Holiday rentals in Jimtown

4.95 out of 5 average rating, 461 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.

Guest house in Healdsburg

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

4.93 out of 5 average rating, 184 reviews

Cottage in Healdsburg

❤The Elegant: A Healdsburg Winery Abode! Hot Tub!❤

❤New! Welcome to the "The Elegant Barn", our newly built stylish Barn Cottage in the HEART of wine country! Our *INSTAWORTHY* barn cottage boasts a HOT TUB, panoramic vineyard VIEWS, comfy furnishings & convertible glass indoor/outdoor doors to bring the outdoors inside! LOCATION, LOCATION, LOCATION! Set on a historic vineyard property on Dry Creek Road, the location of Healdsburg's most famous wineries, and an easy walk, bike ride or drive to many of the best wineries in the area! PETS OK!❤

4.97 out of 5 average rating, 429 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.

Guest suite in Healdsburg

4.93 out of 5 average rating, 444 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, 594 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

4.9 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

Guest house in Healdsburg

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, 169 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.

Guest house in Middletown

4.91 out of 5 average rating, 315 reviews

Love Shack

Come stay in the good vibes of the Love Shack. Built for one of my sons and his sweet love to escape his mother's hearing range.... It was built to be inviting to snuggle up in and enjoy. The cottage is comfortable and charming with a newly added bathroom and kitchen area. The back deck faces the morning sun, where you can sit and drink your morning, coffee . Walking distance to shops and restaurants in Middletown. All folks, races, LGBT friendly.

5 out of 5 average rating, 169 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!

Guest house in Healdsburg

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.

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Other great holiday rentals in Jimtown

Superhost

4.9 out of 5 average rating, 80 reviews

Morning Dew - A Riverfront Healdsburg Home

MargaretRating, 5 stars1 month ago

This place was so quiet, private and beautiful. We got to see a huge deer right next to the house! Great back deck where we spent a ton of time play games ans drinking wine...nice big kitchen, really comfy beds! It is a ways outside of town so a car is necessary and the road there is pretty curvy and dark at night. Cell service is limited out there, but the wifi worked well. Over all our stay was great and our host was very responsive. Would definitely stay here again!

4.71 out of 5 average rating, 7 reviews

Modern Sonoma Home w Private Pool & Vineyard Views

DylanRating, 5 stars4 months ago

We had a wonderful stay. The house is in a great location, very peaceful, but only 10 minutes from town. The weather was too cold to use the swimming pool, but I have not, and it would be incredible during the summer months.

4.97 out of 5 average rating, 34 reviews

Cottage in Kenwood

Zoë Creekside-Tranquil Redwoods in Kenwood

JessicaRating, 5 stars2 weeks 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, 95 reviews

The Sonoma Spyglass | Incredible Views + Sauna

RomaRating, 5 stars2 days ago

Undoubtedly one of out favorite stays. From the moment of booking, the hosts made it a point to keep us in-the-know about what's around the area- from food to activities. Check in instructions were SUPER clear, and the host was responsive to any questions we had. The space itself was INCREDIBLE! Clean, peaceful, and just beautiful. You can tell the hosts have put their heart and soul into the space- there was attention to detail put into everything from the amenities offered, to the floor plan, to the aesthetics. We were here for just a one-night getaway, and admittedly, I always am stressed out about the check out process. Luckily, I had NOTHING to stress about- we didn't have to do dishes or start laundry! It was all taken care of for us upon our checkout. Thank you for an incredible stay! I am sure we will be back!

5 out of 5 average rating, 14 reviews

Flat in Forestville

Enchanting Russian River Retreat

BrendanRating, 5 stars2 weeks 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, 31 reviews

Healdsburg Vineyard Home - 3BD + Den, Spa, Bocce

MatthewRating, 5 stars2 weeks ago

Fantastic home that feels brand new and is just a short walk—about three minutes—to Ridge Winery in Lytton, which turned out to be an unexpected but welcome bonus. The house is beautifully updated and thoughtfully furnished, with great views throughout. The primary bedroom and bathroom are especially spacious, and the other rooms are just as comfortable. All the beds were incredibly cozy. Communication with the hosts was excellent—they were proactive, responsive, and very easy to work with. I also really appreciated their simple and reasonable checkout process: just lock up when you leave. That’s a rare find, as many rentals have a long list of chores despite charging a cleaning fee. The only minor downside was that a few neighboring properties weren’t as well maintained, but given the location in a vineyard setting, it didn’t detract from the experience. I’d absolutely stay here again.

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