Best Short term and Weekly rentals in Healdsburg, CA
9.5 114 reviews
Healdsburg, CA
10/02 – 10/07
$1214/nighttotal: $6070 (5 )
Rendezvous Under The Oaks-pool & Hot Spa
3 4
apartment , Healdsburg
This modern ranch house is situated in the desirable Alexander Valley neighborhood of Healdsburg, just minutes from downtown. It has excellent user, location, and cleanliness ratings. The apartment has a floor area of 2000 square feet and can accommodate up to 8 guests in 3 bedrooms. It features a secluded vineyard setting on an acre of land, a spacious outdoor entertainment area with a pool, spa, bocce and basketball courts, a professionally decorated and furnished interior with hardwood floors and a gourmet kitchen, and a master suite with a free-standing shower and double mirror doored closets.
9.9 15 reviews
Healdsburg, CA
08/20 – 08/23
$801/nighttotal: $2403 (3 )
Healdsburg Victorian Cottage On Vineyard Estate
2 3
apartment , Healdsburg
This 1895 Victorian cottage in Healdsburg's Alexander Valley offers an authentic wine country experience on a working vineyard, located 1.3 miles from Healdsburg Plaza's tasting rooms and Michelin-starred SingleThread. This two-bedroom, two-bathroom rental accommodates up to four guests and features original hardwood floors, a modernized kitchen with a marble island, central air conditioning, two furnished patios with views, and two sitting areas with decorative brick fireplaces.
9.9 162 reviews
Healdsburg, CA
08/20 – 08/23
$1336/nighttotal: $4008 (3 )
Casa Chiquita-the Coziest In Town, 3 Bed, 3 Full Bath, Spa & Pool
1 3
apartment , Healdsburg
This 3-bedroom, 3-bathroom vacation rental home is located less than 8 minutes from downtown Healdsburg, in the rolling hills of Dry Creek Valley. With excellent user, location, and cleanliness ratings, this apartment is an excellent option for travelers visiting Healdsburg. The apartment has an open floor plan with a spacious living area, a dining room, and a well-equipped kitchen. The apartment can accommodate up to 6 guests and features modern amenities such as a Sonos sound system, Xfinity Wi-Fi, and Lutron smart lighting controls. Guests can also enjoy the outdoor amenities, which include a large heated swimming pool, a hot tub, a covered arbor living/dining and cooking area, and a gas fire pit.
10 4 reviews
Healdsburg, CA
07/10 – 07/13
$522/nighttotal: $1566 (3 )
Private Acre+bbq Patio | 5min To Healdsburg Plaza
1 2
apartment , Healdsburg
Casa Campo, a 2-bedroom, 2-bathroom rental, is located on a one-acre property just 5 minutes from Healdsburg Plaza in Dry Creek wine country. This family-friendly guesthouse accommodates up to 4 guests and features a fully equipped kitchen, gas BBQ patio, deep soaking bathtub, and an ergonomic workspace with Wi-Fi, with ample private parking for three vehicles.
9.9 106 reviews
Healdsburg, CA
08/20 – 08/23
$604/nighttotal: $1812 (3 )
Downtown Healdsburg Nest
1 3
apartment , Healdsburg
This Healdsburg apartment rental is located two blocks from the Healdsburg Plaza, offering easy access to downtown restaurants, shops, and tasting rooms. The two-bedroom, one-bathroom unit sleeps four guests and features a fully equipped kitchen with modern appliances, a private patio, in-unit laundry, and high-speed internet; street parking is available on a first-come, first-served basis.
10 17 reviews
Healdsburg, CA
10/02 – 10/07
$617/nighttotal: $3085 (5 )
Healdsburg Vineyard Farmhouse With Game Barn
3 4
apartment , Healdsburg
This Healdsburg vacation rental is located among vineyard rows, 2 miles from Healdsburg Plaza and a 0.2-mile walk to Aperture Cellars. This 1550 sq ft, 3-bedroom, 2-bathroom house accommodates up to 6 guests and features vineyard views, a converted barn game room with ping-pong, a bocce ball court, two living areas with fireplaces, and an EV charger.
