Healdsburg Holiday Rentals

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Check prices for these dates

Tonight
12 Jul - 13 Jul
Tomorrow
13 Jul - 14 Jul
Next weekend
18 Jul - 20 Jul
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25 Jul - 27 Jul

Holiday Rentals in Healdsburg

Experience Limerick Lane Cellars at our Vineyard Farmstay Retreat in Healdsburg
Enjoy a backyard with a swimming pool surrounded by lush landscaping and a shaded pergola.

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
Enjoy cooking in this well-equipped kitchen with a central island, gas stove, and ample counter space.

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
Gorgeous Views, Pool and Hot Tub, 12 mins to HB Plaza
Relax in a serene, setting surrounded by lush greenery and enjoy the inviting pool and patio area.

Gorgeous Views, Pool and Hot Tub, 12 mins to HB Plaza

10.0 out of 10, Exceptional, (166)
"Fantastic and relaxing stay. Beautiful views, comfortable home, peaceful surroundings. Always an excellent place to recharge. "
Gorgeous Views, Pool and Hot Tub, 12 mins to HB Plaza
✨Rustic Cabin in Dry Creek Valley with beautiful views // 5 miles to Plaza ✨
Cozy cabin interior with a central island, dining area, and wooden table.

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

10.0 out of 10, Exceptional, (297)
"We love staying at this cabin. It is peaceful, has a great location, and is the perfect place to unwind."
✨Rustic Cabin in Dry Creek Valley with beautiful views // 5 miles to Plaza ✨
Wooded Restful Retreat, with broad scenic views, outdoor dining
Enjoy cooking in this well-lit kitchen with a large island, double oven, and stainless steel refrigerator.

Wooded Restful Retreat, with broad scenic views, outdoor dining

10.0 out of 10, Exceptional, (308)
"Property is spotless. View is spectacular. Central location to restaurants and vineyards. Host was friendly and helpful! Highly recommend this property. "
Wooded Restful Retreat, with broad scenic views, outdoor dining
✨River View Lodge | Private River Access, Hot Tub, Kayaks & Views
Relax on the deck with a clear view of the forested hillside, featuring a hot tub and comfortable seating.

✨River View Lodge | Private River Access, Hot Tub, Kayaks & Views

9.6 out of 10, Exceptional, (70)
"The property is perfectly located just 10 minutes from central Healdsburg. Great for wine tasting and family time. "
The price is HK$6,824
HK$12,183 total
includes taxes & fees
7 Aug - 8 Aug
✨River View Lodge | Private River Access, Hot Tub, Kayaks & Views
Cypress House & Studio, Walk to Healdsburg Plaza by RedAwning
Stunning two-story building with a central entrance and upper-level balcony offering a scenic view.

Cypress House & Studio, Walk to Healdsburg Plaza by RedAwning

9.8 out of 10, Exceptional, (26)
"House was super convenient to downtown Healdsburg and all the attractions including restaurants, bakeries, coffee shops, wine tastings, and shopping."
Cypress House & Studio, Walk to Healdsburg Plaza by RedAwning
Rivers Breeze – Relaxing Riverside Cabin with Private Suite + Kayaks
Relax in a serene lakeside setting with a hammock and outdoor seating area amidst lush greenery.

Rivers Breeze – Relaxing Riverside Cabin with Private Suite + Kayaks

10.0 out of 10, Exceptional, (13)
"In Healdsburg to visit family and could not have had a more comfortable and lovely place to stay! It was impeccably clean, well located and so cute! We loved it!"
Rivers Breeze – Relaxing Riverside Cabin with Private Suite + Kayaks
Chalk Hill Cottage Close to Wineries
Situated in a serene wooded area, this charming home offers a peaceful retreat with a front porch and lush garden.

Chalk Hill Cottage Close to Wineries

9.8 out of 10, Exceptional, (37)
"The Chalk Hill cottage was the perfect getaway for Sonoma wine lovers. Located in Alexander Valley and close to great wineries."
Chalk Hill Cottage Close to Wineries
Fitch Mtn Lookout- Gorg & Comfy!Pets-Walkable Russian River-Spa under the stars!
Surrounded by lush greenery and a meandering river, this serene valley offers a secluded escape.

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

9.6 out of 10, Exceptional, (167)
"Cool cabin, lots of communication with host. Hummingbirds were amazing, there were hundreds. Didn’t realize both bathrooms were on the lowest floor so the top floor bedroom had a two story walk down when facilities were needed. Roads are extremely narrow to get to house and we were expecting an easier route to the river. Great spot for folks looking for an “off the beaten path” stay. Treehouse feeling was great."
Fitch Mtn Lookout- Gorg & Comfy!Pets-Walkable Russian River-Spa under the stars!
Private 1-bedroom Guest House with Great Amenities
Relax by the pool in a tranquil outdoor space with a patio, table, and comfortable seating.

