Find short term rentals in Healdsburg, CA at the best prices
100 available short term rental offers
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Best Short term and Weekly rentals in Healdsburg, CA
10 85 reviews
Healdsburg, CA
20/08 – 23/08
$2623/nighttotal: $7869 (3 )
Alexander Valley Modern Farmhouse With Vintage Charm - Newly Renovated Pool
3 3
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.
10 112 reviews
Healdsburg, CA
10/07 – 13/07
$1165/nighttotal: $3495 (3 )
Modern, Secluded Retreat - Walk To The Plaza!
1 2
apartment , Healdsburg
This modern cottage is situated on Dry Creek, just 2.4 kilometres from the bustling Healdsburg Plaza, offering a peaceful escape from the town centre. It has consistently received excellent ratings for its location, cleanliness, and overall experience. The cottage spans 107 square metres and comfortably accommodates up to six guests in its two bedrooms and three bathrooms. It boasts a fully equipped kitchen, a private garden, a spacious deck, a Jacuzzi, and an EV charging station, ensuring a comfortable and enjoyable stay.
9.9 39 reviews
Healdsburg, CA
07/09 – 11/09
$636/nighttotal: $2544 (4 )
Puccioni Paradise - Wine Tastings Included
2 2
apartment , Healdsburg
This Healdsburg apartment, situated a 6.4km drive from Healdsburg Plaza, offers a secluded setting amidst vineyards and redwood forests. Sleeping four guests, the self-catering property boasts two bedrooms, a well-equipped kitchen including a dishwasher and microwave, plus an expansive patio ideal for barbecues, and access to a fitness centre and parking.
10 7 reviews
Healdsburg, CA
08/07 – 10/07
$1340/nighttotal: $2680 (2 )
Right In The Heart Of Healdsburg Lies This Charming Two-bedroom House
2 2
apartment , Healdsburg
This Healdsburg house offers convenient access to nearby wineries such as Pezzi King Winery and Seghesio Family Vineyards, and is also within a short distance of outdoor recreational areas including Safari West and Healdsburg Ridge Open Space Preserve (distances unspecified). The two-bedroom, one-bathroom property sleeps four guests and includes amenities such as Wi-Fi, air conditioning, a fridge, microwave, and garden; parking is also available.
9.9 66 reviews
Healdsburg, CA
10/07 – 13/07
$531/nighttotal: $1593 (3 )
Bridle Path Bnb - Private Suite W/ Hot Tub & Views
1 2
B&B , Healdsburg
Bridle Path Bed and Breakfast is situated on a hillside overlooking Healdsburg, just a short drive from the town square and close to the Montage resort, offering a peaceful retreat with stunning views. The property has received excellent ratings for its location, cleanliness, and overall experience. The suite is a self-contained unit with one bedroom and one bathroom, comfortably accommodating two guests. It features a private patio with a hot tub, a kitchenette, a large flat-screen TV, and an outdoor dining area with a radiant heater, providing everything you need for a relaxing and enjoyable stay.
10 3 reviews
Healdsburg, CA
10/07 – 13/07
$699/nighttotal: $2097 (3 )
Scenic Hilltop Villa Room | Wine Country Stay
1 2
house , Healdsburg
Healdsburg Hilltop Villa, a guesthouse situated on a hillside a short distance from Healdsburg's town centre, offers easy access to local wineries and restaurants. This king suite, with a private patio and in-room jacuzzi, sleeps two guests and includes a second bathroom, daily breakfast, shared pool and hot tub access, and stunning vineyard views.
9.0 49 reviews
Healdsburg, CA
20/08 – 23/08
$2100/nighttotal: $6300 (3 )
Heart Of Healdsburg Cottage For 4, Pool, Spa, Fire Pit, Wifi, Bbq
2 3
cottage , Healdsburg
This charming cottage is located in Healdsburg, just one and a half kilometres from the Healdsburg Plaza and the Russian River, in a peaceful residential area. Guests have consistently rated the cottage highly for its cleanliness, location, and overall experience. The two-bedroom cottage spans 93 square metres and comfortably accommodates up to four guests. It boasts a modern kitchen, a relaxing spa tub, a private garden, and a barbecue grill, perfect for enjoying the beautiful Healdsburg weather.
