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Healdsburg Vacation Rentals

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Vacation Rentals in Healdsburg

Cottages at Healdsburg

Cottages at Healdsburg

4 out of 5
425 Foss Street, Healdsburg, CA
The price is $475 per night from Aug 8 to Aug 8
Situated in Healdsburg, this cottage is within a 5-minute walk of Raven Performing Arts Theater, Healdsburg Center for the Arts, and Healdsburg Plaza. Healdsburg ...
4.8/5Exceptional! (28 reviews)
"Everything was so amazing! The room was more spacious than we expected, complete with a little living room and dining table, plus a cute back porch. There was private onsite parking which was so convenient, and the property was in walking distance of the town center. Looking forward to coming back ..."

Reviewed on Jul 27, 2021

Cottages at Healdsburg
Dry Creek Cottage - Healdsburg

Dry Creek Cottage - Healdsburg

Healdsburg, CA
Situated in Healdsburg, this cottage is within 2 mi (3 km) of Healdsburg District Hospital, Simi Winery, and Raven Performing Arts Theater. Wilson Winery and ...
4.8/5Exceptional! (58 reviews)
Wine country getaway
"Lovely (small) guest house across the pool from owners of the property. Close to everything in Healdsburg. Great wine tasting, restaurants, biking, and hiking all nearby. Not walking distance to town but short car ride. Convenient to Highway 101 (but thus some road noise — although not intrusive). ..."

Reviewed on Jul 27, 2021

Dry Creek Cottage - Healdsburg
Elegant - Peaceful - Romantic - Private

Elegant - Peaceful - Romantic - Private

Healdsburg, CA
Located in the heart of Healdsburg, this cottage is within a 10-minute walk of Raven Performing Arts Theater, Healdsburg Center for the Arts, and Healdsburg ...
4.8/5Exceptional! (165 reviews)
Great Location
"The location is primo, just a short few blocks to downtown Healdsberg. The cottage was very clean and the bed was comfortable. However, we found that having only 2 small cups for coffee was simply not enough. It should also be noted that Grandma likes having lots and lots of pictures hanging everywhere. ..."

Reviewed on Jul 19, 2021

Elegant - Peaceful - Romantic - Private
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Art and Wine Estate - 4 Br Home

Art and Wine Estate - 4 Br Home

3.5 out of 5
8409 Westside Rd, Healdsburg, CA
Situated in Healdsburg, this golf vacation home is 0.1 mi (0.2 km) from Russian River and within 6 mi (10 km) of Matrix Winery and Russian River Vineyard. Hartford ...
5/5Exceptional! (1 review)
Go to house in wine country
"Great convenient spot within walking and short drive of several wineries and vineyards everywhere. Quiet and beautiful."

Reviewed on Oct 22, 2019

Art and Wine Estate - 4 Br Home
Modern Luxury Farm House in the Heart of Dry Creek Valley

Modern Luxury Farm House in the Heart of Dry Creek Valley

Healdsburg, CA
Situated in Healdsburg, this vacation home is within 6 mi (10 km) of Sbragia Family Vineyards, Russian River, and Fritz Underground Winery. DeLorimier Winery ...
5/5Exceptional! (2 reviews)
Perfect location
"We have been to the Healdsburg area many times. This house was not only clean and beautiful, but was located perfectly to our favorite wineries, as well as highway access and proximity to town. If you prefer to spend more time at the house, it is very comfortable. Couldn’t have been more ..."

Reviewed on Jul 27, 2021

Modern Luxury Farm House in the Heart of Dry Creek Valley
Redwood River House- Peaceful Riverfront Cottage Minutes From Downtown

Redwood River House- Peaceful Riverfront Cottage Minutes From Downtown

Healdsburg, CA
Situated on the waterfront, this romantic vacation home is 0.1 mi (0.1 km) from Russian River and within 3 mi (5 km) of Healdsburg District Hospital and Healdsburg ...
4.7/5Exceptional! (35 reviews)
Excellent gateaway
"We spent 3 wonderful days at Redwood River house. Excellent property, excellent location, excellent host!"

