We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Healdsburg Vacation Rentals

List your property
Owner log in
Check in
— / — / —
Check out
— / — / —
Guests
0 rooms, 2+ guests
Bedrooms
Any
Bathrooms
Any
Amenities
Show more
Suitability
Show more
Property type
Show more
Distinctive Features
Show more
Distance from
1 mi
94 rentals in Healdsburg.
Sort by:
Tripadvisor Sort

Cabin In An Old Vine Zinfandel Vineyard. Dry Creek Valley. Five Miles To Plaza.

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Healdsburg - Chalk Hill Wine Country Cottage

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Hilltop Hideaway: Bright, Fresh, Modern, Views And Only 2 Miles To Plaza

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Wooded Restful Retreat, with broad scenic views, outdoor dining

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Secluded Valley Retreat

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

4 BR/4 BA Vineyard Retreat - Solar Heated Pool, Spa, Views

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Healdsburg River Front Oasis Retreat.

Rental Home
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Tanda Tula, Wine Country Sanctuary

Rental Home
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Healdsburg Cottage Walk to the Plaza, Workspace

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Healdsburg Bliss House-Sonoma Wine Country Sweeping Panoramic Vineyard Views

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Save time - get the best Healdsburg rentals sent straight to your email!

Superb Healdsburg Location, Spectacular Views, Minutes to Town

Rental Home
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Beautiful Studio Getaway in the Heart of Wine Country

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Healdsburg Villa on a Vineyard with Amazing Poolside Sunsets

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Modern Wine Country Cottage in Historic Healdsburg, Premiere Location

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Dry Creek Farm--Vineyard, Pool and Spa with Stunning View, Dog friendly

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Beautiful Mountain Top retreat less than 10 mins from downtown Healdsburg!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Yea, The Outdoor Kitchen is a Little Crazy (and pool, hot tub, firepit & views)

Rental Home
6 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Casa Chiquita - 3 Bedroom, 3 bath newly remodeled home with spa and pool

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Secluded Luxury Vineyard Estate House and Guest House

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Dry Creek Cottage - Healdsburg

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Modern country cottage: swimming pool, privacy, vineyard & 5 min. to Healdsburg

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Modern, newly built 5 BR home with beautiful views and 50 acres of privacy

Rental Home
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

luxuriously appointed new large guest suite in a landmark Victorian

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Elegant - Peaceful - Romantic - Private

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Contemporary Designer Cottage, Garden View, 3 Blocks From From The Plaza

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Updated cabin, right on Russian River, amazing views & location!

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Top Of The World Dry Creek Views With Hot Tub, POOL and new Tesla charger!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Modern Sophisticated Private Luxurious W/Views & Hot Tub

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Newly Listed 4BR/4.5BA Gorgeous 17 Acre Estate/Pool/Hot Tub/5 mins - Hburg Plaza

Rental Home
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Beautiful Views! Dry Creek Valley Retreat with Deck & Pool, 5 min to Healdsburg

Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Enjoy a Slice Of Country--Two miles to Downtown Healdsburg - Pets Welcome

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Creek Front Vineyard, West Dry Creek Healdsburg CA

Rental Home
6 bedrooms
7 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Luxury Wine Country Home in the Heart of Healdsburg with a Private Pool.

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

4,700 ft 4 bed & 4 bath ranch, 120 acres all to yourself with a lake and farm.

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Safe Retreat: Bicyclists, Birders, Wine Lovers, River Revelers Welcome!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Dog Friendly Vineyard Estate Cottage with Lap Pool and Incredible Views

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Sunset Magazine Meets Healdsburg - Foodies & Wine Lovers

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Close to Plaza/15 Acre Estate/swiming Pool and Bocce Ball

Rental Home
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Lovely Healdsburg Vineyard Home - 3br/2ba (up to 8 guests, children welcome)

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Dry Creek Valley Home and Vineyard

Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

VineHaven- Spa, Gardens, & Spectacular Vineyard Views

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

New Contemporary Home in the Heart of Sonoma Wine Country.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

*LImited Time Discount* Healdsburg Riverside Cottage - Beautiful River Views

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Bunkhouse at Side Road Farm charming one bedroom cottage

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

*New Home* 3 Blocks from Downtown Healdsburg Plaza!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Stunning, contemporary, eco-friendly home on 2.5 acres | Heated Pool & Spa

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Rendezvous Under the Oaks-Pool & hot Spa

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Views, Hot Tub, Fireplace, Semi-Private Beach Close By , Pet-Friendly

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Private 3 Bed + Cottage Wine Country Estate With Pool And More

Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Vineyard Guest House

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
PreviousNext
12
Frequently Asked Questions about Healdsburg





Healdsburg Vacation Rentals
Beautiful Northern California has many fabulous destinations, and the town of Healdsburg in Sonoma County is at the top of the list. And if you are looking for a vacation rental in this slice of world famous wine country, we’ve got you covered. We have a huge variety of Healdsburg vacation rental listings. You might be looking for a large house for the whole family, or a quaint cottage for a special romantic getaway. Whatever your needs and budget, we can help you find the perfect vacation rental that will make your stay in Healdsburg even more amazing. We can also provide you with helpful user reviews of vacation rentals in Healdsburg and the surrounding area, so you’ll be sure to get good value for your money.
More
Healdsburg Vacation Rentals
Beautiful Northern California has many fabulous destinations, and the town of Healdsburg in Sonoma County is at the top of the list. And if you are looking for a vacation rental in this slice of world famous wine country, we’ve got you covered. We have a huge variety of Healdsburg vacation rental listings. You might be looking for a large house for the whole family, or a quaint cottage for a special romantic getaway. Whatever your needs and budget, we can help you find the perfect vacation rental that will make your stay in Healdsburg even more amazing. We can also provide you with helpful user reviews of vacation rentals in Healdsburg and the surrounding area, so you’ll be sure to get good value for your money.
Healdsburg a Slice of Paradise
Small town charm, beautiful landscapes and outstanding weather are just a few of the trademark qualities that make Healdsburg so popular. Healdsburg combines five-star cuisine, rolling hills and world-acclaimed wine growing appellations for an experience you will never forget. When it’s time to relax at the end of the day, why stay in a cramped hotel when you can enjoy the comforts of home in one of our rental cottages, houses or cabins?
Lots of Activities
If you love the vibrant outdoors and colorful festivals, you will love Healdsburg. In April, you can help harvest roses and distill them into fragrant rose oil and rosewater as part of the Classic Perfume Rose Harvest & Distillation Tours. An annual sea food dinner at the Healdsburg Fire Department is also in April. From February to June, enjoy the "Russian River Good Old Days" exhibit at the Healdsburg Museum. And on the first Friday of the month, Williamson Wines sponsors an Epicurean Dinner at the Dry Creek Kitchen at Hotel Healdsburg.
Food, Wine and Fun
Speaking of eating, you won’t want to miss the chance to dine at Healdsburg’s amazing restaurants, including Affronti, Agave Mexican Restaurant &Tequila Bar, Thai Orchid Cuisine, Willi's Seafood & Raw Bar and Zin Restaurant & Wine Bar. And don’t forget to visit the beautiful wine country all around you, featuring names like Alexander Valley, Chalk Hill, Dry Creek Valley, and Russian River Valley. We’re here to help you make the most of your visit to Healdsburg. Let us help you find the perfect cozy cottage, cabin or house to make your stay in Healdsburg one you will always remember.