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Holiday Rentals in Healdsburg

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Our top choices for Healdsburg holiday rentals

1. Wildhaven Sonoma Glamping

Wildhaven Sonoma Glamping
1.0 star property
Healdsburg
9.2 out of 10, Wonderful, (139 reviews)
"Nice place to be in with your dog, very good for comfortable stay"
United States
NEERJA
The price is €100
includes taxes & fees
8 Dec - 9 Dec
Wildhaven Sonoma Glamping

2. Healdsburg Plaza Gem-Hot Tub and Tastings Included

Healdsburg Plaza Gem-Hot Tub and Tastings Included
Healdsburg
9.8 out of 10, Exceptional, (50 reviews)
"Great location and charming cottage. "
United States
Christopher T.
Healdsburg Plaza Gem-Hot Tub and Tastings Included

3. River View Lodge - Hot Tub and Tastings Included

River View Lodge - Hot Tub and Tastings Included
Healdsburg
9.6 out of 10, Exceptional, (75 reviews)
"Wonderful vacation and location. "
United States
Leslie M.
The price is €914
includes taxes & fees
17 Nov - 18 Nov
River View Lodge - Hot Tub and Tastings Included

4. Tranquil Retreat with Pool, Hot Tub, & Game Room

Tranquil Retreat with Pool, Hot Tub, & Game Room
Healdsburg
The price is €779
includes taxes & fees
15 Nov - 16 Nov
Tranquil Retreat with Pool, Hot Tub, & Game Room

5. Hilltop Overlook Room with Views | Private Entrance | Near Downtown Healdsburg

Hilltop Overlook Room with Views | Private Entrance | Near Downtown Healdsburg
Healdsburg
The price is €368
includes taxes & fees
8 Dec - 9 Dec
Hilltop Overlook Room with Views | Private Entrance | Near Downtown Healdsburg

6. 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, (68 reviews)
"Unbelievable property – we will absolutely stay here again –Just fabulous!"
United States
Jeffrey S.
The price is €1,530
includes taxes & fees
9 Nov - 10 Nov
Luxury Private Estate at Zoella Vineyards in the heart of Wine Country

7. Sauna, Cold Plunge & Fire Pit Near Wineries

Sauna, Cold Plunge & Fire Pit Near Wineries
Windsor
10.0 out of 10, Exceptional, (1 review)
"Very accommodating home with all the essentials. Awesome backyard for the dogs, great location and communication. "
United States
Keri S.
The price is €829
includes taxes & fees
9 Nov - 10 Nov
Sauna, Cold Plunge & Fire Pit Near Wineries

8. Cozy Riverfront Cabin - Beach Access & Wood Stove

Cozy Riverfront Cabin - Beach Access & Wood Stove
Guerneville
9.8 out of 10, Exceptional, (30 reviews)
"It was wonderful, we'll be back!"
United States
Jehanne H.
The price is €416
includes taxes & fees
9 Nov - 10 Nov
Cozy Riverfront Cabin - Beach Access & Wood Stove

9. Eastside Eden - Pool, Hot Tub and Tastings Included

Eastside Eden - Pool, Hot Tub and Tastings Included
Healdsburg
9.2 out of 10, Wonderful, (5 reviews)
"This is a great location with wonderful outdoor space and nice layout of the home. A perfect spot for a long weekend or longer. Great views on the wrap around deck. Would definitely come back. "
United States
Dan M.
Eastside Eden - Pool, Hot Tub and Tastings Included

10. 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, (23 reviews)
"Spacious and beautiful property- we had a great time!"
United States
Kirsten G.
The price is €1,000
includes taxes & fees
9 Nov - 10 Nov
Alexander Valley Lodge w/ Pool, Hot tub, Waterfall, Pool table and Tiki Bar

11. Healdsburg Luxury Villa Estate | Private Boutique Stay Near Plaza & Wineries

Healdsburg Luxury Villa Estate | Private Boutique Stay Near Plaza & Wineries
Healdsburg
The price is €1,851
includes taxes & fees
10 Nov - 11 Nov
Healdsburg Luxury Villa Estate | Private Boutique Stay Near Plaza & Wineries