Reviewed on Jul 26, 2021

Redwood River House- Peaceful Riverfront Cottage Minutes From Downtown
Rustic Cabin in Dry Creek Valley With Beautiful Views // 5 Miles to Plaza

Rustic Cabin in Dry Creek Valley With Beautiful Views // 5 Miles to Plaza

Healdsburg, CA
Situated in a rural location, this cabin is within 6 mi (10 km) of Dry Creek Vineyard, Healdsburg Plaza, and Healdsburg Center for the Arts. Raven Performing ...
5/5Exceptional! (149 reviews)
Idyllic Cabin in the Vineyards!
"The cabin is perfect for a peaceful, relaxing time in the middle of beautiful vineyards in the Dry Creek Valley. It is furnished with everything you could possibly want (except maybe a fireplace!). The hosts are accommodating and responsive to your needs. Highly recommended!"

Reviewed on Jul 19, 2021

Rustic Cabin in Dry Creek Valley With Beautiful Views // 5 Miles to Plaza
Yea, The Outdoor Kitchen is a Little Crazy

Yea, The Outdoor Kitchen is a Little Crazy

Healdsburg, CA
This family-friendly Healdsburg resort is located on a river, within 3 mi (5 km) of Russian River and Simi Winery. Healdsburg Ridge Open Space Preserve and Healdsburg ...
5/5Exceptional! (67 reviews)
Wonderful family vacation!
"This house has it all! We spent four days swimming, cooking in the beautiful outdoor kitchen and relaxing. We hope to return next year!"

Reviewed on Jul 27, 2021

Yea, The Outdoor Kitchen is a Little Crazy
Private Wine Country Resort - 4 Br estate

Private Wine Country Resort - 4 Br estate

3.5 out of 5
700 Maybee LN, Healdsburg, CA
This family-friendly Healdsburg vacation home is within 3 mi (5 km) of Mazzocco Winery, Simi Winery, and Healdsburg Ridge Open Space Preserve. Healdsburg District ...
Private Wine Country Resort - 4 Br estate
Historic Cottage Walk To The Plaza

Historic Cottage Walk To The Plaza

Healdsburg, CA
Located in the heart of Healdsburg, this vacation home is within a 5-minute walk of Raven Performing Arts Theater and Healdsburg Center for the Arts. Healdsburg ...
5/5Exceptional! (3 reviews)
Excellent!!!
"Great property! Will definitely stay here again! Wish the listing told us there was a bbq outside we could use. Also, would recommend a wall A/C unit for room upstairs! Everything else was perfect ☺️🙌🏽"

Reviewed on Jul 26, 2021

Historic Cottage Walk To The Plaza
Pet Friendly Wine Country Getaway On The Russian River Just 5 Minutes From Town

Pet Friendly Wine Country Getaway On The Russian River Just 5 Minutes From Town

Healdsburg, CA
This family-friendly Healdsburg vacation home is within 3 mi (5 km) of Russian River, Healdsburg Golf Club, and Healdsburg Museum. Healdsburg District Hospital ...
4.3/5Excellent! (44 reviews)
house lovely
"A little hard to find at first. Maybe a little map with final instructions. Plenty of room for 5 adults"

Reviewed on Jul 26, 2021

Pet Friendly Wine Country Getaway On The Russian River Just 5 Minutes From Town
Healdsburg Bliss House-sonoma Wine Country Panoramic Views

Healdsburg Bliss House-sonoma Wine Country Panoramic Views

Healdsburg, CA
Located in the heart of Healdsburg, this vacation home is within 2 mi (3 km) of Healdsburg Plaza, Healdsburg Center for the Arts, and Healdsburg Museum. Raven ...
4.8/5Exceptional! (83 reviews)
Blissfully happy at Bliss House
"The time we spent at this beautiful property was really enjoyable. The expansive vineyard views made morning coffee and dinner especially pleasant. We will be back!"

