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

A spacious studio guest house is shown, featuring a comfortable queen bed adorned with soft linens. A cozy seating area is present with a plush couch, and a wall-mounted TV is visible. Natural light fills the room through large windows, complemented by wooden beams on the ceiling.

Guesthouse in Healdsburg

4.98 out of 5 average rating, 299 reviews

Alexander Valley: Wine Lover and Cycling Paradise

The Finca Guest House is a beautiful modern & private unit, which offers country seclusion just a short hop into Healdsburg. Three private outdoor spaces for your use! Coffee patio, wine patio, goat patio--your choice! World-class biking out the door. Guest House will be thoroughly cleaned per Airbnb guidelines! *This property has farm animals so no outside animals allowed. See Rules and Policies notes Gas grill w/burner is available for outdoor cooking. NO full kitchen. Sonoma Co. TOT#3191N

Top 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, 454 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

Superhost

Guest suite in Santa Rosa

4.77 out of 5 average rating, 132 reviews

In Law Guest Suite with Bathroom & kitchenette

Please Note the following things before Booking 1) There is NO T.V in the room. 2) Full size bed high platform. Please be aware of the height. 3) No other guest can enter unless booked. 4) 2ND guest is EXTRA $12 must book through Airbnb This is Guest room attach to the main house. Has separate entrance with bathroom & kitchenette inside. Ideal place for guest who check in late and leave early for work/activities without interacting with host Come/Goes at your own time using keypad lock.

Guest favorite

A Tuscan-inspired villa is set among rolling hills and vineyards. The property features a well-maintained front yard with a gravel drive, surrounded by lush grapevines. Elegant seating options are visible near the entrance, framed by vibrant trees and a scenic backdrop of the mountainous landscape.

Guesthouse in Cloverdale

4.94 out of 5 average rating, 235 reviews

Wing in Tuscan Villa with Vineyard and two bedrms

Beautiful Tuscan-inspired villa perched at the northern most corner of Alexander Valley and Sonoma County. Perfect abode to escape the city and experience the beautiful outdoors with luxurious amenities. Cloverdale, Healdsburg & Anderson Valley Wineries all within short drive on Highway 128 wine trail - 1 hour’s drive to coast and town of Mendocino. Modern private space with full kitchen and private bathroom with access to pool, jacuzzi, outdoor kitchen/grill, and fire pit. TOT# 2713N

Guest favorite

The image captures a serene landscape view featuring rolling hills and lush greenery. Sunlight filters through the leaves, illuminating the valley below. A tranquil atmosphere is conveyed by the soft colors of the sky and the natural surroundings.

Guesthouse in Cloverdale

4.94 out of 5 average rating, 127 reviews

Ideal romantic getaway...♥️♥️👨‍❤️‍👨👩‍❤️‍💋‍👩

A lovely studio , with a private entrance, above the world famous Alexander Valley. Just 20 minutes to Geyersville/Healdsburg wineries, shopping and fine dining. A secure gated property in this tranquil area of Northern California, yet just 10 minutes from the charming historic village of Cloverdale awaits. The perfect place to kick back and relax in a calm, stylish space. Let your stress melt away while you enjoy incredible views from your private patio, complete with hot tub.

Top guest favorite

A charming single-story cottage is framed by vibrant plants, showcasing a well-kept lawn. Large windows invite natural light, while a welcoming front door is visible. The surrounding garden features colorful flowers, enhancing the tranquil setting.

Home in Healdsburg

5 out of 5 average rating, 190 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. Guests staying 3+ nights will receive a complimentary bottle of Chardonnay crafted from our vines. Your perfect wine country escape awaits!

Top guest favorite

The interior of the cottage features a spacious sleeping area with a king-sized bed, a soft sofa, and a leather love seat. A large window allows natural light, with curtains providing a touch of color. Nearby, a guitar and a small entertaining space can be seen.

Cottage in Middletown

4.98 out of 5 average rating, 140 reviews

Garden house with gas fireplace

Beautiful new cottage with lots of light, swing, and gas fireplace. Large open space with private deck looking out at Mt St. Helena. In the evening, turn on the outdoor string lights and relax on the swing under the huge oak tree before sinking into the memory foam king size bed. In the morning there is pour over coffee and robes so you can sit outside and sip your coffee. Perfect place to stay for a while, or have a romantic weekend.

Guest favorite

A bright living area features a spacious white sectional couch and a wooden coffee table. An expansive bookshelf holds various items, with a television and fireplace being focal points. Large glass doors open to a garden, bringing in natural light and outdoor views.

Guesthouse in Healdsburg

4.97 out of 5 average rating, 211 reviews

Healdsburg Contemporary Cottage With Lush Backyard Patio

Your private Healdsburg retreat—just a 4-minute walk to downtown wine tasting rooms, restaurants, shops, and the Farmers Market. This stylish guest cottage offers parking in front of a private entry, garden with al fresco dining, BBQ, lounge area, and a fully equipped Pilates studio. Designed with international contemporary art and thoughtful touches, it’s perfect for a weekend escape or a longer stay while house hunting.

Top 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, 128 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!

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

4.93 out of 5 average rating, 122 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!

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, 119 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 *

Superhost

A modern kitchen is seen with stainless steel appliances and a gas range. White cabinetry is paired with a large island, offering additional prep space. Four white chairs surround a glass dining table, while pots and utensils are neatly arranged on the wall.

Cabin in Cobb

4.85 out of 5 average rating, 106 reviews

Cozy Cabin in Cobb Mtn near Harbin Hot Springs

This super cute cabin was recently remodeled with all the modern amenities but still has that rustic and cozy charm of a cabin in the woods! It's the perfect getaway for a small group or family. There is lots to explore in the area but also plenty of fun activities provided at the cabin so you don't even have to leave if you don't want to!