This studio is located just 1.6 kilometres from downtown Healdsburg, surrounded by vineyards and offering a peaceful setting. It has received excellent ratings for its location, cleanliness and overall experience. The studio provides accommodation for two guests and comes with a fully equipped kitchen, a private garden and a patio. Guests can enjoy fresh produce from the garden, explore the area on two complimentary bikes and even take part in a wine tasting experience with the owner, a second-generation vineyard manager.
10 48 reviews
Healdsburg, CA
20/08 – 23/08
411 €/nighttotal: 1233 € (3 )
Slice Of Country
2 3
apartment , Healdsburg
This two-bedroom apartment is situated on a quiet country road just two miles from Healdsburg's bustling centre, offering a peaceful retreat with easy access to the town's attractions. It has consistently received excellent ratings for its cleanliness, location and overall guest experience. The self-contained apartment comfortably accommodates up to four guests and features a well-equipped kitchen, a private garden, a deck and ample parking. Guests can enjoy the convenience of on-site parking, a fully equipped kitchen, and a private garden, perfect for relaxing after a day of exploring the nearby Dry Creek Valley wineries.
9.9 35 reviews
Healdsburg, CA
30/08 – 06/09
708 €/nighttotal: 4956 € (7 )
Luxury 1-br Cottage On 30-acre Healdsburg Vineyard
1 2
apartment , Healdsburg
This charming cottage is situated in the Dry Creek Valley, just 10 kilometres from Healdsburg's town centre and a short drive from the Russian River, offering a peaceful retreat amidst beautiful vineyards. The property has received excellent ratings for location, cleanliness, and overall experience. The cottage is a comfortable and stylish one-bedroom property, perfect for couples seeking a quiet getaway. Guests can enjoy stunning views of the vineyard from the spacious covered porch, relax in the garden, or explore the on-site winery, which produces a variety of award-winning wines.
10 52 reviews
Healdsburg, CA
30/08 – 06/09
314 €/nighttotal: 2198 € (7 )
Guesthouse On Gated 22 Acre Family Ranch, Vineyard
2 2
house , Windsor
This Casita is located in the foothills between Healdsburg and Windsor, just a short drive from the historic Healdsburg Plaza. The property enjoys excellent user, location and cleanliness ratings. The Casita offers 830 square metres of living space plus a 320 square metre patio, accommodating up to four guests. It features a private covered terrace, a fully equipped kitchen, air conditioning, a garden, parking, and internet access.
9.9 292 reviews
Healdsburg, CA
02/10 – 07/10
519 €/nighttotal: 2595 € (5 )
The Wine Ranch
3 4
apartment , Healdsburg
This traditional ranch-style house is located just north of the Healdsburg Plaza, a short 5-minute drive from the Montage Healdsburg, putting you within easy reach of the town's restaurants, shops, and events. This property has received excellent ratings for its location, cleanliness, and overall experience. The house has three bedrooms and two bathrooms, comfortably accommodating up to eight guests. Guests can enjoy a range of amenities, including a bocce court, a deck, and a patio, offering ample space for outdoor relaxation and entertainment.
10 17 reviews
Healdsburg, CA
30/08 – 06/09
615 €/nighttotal: 4305 € (7 )
Healdsburg Vineyard Farmhouse With Game Barn
3 2
apartment , Healdsburg
This farmhouse, located amidst vineyards in Healdsburg, is 200 metres from Aperture Cellars and 800 metres from Christopher Creek Winery, with Healdsburg Plaza 3.7 kilometres away. This 144 square metre dwelling accommodates up to six guests, featuring three bedrooms, two bathrooms, a converted barn game room with a ping-pong table, a bocce ball court, outdoor dining, two living areas with fireplaces, and an EV charger.
9.8 50 reviews
Healdsburg, CA
02/10 – 07/10
485 €/nighttotal: 2425 € (5 )
Rivers Breeze - Wine Tastings Included
3 4
apartment , Healdsburg
This charming riverside property is located just 5.6 kilometres from Healdsburg Plaza and a short drive from local farms, offering a peaceful escape from the town centre. The apartment has received excellent ratings for its cleanliness, location, and overall experience. The property features three bedrooms and two bathrooms, comfortably accommodating up to six guests. Enjoy the well-equipped kitchen, a spacious living area, a garden, a fitness centre, and two kayaks for exploring the river.
