in Healdsburg. Vacation rentals provide amenities such as hot tubs, fire pits, and patios so you'll have everything you need. If you're concerned about cleanliness, a vacation rental can offer a sense of seclusion away from public hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for small groups.