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Vacation rentals in Chianti

Vacation rentals in Chianti

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Chianti

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

  • Waterloo Wine Retreat
    SUPERHOSTEntire guest house · 2 guests · 2 beds · 1 bathroom
    Waterloo Wine Retreat

    Welcome to the Waterloo Wine Retreat! We are located just less than a block away from the heart of downtown Cloverdale where you will find local bars, restaurants, shops and festivities. We are situated close to some of the best wine regions in the area including Dry Creek Valley, Anderson Valley and Napa Valley and only 15 minutes away from Healdsburg. This is truly a wine enthusiast or a cyclist’s paradise.

    What guests are saying:

    “Superhosts ourselves, we had been hosting at our bed and breakfast for nearly 3 months straight and during the pandemic meant a heavy hit sheltering in place with guests. We’ve also been working to feed and help the chronic homeless and had another big set of events on our schedule coming up. We needed a sweet simple private getaway in a darling town with comfort, cleanliness and courtesy to recharge and we received that and more. We arrived during a heat wave and not only had ceiling and floor fans but Kristi offered yet another one. What we needed was some healing lotion since I walked for 4 miles in the sun and had quite a burn. Within minutes there was a large organic lavender lotion left on our cozy porch. There were loads of coffee pods, and a solid basic set of tools plates pans and supplies in the kitchen, like oil, vinegar, jams and cold filtered water, and an ice maker which came in handy. They do not lie! Within 3 minutes you are walking down their lovely main street with landscaped gardens sculptures art and sweet shops we were sad not to see open due to the sheltering. We will definitely come back and thank Kristi and her family for hosting us!”

  • Secluded house between the lake and the stars
    SUPERHOSTEntire cabin · 6 guests · 2 beds · 2 bathrooms
    Secluded house between the lake and the stars

    Secluded two-bedroom plus loft, two-bath A-frame cabin on a wooded acre with a 180-degree lake view. Watch sunrises, sunsets, and night stars from inside or out on the deck. Perfect for getaways, writing, relaxing, quiet, and total privacy (no visible neighbors). Cooled in the summer by a moist-air cooler and warmed in winter by a cozy wood-stove. Includes a fully-equipped kitchen and everything else you need. Easy access to both ends of the lake for restaurants, movies, wineries, boating, etc.

    What guests are saying:

    “This cabin is a little gem with a beautiful view. It was nice and clean and stocked with everything that we needed, including a nice washer and dryer, a fully stocked kitchen, and even basic food items like eggs and milk.Swamp cooler keeps it comfortable when it’s hot and it’s lovely to have the windows open in the evenings to catch the breeze. Richard was extremely helpful and we had no trouble with communication. It was a great value and I can highly recommend staying here! PS - The driveway is a bit steep so it might be a challenge for a low-clearance car, but we just took it slowly and had no problems with our SUV.”

  • The Cobb Haus
    SUPERHOSTEntire cabin · 2 guests · 1 bed · 1 bathroom
    The Cobb Haus

    Welcome to The Cobb Haus! Find us on Instagram @thecobbhaus and online at www dot thecobbhaus dot com for more pictures and current updates! We are located in the quiet neighborhood of Whispering Pines in Cobb, CA. With lots of activities right outside the door, you'll have plenty to do but this is also the perfect retreat to stay in and relax!

    What guests are saying:

    “This cabin is everything you’re looking for! Insanely beautiful surroundings, super cozy setting, incredibly hip style, this place is straight out of a professional instagram account (no seriously, they have an Instagram account @thecobbhaus and it’s just as awesome as it looks!) We were only there a couple days but it already felt like home and we were sad to leave. My only pro tip is if you go in the summer, bring some fans because it can get pretty warm and there is no AC. But other than that, it was seriously the best way to celebrate our 14 year anniversary (and to get out of the house and travel a little bit after SIP). We are locking this incredible place away for future stays! Thanks again Hope and Tom!”

Holiday rentals for every style

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Popular amenities for Chianti holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Chianti

Alexander Valley: Wine Lover and Cycling Paradise
SUPERHOSTEntire guest house
Alexander Valley: Wine Lover and Cycling Paradise
Price:€132 / night
Charming Clearlake cottage
SUPERHOSTEntire bungalow
Charming Clearlake cottage
Price:€106 / night
Dry Creek Valley Vineyard Cottage Long Term Stay
SUPERHOSTEntire cottage
Dry Creek Valley Vineyard Cottage Long Term Stay
Price:€95 / night
Contemporary Vineyard Retreat
SUPERHOSTEntire house
Contemporary Vineyard Retreat
Price:€265 / night
Stay on Pony Ranch Vineyard Estate
SUPERHOSTEntire guest suite
Stay on Pony Ranch Vineyard Estate
Price:€174 / night
Downtown Cottage - Walk to Plaza!
Entire guest house
Downtown Cottage - Walk to Plaza!
Price:€106 / night
Cobb Tree House
SUPERHOSTEntire cabin
Cobb Tree House
Price:€93 / night
Great Geyserville Apartment
SUPERHOSTEntire flat
Great Geyserville Apartment
Price:€132 / night
Have an Adventure, not just a place to stay
Hut
Have an Adventure, not just a place to stay
Price:€110 / night
Luxurious, Private, Healdsburg Guest House
Entire cottage
Luxurious, Private, Healdsburg Guest House
Price:€247 / night
Romantic Woodland Cabin 3 minutes to Clear Lake
SUPERHOSTEntire cabin
Romantic Woodland Cabin 3 minutes to Clear Lake
Price:€57 / night
The Dogwood Lodge
SUPERHOSTEntire cabin
The Dogwood Lodge
Price:€90 / night
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