9.9 119 reviews
Healdsburg, CA
30/08 – 06/09
880 €/nighttotal: 6160 € (7 )
Views, Hot Tub, Sauna, Cold Plunge, Cinema!
2 2
apartment , Healdsburg
This Healdsburg apartment is situated in a peaceful area, just a short drive from the town square and its many restaurants and shops, offering stunning views of the surrounding vineyards. It has received excellent ratings for user experience, location, and cleanliness. The property is a spacious two-bedroom, two-bathroom dwelling with a guest capacity of four people. Guests have access to a private deck, garden, wine cave, hot tub, gym, and a detached office room, ideal for remote working.
9.9 177 reviews
Healdsburg, CA
20/08 – 23/08
507 €/nighttotal: 1521 € (3 )
Updated Russian River Cabin (Beach/river Access!)
1 3
cabin , Healdsburg
This charming riverside retreat is located just a short drive from Healdsburg and the Dry Creek Valley wineries, offering a peaceful escape from the hustle and bustle of city life. The property has received excellent ratings for its location, cleanliness and overall experience. The cottage offers a flexible layout with two bedrooms and a spacious living area, comfortably accommodating up to six guests. Guests can enjoy a range of amenities including a fully equipped kitchen, a private outdoor area with a terrace and garden, and a range of water sports equipment such as a canoe, kayak and paddleboards.
9.8 99 reviews
Healdsburg, CA
02/10 – 07/10
757 €/nighttotal: 3785 € (5 )
Dry Creek Ranch ~ (Tariff Discount) Hot Tub & Pool
3 4
apartment , Healdsburg
This three-bedroom apartment is conveniently located just 2.2 kilometres from Healdsburg’s town square, offering easy access to the region's renowned wineries and vineyards. The apartment has received excellent ratings for its cleanliness, location, and overall experience. This spacious property provides ample room for up to six guests, with a separate pool house offering additional living space. The apartment boasts a fully equipped kitchen, a private garden, a swimming pool, a hot tub, and a Tesla charger, making it ideal for a relaxing and comfortable stay.
9.3 272 reviews
Healdsburg, CA
07/09 – 11/09
390 €/nighttotal: 1560 € (4 )
Rockhouse Suites
1 2
studio , Healdsburg
This studio apartment is situated just outside of Healdsburg, offering easy access to both the town's attractions and the surrounding countryside, making it ideal for exploring the area. The property enjoys excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable stay. The studio apartment offers 74 square metres of space, comfortably accommodating two guests. Amenities include a fully equipped kitchenette, a private patio, cable TV, Wi-Fi, plush bathrobes and access to a tranquil garden, providing everything you need for a relaxing getaway.
10 311 reviews
Healdsburg, CA
30/08 – 06/09
382 €/nighttotal: 2674 € (7 )
Luxurious, Private, Healdsburg Guest Cottage
1 2
house , Healdsburg
This charming cottage is situated in Healdsburg, just a short walk from the town's best restaurants, wineries, shops, and the Russian River, offering a peaceful escape in a vibrant setting. The cottage boasts excellent ratings for location, cleanliness, and user experience, ensuring a comfortable and enjoyable stay. The cottage comfortably accommodates two guests in one bedroom and one bathroom. Enjoy the private hot tub, a continental breakfast, and a garden area, along with access to the garage and internet.
Best family friendly Healdsburg, CA holiday rentals
Among the 114 accommodations in Healdsburg, CA, here are the 4 best family friendly rentals
10 85 reviews
Healdsburg, CA
02/10 – 07/10
1558 €/nighttotal: 7790 € (5 )
Alexander Valley Modern Farmhouse With Vintage Charm - Newly Renovated Pool
3 4
apartment , Healdsburg
This Healdsburg apartment is situated just 1.4 kilometres from Jordan Vineyard & Winery and within 5 kilometres of the Russian River, offering easy access to renowned wineries and scenic landscapes. The apartment has consistently received excellent ratings for its cleanliness, location, and overall experience. The apartment features three bedrooms and four bathrooms across 274 square metres of living space. Guests can enjoy a range of amenities including a private pool, a fenced garden, a fitness centre, a bar, and a terrace with stunning lake views.