Reviewed on Jul 14, 2021

Healdsburg Bliss House-sonoma Wine Country Panoramic Views
Choice Getaway With Hot Tub - Near Wineries, Dining - 2 Bedroom Home

Choice Getaway With Hot Tub - Near Wineries, Dining - 2 Bedroom Home

3.5 out of 5
815 Dry Creek Rd, Healdsburg, CA
Situated in Healdsburg, this golf vacation home is within 2 mi (3 km) of Wilson Winery, Healdsburg District Hospital, and Simi Winery. Raven Performing Arts ...
Choice Getaway With Hot Tub - Near Wineries, Dining - 2 Bedroom Home
3br W/ Pool, Hot Tub & Guest Suite 3 Bedroom Home

3br W/ Pool, Hot Tub & Guest Suite 3 Bedroom Home

4 out of 5
788 Magnolia Dr Entire Property, Healdsburg, CA
Situated in Healdsburg, this golf vacation home is 0.2 mi (0.3 km) from Russian River and within 3 mi (5 km) of Healdsburg Plaza and Healdsburg Center for the ...
3br W/ Pool, Hot Tub & Guest Suite 3 Bedroom Home
Wooded Restful Retreat, With Broad Scenic Views, Outdoor Dining

Wooded Restful Retreat, With Broad Scenic Views, Outdoor Dining

Healdsburg, CA
Located in the heart of Healdsburg, this resort is 0.3 mi (0.5 km) from Russian River and within 3 mi (5 km) of Healdsburg Golf Club and Healdsburg Museum. Pezzi ...
4.9/5Exceptional! (153 reviews)
Beautiful mountain home
"We were in town for a wedding in the vineyards and our stay at your home was really great. The kitchen had everything you could possibly need including spices and other incidentals which was very helpful and prevented an extra trip to town."

Reviewed on Jul 10, 2021

Wooded Restful Retreat, With Broad Scenic Views, Outdoor Dining
Private Wine Country Retreat-luxury Estate, Pool, hot Tub, 3 Miles to Town

Private Wine Country Retreat-luxury Estate, Pool, hot Tub, 3 Miles to Town

Healdsburg, CA
This family-friendly Healdsburg vacation home is located in a rural location, within 3 mi (5 km) of Mazzocco Winery, Simi Winery and Healdsburg Ridge Open Space ...
4.9/5Exceptional! (18 reviews)
70th Birthday Celebration
"Sienna is even more beautiful than what you see in the photos. The outdoor areas are so peaceful. We made pizzas in the stone pizza oven, built a fire and had a chocolate tasting in the area below, swam in the warm pool, enjoyed the hot tub...I can't say enough about the lovely setting and property. ..."

Reviewed on May 26, 2021

Private Wine Country Retreat-luxury Estate, Pool, hot Tub, 3 Miles to Town
Downtown Suites ONE - Near Raven Performing Arts Theater

Downtown Suites ONE - Near Raven Performing Arts Theater

4 out of 5
415A Healdsburg Ave., Healdsburg, CA
Located in the heart of Healdsburg, this beach aparthotel is within a 5-minute walk of Raven Performing Arts Theater, Healdsburg Plaza, and Healdsburg Center ...
5/5Exceptional! (10 reviews)
Great location and property!
"We really enjoyed our stay. The location was very central and we easily walked around downtown. The apartment itself was clean, spacious, and a great place to spend time. Very happy with our stay!"

Reviewed on Mar 20, 2020

Downtown Suites ONE - Near Raven Performing Arts Theater
Riverfront Getaway Only 5 Minutes to Healdsburg - Hot Tub, Kayaks, River Access

Riverfront Getaway Only 5 Minutes to Healdsburg - Hot Tub, Kayaks, River Access

Healdsburg, CA
Nestled on the beach, this Healdsburg vacation home is within 3 mi (5 km) of Russian River, Healdsburg Golf Club, and Healdsburg District Hospital. Healdsburg ...
4.8/5Exceptional! (28 reviews)
Fun experience, we enjoyed being there with some reservations.
"The home was clean and very attractive with many nice amenities like the hot tub and the kayak and paddle boat and river. The steps down to the river were dangerous especially with no railing where the steps slanted downward. The Master bedroom was very light especially when the neighbor left their ..."

