Villas and Holiday homes in Healdsburg, CA

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Healdsburg, CA holiday homes
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65 Villa rentals in Healdsburg, CA

Discover Central Holiday Homes in Healdsburg, CA

Position yourself moments from excellent independent bistros and famous landmarks with central holiday homes in Healdsburg, CA.

Stunning Dry Creek Road Estate - Healdsburg, CA
10 7 reviews

Stunning Dry Creek Road Estate

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.
Luxe Guest Suite In Dry Creek 5 Mins From Town! - Healdsburg, CA
10 167 reviews

Luxe Guest Suite In Dry Creek 5 Mins From Town!

house, Healdsburg
This charming guest suite is located just 5 kilometres from the centre of Healdsburg, in the picturesque Dry Creek Valley, a renowned wine region. It has received excellent ratings for location, cleanliness and user experience.
This self-contained accommodation is ideal for couples, with one bedroom and one bathroom. Enjoy the stunning vineyard views from your private lanai, relax in the hot tub, and take advantage of the fully equipped kitchen, washer and dryer.
Enjoy A Slice Of Country--two Miles To Downtown Healdsburg - Healdsburg, CA
10 65 reviews

Enjoy A Slice Of Country--two Miles To Downtown Healdsburg

cottage, Healdsburg
This charming cottage is located just under 3km from the centre of Healdsburg Plaza, nestled in a peaceful rural setting with vineyard views. It has received excellent reviews from previous guests.
The cottage offers 102 square metres of space and can accommodate up to 4 guests. It comes complete with a fully equipped kitchen, a private deck, a jacuzzi, a garden and a spa, making it ideal for a relaxing getaway.
River View Lodge - Hot Tub And Tastings Included - Healdsburg, CA
9.5 213 reviews

River View Lodge - Hot Tub And Tastings Included

house, Healdsburg
River View Lodge is located in Healdsburg, just 23 kilometres from Safari West and 18 kilometres from Charles M. Schulz Sonoma County Airport. The lodge has received excellent ratings for its cleanliness, location, and overall experience.
This three-bedroom lodge spans 149 square metres and comfortably accommodates up to eight guests. The lodge offers a range of amenities, including a fully equipped kitchen, a hot tub, a garden, a tennis court, and free parking.

Best family friendly Healdsburg, CA villas and holiday home

Among the 65 accommodations in Healdsburg, CA, here are the 4 best family friendly villas and holiday homes

Private Acre With Bbq, Patio, 5min To Healdsburg Plaza - Healdsburg, CA
No reviews

Private Acre With Bbq, Patio, 5min To Healdsburg Plaza

house, Healdsburg
Casa Campo is a detached property situated on a one-acre plot in Dry Creek wine country, a mere five minutes by car from Healdsburg's central plaza.
This family-friendly accommodation for four guests features two bedrooms, two bathrooms with a deep soaking tub, a fully equipped kitchen with an induction hob, air conditioning, Wi-Fi, and private parking for three vehicles, with a gas BBQ and outdoor seating area ideal for enjoying the surroundings.
Villa Terra Bella, By Vinifera Homes - Healdsburg, CA
9.8 8 reviews

Villa Terra Bella, By Vinifera Homes

house, Windsor
Villa Terra Bella, a six-bedroom property in Windsor, California, boasts a seven-acre vineyard setting, situated 2.6 km from KIN Windsor and 2.7 km from Windsor Town Green.
This luxurious holiday home sleeps twelve guests and offers a chef's kitchen, private pool, basketball court, BBQ, shuffleboard, and proximity to several renowned wineries.
The Estate Villa - Healdsburg, CA
10 11 reviews

The Estate Villa

house, Healdsburg
The Estate Villa at NewTree Ranch, a luxurious property in Sonoma County's wine country, is situated 1.6km from Healdsburg's restaurants and shops.
This 4-bedroom, 4-bathroom villa sleeps 8 guests and boasts a chef's kitchen, private lake, solar-heated pool (May-October), fitness centre, stables, and access to hiking trails; on-site activities include interacting with farm animals and enjoying massages.
Alexander Valley Modern Farmhouse With Vintage Charm  - Newly Renovated Pool - Healdsburg, CA
10 89 reviews

Alexander Valley Modern Farmhouse With Vintage Charm - Newly Renovated Pool

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.