9.9 34 reviews
Healdsburg, CA
07/09 – 11/09
$728/nighttotal: $2912 (4 )
Vintage Retreat With Spa Near Healdsburg
3 2
apartment , Healdsburg
This Healdsburg apartment, situated 3.2 kilometres from the town centre and close to Dry Creek Valley vineyards, offers easy access to Healdsburg's attractions. The 150 square metre self-catering property sleeps six, boasting three bedrooms, two bathrooms, a private redwood deck with a six-person hot tub, a well-equipped kitchen with a double oven, and free parking for three cars.
10 132 reviews
Healdsburg, CA
10/07 – 13/07
$712/nighttotal: $2136 (3 )
2 Bedroom Flat In Downtown Healdsburg
1 2
apartment , Healdsburg
This upstairs flat is located a short walk from Healdsburg's historic downtown plaza, surrounded by restaurants, bars, and tasting rooms. It has received excellent ratings for location, cleanliness, and overall user experience. The flat has two bedrooms, each with a queen-sized bed, accommodating up to four guests. The kitchen is fully equipped with modern appliances, and the living area features a leather sofa and coffee table, perfect for relaxing or entertaining.
9.9 15 reviews
Healdsburg, CA
08/07 – 10/07
$614/nighttotal: $1228 (2 )
Harmon King
1 2
B&B , Healdsburg
This charming bed and breakfast is located just a short drive from the centre of Healdsburg, offering a tranquil escape amidst the surrounding woodland. It has consistently received excellent ratings for its cleanliness, location, and overall guest experience. The accommodation has one bedroom and one bathroom, comfortably sleeping two guests. It features a private balcony with wooded views, a hand-loomed bed throw, and a welcoming atmosphere. Guests can enjoy the on-site swimming pool, garden, and parking, as well as the convenience of air conditioning and internet access.
9.6 66 reviews
Healdsburg, CA
20/08 – 23/08
$424/nighttotal: $1272 (3 )
Adventures Surround This Charming 2bedroom Home.
1 3
apartment , Windsor
This Foothills of Windsor house, minutes from local wineries and a 48km drive from Calistoga, offers direct access to a regional park with lakes and hiking trails. The self-contained property sleeps four in two bedrooms and two bathrooms, boasting a well-equipped kitchen, private garden with barbecue, swimming pool, jacuzzi, and parking; nearby amenities include tennis courts and a playground.
10 40 reviews
Healdsburg, CA
10/07 – 13/07
$561/nighttotal: $1683 (3 )
Modern Vineyard Farmhouse - Cabernet Room
1 2
gîte , Healdsburg
This Healdsburg vineyard cottage is situated in Dry Creek Valley, a short 5km drive from Healdsburg Plaza. The self-catering unit sleeps two guests, offering a king-size bed, private bathroom with shower, mini-fridge, coffee facilities, central heating and air conditioning, plus a wrap-around porch with vineyard views and picnic table.
Best family friendly Healdsburg, CA Short term rentals
Among the 100 accommodations in Healdsburg, CA, here are the 4 best family friendly rentals
10 221 reviews
Healdsburg, CA
08/07 – 10/07
$1475/nighttotal: $2950 (2 )
Wake Up In Your Own Private Vineyard - Healdsburg
3 2
apartment , Healdsburg
This private house is situated just a few kilometres from the centre of Healdsburg, surrounded by vineyards and offering a peaceful escape from the town's bustle. It has received excellent ratings for location, cleanliness and overall experience. The house is spacious, covering 232 square metres and accommodating up to six guests across three bedrooms and two bathrooms. Guests can enjoy a fully equipped kitchen, a terrace and garden, and explore the estate's vineyards.
9.8 356 reviews
Healdsburg, CA
02/10 – 07/10
$815/nighttotal: $4075 (5 )
Peaceful Location, Hot Tub, Fire Pit, Game Room!