10 3 reviews
Healdsburg, CA
07/09 – 11/09
565 €/nighttotal: 2260 € (4 )
Farmstay With Pool And Wine Tastings Included
3 2
apartment , Geyserville
This historic winery estate flat in Geyserville offers vineyard views and is located just 200 metres from Trentadue Winery, with Healdsburg Plaza a short drive away. This family-friendly accommodation sleeps six guests and features three bedrooms, three bathrooms, air conditioning, a private swimming pool, a garden, parking, and complimentary wine tastings at four local wineries.
9.8 132 reviews
Healdsburg, CA
02/10 – 07/10
458 €/nighttotal: 2290 € (5 )
Riverside Cottage: Access And River Views- 1 Miles From Downtown Healdsburg
1 4
apartment , Healdsburg
This charming cottage is situated just a short drive from Healdsburg's downtown Plaza, offering easy access to the town's restaurants, shops, and wineries. The property enjoys excellent ratings for location, cleanliness, and overall user experience. The two-bedroom dwelling comfortably accommodates up to six guests and boasts a well-equipped kitchen, a private hot tub, and a wraparound veranda with stunning views of the Russian River. Guests can enjoy the vintage charm of the cottage, complete with modern amenities, and take advantage of the seasonal river access during the summer months.
10 159 reviews
Healdsburg, CA
30/08 – 06/09
457 €/nighttotal: 3199 € (7 )
Historic Queen Anne Victorian In The Heart Of Windsor
3 2
apartment , Windsor
This holiday home is ideally situated in central Windsor, just a short walk from the Dom Whitney Tasting Lounge and Powell's Sweet Shoppe, and 4.3 km from Windsor Golf Club. The property has received excellent ratings for location, cleanliness and overall experience. The three-bedroom house, with a floor area of 169 square metres, comfortably accommodates up to six guests. The house offers a range of amenities, including a fully equipped kitchen, a private garden with a terrace, a Jacuzzi, a spa, and free Wi-Fi.
Best Healdsburg, CA holiday rentals with parking
9.8 6 reviews
Healdsburg, CA
07/09 – 11/09
563 €/nighttotal: 2252 € (4 )
Vinehaven - 3bd Healdsburg Retreat With Spa
3 2
apartment , Healdsburg
This Healdsburg apartment, situated 3.2km from the town centre, offers easy access to Dry Creek Valley vineyards and is within easy reach of restaurants, shops, and the Raven Performing Arts Theatre. The 150 sq m property boasts three bedrooms, two bathrooms, sleeps six, and includes a well-equipped kitchen, a private redwood deck with a hot tub, and parking; two dogs are welcome.
10 1 review
Healdsburg, CA
20/08 – 23/08
565 €/nighttotal: 1695 € (3 )
Private Acre+bbq Patio | 5min To Healdsburg Plaza
2 3
apartment , Healdsburg
Casa Campo is a secluded two-bedroom, two-bathroom cottage situated on a one-acre property just 5 minutes from Healdsburg's Downtown Plaza and the wineries of Dry Creek Valley. This 89-square-metre cottage comfortably accommodates four guests with a fully equipped kitchen, private patio with a gas BBQ, and in-unit laundry, all within easy reach of Healdsburg's attractions.
This Healdsburg mountainside property is situated within 3.2km of Ridge Vineyards, Mazzocco Winery, and Simi Winery, and 4.8km from the Krug Event Center. This six-bedroom, six-bathroom house boasts 288 square metres of living space, a private pool, jacuzzi, and game room, accommodating up to ten guests and offering self-catering facilities.
