Holiday rentals in Chianti

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Top-rated holiday rentals in Chianti

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

Guest favourite

Home in Healdsburg

4.96 out of 5 average rating, 429 reviews

Dry Creek Valley Cottage

Enjoy your stay in beautiful Dry Creek Valley, a pastoral rural setting surrounded by vineyards and local wineries, minutes from Healdsburg's historic quaint downtown plaza. The cottage is 480 square feet with big windows, high ceilings and its own private entrance. There is parking right in front. It has kitchen amenities (coffee and tea pot, mini refrigerator, toaster and microwave), living room and bathroom with a mosaic tile shower. Right across the way you can take a lovely walk or run alongside the vineyards or you can rent a bike to explore the beauty of the valley. If you enjoy hiking, seasonal kayaking or canoeing there are opportunities all around us to explore as well. Our property has multiple fruit trees and we will be happy to share whatever bounty is in season when you arrive. The water here is also clean spring fed and very tasty and the sky at night is full of stars! You can enjoy sitting in the front yard which is bordered by a dozen Redwood trees or you can picnic in our big back yard among the fruit trees. We also have 2 female dogs who are quite friendly if you'd like to meet them. We would be happy to welcome you to Sonoma County and insure that your stay here is enjoyable.

26 Mar – 2 Apr

$266 SGD per night
Guest favourite

Guest house in Healdsburg

4.98 out of 5 average rating, 246 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

2–9 Sep

$254 SGD per night
Guest favourite

Guest house in Gualala

4.97 out of 5 average rating, 779 reviews

Casita In The Redwoods

Casita In The Redwoods - On the Coast! This beautiful guesthouse has a private garden setting. Come shoot hoops on our basketball court. We're a seven minute drive to Gualala Point Beach, where one can park and enjoy a scenic, short 15 minute or 30 minute walk to the beach. "Gualala" means "Where The River Meets The Ocean." We are minutes away from the Gualala River - kayaking, The Gualala Arts Center, The Sea Ranch Golf Links, the Gualala Township shops, galleries, restaurants, and services.

5–12 Jun

$175 SGD per night

Popular amenities for Chianti holiday rentals

Other great holiday rentals in Chianti

Guest favourite

Guest house in Gualala

4.93 out of 5 average rating, 126 reviews

Cosy Eco Studio tucked into the Redwoods

10–17 May

$128 SGD per night
Guest favourite

Guest house in Sebastopol

4.93 out of 5 average rating, 674 reviews

Sun Drenched Flat

1–8 Jul

$185 SGD per night
Superhost

Home in Clearlake Oaks

4.89 out of 5 average rating, 236 reviews

Cozy Cottage: Panoramic Lake View, WiFi, Deck

5–12 Jun

$165 SGD per night
Superhost

Cottage in Sebastopol

4.92 out of 5 average rating, 200 reviews

Stunning Sauna Cottage Retreat on Private Vineyard

31 Dec – 7 Jan

$390 SGD per night
Guest favourite

Cabin in Cazadero

4.98 out of 5 average rating, 799 reviews

Architect cabin in the Redwoods

9–16 Jan

$213 SGD per night
Superhost

Villa in Healdsburg

4.94 out of 5 average rating, 108 reviews

Hilltop Vista Villa

30 Dec – 6 Jan

$609 SGD per night
Guest favourite

Guest suite in Forestville

4.97 out of 5 average rating, 152 reviews

Forest Gem: peaceful retreat hot tub and firepit

15–22 May

$207 SGD per night
Guest favourite

Guest house in Healdsburg

4.96 out of 5 average rating, 101 reviews

Dog Friendly Healdsburg / Dry Creek Valley Cottage

9–16 Mar

$690 SGD per night
Guest favourite

Cabin in Geyserville

4.93 out of 5 average rating, 14 reviews

Wine Ranch Private Cabin with Views

4–11 Sep

$358 SGD per night
Guest favourite

Guest house in Cloverdale

4.94 out of 5 average rating, 72 reviews

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

8–15 May

$235 SGD per night
Guest favourite

Home in Cobb

4.88 out of 5 average rating, 32 reviews

Cobb Mountain Chalet Main House

28 Nov – 5 Dec

$144 SGD per night
Superhost

Cabin in Cobb

4.85 out of 5 average rating, 34 reviews

Cozy vintage cabin w fireplace + deck in the woods

22–29 Apr

$196 SGD per night

Destinations to explore

  1. Airbnb
  2. United States
  3. California
  4. Sonoma County
  5. Chianti