Healdsburg Vacation Rentals

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Vacation Rentals in Healdsburg

Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg
Fridge, microwave, oven, stovetop

Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg

10.0 out of 10, Exceptional, (63)
"Gorgeous property and excellent communications with owner and property manager. Well stocked kitchen and so many wonderful things to enjoy!"
Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg
Clear Lake Cottages & Marina
View from property

Clear Lake Cottages & Marina

2.5 star property
9.0 out of 10, Wonderful, (320)
"Great stay!"
$154 nightly
The price is $172
Oct 8 - Oct 9
Total with taxes and fees
Clear Lake Cottages & Marina
Incredibly Beautiful, Private, Unique Home Perched On The Bluff At Ocean's Edge!
Smart TV, fireplace, DVD player, books

Incredibly Beautiful, Private, Unique Home Perched On The Bluff At Ocean's Edge!

10.0 out of 10, Exceptional, (397)
"We love this rental! Perfect for a couple or a family that doesn’t mind sharing a bed :) amazing hosts and most incredible view. "
Incredibly Beautiful, Private, Unique Home Perched On The Bluff At Ocean's Edge!
The Ranch at Lake Sonoma
Front of property

The Ranch at Lake Sonoma

1.0 star property
10.0 out of 10, Exceptional, (1)
"The location is fantastic, with a spectacular view on the lake if you choose a lakeview. A very genuine welcome from The Ranch team, with all detailed explanations, a map to help you to navigate around. For our first time going camping, we want definitely to come back there !"
$59 nightly
The price is $68
Oct 3 - Oct 4
Total with taxes and fees
The Ranch at Lake Sonoma
7 Bedroom Oceanfront in Dillon Beach with spa
Dining

7 Bedroom Oceanfront in Dillon Beach with spa

9.4 out of 10, Exceptional, (162)
"Amazing property with stunning views. Owner is prompt with communication, and the amenities are as advertised. Would stay again or recommend to anyone!"
$1,854 nightly
The price is $2,094
Oct 5 - Oct 6
Total with taxes and fees
7 Bedroom Oceanfront in Dillon Beach with spa
Riverfront Cottage in Wine Country - Seasonal River Access - Dogs Stay for Free!
Terrace/patio

Riverfront Cottage in Wine Country - Seasonal River Access - Dogs Stay for Free!

9.8 out of 10, Exceptional, (345)
"We enjoyed our stay at this well equipped and designed cottage. We loved the decks and location on the river. "
Riverfront Cottage in Wine Country - Seasonal River Access - Dogs Stay for Free!
Oceanfront - Hot Tub - Newly Remodeled Cottage
Outdoor spa tub

Oceanfront - Hot Tub - Newly Remodeled Cottage

9.8 out of 10, Exceptional, (393)
"Perfect getaway and the hot tub was a hit. "
Oceanfront - Hot Tub - Newly Remodeled Cottage
COZY—Dog-Friendly—Perfect for Couples!!! 2025 DISCOUNT for 5-10 days—ASK!!!
Beach

COZY—Dog-Friendly—Perfect for Couples!!! 2025 DISCOUNT for 5-10 days—ASK!!!

9.6 out of 10, Exceptional, (187)
"Perfect get away for my wifes 60th."
COZY—Dog-Friendly—Perfect for Couples!!! 2025 DISCOUNT for 5-10 days—ASK!!!
Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella
Fridge, microwave, oven, stovetop

Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella

10.0 out of 10, Exceptional, (66)
"Smooth check-in process. Close to plenty of vineyards. Very friendly staff. "
Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella
Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard
Interior

Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard

9.8 out of 10, Exceptional, (457)
"It was great as always"
Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard
ON A BLUFF WITH 180 DEGREE CLOSE WATER VIEWS SHORT WALK TO THE BEACH
Interior

ON A BLUFF WITH 180 DEGREE CLOSE WATER VIEWS SHORT WALK TO THE BEACH

9.2 out of 10, Wonderful, (215)
"The location can’t be beat, the views are incredible. We had a few issues that were handled with great satisfaction by the owner. "
$712 nightly
The price is $787
Oct 9 - Oct 10
Total with taxes and fees
ON A BLUFF WITH 180 DEGREE CLOSE WATER VIEWS SHORT WALK TO THE BEACH
Panoramic Ocean View--3 Min Walk To Beach
Dining

