Healdsburg Holiday Rentals

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Holiday Rentals in Healdsburg

Healdsburg Modern home, 3BR/3.5BA pool, hot tub, outdoor kitchen, WiFi

10.0 out of 10, Exceptional, (13)
"My very Best VRBO rental experience. Property was even better than expected, very comfortable beds and bedding. Fully equipped kitchen with all necessities. Thoughtful property management and communications. This is a property I would book again without hesitation. "
Healdsburg Modern home, 3BR/3.5BA pool, hot tub, outdoor kitchen, WiFi

✨Rustic Cabin in Dry Creek Valley with beautiful views // 5 miles to Plaza ✨

10.0 out of 10, Exceptional, (280)
"Charming cabin among the vineyard. Very comfortable, host is very informative. Love the location close to Healdsburg. This was our second visit, we hope to return again."
✨Rustic Cabin in Dry Creek Valley with beautiful views // 5 miles to Plaza ✨

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

10.0 out of 10, Exceptional, (144)
"Beautiful setting with a wonderful home. Loved the location near Healdsburg. Everything was convenient. The property manager was fantastic!"
4 BR/4 BA Vineyard Retreat - Solar Heated Pool, Spa, Views

Fitch Mtn Lookout- Gorg & Comfy!Pets-Walkable Russian River-Spa under the stars!

9.6 out of 10, Exceptional, (165)
" Place is a real gem: Beautiful views of the Russian River valley from the house and from several decks; Spacious and comfortable inside; Hot tub outside on deck with beautiful view of the valley; easy walk to water. We also did some nearby hikes and spent time in the lovely town of Healdsburg. Owner Stephen and manager Tenay were great hosts."
Fitch Mtn Lookout- Gorg & Comfy!Pets-Walkable Russian River-Spa under the stars!

Experience Limerick Lane Cellars at our Vineyard Farmstay Retreat in Healdsburg

10.0 out of 10, Exceptional, (29)
"Our stay was lovely. The property is absolutely beautiful!! We were a group of 7 on our annual college reunion trip and the layout fit us well. The house is well appointed - wish there was an additional half bath in the house to make it more accommodating for those in the front of the home. It took a long time for the water to warm up in all the sinks and showers - guessing the pipes are old and the ground is cold. We enjoyed our tasting next door among the barrels."
Experience Limerick Lane Cellars at our Vineyard Farmstay Retreat in Healdsburg

February SPECIAL 𝑳𝒖𝒙𝒖𝒓𝒚 𝑷𝒓𝒊𝒗𝒂𝒕𝒆 𝑬𝒔𝒕𝒂𝒕𝒆 𝒂𝒕 𝒁𝒐𝒆𝒍𝒍𝒂 𝑽𝒊𝒏𝒆𝒚𝒂𝒓𝒅.𝑷𝑶𝑶𝑳&𝑺𝑷𝑨!𝑮𝑨𝑴𝑬𝑹𝑶𝑶𝑴!

9.6 out of 10, Exceptional, (57)
"I had a group of 10 people staying at Zoella Vineyard for my birthday and the place was so perfect for us. The house was massive and had tons of amenities and games. The pool and hot tub were awesome too! If you have a big group and want to enjoy the beautiful Sonoma in a gorgeous house, this is the place to be!"
The price is AU$2,542
includes taxes & fees
17 Mar - 18 Mar
February SPECIAL 𝑳𝒖𝒙𝒖𝒓𝒚 𝑷𝒓𝒊𝒗𝒂𝒕𝒆 𝑬𝒔𝒕𝒂𝒕𝒆 𝒂𝒕 𝒁𝒐𝒆𝒍𝒍𝒂 𝑽𝒊𝒏𝒆𝒚𝒂𝒓𝒅.𝑷𝑶𝑶𝑳&𝑺𝑷𝑨!𝑮𝑨𝑴𝑬𝑹𝑶𝑶𝑴!

Private Luxury home in Healdsburg with Vineyard, Sauna, Hot tub, Tesla Charger

10.0 out of 10, Exceptional, (2)
"Stunning property! The perfect getaway for a girls weekend. "
Private Luxury home in Healdsburg with Vineyard, Sauna, Hot tub, Tesla Charger

Renovated farmhouse with vineyard views, bocce ball court, Ping-Pong, basketball

10.0 out of 10, Exceptional, (10)
"Everything about this property was outstanding! Spotless, well equipped, comfortable, spacious, indoor and outdoor relaxation areas, easy access to the freeway while being tucked away in the vineyard, bocce, ping pong, ample outdoor seating. We were blown away! Every detail was thought of and provided. We loved the natural light throughout. Comfortable beds and plenty of linens. This will be our home away from home when we visit Sonoma County!"
Renovated farmhouse with vineyard views, bocce ball court, Ping-Pong, basketball

Casa Pavone: Serene Escape w/ Pool & Pizza Oven

Casa Pavone: Serene Escape w/ Pool & Pizza Oven

Mountain Cottage near Russian River, hiking & downtown, family and pet friendly

9.2 out of 10, Wonderful, (55)
"Cute property! It’s a little rustic, but has everything you need. The location is beautiful and convenient to Healdsburg. "
Mountain Cottage near Russian River, hiking & downtown, family and pet friendly

