Vacation rentals in Chalk Hill AVA

4.98 out of 5 average rating, 291 reviews

Guesthouse in Healdsburg

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

4.97 out of 5 average rating, 426 reviews

Guest suite in Windsor

Private Entrance Suite in Heart of Wine Country

Situated in an upscale neighborhood, this exquisite guest suite boasts a private entrance on a safe, quiet cul-de-sac in the heart of the wine country. The en-suite is perfect for a romantic getaway, comfortable for an infant or small child, and ideal for the business traveler. We are 5 miles from Healdsburg and 3 from the Sonoma Co. Airport. Three parks within 4 miles encompass over 20 miles of hiking/biking. The Russian River, Redwoods, and Sonoma Coast are only a short, panoramic drive away.

Shipping container in Santa Rosa

4.98 out of 5 average rating, 123 reviews

Luxury Container Home w Infinity Pool + 360 Views

Enjoy the sounds of nature from your own private 12 acre oasis in this unique container home. Set on a private road, and built on a ridge with incredible 360-degree panoramic views from sunrise to sunset, this modern dwelling has been thoughtfully crafted with simplicity and indoor-outdoor living at the forefront of design. From the valley views to the distant mountains, every room feels a part of nature. Enjoy your private oasis from the infinity pool and spa, w views overlooking wine country.

Guest suite in Healdsburg

4.93 out of 5 average rating, 442 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

4.93 out of 5 average rating, 592 reviews

Healdsburg Garden House

Enjoy a real Sonoma County Experience Best Value in the Valley Organic grapes, hops, flower and vegetable gardens Centrally located home away from home Large Covered Redwood Deck with Gas Grill NEW A/C and Heating (controls in each bedroom) Super clean and sanitized Private, spacious & comfortable Fully Stocked Kitchen w/ Dishwasher 50” HDTV’s in each room (HBO, Showtime, Netflix, YouTube…) 1 GB High Speed Ethernet Level Walk to Town Square and Russian River Beach TOT # 798N

4.96 out of 5 average rating, 268 reviews

Home in Clearlake Oaks

Top of the World View of Clear Lake and Mountains

If you’re looking to getaway, this home high in the hills surrounding beautiful Clear lake, is the retreat for you! Enjoy panoramic views of the lake and mountains. Very quiet, the perfect stop between the redwood trees and the Bay Area Relax on the deck shaded by mature oak trees and watch the osprey’s gliding below you or use the house as a jumping off point. Mendocino National Forest, just 20 minutes away, offers endless possibilities: mountain bike and explore the local trails

4.9 out of 5 average rating, 120 reviews

Healdsburg 2br Cottage with Private Yard!

Relax at our renovated private guesthouse a 5 min drive (1 mi) from the Healdsburg Plaza. Updated 2 br/ 1 ba home with private yard and outdoor dining and lounge areas. Our layout is ideal for one family or friends traveling together as the one bathroom is accessed through the primary bedroom. Perfect for a wine country getaway- convenient location just outside of Healdsburg city limits in a vineyard adjacent neighborhood. We love kids and welcome them! Permit #TVR22-0119

4.96 out of 5 average rating, 118 reviews

Guesthouse in Healdsburg

Mediterranean Getaway with breakfast Healdsburg

An attractive, ultra-romantic, almost-a-cottage Bed&Breakfast is waiting for you in our restored 1930s-era home in a peaceful corner of northern Sonoma County. Ours is a quiet rural road nestled in beautiful oaks, redwoods, California bay, and buckeye trees near the bottom of Fitch Mountain, some 100’ above the Russian Rive. Fitch Mountain is known for its interesting local history, eclectic building styles, beautiful views, secluded neighborhoods, and friendly spirit.

4.93 out of 5 average rating, 167 reviews

Villa in Healdsburg

Hilltop Vista Villa

Set on an Acre by Fitch Mountain Park and Open Space Preserve, Hilltop Vista Villa offers a quiet private setting, spectacular views of world class vineyards, private access to hiking trails and proximity to the Russian River beach. This inviting single level retreat has an open floor plan with lots of sunshine. The open kitchen features stainless steel appliances, custom cabinetry, and a granite topped island. The Master Suite includes a custom soaking tub.

5 out of 5 average rating, 167 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!