9.5 208 reviews
Healdsburg, CA
19/08 – 24/08
547 €/nighttotal: 2735 € (5 )
Serene Riverfront Cottage In Healdsburg Views Kayaks 1 5 Mile To Downtown
2 2
house , Healdsburg
Redwood River Lodge is a beachfront property located just 14 miles from the Luther Burbank Center for the Arts in Healdsburg, with Safari West and the Petrified Forest both a short drive away. The lodge has received excellent ratings for its location, cleanliness, and overall user experience. This two-bedroom holiday home spans 111 square metres and comfortably sleeps up to six guests. Amenities include a fully equipped kitchen, a private patio, a Jacuzzi, a tennis court, and free parking, making it ideal for a relaxing and enjoyable stay.
Frequently asked questions about holiday rentals in Healdsburg, CA
What are some interesting places to visit in or near Healdsburg, CA?
Healdsburg is a great base for exploring the Sonoma County wine region. There are plenty of vineyards to visit, like the stunning Alexander Valley Vineyards, or the historic Castello di Amorosa. If you're looking for something a little different, the Healdsburg Museum is worth a visit, or head to the Russian River for kayaking or fishing.
What are the best Airbnb and holiday rentals in Healdsburg, CA?
Which walking or cycling routes are the best in Healdsburg, CA?
The Healdsburg Plaza is lovely for a stroll and you can pick up a map from the Healdsburg Chamber of Commerce. For a longer walk or cycle, the Healdsburg to Windsor Trail is a great option. If you're feeling adventurous, the Healdsburg to Cloverdale Rail Trail is a longer, but scenic, cycle route.
What are the most popular Airbnbs in Healdsburg, CA?
What sports or outdoor activites can visitors enjoy in and around Healdsburg, CA?
Healdsburg is a great place for outdoor activities. There are plenty of hiking trails in the surrounding hills, like the Fitch Mountain Trail. You can also go kayaking or canoeing on the Russian River, or go fishing. The Healdsburg Golf Course is a good option for a round of golf.
What are the best holiday rentals with a pool in Healdsburg, CA?
What other towns or cities can be easily accessed from Healdsburg, CA?
Healdsburg is well-positioned for exploring Sonoma County. You can easily get to Santa Rosa, which is about 20km away, or head west to the Pacific coast and visit towns like Bodega Bay or Jenner. If you want to explore further afield, San Francisco is about a 1.5-hour drive.
What are the best rentals for families and kids in Healdsburg, CA?
What amenities are commonly available in vacation rentals in Healdsburg, CA?
Vacation rentals in Healdsburg are typically well-equipped, with most offering things like kitchens, laundry facilities, and Wi-Fi. Many also have private patios or decks, and some even have swimming pools or hot tubs. You'll find a variety of sizes and styles to choose from, so there's something for everyone.
What are the best rentals or Airbnbs with a jacuzzi in Healdsburg, CA?
What time of year is best to rent a vacation rental Healdsburg, CA?
Healdsburg is a great place to visit year-round, but the best time to visit depends on your preferences. Spring and autumn are lovely for mild weather and beautiful scenery. Summer is warm and sunny, perfect for swimming and outdoor activities. Winter can be rainy, but it's also a good time for wine tasting and exploring the local shops and restaurants.
Destinations nearby
Best Healdsburg, CA holiday rentals with a balcony
Healdsburg, CA
07/09 – 11/09
504 €/nighttotal: 2016 € (4 )
Cottages At Little Saint
1 2
resort , Healdsburg
The Cottages at Healdsburg is conveniently located in the centre of Healdsburg, just a short walk from the town square and its shops and restaurants. The charming atmosphere of the surrounding area provides a relaxing and enjoyable experience for visitors. The cottages offer comfortable accommodation for up to two guests. Guests can enjoy a range of amenities, including a swimming pool, a restaurant, and a terrace or balcony.
9.0 1 review
Healdsburg, CA
02/10 – 07/10
697 €/nighttotal: 3485 € (5 )
Mill Creek By Avantstay Modern Design Patio Hot Tub
2 4
house , Healdsburg
Mill Creek by AvantStay, a modern Healdsburg property, is situated 5.3km from Healdsburg Plaza and 17.7km from the Charles M. Schulz Sonoma County Airport. This two-bedroom, two-bathroom house boasts 130 square metres of living space, accommodating up to 10 guests and featuring a private plunge pool, hot tub, sauna, and free Wi-Fi; nearby attractions include the Luther Burbank Center for the Arts (22.5km) and Safari West (37km).