10 14 reviews
Healdsburg, CA
07/08 – 07/10
$762/nighttotal: $1524 (2 )
Healdsburg Victorian Cottage On Vineyard Estate
2 2
apartment , Healdsburg
This 1895 Victorian cottage is located in Alexander Valley wine country, 1.3 miles from Healdsburg Plaza's tasting rooms and restaurants, and within walking distance to Tongue Dancer Wines (0.4 miles) and Arnot-Roberts (0.8 miles). This 1670 square foot rental sleeps 4 guests in 2 bedrooms and 2 bathrooms, featuring a modernized kitchen with a marble island and induction oven, air conditioning, internet, a terrace, garden, and parking for 2 vehicles.
10 65 reviews
Healdsburg, CA
09/07 – 09/11
$473/nighttotal: $1892 (4 )
Enjoy A Slice Of Country--two Miles To Downtown Healdsburg
2 2
cottage , Healdsburg
This charming cottage is located just under two miles from the Healdsburg Plaza, offering a peaceful rural setting with vineyard views. Guests consistently rate this property as excellent for its comfort and amenities. This two-bedroom, one-bathroom cottage can comfortably accommodate four guests. Enjoy the private deck with outdoor seating, a Jacuzzi, and a well-equipped kitchen, plus the convenience of a pet-friendly environment and easy access to the Dry Creek Valley wine region.
Healdsburg, CA
08/20 – 08/23
$562/nighttotal: $1686 (3 )
Bermudes Family Vineyard View Healdsburg House
1 3
apartment , Healdsburg
This vineyard residence in Healdsburg's Alexander Valley offers a unique stay, located a short 8-minute drive from Healdsburg town square and within walking distance of Jordan Winery. This pet-friendly apartment accommodates up to 6 guests with 2 bedrooms, a rec room, an upgraded kitchen, and expansive outdoor space featuring vineyard views, a BBQ, and dining area.
9.6 21 reviews
Healdsburg, CA
10/02 – 10/07
$414/nighttotal: $2070 (5 )
River Retreat - Hot Tub And Tastings Included
2 4
apartment , Healdsburg
This Healdsburg bungalow, situated in a peaceful neighborhood just five minutes from downtown Healdsburg and directly across from the Russian River, offers easy access to kayaking, swimming, and local restaurants. This two-bedroom, one-bathroom rental sleeps six guests comfortably, boasting a fully equipped kitchen, private hot tub, outdoor decks with a gas BBQ and ping pong table, and proximity to Healdsburg's tasting rooms and shops.
9.9 292 reviews
Healdsburg, CA
10/02 – 10/07
$600/nighttotal: $3000 (5 )
The Wine Ranch
3 4
apartment , Healdsburg
This traditional ranch-style home is situated in a tranquil residential area just 5 minutes from the vibrant heart of Healdsburg. It received excellent ratings for its location, cleanliness, and user experience. The home offers a modern farmhouse interior with 3 bedrooms, 2 bathrooms, and a guest capacity of 8. Amenities include a fully equipped kitchen, comfortable furnishings, air conditioning, a garden, parking, and access to Wi-Fi. The property also boasts nearly 3/4 of an acre of outdoor space, including a bocce court, deck, and patio, perfect for relaxation and entertainment.
9.9 89 reviews
Healdsburg, CA
09/07 – 09/11
$507/nighttotal: $2028 (4 )
Creekside Cottage
1 2
apartment , Healdsburg
This two-bedroom, two-bathroom Healdsburg cottage is located near the Russian River and a short drive from the town's downtown area. The cottage features a spacious deck with a pergola, an outdoor dining table and a grill, as well as a separate guest house with its own bedroom and bathroom.
Traveler-Approved Family Short-Term Rentals in Healdsburg, CA
Keep the little ones entertained in Healdsburg, CA by choosing a family rental located just steps away from the city’s top attractions.