Panoramic Ocean View--3 Min Walk To Beach

9.6 out of 10, Exceptional, (323)
"The cabin is well supplied and so close to the beach. Comfortable and sweet."
Panoramic Ocean View--3 Min Walk To Beach
Casa Bella Estate in Wine Country w/ New Pool!
Outdoor dining

Casa Bella Estate in Wine Country w/ New Pool!

9.6 out of 10, Exceptional, (132)
"Cozy Location for a Corporate retreat!"
$3,066 nightly
The price is $3,432
Oct 10 - Oct 11
Total with taxes and fees
Casa Bella Estate in Wine Country w/ New Pool!
Romantic, Dramatic Views! Full calendar https://www.vrbo.com/81742?dateless=true
Smart TV, fireplace, books, music library

Romantic, Dramatic Views! Full calendar https://www.vrbo.com/81742?dateless=true

10.0 out of 10, Exceptional, (282)
"Lovely house, setting and host!"
Romantic, Dramatic Views! Full calendar https://www.vrbo.com/81742?dateless=true
Romantic King Bed Studio ~ STUNNING VIEWS Bodega Bay - Perched over the water!
Interior

Romantic King Bed Studio ~ STUNNING VIEWS Bodega Bay - Perched over the water!

9.4 out of 10, Exceptional, (346)
"The property was beautiful and perfect! We absolutely loved our stay here, and are looking forward to coming back again."
$547 nightly
The price is $605
Oct 7 - Oct 8
Total with taxes and fees
Romantic King Bed Studio ~ STUNNING VIEWS Bodega Bay - Perched over the water!
Sonoma Luxury, Enchanting Sonoma Home, Walkable to the Square, Sleeps 10
Interior

Sonoma Luxury, Enchanting Sonoma Home, Walkable to the Square, Sleeps 10

9.8 out of 10, Exceptional, (154)
"Beautiful property in a good location not far from Sonoma Square. Our friends really enjoyed staying there !"
Sonoma Luxury, Enchanting Sonoma Home, Walkable to the Square, Sleeps 10
Malibu of the North Oceanfront w 3 Suites
TV, fireplace, offices

Malibu of the North Oceanfront w 3 Suites

7.8 out of 10, Good, (8)
Malibu of the North Oceanfront w 3 Suites
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
Interior

Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021

10.0 out of 10, Exceptional, (245)
"Loved the house and location! "
$1,934 nightly
The price is $2,189
Nov 2 - Nov 3
Total with taxes and fees
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
Backyard Garden Oasis
Property grounds

Backyard Garden Oasis

3.0 star property
9.6 out of 10, Exceptional, (50)
"Cute garden area, quiet, nice all inclusive spot"
$194 nightly
The price is $216
Oct 5 - Oct 6
Total with taxes and fees
Backyard Garden Oasis
Bright Home 800 Feet from Salmon Creek Beach w/ Wood Stove & Pool Table
Interior

Bright Home 800 Feet from Salmon Creek Beach w/ Wood Stove & Pool Table

8.2 out of 10, Very Good, (47)
"Walking distance to the beach and a warm and inviting space to return to. Perfect for our weekend getaway."
Bright Home 800 Feet from Salmon Creek Beach w/ Wood Stove & Pool Table
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

Find out more about Healdsburg

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 $68 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

Explore a world of travel with Expedia

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?

7 Bedroom Oceanfront in Dillon Beach with spa: This vacation home rental outside of Healdsburg is located on the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub.

How many vacation rentals are there in Healdsburg?

Expedia has 139 vacation rentals for your stay in Healdsburg.

What can I see and do in Healdsburg?

Enjoy the outdoors at Russian River and Healdsburg Ridge Open Space Preserve, or simply take in cultural attractions like Healdsburg Museum and Raven Performing Arts Theater. 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.