Search Holiday Rentals in Healdsburg

    price find illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Save instantly and earn perks with One Key
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Top Holiday Rentals in Healdsburg

Experience Limerick Lane Cellars at our Vineyard Farmstay Retreat in Healdsburg

10.0 out of 10, Exceptional, (32)
"Absolutely wonderful stay. The house was beautiful and clean, with multiple spacious common areas for family time. The Limerick Lane team was also incredibly communicative and accommodating throughout. 100% recommend."
Experience Limerick Lane Cellars at our Vineyard Farmstay Retreat in Healdsburg

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

10.0 out of 10, Exceptional, (61)
"Great stay, recommend in every way"
Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg

Clear Lake Cottages & Marina

2.5 star property
9.0 out of 10, Wonderful, (314)
"The cabin was very clean and it was in a nice and quiet location."
The price is £175
includes taxes & fees
10 Jul - 11 Jul
Clear Lake Cottages & Marina

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 !"
The price is £50
includes taxes & fees
27 Jul - 28 Jul
The Ranch at Lake Sonoma

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

10.0 out of 10, Exceptional, (383)
"Super clean and comfortable with an amazing view. We hope to be back! "
Incredibly Beautiful, Private, Unique Home Perched On The Bluff At Ocean's Edge!

Panoramic Ocean View--3 Min Walk To Beach

9.6 out of 10, Exceptional, (310)
"Great place to stay. Perfect walk to the beach and very relaxing. Loved the view from the deck. Great kitchen, clean house and comfortable bed. "
Panoramic Ocean View--3 Min Walk To Beach

Unobstructed ocean views in a cozy setting

10.0 out of 10, Exceptional, (42)
"Our stay here was wonderful, very cute beach house and wonderful view of the ocean. "
Unobstructed ocean views in a cozy setting

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

9.6 out of 10, Exceptional, (177)
"Nice, clean, small duplex perfect for two people, within walking distance to the bay and stores. Dog friendly!"
COZY—Dog-Friendly—Perfect for Couples!!! 2025 DISCOUNT for 5-10 days—ASK!!!

Oceanfront - Hot Tub - Newly Remodeled Cottage

9.8 out of 10, Exceptional, (383)
"Our third stay and first time booking three nights which seems to be the sweet spot for an extended weekend since you get two full days to relax along the coast. Already can't wait to book our next visit to this charming property!"
Oceanfront - Hot Tub - Newly Remodeled Cottage

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

8.0 out of 10, Very good, (41)
"Clean, heater worked great, comfy beds, lots of room, loved the views"
Bright Home 800 Feet from Salmon Creek Beach w/ Wood Stove & Pool Table

Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard

9.8 out of 10, Exceptional, (438)
"We had a great time finding a relaxing spring break spot. Gorgeous views and comfortable house. Great location. "
Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard

Bodega Bay on the Edge of Pacific Ocean

9.6 out of 10, Exceptional, (148)
"Perfect stay"
Bodega Bay on the Edge of Pacific Ocean

Luxury 3-bedroom Estate surrounded by a 20-acre vineyard and 30-mile views.

10.0 out of 10, Exceptional, (5)
"We had a pleasant stay at the property over the Memorial Day weekend. It’s away from the crowds but yet 15 mins from Sonoma Lake for water sports and 30 mins from Healdsburg. Amazing view and great time in the pool. "
Luxury 3-bedroom Estate surrounded by a 20-acre vineyard and 30-mile views.

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

9.8 out of 10, Exceptional, (328)
"We enjoyed our stay! So much to see and do in the RR valley! "
Riverfront Cottage in Wine Country - Seasonal River Access - Dogs Stay for Free!

Escape to Wine County in your independant Cottage in Downtown Calistoga

9.8 out of 10, Exceptional, (19)
"We have stayed many times at the Cottage Grove Inn and it never disappoints. "
The price is £306
includes taxes & fees
14 Jul - 15 Jul
Escape to Wine County in your independant Cottage in Downtown Calistoga

Dog-Friendly Oceanfront Home with Gorgeous Views, a Private Hot Tub

8.6 out of 10, Excellent, (147)
"We enjoyed our stay very much, even with the electricity off for several hours. There was so much to see and enjoy. "
Dog-Friendly Oceanfront Home with Gorgeous Views, a Private Hot Tub

Renovated home w/ breathtaking views of the bay and new hot tub

10.0 out of 10, Exceptional, (45)
"Thank you - fantastic place with a great view. We would highly recommend the property to anyone looking on VRBO. "
The price is £578
includes taxes & fees
13 Jul - 14 Jul
Renovated home w/ breathtaking views of the bay and new hot tub

Ocean Front/3 minute walk/Hotub/Sauna/Pets/Massage Chair/Pinball/Pac-Man Machine

9.0 out of 10, Wonderful, (294)
"Very good overall stay, comfortable and unbeatable location"
Ocean Front/3 minute walk/Hotub/Sauna/Pets/Massage Chair/Pinball/Pac-Man Machine

Beautiful Coast Home 3 Minutes From Beach!

8.0 out of 10, Very good, (8)
"The home was beautiful, comfortable and clean and lots of amenities."
The price is £574
includes taxes & fees
5 Aug - 6 Aug
Beautiful Coast Home 3 Minutes From Beach!

4.5 Bedrooms, 3 Baths, 2 Kitchens, 180 degree views and a 'Man Cave'

9.2 out of 10, Wonderful, (177)
"The house was spacious and welcoming. There was plenty to do for all ages. Gaines, pool table, hot tub. Plenty of room to spread out. We enjoyed our time."
4.5 Bedrooms, 3 Baths, 2 Kitchens, 180 degree views and a 'Man Cave'
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.
Save an average of 15% on thousands of hotels when you're signed in

Frequently asked questions

Are there holiday rentals in Healdsburg?

Yes, there are holiday rentals in Healdsburg close to SingleThread Farm at Dry Creek, 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 top-notch restaurants and wineries.

What are some of the best holiday rentals that Healdsburg has to offer?

Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg: This highly rated holiday home rental in Healdsburg is located in a rural location, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Healdsburg?

Expedia has 141 holiday 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 Wilson 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.