Vacation rentals in Chianti

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Top-rated vacation rentals in Chianti

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite

An airy living space is highlighted by high-beamed ceilings and large windows, allowing plenty of natural light. A gray sofa and two brown leather chairs are arranged around a round coffee table on a light-colored rug. The adjacent dining area features a wooden table, surrounded by various chairs.

Home in Healdsburg

5.0 out of 5 average rating, 123 reviews

Healdsburg House - Chiquita Road

Relax with the whole family at this peaceful and private home mins to the Healdsburg Square, Montage Resort, and Dry Creek/Alexander Valley Wineries. The updated home features an open concept kitchen, two family rooms, and a sparkling hot tub on 1.5 private acres surrounded by vineyards and oak trees. Cruise your bike to town or head directly out Chiquita Road to some of the world's greatest cycling. 2.4 miles to the Montage Resort. 2.5 miles to the Healdsburg Square. Welcome to Wine Country!

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Guest favorite

The image displays a sunny outdoor pool area surrounded by comfortable lounge chairs. Two shaded cabanas offer shelter, while vibrant orange and red canopies provide additional shade. Lush green hills are visible in the background, contributing to a serene atmosphere.

Home in Cloverdale

4.87 out of 5 average rating, 126 reviews

Woodhawk Manor of Alexander Valley

Welcome to Woodhawk Manor! We have completed our remodel. Previous guests will now find en suite bathrooms for the four main bedrooms, plus a new tub in the master bath. Brand new hardwood floors adorn the home with freshly painted walls and ceilings to add to the charm. As of May 2024, an outdoor kitchen is available for you at the swimming pool. The property is now gated and fenced, giving you additional exclusivity on your special getaway. We invite you to come and stay at Woodhawk Manor

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Guest favorite

A spacious guest house is set within a picturesque vineyard estate, featuring a distinct architectural style with multiple gabled rooftops. The driveway leads to a well-maintained entrance, surrounded by lush landscaping and mature trees, providing a serene and welcoming arrival experience.

Guest suite in Healdsburg

4.93 out of 5 average rating, 481 reviews

Pony Ranch Vineyard Estate with Pool

Guest House with private entrance on gorgeous gated Vineyard Estate. Overlooks pool and vineyards with views to Mount St. Helena. Gas fireplace, refrigerator, microwave, Keurig coffee maker, queen bed. Seasonal private pool with fabulous views, occasionally shared with owners. Toilet and sink separate from shower. 8 minutes to the Healdsburg Plaza. Less than a mile from 3 wineries, very close to dozens more. Agricultural Education Programs available. Sonoma County TOT Certificate 1362N

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Superhost

A wooden bridge connects the ground to a treehouse elevated among tall trees. The treehouse features large windows and a circular design, surrounded by lush greenery. A sturdy netting lines the sides of the walkway, ensuring safety while traversing to this unique retreat.

Treehouse in Bodega Bay

4.94 out of 5 average rating, 236 reviews

Eagle's Nest Treehouse Farm Stay

Eagle's Nest Treehouse Farm Stay is a tranquil, secluded, luxurious, romantic wilderness experience in a private forest on a 400 acre working ranch. Thirty feet above the forest floor you are nestled in a gorgeous, well-appointed suite of 1,000 year old polished redwood, with bathroom and amazing copper/glass forest-view shower. Explore hiking trails through the forest and learn about ranch operations (Highland cattle, goats and ducks). See guest comments in the space description.

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Top guest favorite

Home in Healdsburg

4.93 out of 5 average rating, 179 reviews

Modern Healdsburg Retreat • Hot Tub, Bocce & Views

Vineyard views + hot tub under the stars—modern Healdsburg, 5 min to the Plaza. Set in Dry Creek Valley, this design-forward retreat feels a world away—yet you’re minutes from top wineries, tasting rooms, and dining. Slow mornings with coffee overlooking the vines. Golden-hour dinners outside. Evenings in the hot tub with sunset views and total privacy. Designed for relaxed Wine Country living with bocce, outdoor lounge spaces, and seamless indoor-outdoor flow.

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Top guest favorite

Cottage in Geyserville

4.99 out of 5 average rating, 180 reviews

Country Carriage House in Downtown Geyserville

Linger over coffee on your quaint patio amongst 6 acres downtown in sweet Geyserville. An industrial loft vibe with wine country bones—the cottage is modern/rustic meets country-correct. Immerse yourself in country life or walk to downtown Geyserville for an Aperol Spritz. Truly where design meets refuge. Goats, horses, dogs, one heifer 🐄 named Francis, and one farm cat named Leo on property. Fully fenced front yard and back patio!