1 4
apartment , Healdsburg
This apartment is situated just 5 kilometres from the centre of Healdsburg, in a peaceful location close to the Russian River and Fitch Mountain. The property has received excellent ratings for its location, cleanliness and overall user experience. The apartment is ideal for families or groups of up to six guests, with three bedrooms and two bathrooms. Amenities include a fully equipped kitchen, a games room with a pool table, a hot tub, a garden with a fire pit and outdoor dining area, and parking.
9.3 16 reviews
Healdsburg, CA
20/08 – 23/08
$797/nighttotal: $2391 (3 )
Windsor Home With Sauna & Outdoor Fire Pit
1 3
apartment , Windsor
This 3-bedroom house is located in Windsor, California, offering a comfortable stay close to local attractions and 3.2 kilometres from Windsor Golf Course. This pet-friendly accommodation for up to 8 guests boasts a private sauna, ice bath, fully equipped kitchen, BBQ grill, fire pit, air conditioning, Wi-Fi, washer/dryer, and free parking.
10 1 review
Healdsburg, CA
20/08 – 23/08
$913/nighttotal: $2739 (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.
Best Healdsburg, CA lodging with a kitchen
9.8 143 reviews
Healdsburg, CA
08/07 – 10/07
$509/nighttotal: $1018 (2 )
Healdsburg 2br Cottage With Private Yard!
1 2
apartment , Healdsburg
This charming guesthouse is located just 1.6 kilometres from Healdsburg Plaza, a vibrant hub of restaurants, shops, and attractions, and is situated in a peaceful vineyard-adjacent neighbourhood. The guesthouse has received excellent ratings for its cleanliness, location, and overall user experience. The guesthouse offers two bedrooms and one bathroom, accommodating up to four guests. The property features a private garden, a fully equipped kitchen with a fridge and freezer, air conditioning, and free Wi-Fi, making it a comfortable and convenient base for exploring the Healdsburg area.
10 3 reviews
Healdsburg, CA
07/09 – 11/09
$745/nighttotal: $2980 (4 )
Puccioni Paradise - Wine Tastings Included
2 2
apartment , Healdsburg
This Healdsburg holiday home boasts a mountain setting, conveniently located within 9.6km of Healdsburg Plaza, the Center for the Arts, Matrix Winery, Raven Performing Arts Theatre, and the Healdsburg Museum. The 77 square metre property sleeps four guests in three bedrooms and one bathroom, and features a fully equipped kitchen, Wi-Fi, a terrace, garden, spa, and tennis court.
9.7 157 reviews
Healdsburg, CA
02/10 – 07/10
$1069/nighttotal: $5345 (5 )
Modern Home In Hburg Wine Country
1 4
apartment , Healdsburg
This modern apartment is situated just a short distance from Healdsburg's town square, offering easy access to the area's renowned wine regions, including Russian River, Dry Creek, Alexander Valley, and Anderson Valley. It has received excellent ratings for its location, cleanliness, and overall experience. The apartment features a spacious open plan layout with expansive decks, comfortably accommodating up to six guests. It offers a fully equipped kitchen, a comfortable living area, and a range of amenities including radiant floor heating, air conditioning, ceiling fans, and a washer/dryer, making it perfect for a relaxing stay in Healdsburg.
9.4 3 reviews
Healdsburg, CA
20/08 – 23/08
$940/nighttotal: $2820 (3 )
Riverbend Retreat - Hot Tub And Tastings Included
2 3
apartment , Healdsburg
This Healdsburg holiday home is located a short drive from Healdsburg Plaza and offers direct access to the Russian River's sandy beachfront across the street. The 158 square metre property boasts two bedrooms, two bathrooms, sleeps six guests, and includes a fully equipped kitchen, Jacuzzi, private hot tub, and high-speed internet.
Frequently Asked Questions about short term rentals in Healdsburg, CA
What are the best short term rentals in Healdsburg, CA?
Best Healdsburg, CA lodging with laundry available
10 17 reviews
Healdsburg, CA
08/07 – 10/07
$1003/nighttotal: $2006 (2 )
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.
