Vacation 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.

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

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

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!

4.93 out of 5 average rating, 337 reviews

Healdsburg Cottage-Workspace, Walk to Plaza

This light-filled cottage is a comfortable, easy to access hide-away in a friendly, historic neighborhood just 5 blocks from the Healdsburg Plaza. Have a glass of wine or dine at your own picnic table in the private, garden setting. Relax in the adirondack chairs. Build a fire in the fire pit (weather permitting). It's an easy stroll into town for wine tasting, shopping or dinner. Transient Occupancy Tax (TOT) of 16% is included in the price.

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, 281 reviews

Cottage in Healdsburg

Luxurious, Private, Healdsburg Guest Cottage

1083 Guest House is a Healdsburg find; comfortable luxury in a spacious private cottage with terrific amenities 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 destination for your personal romantic getaway to enjoy all that the Wine Country has to offer.

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Other great vacation rentals in Jimtown

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.

4.98 out of 5 average rating, 57 reviews

Home in Geyserville

Healdsburg Wine Country Oasis, Hot Tub & Bocce

MarlenaRating, 5 stars4 weeks ago

We had the pleasure of staying in this beautiful home. The pictures and description were very accurate. Jonathan is very responsive. It was super close to the wedding venue and we had a lovely time. If you are in the Geyserville area, you will not be disappointed if you rent this house. It was beautiful and perfect.

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.

4.99 out of 5 average rating, 75 reviews

Cabin in Cobb

Little Falling Water - Mid-Mod Masterpiece

RichardRating, 5 stars3 weeks ago

The feeling of a treehouse, with the amenities of an actual home, infused with laid back, Northern California vibes. Also an architectural marvel with construction directly over the small stream. Time spent on the deck with the trees overhead and the stream below seems to slow down. Add in a lovely collection of prints, paintings, and sculptures, and very kind hosts, and you have a wonderful AirBnb. Very grateful to have had the opportunity to stay here.

5 out of 5 average rating, 30 reviews

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

MatthewRating, 5 stars1 week 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, 94 reviews

Cabin in Cazadero

Ocean View Forest Retreat I Dog Friendly I Hot Tub

AlisonRating, 5 stars5 days 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