Holiday rentals in Chalk Hill AVA

4.95 out of 5 average rating, 461 reviews

Home in Healdsburg

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.

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Cottage in Sebastopol

4.9 out of 5 average rating, 332 reviews

Stunning Sauna Cottage Retreat on Private Vineyard

Welcome to our private, renovated, personal spa in the woods. Including a large wood-burning Finnish sauna, it features a picturesque deck with hot/cold plunge over breathtaking untouched forest with fire pit vineyard-side. This all-cedar cottage is nested below Halleck Vineyard, one of Sonoma County’s prestigious wineries. A perfect retreat, you are centrally located for the best Sonoma has to offer Sonoma County Wine Tastings (0-20 mins) Bodega Bay (20 mins) Armstrong Giant Redwoods (30 mins)

4.98 out of 5 average rating, 291 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

4.97 out of 5 average rating, 427 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, 128 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.

4.95 out of 5 average rating, 718 reviews

Cottage in Occidental

The Perch

Overlooking a fern grotto and redwood valley, The Perch, our newly renovated room lets you experience nature up close. Come unwind and luxuriate in nature. Limited cell service. The room INSIDE has a bed, toilet, sink, mini-fridge, microwave, and electric hot water kettle. OUTSIDE a claw foot tub/shower, private deck & outside kitchen with a gas burner stove. Very rural. We live full-time on the property, there are communal and private areas for guests TOT#3345N, Permit#:THR18-0032

4.93 out of 5 average rating, 592 reviews

Home in Healdsburg

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, 119 reviews

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, 168 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, 169 reviews

Home in Healdsburg

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, 204 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.

4.99 out of 5 average rating, 283 reviews

Luxurious, Private, Healdsburg Guest Cottage

1083 Guest House is comfortable luxury in a spacious private cottage within walking distance of four-star restaurants, wineries, fabulous boutique shopping, and the Russian River. Your secluded cottage is nestled in the trees with views of a wooded area and is the perfect base for your Wine Country get away. There is no stove/oven due to zoning/licensing so the cottage has a microwave, small air fryer, toaster and bbq.

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Other great holiday rentals in Chalk Hill AVA

5 out of 5 average rating, 13 reviews

Yurt in Monte Rio

Tiny House + Yurt Nature Retreat

SabinaRating, 5 starstoday

Christy was a wonderful host—very kind, welcoming, and always helpful when we needed anything. Her place is tucked away in a beautiful wooded area, which made for such a peaceful and relaxing stay. The surroundings were quiet and serene, perfect for a getaway. I’d definitely stay here again!

4.8 out of 5 average rating, 60 reviews

Cottage in Healdsburg

Charming Cottage in Sonoma Wine Country

TomRating, 5 stars6 days ago

Beaux Maison Sonoma is a true gem. This Airbnb is in the hills of Healdsburg, CA, in a beautiful, quiet, and private location. The house is charming and cozy, and the host is very helpful and responsive to all my questions. I have already marked this property as a favorite and I will definitely be back.

5 out of 5 average rating, 14 reviews

Flat in Forestville

Enchanting Russian River Retreat

BrendanRating, 5 stars1 week ago

My wife and I enjoyed an absolutely delightful 4-night visit. Perfect place for a quiet, peaceful home base from which to enjoy all that the Russian River area has to offer. Kathy and Mike are very thoughtful and generous hosts. Their care and attention to detail to ensure their guests have everything they need to have as comfortable and enjoyable a stay as possible was evident throughout our visit. Highly recommended!

5 out of 5 average rating, 95 reviews

Cabin in Cazadero

Ocean View Forest Retreat I Dog Friendly I Hot Tub

AlisonRating, 5 stars1 week ago

Our stay was. perfection. Of course the scenery is the main attraction but this cabin made it all the more amazing. Loved the rustic feel, with just the right amount of fun, creative interior design. Everything you could want was always right there, easy to find. We spent most of our time on the deck, unwinding from our busy lives and I hope to do it again soon! Thank you

4.97 out of 5 average rating, 87 reviews

Home in Calistoga

Calistoga Tejas Trails

AndyRating, 5 stars1 week ago

Great location with a great host for a peaceful trip to Northern Napa and Sonoma Valleys.

Home in Windsor

5 out of 5 average rating, 36 reviews

Private Villa With Stunning Views

DavidRating, 5 stars15 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.

4.97 out of 5 average rating, 64 reviews

Home in Calistoga

Calistoga Hills Hideaway on 22 Acres

LesRating, 5 stars2 weeks ago

Although a little challenging to reach Josh’s place from civilization, the beautiful surroundings and comfortable and roomy house make the journey worthwhile. His place is spotless and very well equipped. We had a small issue getting in, and he was immediately and fully responsive. Everything you could want both inside the house and outside are provided. The view from the front deck is gorgeous and the environment is totally peaceful. Getting to Calistoga is fairly easy, St. Helena is not too far and Healdsberg takes about 25 minutes. Driving back in the dark is a little challenging, but you’ll get used to it. All-in-all, this is a special place and well-worth the drive. You’ll love it.