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Top guest favorite

A bright bedroom is furnished with a metal bed frame topped with white linens. Soft gray curtains frame the window, allowing natural light to fill the space. A dark dresser stands against the wall, and a small area rug adds texture to the floor.

Apartment in Cloverdale

4.94 out of 5 average rating, 143 reviews

2 Bedroom Flat With Short Walk to Downtown

Keep it simple at this peaceful and centrally-located place. Our 100+ year old vacation home has a classic vintage vibe with newly renovated modern touches. The upstairs apartment features 2 bedrooms and 1 bathroom. It is only half a block from downtown Cloverdale where you’ll find restaurants, bars, shopping and live music in the summer. This is the perfect place to enjoy a family vacation or a friends getaway!

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Guest favorite

An elegant wrought iron gate features a circular emblem at its center, framed by tall brick pillars. Lush greenery surrounds the entrance, with oak trees providing shade and creating a serene atmosphere. A gravel driveway leads up to the gate, inviting guests into the private property.

Home in Cloverdale

4.99 out of 5 average rating, 134 reviews

Peaceful Hilltop Retreat - Deck, Privacy & Views

The Ranch House is completely remodeled and boasts new bamboo floors, quartz countertops and custom-made cabinets in kitchen and baths, with three bedrooms. A hillside home, quiet location with amazing views of the mountains and valleys surrounding. You'll love the convenient location but the complete privacy. Perfect spot to relax after a day at the lake or wine tasting. We are just minutes rom the Russian River!

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Top guest favorite

A serene outdoor space is showcased, featuring a sparkling pool surrounded by neatly arranged white lounge chairs. Lush greenery and blooming shrubs create a natural border, enhancing the tranquil atmosphere.

Home in Geyserville

4.98 out of 5 average rating, 120 reviews

Historic Home; Walk to Cyrus, Diavola, Catelli's

This remodeled historic home is a Sonoma County Historic Landmark, called "The Bosworth, 1904," after the family who built it at the turn of the century. Beautifully restored, this 4 bed/4 bath home is two blocks from Geyserville's restaurants and wineries and a 10 minute drive from downtown Healdsburg and all the wineries the Anderson Valley and Dry Creek have to offer. TOT# 2463N

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Top guest favorite

A hot tub is positioned on a grassy area, offering a view of rows of grapevines against a serene sunset. Colorful flowers are visible nearby, complementing the natural surroundings.

Home in Healdsburg

5.0 out of 5 average rating, 268 reviews

10-Acre Vineyard Cottage w/Hot Tub + Bocce Court

Escape to a private and peaceful retreat surrounded by Russian River Valley Chardonnay and olive trees. Set on 10 acres of producing vines, our cottage offers vineyard views, a bocce court, fire pit, garden, cruiser bikes, and a sparkling hot tub. Immerse yourself in world-class food, wine, cycling, and nature. Your perfect wine country escape awaits!

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Guest favorite

The spacious bedroom features natural wood beams and hardwood floors, creating a cozy atmosphere. A large bed with soft linens is flanked by windows that let in natural light. A desk and chair are positioned neatly beside the bed, complementing the room's inviting design.

Farm stay in Healdsburg

4.92 out of 5 average rating, 101 reviews

Eco Modern Casita in the Vineyards

Land + Local Farmstay is located just 10 minutes outside the town of Healdsburg, surrounded by organic vineyards and rolling hills of the Dry Creek Valley. The standalone casita has a separate entrance for your privacy, features organic linens, eco bath products, herbal tea from our product line, and local organic coffee. Sonoma County TOT 4670N

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Top guest favorite

A covered hot tub is surrounded by curtain drapes and string lights, providing a cozy ambiance. The tub is filled with water that displays a soothing green hue, inviting relaxation in a tranquil outdoor setting.

Home in Geyserville

4.99 out of 5 average rating, 142 reviews

Updated 5 BR house w/ hot tub - walk to downtown!

Enjoy the wine country with this newly remodeled 5 bedroom home located within walking distance to downtown Geyserville. Relax in the backyard which features a hot tub, outdoor fire pit, BBQ, and a dining table. Or take a short walk to some of Sonoma County's best restaurants and wine tasting rooms. * No parties! This is a quiet neighborhood *

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