10 1 review
Healdsburg, CA
08/20 – 08/23
$707/nighttotal: $2121 (3 )
Windsor Home With Sauna & Outdoor Fire Pit
3 3
apartment , Windsor
This Windsor apartment is located a short drive from the Windsor Town Green, Russian River, and Sonoma County wineries. This 1800 sq ft home offers 3 bedrooms, 2 bathrooms, and can accommodate up to 8 guests with amenities including air conditioning, Wi-Fi, a full kitchen, BBQ grill, fire pit, private sauna, and ice bath.
10 113 reviews
Healdsburg, CA
09/07 – 09/11
$2815/nighttotal: $11260 (4 )
The Quails Crossing-healdsburg Vineyard Home
4 2
apartment , Windsor
This Windsor vacation home is centrally located, within 6 miles of attractions like the Dom Whitney Tasting Lounge, Powell's Sweet Shoppe, Pezzi King Winery, Healdsburg Plaza, and the Healdsburg Center for the Arts. This 3000-square-foot house sleeps eight guests and boasts a private pool, Jacuzzi, spa, and fully equipped kitchen, plus free Wi-Fi.
10 121 reviews
Healdsburg, CA
09/07 – 09/11
$1790/nighttotal: $7160 (4 )
Luxury Retreat W/ Pool, Hot Tub & Sauna
1 2
apartment , Healdsburg
This private vineyard estate is located in the rolling hills of the Dry Creek Valley, just minutes from the Healdsburg Plaza and famed Dry Creek and Alexander Valley Vineyards. The three-bedroom, three-bathroom villa boasts a modern design with comfortable furnishings, a gourmet kitchen, a spacious deck, and a luxurious spa, sauna, and fire pit.
10 196 reviews
Healdsburg, CA
07/10 – 07/13
$2617/nighttotal: $7851 (3 )
5 Bedroom, 6.5 Bath Luxury Home On 3+ Acres, 5 Min To Square
5 2
apartment , Healdsburg
This family-friendly vacation home is located in a peaceful rural setting just outside of Healdsburg, within a 3km radius of the Healdsburg Plaza, Museum, and Raven Performing Arts Theater. This property has received excellent user ratings and is perfect for families or groups of friends. The home features 5 bedrooms and 7 bathrooms, spanning 4,600 square feet, and comfortably accommodates up to 12 guests. Enjoy a private pool, fenced yard, sauna, spa tub, fully equipped kitchen, fireplace, and other modern amenities for a relaxing and enjoyable stay.
Best Healdsburg, CA lodging with a kitchen
9.7 157 reviews
Healdsburg, CA
07/10 – 07/13
$818/nighttotal: $2454 (3 )
Modern Home In Hburg Wine Country
1 2
apartment , Healdsburg
This 3-bedroom, 4-bathroom apartment is only a few miles from Healdsburg's town square, giving easy access to the city's attractions. With excellent user, location, and cleanliness ratings, this modern open design apartment offers abundant natural light and a fully equipped kitchen. Accommodating up to 6 guests, the apartment features expansive decks and open spaces for indoor-outdoor living. Guests can enjoy access to outdoor activities such as boating, fishing, hiking, and kayaking, as well as amenities like air conditioning, a garden, parking, and exterior security cameras for added peace of mind.
9.9 66 reviews
Healdsburg, CA
07/10 – 07/13
$380/nighttotal: $1140 (3 )
Bridle Path Bnb - Private Suite W/ Hot Tub & Views
1 2
B&B , Healdsburg
Bridle Path Bed and Breakfast is located just outside Healdsburg's town square, close to the Montage resort and offering a peaceful setting. It has earned excellent ratings for its cleanliness, location, and overall experience. The single-unit property can accommodate two guests and features a private bedroom, den, bathroom, and patio with a hot tub. Enjoy a continental breakfast, relax in the garden, and take advantage of amenities like a fitness center, jacuzzi, and kitchen with a fridge, freezer, and microwave.
9.4 13 reviews
Healdsburg, CA
08/20 – 08/23
$1191/nighttotal: $3573 (3 )
Modern Sonoma Home W Private Pool & Vineyard Views
3 3
apartment , Healdsburg
This modern, rustic home is located in the quiet countryside of Sonoma, just minutes from Healdsburg's restaurants and shops and steps away from renowned wineries. The apartment offers a spacious living area, a fully equipped kitchen, and three bedrooms, comfortably accommodating up to six guests. Guests can enjoy a private pool, a large outdoor space with a heated shower, and a surround-sound speaker system.