10 6 reviews
Healdsburg, CA
02/10 – 07/10
3186 €/nighttotal: 15930 € (5 )
Stunning Dry Creek Road Estate
4 4
apartment , Healdsburg
This stunning four-bedroom property is situated in the Dry Creek Valley, just eight minutes from Healdsburg's town square, offering easy access to the area's charming shops, restaurants, and wineries. The house consistently receives excellent ratings for its location, cleanliness, and overall guest experience. The property spans 390 square metres and comfortably accommodates up to 10 guests. It features a heated swimming pool, a Jacuzzi, a spacious terrace, a garden, and a well-equipped kitchen, perfect for hosting large gatherings or enjoying a relaxing getaway.
10 27 reviews
Healdsburg, CA
20/08 – 23/08
5088 €/nighttotal: 15264 € (3 )
The Estate Villa
4 3
house , Healdsburg
The Estate Villa at NewTree Ranch is a 120-acre private estate located just 4.7 miles outside of Healdsburg, California, offering easy access to the town's restaurants, wineries, and shops. This luxurious property has received excellent user ratings and provides a secluded and tranquil escape from the hustle and bustle of Healdsburg. This spacious villa spans 437 square metres and comfortably accommodates up to eight guests. The villa offers a range of amenities, activities, and features, including a private lake, a solar-heated swimming pool, a well-equipped gym, a chef's kitchen, and a dedicated concierge team to curate personalised experiences.
Best pet friendly Healdsburg, CA holiday rentals
Among the 114 accommodations in Healdsburg, CA, here are the 4 best pet friendly rentals
10 131 reviews
Healdsburg, CA
02/10 – 07/10
1899 €/nighttotal: 9495 € (5 )
Tandatula, Wine Country Sanctuary With Pool, Hot Tub, Bocce, Fire Pits And More!
4 4
apartment , Healdsburg
This Healdsburg holiday home, situated in the Dry Creek Valley of Northern Sonoma County, is an hour's drive (approximately 80km) north of San Francisco and minutes from Dry Creek Vineyard and Healdsburg's attractions. This 288-square-metre property comprises a main house, cottage, and studio, sleeping up to 10 guests, and boasts a pool, hot tub, tennis court, fitness centre, and 1.25 acres of landscaped grounds with vineyards, offering bocce ball, croquet, and a games barn.
9.9 89 reviews
Healdsburg, CA
07/09 – 11/09
438 €/nighttotal: 1752 € (4 )
Creekside Cottage
1 2
apartment , Healdsburg
This two-bedroom cottage is situated just a short drive from Healdsburg’s town centre, offering easy access to the region’s wineries and restaurants. The property features a private guest house, an expansive deck with a pergola, and a tranquil creekside setting, ideal for families or groups of up to six guests.
10 1 review
Healdsburg, CA
30/08 – 06/09
2559 €/nighttotal: 17913 € (7 )
The Barn Villa
2 2
apartment , Healdsburg
This modern barn villa is situated in the countryside near Healdsburg, California, just 12-15 minutes from the town centre and a short drive from the Healdsburg Ridge Open Space Preserve. The villa is a peaceful retreat, offering a unique farm stay experience. The property has two bedrooms and two bathrooms, accommodating up to four guests. It features a 111 square metre living space with a fully equipped kitchen, a spacious garden, an outdoor Balinese tub, and a Japanese tea garden.
9.8 251 reviews
Healdsburg, CA
19/08 – 24/08
416 €/nighttotal: 2080 € (5 )
❤The Elegant: A Healdsburg Winery Abode! Hot Tub!❤
1 2
apartment , Healdsburg
This charming cottage is situated on Dry Creek Road in Healdsburg, just 1.6km from the town centre and its wineries, restaurants, and tasting rooms. It has received excellent ratings for its location, cleanliness, and overall experience. The property offers a spacious layout with two bedrooms and two bathrooms, accommodating up to four guests. Enjoy panoramic vineyard views from the wrap-around deck, relax in the private hot tub, and make use of the fully equipped kitchen, Tesla charging station, and pet-friendly fenced yard.