Frequently asked questions about villa rentals in Healdsburg, CA

  • What are the must-see attractions in and around Healdsburg, CA?

    Healdsburg is a charming town with plenty to offer. You've got to visit the Healdsburg Plaza, a beautiful square with shops and restaurants. The Healdsburg Museum is also a must-see, showcasing the history of the area. For a taste of the local wine scene, head to the Healdsburg Wine Country Visitor Center and the Russian River Valley.
  • What are the best holiday homes in Healdsburg, CA?

  • What types of wildlife can travelers expect to see in the area of Healdsburg, CA?

    You'll likely spot deer, rabbits, and squirrels in the area, especially in the early morning or late evening. If you're lucky, you might even catch a glimpse of a coyote or a bobcat, but they tend to be more elusive. The Russian River is also home to a variety of birds, including herons, egrets, and ducks.
  • What are the best holiday homes with a pool in Healdsburg, CA?

  • What is the best time to visit Healdsburg, CA?

    The best time to visit Healdsburg really depends on what you're looking for. For warm weather and outdoor activities, spring (April-May) and autumn (September-October) are ideal. If you're a wine enthusiast, you'll want to visit during harvest season in autumn, but be prepared for crowds. Summer can be hot and crowded, but there are plenty of events and festivals to enjoy.
  • What are the best holiday homes with a jacuzzi in Healdsburg, CA?

  • When is it easiest to book a villa rental in Healdsburg, CA?

    You'll find the best deals on villa rentals in Healdsburg during the shoulder seasons, like spring or autumn. Summer and autumn are peak season, so booking in advance is essential. If you're flexible with your dates, you might find better deals during the week compared to weekends.
  • What are the best holiday homes for families and kids in Healdsburg, CA?

  • What are the top hiking trails near Healdsburg, CA?

    There are some great hiking trails around Healdsburg. The Armstrong Redwoods State Natural Reserve is a must-visit for its towering redwood trees. The Fitch Mountain Trail offers stunning views of the surrounding countryside. For a shorter walk, the Healdsburg Ridge Trail is a great option.
  • What are the best pet friendly holiday homes in Healdsburg, CA?

  • What are the advantages of renting a house or a villa in Healdsburg, CA

    Renting a villa in Healdsburg gives you more space and privacy than a hotel. You'll have access to a fully equipped kitchen, so you can save money by cooking some of your meals. Many villas also offer outdoor living spaces, perfect for relaxing and enjoying the beautiful surroundings.
  • What are the best holiday homes with parking in Healdsburg, CA?

  • Are there popular destinations near Healdsburg, CA?

    Yes, there are plenty of popular destinations near Healdsburg. You can easily visit the charming towns of Guerneville, Cloverdale, and Sebastopol. For a day trip, head to the coast and explore the beaches and tide pools of Bodega Bay. If you're looking for a more adventurous outing, visit the Armstrong Redwoods State Natural Reserve, just a short drive from Healdsburg.

Popular destinations

Best Healdsburg, CA villas and holiday homes with a garden

Updated Russian River Cabin (Beach/river Access!) - Healdsburg, CA
9.9 184 reviews

Updated Russian River Cabin (Beach/river Access!)

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.
Luxurious Estate With Hot Tub And Pool - Stunning Wine Country Haven - Healdsburg, CA
No reviews

Luxurious Estate With Hot Tub And Pool - Stunning Wine Country Haven

house, Healdsburg
This exclusive Wine Country retreat is a private, gated estate located on the Russian River, just a few minutes' drive from the centre of Healdsburg.
This sprawling property offers over 492 square metres of living space across three separate dwellings, accommodating up to 12 guests with resort-style amenities including a solar-heated swimming pool, year-round hot tub, and bocce ball court.
Mediterranean Getaway With Breakfast Healdsburg - Healdsburg, CA
9.9 209 reviews

Mediterranean Getaway With Breakfast Healdsburg

house, Healdsburg
This Healdsburg guesthouse is situated in a peaceful wooded area of Northern Sonoma County, near the base of Fitch Mountain, approximately 1.4 kilometres from Healdsburg Plaza and 0.8 kilometres from the Russian River.
The self-catering unit offers a queen-sized bed, private patio with a translucent roof and gas heater, a gourmet continental breakfast, and is within walking distance of the 173-acre Fitch Mountain Nature Preserve, accommodating up to two guests.
Luxury Villa, 7  Minutes From Healdsburg  Plaza. - Healdsburg, CA
10 67 reviews