4.97 out of 5 average rating, 588 reviews

Farm stay in Healdsburg

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. 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

4.97 out of 5 average rating, 204 reviews

Guesthouse in Healdsburg

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.

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Other great vacation rentals in Chalk Hill AVA

5 out of 5 average rating, 25 reviews

Cuvée House

EmilyRating, 5 stars1 month ago

We had a great stay at the Cuvee house. Sarah was extremely responsive and helpful throughout the trip which made this stay even better. The place was super cute and comfortable and it's located right behind a bubble bar which was fun to go to before dinner. The location can't be beat as it's right around the corner from the square and lots of shops and restaurants. Thanks for a great stay, we'd definitely come again.

4.97 out of 5 average rating, 34 reviews

Cottage in Kenwood

Zoë Creekside-Tranquil Redwoods in Kenwood

JessicaRating, 5 stars1 week ago

Wow! This property is absolutely stunning. Private and peaceful, it’s straight out of a magazine! Just 6 minutes from the most beautiful hiking trail, Goodlove Trail and just minutes to drive to some of the most beautiful wineries! We truly enjoyed our stay and would love to visit again!

Place to stay in Sebastopol

5 out of 5 average rating, 93 reviews

The Sonoma Spyglass | Incredible Views + Sauna

CheyenneRating, 5 stars5 days ago

Wow, this place is stunning. Not only the view, but the home itself is honestly incredible. It was so clean, modern & refreshing. The hosts thought of everything that we might have needed for our stay, including water, non alcoholic wine & even epson salt for the bath! I can't believe we were lucky enough to stay here. I couldn't recommend it more! Thank you for giving us such a wonderful experience!

5 out of 5 average rating, 32 reviews

Apartment in Healdsburg

Downtown Healdsburg Perch

ChelseaRating, 5 stars4 weeks ago

This place is fabulous! Perfect location, right in the center of town with tons of shops, restaurants, etc. within steps of our front door. The unit itself is spectacular - spacious, beautifully designed, elegant... everything we wanted and more! We had 2 minor issues with the AC and hot water in the shower but overall, everything was great. Megan was extremely responsive and even went out of her way to buy a clothing steamer for the unit when I inquired if there was one… she is the best! The welcome bottle of bubbly was a lovely touch, too. We’d stay here again in a heartbeat.

5 out of 5 average rating, 76 reviews

Healdsburg House - Chiquita Road

BartRating, 5 stars4 weeks ago

We had a wonderful stay at Katherine’s home. Plenty of room for 3 couples with very comfortable accommodations. The setting is beautiful and serene among the huge oak trees. We were able to instantly settle in and relax and enjoy the house and the surroundings. The kitchen was fantastic and very well stocked for everything we needed. We would come back to Katherine’s home in a heartbeat and are happy to give it our highest recommendation.

Home in Windsor

5 out of 5 average rating, 36 reviews

Private Villa With Stunning Views

DavidRating, 5 stars14 months ago

The guest house, the grounds, the vineyard, and the surrounding hills provided a uniquely beautiful spot for our family vacation. We felt alone on a private vineyard with views for miles, but we were also only 10 minutes from stores and restaurants. The grounds outside the guest house were spectacular, well maintained, and safe for our toddler. David was responsive and very helpful. He hosted us in his home for a wine tasting and shared his knowledge, passion, and the beautifully balanced wines he has produced. By far, this was the best Airbnb experience we’ve ever had — and maybe the best vacation.

5 out of 5 average rating, 52 reviews

Guesthouse in Santa Rosa

Wine Country Guest Cottage

AnneRating, 5 stars1 week ago

Everything was even better in person! My wife and I did not want to leave this beautiful sanctuary at the end of our trip. The "cottage" — aka luxury condo—is a standalone unit above the garage. Even though the main house is right there, we had 100% privacy and the pool area all to ourselves for the entire stay. The unit is perfect for 2 adults, beautifully decorated, very clean and filled with sunlight. We appreciated the laundry room and oversized closet so we could unpack and feel at home. Beautiful vineyard views from the bed and the 2-person shower were highlights. The cute back porch has a cafe table perfect for morning coffee—directly to the left is a wonderful coast redwood. We saw deer, fox, and birds from the property. Easy drives to Guerneville/ Armstrong Redwood Reserve, Healdsburg, Sebastopol, Sonoma Coast State Park, Santa Rosa, and of course there are SO many wineries just minutes away. We hope to return!