Healdsburg Vacation Rentals from $127: Search Short-Term Rentals

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

Panoramic Ocean Views walk to the Beach : This vacation home rental outside of Healdsburg is equipped with a balcony, air-conditioning, and laundry facilities to help you feel comfortable during your stay. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family.

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Healdsburg vacation rentals

Deluxe Cabin, 1 Queen Bed, Patio, Garden View | Laptop workspace, WiFi (free), bed sheets

1. Wildhaven Sonoma Glamping

Healdsburg

Yilin

$112 nightly

Sep 1 - Sep 2

Total with taxes and fees

2. Hillside Hideaway in the Redwoods

Guerneville

Kristin G.

$320 nightly

Aug 3 - Aug 4

Total with taxes and fees

3. Tranquil Redwood Retreat

Guerneville

Alex A.

$315 nightly

Aug 10 - Aug 11

Total with taxes and fees

4. Peaceful Redwood Hideaway - Hot Tub, A/C, Walk to Russian River and Downtown

Guerneville

Melissa R.

$440 nightly

Aug 4 - Aug 5

Total with taxes and fees

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

Geyserville

Gina I.

$341 nightly

Aug 17 - Aug 18

Total with taxes and fees

6. Wildflower

Windsor

Keri S.

$732 nightly

Sep 1 - Sep 2

Total with taxes and fees

7. Heart of Wine Country, Cute Cottage w/Hot Tub

Windsor

Rod H.

$581 nightly

Aug 2 - Aug 3

Total with taxes and fees

Coffee/tea maker, fridge, microwave, oven

8. Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape

Northwest Santa Rosa

kevin c.

$384 nightly

Aug 11 - Aug 12

Total with taxes and fees

View all properties

Find vacation rentals that suit your style

Cabins

Private vacation homes

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Healdsburg Hotel Reviews

The Lodge at Healdsburg, Tapestry Collection by Hilton

8/10 Good

"Our stay was comfortable and the staff was friendly. However, being "senior citizens" when I asked about a bell man for our bags, we had not assistance at all. In the end, we discovered several carts to make carrying our carts easier. They were pointed out to us and we had to discover them accidentally. Food service was not that impressive. Our room was clean and neat and comfortable, though."

Dry Creek Inn MOD Collection by Sonesta

8/10 Good

"Area was near a gas station, and 2 breakfast spots, fairly near a trail to walk/bike downtown. Staff were so friendly and provided great information. Room had a motel vibe, but clean and felt safe! Pool was pretty small, didn't use. Brought my doggy and our stay went well, not many spots for her to use the potty but it was sufficient."

Liora Estate

10/10 Excellent

"The Liora Estate Hotel is gorgeous. Our high end restaurant was just around the corner. The location is right in the middle of things. The valet parking is complimentary and a real convenience. My favorite amenity was the spectacular breakfast delivered to the room in a basket. Everything you need to start the day."

Wildhaven Sonoma Glamping

8/10 Good

"Swimming in the river was the best part of the trip. Bring your water shoes; there are rocks and I almost lost my sandals three times . Bring an extra fan for the tent. If you are in a tent; bring a portable umbrella for the outside. Our bench was not covered by the trees most of the day and the sun was strong. It is hot in the tent during the summer; that’s when you go swimming or hiking during the day. We recommend going to riverfront park trail; it’s an easy hike 20 mins drive from wildheaven. And it is beautiful there. Oh bring a hoodie for the night time; it gets cold at night. Hot days and cold nights in the summer."

Find out more about Healdsburg

Everything you need to know about Healdsburg vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Healdsburg vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Healdsburg vacation 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 low season months. For more hustle and bustle, you may prefer to visit Healdsburg in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $127 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Healdsburg rentals

At Expedia, we put the best Healdsburg vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Healdsburg?

Yes, there are vacation rentals in Healdsburg near Healdsburg Center for the Arts, 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 top-notch restaurants and wineries.

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

Panoramic Ocean Views walk to the Beach: This vacation home rental outside of Healdsburg is equipped with a balcony, air-conditioning, and laundry facilities to help you feel comfortable during your stay. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family.

How many vacation rentals are there in Healdsburg?

Expedia has 140 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.

Room 1

Check prices for these dates

Our top choices for Healdsburg vacation rentals

1. Wildhaven Sonoma Glamping

2. Hillside Hideaway in the Redwoods

3. Tranquil Redwood Retreat

4. Peaceful Redwood Hideaway - Hot Tub, A/C, Walk to Russian River and Downtown

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

6. Wildflower

7. Heart of Wine Country, Cute Cottage w/Hot Tub

8. Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape

9. Heron House - Hot Tub and Wine Tastings Included

10. Wine Country Cottage Escape

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

12. Russian River Brew-cation Home

13. Rivers Breeze - Wine Tastings Included

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

15. River View Lodge - Hot Tub and Tastings Included

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

17. The Dragonfly - Healdsburg with Pool, Hot Tub and Tastings Included

18. The Grove on Alexander Valley

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

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

Find vacation rentals that suit your style

Top Healdsburg Hotel Reviews

The Lodge at Healdsburg, Tapestry Collection by Hilton

Hotel Trio Healdsburg

Dry Creek Inn MOD Collection by Sonesta

Calderwood Inn

Fairview Inn and Suites

Grape Leaf Inn

Liora Estate

Wildhaven Sonoma Glamping

Appellation Healdsburg

Find out more about Healdsburg

Explore a world of travel with Expedia

Frequently asked questions

Expedia's Latest Trends