10 30 reviews
Healdsburg, CA
20/08 – 23/08
$1907/nighttotal: $5721 (3 )
Dry Creek Modern
3 3
apartment , Healdsburg
Apartment rental listing for up to 6 people with an excellent rating of 100% based on 30 reviews. This accommodation is based in Healdsburg. Facilities and services include a bar, an iron and a sauna. Take advantage of the jacuzzi in this apartment.
9.9 67 reviews
Healdsburg, CA
20/08 – 23/08
$1115/nighttotal: $3345 (3 )
7 Acre Hilltop Compound
1 3
apartment , Healdsburg
This charming cottage is situated just 3.2 kilometres from Healdsburg's town square, offering stunning views of the Dry Creek Valley vineyards. It has received excellent ratings for location, cleanliness, and user experience. The cottage boasts an open-plan design, creating a spacious and tranquil atmosphere. Guests can enjoy a private courtyard, a fully equipped kitchen, air conditioning, and a garden, perfect for relaxing and enjoying the beautiful surroundings.
10 52 reviews
Healdsburg, CA
10/07 – 13/07
$960/nighttotal: $2880 (3 )
Downtown Healdsburg Perch
1 2
apartment , Healdsburg
This Healdsburg apartment, situated above the main street, offers easy access to numerous restaurants, tasting rooms, and shops. The one-bedroom flat boasts a spa-like bathroom, a convenient kitchenette, and sleeps two guests, enjoying unique features such as its location in a converted Quonset hut above Healdsburg's main street and proximity to a world-class gallery.
Best Healdsburg, CA lodging with air conditioning
10 45 reviews
Healdsburg, CA
08/07 – 10/07
$1236/nighttotal: $2472 (2 )
Cuvée House
1 2
apartment , Healdsburg
This charming Queen Anne Victorian property is situated on a quiet street just a short walk from Healdsburg Plaza, offering easy access to the town's restaurants, galleries, and shops. The apartment has received excellent ratings for its location, cleanliness, and overall experience. The apartment has two bedrooms and one bathroom, comfortably accommodating up to four guests. Amenities include a fully equipped kitchen, private parking, and keyless entry, making it a convenient and comfortable base for exploring Healdsburg.
9.3 121 reviews
Healdsburg, CA
10/07 – 13/07
$572/nighttotal: $1716 (3 )
Bella Villa Messina
1 2
B&B , Healdsburg
Bella Villa Messina is a Healdsburg guesthouse conveniently located 3.9km from Healdsburg Plaza and 18km from Charles M. Schulz Sonoma County Airport. This one-bedroom, one-bathroom guest house sleeps up to three guests and offers air conditioning, a terrace, a spa, parking, and a continental breakfast.
10 216 reviews
Healdsburg, CA
02/10 – 07/10
$2937/nighttotal: $14685 (5 )
Large Outdoor Kitchen, Pool, Hot Tub, Firepit...8 Mins From Healdsburg Plaza
4 4
apartment , Healdsburg
This family-friendly house is located on a river in Healdsburg, within a 3km radius of Jordan Vineyard & Winery and Medlock Ames Winery, and within 5km of Russian River and Simi Winery. The house has consistently received excellent ratings from previous guests for its cleanliness, location, and overall experience. The property spans 260 square metres and comfortably accommodates up to 8 guests. Enjoy a range of amenities including a private pool, fitness centre, spa tub, barbecue grills, and a fully equipped kitchen, making it perfect for a relaxing and enjoyable stay.
Healdsburg, CA
20/08 – 23/08
$785/nighttotal: $2355 (3 )
Bermudes Family Vineyard View Healdsburg House
1 3
apartment , Healdsburg
This vineyard apartment in Healdsburg's Alexander Valley offers a unique stay, situated just 8 kilometres from Healdsburg town square and a short walk from Jordan Winery. This property accommodates up to six guests across two bedrooms and a rec room with Murphy beds, featuring an upgraded kitchen, air conditioning, Wi-Fi, and expansive outdoor space for dining and barbecuing with vineyard views.