Private 1-bedroom Guest House with Great Amenities

10.0 out of 10, Exceptional, (11)
"Our group had a wonderful time. The property was perfect in every way & would certainly rent again if lucky enough to return to Healdsburg."
Private 1-bedroom Guest House with Great Amenities
4 BEDROOM plus PRIVATE DEN, 6 1/2 BATH LUXURY HOME ON 3+ ACRES, 5 MIN TO SQUARE
Relax in a serene outdoor oasis with a pool, hot tub, and comfortable seating areas.

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

10.0 out of 10, Exceptional, (191)
"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
Vineyard Vue--Remodeled farmhouse w/ Vineyard Views and wrap around porch.
Enjoy cooking in this well-equipped kitchen with a central island, bar stools, and stainless steel appliances.

Vineyard Vue--Remodeled farmhouse w/ Vineyard Views and wrap around porch.

10.0 out of 10, Exceptional, (34)
"This is a meticulous property in an amazing location. The house is spacious with comfortable separated sleeping and bathroom accommodations. Perfect for our group. Easy access to town as well as innumerable delicious wineries in the area."
Vineyard Vue--Remodeled farmhouse w/ Vineyard Views and wrap around porch.
Walk to Downtown Healdsburg--Luxury Healdsburg Vacation Rental
Relax by the serene pool surrounded by lush greenery and tropical plants.

Walk to Downtown Healdsburg--Luxury Healdsburg Vacation Rental

10.0 out of 10, Exceptional, (29)
"Great proximity to wine and town. Loved it! Leah is great"
Walk to Downtown Healdsburg--Luxury Healdsburg Vacation Rental
Healdsburg Wine Country Getaway with Panoramic Valley Views -5 min from downtown
Relax in this inviting living room with a fireplace, flat-screen TV, and sliding glass doors leading to a balcony with a scenic view.

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

10.0 out of 10, Exceptional, (251)
"Our group had a fantastic stay at this property. The location is amazing - minutes from downtown Healdsburg but just far enough to feel a bit secluded. Tons of great wineries nearby (I recommend De La Montanya)."
Healdsburg Wine Country Getaway with Panoramic Valley Views -5 min from downtown
Vineyards Edge - Pool, Hot Tub, Bikes, Pets Welcome, Fire Pit- 1mi to Downtown
Relax in a serene outdoor oasis with a comfortable seating area, bar, and hot tub under a shaded pergola.

Vineyards Edge - Pool, Hot Tub, Bikes, Pets Welcome, Fire Pit- 1mi to Downtown

10.0 out of 10, Exceptional, (9)
"This was one of the most incredible VRBOs I have ever stayed at. Far exceeded every expectation and the hosts were so nice and communicative."
Vineyards Edge - Pool, Hot Tub, Bikes, Pets Welcome, Fire Pit- 1mi to Downtown
Private Vineyard Haven--walk to the HBG Square!
Relax by the pool under a shaded pergola with a comfortable bench and nearby table.

Private Vineyard Haven--walk to the HBG Square!

9.8 out of 10, Exceptional, (59)
"The house was exactly as described. Lovely home and garden area. Perfect location to explore Healdsburg and surrounding area"
Private Vineyard Haven--walk to the HBG Square!
Healdsburg Home with Magnificent Vineyard View by RedAwning
Guests can enjoy a patio with a table and chairs, surrounded by lush greenery and a wooden fence.

Healdsburg Home with Magnificent Vineyard View by RedAwning

10.0 out of 10, Exceptional, (18)
"Had a great stay!"
Healdsburg Home with Magnificent Vineyard View by RedAwning
Vinehaven - 3BD Healdsburg Retreat with Spa
Relax amidst a serene garden setting with vibrant flowers and a picturesque vineyard backdrop.

Vinehaven - 3BD Healdsburg Retreat with Spa

10.0 out of 10, Exceptional, (1)
"We had a lovely stay at Vinehaven as we explored Sonoma County. Thanks so much!"
Vinehaven - 3BD Healdsburg Retreat with Spa
Renovated farmhouse with vineyard views, bocce ball court, Ping-Pong, basketball
Relax in this spacious room with a ping pong table and comfortable seating area.

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

10.0 out of 10, Exceptional, (12)
"We had the best time at Bird & Barrel!! Every detail was thought through and the home was beautiful. The location was incredible, so close to town and wineries. We had the perfect weekend and can’t recommend it enough!!! We can’t wait to come back!"
Renovated farmhouse with vineyard views, bocce ball court, Ping-Pong, basketball
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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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?

COZY—Dog-Friendly—Perfect for Couples!!! 2025 DISCOUNT for 5-10 days—ASK!!!: This holiday home rental outside of Healdsburg is located on the waterfront, and offers a selection of books, WiFi and a Smart TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Healdsburg?

Expedia has 142 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 SingleThread Farm at Dry Creek 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.