12. Elegant Vineyard Living at a Private Wine Country Estate

Elegant Vineyard Living at a Private Wine Country Estate
Windsor
8.4 out of 10, Very good, (6 reviews)
"What an amazing place! The hosts made it very easy to be prepared for our stay."
United States
Eric B.
Elegant Vineyard Living at a Private Wine Country Estate

13. 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)
"very nice space "
United States
kevin c.
The price is €315
includes taxes & fees
9 Nov - 10 Nov
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape

14. Vineyard View Retreat • Fire Pit • Wine Tasting Perks

Vineyard View Retreat • Fire Pit • Wine Tasting Perks
Healdsburg
9.8 out of 10, Exceptional, (19 reviews)
"Great place. Quiet, very clean, close to Healdsburg, grocery stores, etc. Very helpful and nice host. We would definitely stay here again when in the area."
United States
Mark R.
The price is €340
includes taxes & fees
2 Dec - 3 Dec
Vineyard View Retreat • Fire Pit • Wine Tasting Perks

15. 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, (85 reviews)
"Great Home. Decent value.Didn’t realize the street were gonna be so compacted with houses very small streets"
United States
Melissa M.
The price is €539
includes taxes & fees
9 Nov - 10 Nov
Sonoma Wine Country Getaway | Winemaker’s Home with Modern Comforts

16. Russian River Retreat: Private Beach & DogFriendly

Russian River Retreat: Private Beach & DogFriendly
Forestville
10.0 out of 10, Exceptional, (1 review)
"Love this place so much! Will rent it every year for my birthday if they’ll let me!"
United States
Anna K.
The price is €523
includes taxes & fees
13 Nov - 14 Nov
Russian River Retreat: Private Beach & DogFriendly

17. Modern Cabin Retreat w/ Swim Spa, Hot Tub & A/C

Modern Cabin Retreat w/ Swim Spa, Hot Tub & A/C
Forestville
10.0 out of 10, Exceptional, (10 reviews)
"Loved our stay. Well stocked kitchen and close to some great little wineries."
United States
Ellen B.
The price is €452
includes taxes & fees
9 Nov - 10 Nov
Modern Cabin Retreat w/ Swim Spa, Hot Tub & A/C

18. Rocktop Lodge - Pool, Sauna, Hot Tub, Private Dock

Rocktop Lodge - Pool, Sauna, Hot Tub, Private Dock
Forestville
Rocktop Lodge - Pool, Sauna, Hot Tub, Private Dock

19. Country Carriage House in Downtown Geyserville, Vineyard Views

Country Carriage House in Downtown Geyserville, Vineyard Views
Geyserville
10.0 out of 10, Exceptional, (5 reviews)
"Cozy, rustic, and with all great amenities."
United States
Gina I.
The price is €332
includes taxes & fees
3 Dec - 4 Dec
Country Carriage House in Downtown Geyserville, Vineyard Views

20. Tranquil Redwood Retreat

Tranquil Redwood Retreat
Guerneville
8.8 out of 10, Excellent, (13 reviews)
"Perfect hun for enjoying downtown guernville "
United States
Alex A.
The price is €302
includes taxes & fees
9 Nov - 10 Nov
Tranquil Redwood Retreat
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

Find out more about Healdsburg

Everything you need to know about Healdsburg holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Healdsburg holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Healdsburg holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Healdsburg holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Healdsburg. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Healdsburg holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Healdsburg holiday rentals we have selected for you start as low as €100 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Healdsburg rentals

At Expedia, we put the best Healdsburg holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Healdsburg rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Healdsburg holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Healdsburg. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Healdsburg?

Yes, there are holiday rentals in Healdsburg close to Healdsburg Center for the Arts, or you can select a more secluded option if you're looking for 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 are some of the best holiday rentals that Healdsburg has to offer?

DOG-FRIENDLY, COZY—PERFECT 4 COUPLES—Close to EVERYTHING. SPECIAL DISCOUNTS!: This holiday 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 holiday rentals are there in Healdsburg?

Expedia has 135 holiday 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 holiday rentals like in Healdsburg?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Healdsburg. Holiday rentals provide amenities such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from public hotel lifts and lobbies packed with people while still allowing you to travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for a family trip or a small group gathering.