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

10.0 out of 10, Exceptional, (57)
"This place is excellent. Karen was such a lovely host, and property manager Alexa was so helpful. The photos really don't do this place justice--it's so lovely. A peak moment for me was watching a hot-air ballon on the horizon from the shower window on our first morning there. It was just magical. There is plenty of room for 10 people to sleep comfortably. The house has all the amenities. We were able to heat the pool so the kids were swimming all day long in the middle of February. They had a...
Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg

Wooded Restful Retreat, with broad scenic views, outdoor dining

10.0 out of 10, Exceptional, (300)
"The house,view, communications and cleanliness were exactly as promised—excellent. We felt welcomed and at home. With the information Cynthia provided, we did everything we wanted easily. Thank you. "
Wooded Restful Retreat, with broad scenic views, outdoor dining

Four Sisters Escape sleeps 10, Healdsburg pool

Four Sisters Escape sleeps 10, Healdsburg pool

Sanctuary on Lytton -- a true Sanctuary in the heart of wine country!

10.0 out of 10, Exceptional, (28)
"Such a fun property to stay at for an extended weekend! Great location and the hosts were easy to communicate with! "
Sanctuary on Lytton -- a true Sanctuary in the heart of wine country!

Healdsburg Wine Country Getaway with Panoramic Valley Views -5 min from downtown

10.0 out of 10, Exceptional, (239)
"This property was perfect for our girls trip. The location could not be any better with it being so close to downtown Healdsburg and access to the highway for other excursions. The pictures do not do the view justice; we found ourselves planning dinners at the house just so we could enjoy it more. The beds were comfortable, plenty of seating in the dining and loving rooms, and the kitchen had ample supplies. We would highly recommend and are already planning our next stay!"
Healdsburg Wine Country Getaway with Panoramic Valley Views -5 min from downtown

Walk to Downtown Healdsburg--Luxury Healdsburg Vacation Rental

10.0 out of 10, Exceptional, (26)
"Great location that’s walkable and bike able to wineries and downtown, very helpful and welcoming hosts, super comfortable space with an awesome game room. "
Walk to Downtown Healdsburg--Luxury Healdsburg Vacation Rental

Private Vineyard Haven--walk to the HBG Square!

9.8 out of 10, Exceptional, (53)
"A very lovely spot -- well-appointed, clean, and everything worked without a hitch! Loved the birdsong in the morning and sitting in the hot tub under the stars at night. Beds were comfortable and it was nice and quiet at night for sleeping.I will note for others that it appears on your mapping software as if you might be able to walk into town from the property, but there are no sidewalks or shoulders on the local roads, so it's a bit sketchy to do so, especially at night."
Private Vineyard Haven--walk to the HBG Square!

Charming Retreat near Healdsburg – 3 BD + Den, Outdoor Dining

10.0 out of 10, Exceptional, (9)
"Loved the proximity to Healdsburg, the dry creek area and the Russian river valley. Very comfortable furniture. "
Charming Retreat near Healdsburg – 3 BD + Den, Outdoor Dining

4 BEDROOM plus PRIVATE DEN, 6 1/2 BATH LUXURY HOME ON 3+ ACRES, 5 MIN TO SQUARE

10.0 out of 10, Exceptional, (189)
"We stayed here for husband’s birthday weekend. Beautiful property. It had everything we needed for a relaxing weekend away. "
4 BEDROOM plus PRIVATE DEN, 6 1/2 BATH LUXURY HOME ON 3+ ACRES, 5 MIN TO SQUARE

The Roost - Garden Studio

10.0 out of 10, Exceptional, (11)
"Loved the location of this cute studio. We were able to walk around Healdsburg and enjoy shopping and all of the delicious restaurants."
The Roost - Garden Studio
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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Other types of properties in Healdsburg you may be interested in

Montage Healdsburg

5.0 star property
9.4 out of 10, Exceptional, (89)
"Impeccable in every way! "
The price is AU$1,520
includes taxes & fees
1 Apr - 2 Apr
Montage Healdsburg

H2Hotel

4.0 star property
9.4 out of 10, Exceptional, (628)
"Love the service and location! "
The price is AU$548
includes taxes & fees
12 Mar - 13 Mar
H2Hotel

The Lodge at Healdsburg, Tapestry Collection by Hilton

3.5 star property
9.0 out of 10, Wonderful, (243)
"I loved this property! The rooms, overall ambiance, and staff were all great! I’ll be back again! "
The price is AU$293
includes taxes & fees
17 Mar - 18 Mar
The Lodge at Healdsburg, Tapestry Collection by Hilton
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.

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 wineries and top-notch restaurants.

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

4 BR/4 BA Vineyard Retreat - Solar Heated Pool, Spa, Views: 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 private balcony, a private garden and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Healdsburg?

Expedia has 147 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 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.