10 59 reviews
Healdsburg, CA
07/08 – 07/10
$725/nighttotal: $1450 (2 )
Luxe Healdsburg 3br Home + Comp Ridge Wine Tasting
1 2
apartment , Healdsburg
This luxurious Healdsburg home is ideally located near Healdsburg Plaza, the Russian River, and Dry Creek Valley wineries, offering easy access to Healdsburg's attractions. The three-bedroom house features a spacious layout with a den/game room, accommodating up to eight guests, and boasts a fully equipped kitchen, a hot tub, and a landscaped yard with a fire pit.
Frequently Asked Questions about short term rentals in Healdsburg, CA
Which top landmarks shouldn't you miss in and around Healdsburg, CA?
Healdsburg Plaza is a must-see, with its charming shops and restaurants. You can't miss the Healdsburg Museum, which showcases local history and art. And just outside of Healdsburg, you'll find the stunning Russian River, perfect for kayaking or just relaxing by the water.
What are the best short term rentals in Healdsburg, CA?
What notable natural landmarks are near Healdsburg, CA?
The Russian River is a popular destination for swimming, fishing, and kayaking. Just a short drive away is Armstrong Redwoods State Natural Reserve, with its towering redwood trees. And for stunning views, head to the top of Fitch Mountain for a panoramic vista of the surrounding area.
What are the best short term rentals with a pool in Healdsburg, CA?
What family-friendly activities are available near Healdsburg, CA?
The Healdsburg Farmers Market is a great place to spend a Saturday morning, with plenty of kid-friendly activities and delicious food. The Healdsburg Aquatic Center offers swimming lessons and a splash pad for the little ones. And for a fun day out, head to the Safari West Wildlife Preserve, where you can see exotic animals from around the world.
What are the best short term rentals with a jacuzzi in Healdsburg, CA?
What kind of weather can travelers expect in Healdsburg, CA?
Healdsburg enjoys a Mediterranean climate with warm, dry summers and mild, wet winters. Expect temperatures in the 70s and 80s Fahrenheit during the summer months and in the 40s and 50s during the winter months. Pack layers, as the weather can be unpredictable.
What are the best short term rentals for families and kids in Healdsburg, CA?
What major cities can be found near Healdsburg, CA?
Healdsburg is located about 60 miles north of San Francisco and about 40 miles west of Santa Rosa. It's also a short drive to the charming town of Sebastopol, known for its apple orchards and wineries.
Destinations nearby
Best Healdsburg, CA lodging with laundry available
10 85 reviews
Healdsburg, CA
09/07 – 09/11
$1831/nighttotal: $7324 (4 )
Alexander Valley Modern Farmhouse With Vintage Charm - Newly Renovated Pool
3 2
apartment , Healdsburg
This Healdsburg vacation rental is located near the Russian River, about 1.5 km from Jordan Vineyard & Winery and within 5 km of other renowned wineries. The property has excellent user, location, and cleanliness ratings. The 3-bedroom, 4-bathroom home features a spacious 2950 square feet layout. Enjoy a private pool, a fenced yard, a barbecue grill, a fireplace, a fully equipped kitchen, a fitness center, a garden, and a bar.
10 38 reviews
Healdsburg, CA
08/20 – 08/23
$3265/nighttotal: $9795 (3 )
Riverstone Estate Sleeps 12 Pool Bocce Spa
5 3
apartment , Healdsburg
This family-friendly vacation home is located on the waterfront in Healdsburg, within a mile of the Russian River, Pezzi King Winery, and within two miles of the Healdsburg Museum and Healdsburg Plaza. The home has earned excellent ratings for its location, cleanliness, and overall experience. This spacious five-bedroom home, with a sofa bed, accommodates up to 12 guests and offers a private pool, spa tub, fitness center, and tennis court. The home also includes a fully equipped kitchen, barbecue grills, and a terrace for enjoying the beautiful Healdsburg scenery.
