Places to stay near Healdsburg Plaza

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Top-rated holiday rentals near Healdsburg Plaza

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Top Guest favourite
The exterior of a charming cottage is framed by lush greenery and features a welcoming entrance with wooden doors. A stone pathway leads to the home, which is complemented by vibrant foliage and a pergola adorned with vines.
Home in Healdsburg
4.96 out of 5 average rating, 479 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 favourite
The exterior of the barn cottage is featured, showcasing a two-story structure with large windows illuminated in a warm glow. The entrance is adorned with wooden doors and a star accent. A spacious deck is visible above, providing an inviting outdoor space.
Cottage in Healdsburg
4.92 out of 5 average rating, 242 reviews

❤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!❤

Top Guest favourite
A leather sectional sofa in a warm shade of brown is positioned against a neutral wall. Above it, a colorful painting of autumn trees adds a touch of artistry. A wooden coffee table sits nearby, featuring small decorative elements and a remote control.
Apartment in Healdsburg
4.98 out of 5 average rating, 123 reviews

2 Bedroom Flat In Downtown Healdsburg

Enjoy a stylish experience at this centrally-located upstairs apartment. Tucked away in a building surrounded by restaurants, bars, and tasting rooms just a few blocks from the historic downtown plaza this art gallery meets air B&b focuses on the intersection of modern art and ancient tradition. You'll find paintings, sculptures, and artistic touches around every corner of this luxuriously modern flat. Enjoy exceptional accommodations with two separate bedrooms, each with a queen-sized bed.

Guest favourite
A wooden bridge connects the ground to a treehouse elevated among tall trees. The treehouse features large windows and a circular design, surrounded by lush greenery. A sturdy netting lines the sides of the walkway, ensuring safety while traversing to this unique retreat.
Treehouse in Bodega Bay
4.95 out of 5 average rating, 197 reviews

Eagle's Nest Treehouse Farm Stay

Eagle's Nest Treehouse Farm Stay is a tranquil, secluded, luxurious, romantic wilderness experience in a private forest on a 400 acre working ranch. Thirty feet above the forest floor you are nestled in a gorgeous, well-appointed suite of 1,000 year old polished redwood, with bathroom and amazing copper/glass forest-view shower. Explore hiking trails through the forest and learn about ranch operations (Highland cattle, goats and ducks). See guest comments in the space description.

Top Guest favourite
A hot tub is positioned on a grassy area, offering a view of rows of grapevines against a serene sunset. Colorful flowers are visible nearby, complementing the natural surroundings.
Home in Healdsburg
5 out of 5 average rating, 223 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 favourite
A bright living area features a spacious white sectional couch and a wooden coffee table. An expansive bookshelf holds various items, with a television and fireplace being focal points. Large glass doors open to a garden, bringing in natural light and outdoor views.
Guesthouse in Healdsburg
4.97 out of 5 average rating, 236 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.

Top Guest favourite
A spacious outdoor deck is furnished with a large sectional sofa and several lounge chairs, all adorned with blue cushions. A wooden coffee table sits in the center, surrounded by lush greenery and trees, creating a serene and private atmosphere.
Guesthouse in Healdsburg
4.99 out of 5 average rating, 305 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.

Top Guest favourite
The cottage exterior features light green siding, surrounded by lush greenery and flowering plants. A cozy adirondack chair with striped cushions is positioned nearby, inviting relaxation. The front door is framed by decorative vines and a star accent, enhancing the welcoming entrance.
Guesthouse in Healdsburg
4.94 out of 5 average rating, 367 reviews

Romantic Cottage | Walk to Healdsburg Plaza

Welcome to this light-filled cottage in a friendly historic neighborhood, just a short walk from the Healdsburg Plaza. Enjoy coffee or local wine at the private garden picnic table, relax in Adirondack chairs, or gather around the fire pit on cool evenings (weather permitting). Walk to town for wine tasting and dining, bike quiet back roads, hike nearby redwood trails, or take a scenic drive to the Sonoma Coast.

Guest favourite
A spacious outdoor seating area features a comfortable sofa with plush cushions facing the ocean. The scene captures the soothing waves and rugged coastline, complemented by a fire feature at the center, all under a beautiful sky transitioning from day to evening.
Cottage in Bodega Bay
4.85 out of 5 average rating, 322 reviews

Surfscape Beach House, Beach & Ocean views

Surfscape Beach House 2 Bedroom 2 Bathroom With Secluded Beach. Welcome to our beach house for the 'Ultimate Pacific Coast Surf Experience'. Perched atop a cliff overlooking the Pacific approximately 4 miles north of Bodega Bay. The photo's will depict views from the actual property and the beautiful coastal inspired interior. You will have your own private stairs down to a sheltered, secluded beach.

Top Guest favourite
The modern exterior of the property is highlighted by dark siding and large windows. Lush greenery and colorful plants frame the entrance, which features a pathway leading to a welcoming porch. Tall trees surround the buildings, enhancing the tranquil atmosphere.
Cottage in Healdsburg
5 out of 5 average rating, 107 reviews

Modern, Secluded Retreat - Walk to the Plaza!

Beautiful modern getaway right on Dry Creek! This secluded, peaceful property has a full kitchen, huge deck, two king bedrooms with in-suite bathrooms and a king Murphy bed and full bath in the living space. The popular Healdsburg Plaza, with all its shops and restaurants, is just a 15-minute walk away. A family of foxes often makes early morning visits and we once saw an otter in the river.

Guest favourite
A modern living room features two comfortable armchairs and a sleek sofa, complemented by a coffee table adorned with a globe. A flat-screen TV is mounted on the wall, and natural light fills the space through large windows. An inviting atmosphere is created by neutral tones.
Holiday home in Healdsburg
4.97 out of 5 average rating, 99 reviews

Downtown Healdsburg Nest

You can't get any closer to all that Healdsburg has to offer. Just two blocks from the charming Plaza, this fully furnished, upstairs 2 bdr apartment has everything you need for a quick trip to Wine Country or longer-term stay. High-speed internet and all the comforts of home. Steps away from world-class restaurants, tasting rooms, shops, galleries, and music venues.

Top Guest favourite
Home in Healdsburg
4.93 out of 5 average rating, 632 reviews

Healdsburg Garden House

Close to the fun Clean and Cozy House Recently redecorated Sonoma style Central jump off point for all of Sonoma Covered Redwood Deck with Gas Grill New A/C and Heating Private Fully Stocked Kitchen w/ Dishwasher 50” HDTVs 1 GB High Speed Ethernet One mile to Town Square Russian River Beach nearby TOT # 798N

Popular amenities for holiday rentals near Healdsburg Plaza

  1. Airbnb
  2. United States
  3. California
  4. Sonoma County
  5. Healdsburg
  6. Healdsburg Plaza