Luxury Villa, 7 Minutes From Healdsburg Plaza.

house, Healdsburg
This renovated villa is situated just a few kilometres from the centre of Healdsburg, close to wineries, restaurants and shops. The property enjoys excellent ratings for user experience, location and cleanliness.
The house has three bedrooms and four bathrooms, comfortably accommodating up to six guests. Amenities include a swimming pool, Jacuzzi, gym, Peloton, game room, high-speed internet, a gourmet kitchen and a pizza oven, as well as a garden and a bar.

Best Healdsburg, CA villas and holiday homes with parking

Guesthouse On Gated 22 Acre Family Ranch, Vineyard - Healdsburg, CA
10 55 reviews

Guesthouse On Gated 22 Acre Family Ranch, Vineyard

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.
A Grass-roofed Earthen Hobbit Hut - Healdsburg, CA
8.9 435 reviews

A Grass-roofed Earthen Hobbit Hut

cabin, Geyserville
Isis Oasis Sanctuary is situated in Geyserville, a short 10-kilometre drive from the renowned Healdsburg and the Russian River.
This unique B&B offers a cob hut crafted by sculptor Miguel Elliott, a spiritual retreat atmosphere, and a community garden, as well as a spacious dining pavilion with a fireplace and a small library.
Designer Cottage | Garden Oasis | Walk To Plaza - Healdsburg, CA
9.9 255 reviews

Designer Cottage | Garden Oasis | Walk To Plaza

house, Healdsburg
This studio apartment is conveniently located in Healdsburg, just a short walk from the town centre and its bustling Plaza area, home to shops, galleries and the farmers' market. It has received excellent ratings for its cleanliness, location and overall experience.
The apartment is ideal for a couple, offering a comfortable and well-equipped space for a relaxing stay. Guests can enjoy a private gated cottage, a fully equipped Pilates studio, a skylighted shower room, an outdoor lounge and dining area with a BBQ, and international contemporary art throughout.
"Luxe Barn-stay" At Moniclaire Vineyards - Healdsburg, CA
9.8 332 reviews

"Luxe Barn-stay" At Moniclaire Vineyards

gîte, Healdsburg
This charming cottage is located in the vineyards of the Russian River Valley, just a short drive from the town of Healdsburg. The property has excellent ratings for location, cleanliness and user experience.
This self-catering property sleeps four guests and features a spacious living room, a fully equipped kitchen, and a private bathroom. Guests can enjoy a private pool, a garden, and a complimentary bottle of wine upon arrival.

Compare Holiday Homes with a Pool in Healdsburg, CA

A holiday home in Healdsburg, CA with a swimming pool makes enjoying a proper swim in the heart of the city remarkably convenient.

The Estate Villa - Healdsburg, CA
10 27 reviews

The Estate Villa

house, Healdsburg
Wine Country Estate - Healdsburg, CA
10 13 reviews

Wine Country Estate

house, Healdsburg

Find the Best Luxury Holiday Homes in Healdsburg, CA

Upscale holiday homes in Healdsburg, CA offer a memorable stay with premium amenities designed for those who appreciate the finer things.

The Roost - Garden Studio - Healdsburg, CA
10 69 reviews

The Roost - Garden Studio

house, Healdsburg

Browse Holiday Homes with a Hot Tub in Healdsburg, CA

Returning to a hot tub after a day in the city is a luxury provided by these premier holiday homes in Healdsburg, CA.

Pezzi King Wine Lovers Retreat In Healdsburg - Healdsburg, CA
9.7 59 reviews

Pezzi King Wine Lovers Retreat In Healdsburg

gîte, Healdsburg
River Retreat - Hot Tub And Tastings Included - Healdsburg, CA
No reviews

River Retreat - Hot Tub And Tastings Included

house, Healdsburg
Heron House - Hot Tub And Wine Tastings Included - Healdsburg, CA
9.9 101 reviews

Heron House - Hot Tub And Wine Tastings Included

house, Healdsburg
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