10 112 reviews
Healdsburg, CA
07/10 – 07/13
$833/nighttotal: $2499 (3 )
Modern, Secluded Retreat - Walk To The Plaza!
1 2
apartment , Healdsburg
This modern cottage is located in Healdsburg, just a 15-minute walk from the Healdsburg Plaza, offering easy access to shops, restaurants, and attractions. It's also situated on Dry Creek, providing a peaceful retreat from the bustling town. This cottage has received excellent ratings for its location, cleanliness, and overall user experience. This 1,150 square foot cottage comfortably sleeps six guests in its two bedrooms and three bathrooms. Guests can enjoy a fully equipped kitchen, a private jacuzzi, a spacious deck, and access to the river for relaxing and enjoying the beautiful California weather.
10 2 reviews
Healdsburg, CA
07/10 – 07/13
$3212/nighttotal: $9636 (3 )
Luxurious Enchanting Healdsburg Estate Style Retreat, Sleeps 12, Pool, Firepit
6 2
apartment , Healdsburg
This Healdsburg estate rental, near the Russian River and a 5-minute drive (1.83 miles) from Healdsburg Plaza, offers unparalleled privacy on a gated property with river views. The 5300+ square-foot family compound features six bedrooms, seven bathrooms, and accommodates up to twelve guests, boasting a solar-heated pool (seasonal), hot tub, and various recreational amenities including a bocce ball court, horseshoe pit, and basketball hoop.
Best Healdsburg, CA lodging with air conditioning
8.8 449 reviews
Healdsburg, CA
08/20 – 08/23
$727/nighttotal: $2181 (3 )
Calderwood Inn
2 3
B&B , Healdsburg
Calderwood Inn is a highly-rated B&B in the heart of Healdsburg, just a 10-minute walk from Healdsburg Plaza and renowned wineries like Optima Winery and Seghesio Winery. The property offers a charming ambiance with individually decorated rooms and personalized amenities. The B&B features 100-square-foot rooms with a private bathroom and a maximum guest capacity of 2. Guests can enjoy a complimentary welcome drink, gourmet breakfast, and access to a nearby spa. The inn also provides concierge services to assist with arrangements and ensure a seamless stay.
9.9 77 reviews
Healdsburg, CA
08/20 – 08/23
$592/nighttotal: $1776 (3 )
Downtown Healdsburg Hideaway
1 3
apartment , Healdsburg
This Healdsburg apartment rental is ideally located in the downtown business district, two blocks from Healdsburg Plaza and minutes from Dry Creek, Alexander Valley, and Russian River Valley wineries. The two-bedroom, one-bathroom unit sleeps four adults, features a sleek design with modern appliances including a Nespresso machine, in-unit laundry, and street parking; no children under 12 are permitted.
9.9 34 reviews
Healdsburg, CA
09/07 – 09/11
$521/nighttotal: $2084 (4 )
Vintage Retreat With Spa Near Healdsburg
3 2
apartment , Healdsburg
This Healdsburg vacation rental, a 1600-square-foot apartment, is located two miles from downtown Healdsburg and offers easy access to Dry Creek Valley wineries. The three-bedroom, two-bathroom unit features a private redwood deck with a six-person hot tub, a spacious open-plan layout, and parking for three vehicles; it comfortably accommodates up to six guests and allows two dogs.
9.8 143 reviews
Healdsburg, CA
09/07 – 09/11
$317/nighttotal: $1268 (4 )
Healdsburg 2br Cottage With Private Yard!
1 2
apartment , Healdsburg
This charming guesthouse is located just a short drive from Healdsburg Plaza, offering easy access to the town's shops, restaurants, and wineries. The home has consistently received excellent ratings for its cleanliness, location, and overall experience. The guesthouse has two bedrooms and one bathroom, comfortably accommodating up to four guests. Enjoy the modern amenities, including a Nespresso coffee maker, Parachute towels, and Evenfall hemp linens, as well as the private yard with a separate gated entrance.