Holiday rentals in Chianti

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

Raven Haven: Cozy Forest Storybook Cabin w Hot Tub

Nestled among majestic redwoods in the historic Rio Nido hamlet near Guerneville, Raven Haus is a delightful Hansel and Gretel cottage. Surrounded by towering firs, the whimsical charm of this cottage captures the essence of a bygone era. Located just a mile from the renowned Korbel vineyards and tasting room, guests can explore the local wine scene. The proximity to the popular Rio Nido Lodge and Roadhouse offers convenient options for dining, drinks, and entertainment within walking distance.

The Black Sheep - Wine Country • Hot Tub • Theater

This bold, eclectic 2000 sqft cabin provides a unique bohemian experience and a spacious calm retreat, ideal for multiple couples or families. The Black Sheep is nestled among the redwoods and perfectly situated for the Russian River (4min), wine tasting (8min), restaurants (10min), and the Armstrong Redwoods preserve. After a day spent floating on the river or tasting some of the best wines in the world, soak in the hot tub, BBQ, or watch a movie/karaoke/play games on the 12ft movie screen!

Cozy vintage cabin with fireplace near hot spring

Our rustic wood cabin is nestled among pine trees in the little village of Cobb Mountain, close to Harbin hot springs, Clear Lake, and just north of Napa valley wine country. Enjoy being surrounded by forest while you relax in the hammock or bbq on the deck. Step back in time in the vaulted wood rooms, warm fireplace, modern amenities including A/C and comfy bedding. A short walk to the swimming pool, little stream, general store and cafe. A perfect romantic getaway, or for the whole family!

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

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.

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.

Gracianna Winery Vineyard Loft - Farm Stay

Costs vary based on availability. Luxury estate loft in Gracianna Winery's vineyard on Westside Road's Miracle Mile of Pinot Noir in Healdsburg includes equipped kitchen with new gas Wolf Range. Pick up breakfast needs before arriving. Vineyard machines may work overnight with lights & disruptive noises, especially during the summer and harvest is in late August early Sept. TASTING ROOM CLOSED DECEMBER 1 - MARCH 31. LOFT AVAILABLE YEAR ROUND. TOT #3294N

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!

Summer at the Cazadero Cabin

The Cabin is a perfect place to spend a cheerful summer!, a swimming hole nearby and all the coastal delights only 20 min away! Delightful, comfortable and romantic; bright, airy but cozy, the cabin is the perfect place for two. A large deck, a fire pit and a Finnish sauna are some of the amenities. the interior is updated and renovated and expresses a scandinavian sensibility culminating in an efficient and minimalistic design.

Rustic Yet Luxurious Cabin in the Redwoods

This rustic yet luxurious cabin is the perfect place to unplug. Walk through the woods, relax by a fire, and enjoy the food and wine of the Russian River Valley. 10 minutes from the beach. Minutes from Occidental, Graton, Forestville, and Guerneville. House has a full bathroom, bedroom downstairs with a Cal King bed and one upstairs with two twin beds. 5 acres in the redwoods, trampoline, fire pit area, high-speed Internet.

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!