Reviewed on Jul 5, 2021

Riverfront Getaway Only 5 Minutes to Healdsburg - Hot Tub, Kayaks, River Access
Luxe Penthouse on the River

Luxe Penthouse on the River

Healdsburg, CA
Situated on a river, this property is 0.1 mi (0.1 km) from Russian River and within 3 mi (5 km) of Healdsburg District Hospital and Healdsburg Golf Club. Healdsburg ...
5/5Exceptional! (1 review)
Great stay at beautiful new property
"Great stay at a beautiful, brand new property. Well decorated, well stocked, and comfortable furniture. Beds were great with high end linens. Kitchen stocked with high end appliances and wares. Highly recommend!"

Reviewed on Jun 29, 2021

Luxe Penthouse on the River
Art and Wine Estate - Vineyards, Pool, Garden

Art and Wine Estate - Vineyards, Pool, Garden

Healdsburg, CA
This family-friendly Healdsburg vacation home is located on a river, 0.1 mi (0.2 km) from Russian River, and within 6 mi (10 km) of Matrix Winery and Russian ...
4.4/5Excellent! (8 reviews)
Great property
"We had an amazing time at this beautiful property. Fully stocked kitchen, beautiful grounds, and wonderful outside area to sit abs enjoy the beautiful scenery. Would absolutely stay here again"

Reviewed on Jun 13, 2021

Art and Wine Estate - Vineyards, Pool, Garden
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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.

Large Group Rentals Healdsburg

Healdsburg Exclusive - Golden Retreat

Healdsburg Exclusive - Golden Retreat

Healdsburg, CA
Healdsburg Exclusive - Golden Retreat
Magical Vineyard Setting - Alexander Valley Ranch

Magical Vineyard Setting - Alexander Valley Ranch

Healdsburg, CA
Magical Vineyard Setting - Alexander Valley Ranch
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.

Large Group Cabins Healdsburg

Wine Country Retreat - 3 Br Home

Wine Country Retreat - 3 Br Home

3.5 out of 5
14271 Highland Ave, Guerneville, CA
Wine Country Retreat - 3 Br Home
4br Rocktop Lodge W/ Pool & Hot Tub 4 Bedroom Home

4br Rocktop Lodge W/ Pool & Hot Tub 4 Bedroom Home

3.5 out of 5
12422 Westside Road, Forestville, CA
4br Rocktop Lodge W/ Pool & Hot Tub 4 Bedroom Home
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.

Choosing the perfect Healdsburg rental

You've likely stayed at countless hotels. Maybe it's time to try a vacation rental to experience the area like a local.

This walkable location allures bargain hunters, shoppers, and foodies, but all visitors will be charmed by its riverside setting. Families will find plenty of fun activities in the area, such as biking and canoeing. Grown-ups might appreciate the wineries in town, and maybe find some time for being pampered at a spa.

Dining in Healdsburg

Healdsburg is praised for its cafés, beer, and coffeehouses. If you'd rather eat in, that's simple too, since most vacation rentals come with full-size kitchens.

Sightseeing around Healdsburg

Kendall-Jackson Wine Estate and Gardens, Petrified Forest, and Old Faithful Geyser of California are some top sights around Healdsburg. Ready for some fun for the whole family? Check out Pee Wee Golf and Arcade. Unwind in the green spaces with stops at Lake Sonoma and Healdsburg Ridge Open Space Preserve. For more things to do, spend the day at Pezzi King Winery or Simi Winery.

Booking your rental on Expedia

Book your vacation rental in Healdsburg easily and safely on Expedia. We can even help you contact the property owner to make special arrangements. You're sure to have a memorable trip with the convenience of a short-term rental.

Frequently asked questions