Pet-friendly vacation rentals in Healdsburg

4.91 out of 5 average rating, 365 reviews

A wooden deck invites relaxation, surrounded by lush trees. Soft, inviting seating is positioned next to a small table with a vase of flowers. Large glass doors provide access to the interior, reflecting warm natural light.

Cottage in Sebastopol

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)

4.93 out of 5 average rating, 198 reviews

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

❤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!❤

4.95 out of 5 average rating, 482 reviews

A modern living area features a high wood-beam ceiling with large windows offering lush outdoor views. A round dining table is surrounded by chairs, while a cozy seating arrangement includes a dark sofa and coffee table. A wood stove adds warmth to the space.

Cottage in Forestville

Cosmo Beach: Riverfront Sanctuary

Riverfront dog friendly 1.5 acre oasis on the Russian River. The property is private, lush, serene & sunny, with access to a huge private beach. The house is modern yet rustic & is fully equipped. It has gorgeous river valley/redwood/bridge views, decks, spa, boats, fireplace, serious kitchen, fruit trees, grapevines & wildlife. Centrally located between Healdsburg, Sebastopol & the Sonoma Coast. Fantastic wineries, trails & redwoods are minutes away. 3 beaches & river park are only steps away

A bright yellow exterior is complemented by vibrant flowers in front of the window. Lush greenery surrounds the area, highlighting a tranquil outdoor space. The view includes trees and open fields, suggesting a peaceful and natural setting.

4.93 out of 5 average rating, 611 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, 163 reviews

A spacious sleeping area features a large bed adorned with a patterned blanket and decorative pillows. Natural wood walls and ceiling add warmth, while large windows provide forest views. Nightstands are placed on either side of the bed, each with a lamp for soft lighting.

Treehouse in Bodega Bay

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.

5 out of 5 average rating, 667 reviews

Home in Graton

Eco Luxury Private Sanctuary / The Farmhouse Oasis

**Very Important** Please read description below and “Other things to note” at the bottom of this section before contacting us. • Adults Only • Private Sunny 1 Bedroom, 2 full bathroom 900 sq ft stand alone home • Private Backyard with Pool, Sauna, Outdoor Shower, and Outdoor Bathtub • Luxurious Modern Farmhouse Style • Created to feel like a boutique hotel experience • In the heart of wine country Sebastopol/ West Sonoma • Eco-Friendly products used • Strict covid cleaning protocols

A charming single-story cottage is framed by vibrant plants, showcasing a well-kept lawn. Large windows invite natural light, while a welcoming front door is visible. The surrounding garden features colorful flowers, enhancing the tranquil setting.

5 out of 5 average rating, 188 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!

4.83 out of 5 average rating, 130 reviews

Three-Building Healdsburg Homestead with Wine Barn

Your Healdsburg Homestead for launching wine country adventure! Recently remodeled, 3 buildings on 1/2 acre, including a barn with a winetasting bar & game room! Great for families and groups. Perfectly located for cycling on the legendary Eastside/Westside loop. For wine lovers, we are across the street from Rodney Strong Vineyard and the amazing sparkling wines of the beautiful J Vineyard. Best of all, Healdsburg Plaza is just a short hop away!

A pathway leads to a welcoming front porch, flanked by greenery and blooming flowers. The light-colored home is partially shaded by surrounding trees, creating a serene approach. The yard features fresh landscaping with mulch and various plants, enhancing the inviting entrance.

4.88 out of 5 average rating, 334 reviews

Peaceful location, hot tub, fire pit, game room!

Feel your stress melt away as you wind your way down a country road to our little piece of heaven in wine country. Our cozy home is a great starting place for your Healdsburg adventures! Private yard, super comfortable beds, well equipped kitchen, cozy living room with fireplace, free wifi and cable, game room with pool table, poker, Skee-ball plus a wonderful outdoor dining area. Just a 5 minute drive to downtown Healdsburg.

4.97 out of 5 average rating, 211 reviews

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

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.

An outdoor space features a well-maintained lawn leading to a gravel pathway. Two black lounge chairs sit on the gravel, overlooking lush vineyards and rolling hills illuminated by soft sunset hues in the distance.

4.92 out of 5 average rating, 142 reviews

Dry Creek Retreat- Bocce, Hot Tub, EV Charger

Ideally located 5 minutes from the Healdsburg Square on Dry Creek Road, this home has it all! Newly renovated home has spectacular vineyard views on a magical 1/2 acre lot, a hot tub, Bocce ball court, large deck, and a fully stocked kitchen. We pride ourselves on keeping the house fully stocked with everything our guests may need & spotlessly clean! World class food, wine, cycling, and nature are at your fingertips here!