Holiday houses in Glen Ellen

The spacious outdoor deck is illuminated in the evening glow, featuring multiple seating areas, a dining table, and a hot tub. Large glass doors provide a view into the inviting interior, framed by tall redwood trees, creating a serene ambiance.

4.99 out of 5 average rating, 304 reviews

Quiet Wine County Retreat with Bocce and Hot tub!

Central wine country location Close to wineries, tasting rooms, gourmet market, french bakery & restaurants New luxury 3-BR, 2.5 bath Hot tub & bocce ball We can host 5 adults + 2-3 kids Quiet spacious home nestled in the redwoods on 1/2 acre Complimentary pastries from local bakery Linens, towels, spa robes & toiletries provided Complimentary coffee, tea & sugar Huge outdoor decks with 3 seating areas, dining table, fire-pit Corn-hole, giant jenga & board games Kids’ books, games & baby items

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The home is framed by lush greenery and vibrant plants, with a patio featuring outdoor furniture. Warm light spills from the windows, hinting at a cozy interior. A barbecue grill is positioned nearby, providing an inviting space for outdoor gatherings.

4.96 out of 5 average rating, 114 reviews

Vineyard Haven: Pool, Hot Tub & Wine Country Charm

Property is managed by Inspired in Sonoma. Welcome to your private wine-country vineyard haven, nestled on an acre of quiet woodland in the heart of Kenwood, California—a serene pocket of Sonoma Valley where golden light filters through oak trees, and every day feels like a celebration of good living. This spacious elegantly appointed 3-bedroom house, swimming pool and Hot Tub invites up to eight guests to unwind, reconnect, and savor the beauty of Kenwood’s vineyards, tasting rooms, and parks.

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4.95 out of 5 average rating, 308 reviews

A spacious bedroom features a comfortable, well-dressed bed with neutral-toned linens and decorative pillows. Floor-to-ceiling windows offer a view of the garden patio, while artwork adorns the walls. A bedside table displays a lamp, adding functionality to the inviting space.

Guesthouse in Kenwood

Casa de Vincenzi

Beautiful, immaculate private studio, situated in Kenwood village with separate entrance and garden patio offers a quiet retreat in the heart of Sonoma Valley. Walking distance to world class tasting rooms and restaurants. Close to Sonoma, Glen Ellen and fave parks. Enjoy your ensuite bathroom with fluffy towels and toiletries. Indoor or outdoor dining to enjoy wine, tea, conversation, TV or wifi. Sleep in the quiet of your comfy King size bed. TOT (Transient Occupancy Tax) included. TOT #3720N

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5 out of 5 average rating, 222 reviews

Tiny home in Sebastopol

The Sonoma Spyglass | Incredible Views + Sauna

🏵️ Featured as one of “California’s Most Wishlisted Airbnbs!” 🏵️ 🌈 Come enjoy deep rest, romance & rejuvenation! ❤️ 🌺 Our Sonoma Spyglass is a gorgeous retreat, designed and built by Artistree Home, seamlessly blending sustainability with a deep connection to nature. 🍇 Tucked in the heart of Sonoma’s wine country, the space offers access to nearby walks and local wineries. Soak in the tub with incredible views or enjoy the detached barrel sauna for a perfectly relaxing stay. 🌺🙏 🌺

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A comfortable living room is displayed, featuring a leather sectional couch complemented by decorative cushions. A television is positioned nearby, with a stylish wooden coffee table in front. Warm light filters through a large window, illuminating the open kitchen area with modern appliances.

4.97 out of 5 average rating, 127 reviews

Fireside Sips & Oak Dreams in Sonoma Valley

Ultimate wine country escape! Stylish 3-bedroom, 1-bathroom oasis nestled in serene Sonoma Valley. Charming getaway features an equipped kitchen, inviting outdoor patios, BBQ grill, outdoor games, and cozy fire pit, perfect for enjoying stunning wooded backdrop. Unwind on the Peloton bike or indulge in board games. Ideal destination! Downtown Glen Ellen and Kenwood wineries are just a five-minute drive away. A perfect balance of seclusion and convenience await you. Pets are allowed, with fee.

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4.97 out of 5 average rating, 159 reviews

Home in Sonoma

Stunning Sonoma | HOT TUB | Game Room | Sleeps 6

Enjoy stunning views of Sonoma! Welcome to Sonoma Vista, minutes from renowned wineries and Downtown Sonoma. Perfect perch for families, couples! Nestled in oak-studded hills, this modern haven boasts three bedrooms, two sleek bathrooms with heated floors, and remote-work-friendly desks. Indulge in a mid-century bar, chef's kitchen, and a jaw-dropping game room. Outside, a vast deck with dining, fire pit, and lounge seating awaits. Immerse yourself in wine country luxury at Sonoma Vista!

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A bright and airy living space features large windows with views of the outdoors. Comfortable seating includes a green sofa and two armchairs. A round marble coffee table sits in front of the sofa, while a dining table is situated nearby. Natural light enhances the welcoming atmosphere.

4.99 out of 5 average rating, 168 reviews

GlenEllenHaven/HotTub/YogaYurt/EvCHGR/Pet Friendly

*5 min Glen Ellen/Kenwood. *20 min to Sonoma/Santa Rosa *45 min Napa Welcome to Glen Ellen Haven, a private 2 bd 1 bath cottage surrounded by organic cabernet vineyards offering views of Sonoma Mountain from expansive deck. We invite you to relax in the hot tub after a day of wine tasting or hiking, practice your daily yoga habit in the 300 sq ft yurt (ask about Sound Healing/Yoga Instructor recommendations), or relax and enjoy the views from our deck. One dog allowed max 25lbs, $150 pet fee.

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Superhost

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

4.94 out of 5 average rating, 236 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.

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4.99 out of 5 average rating, 255 reviews

A cozy living area showcases a rustic brick fireplace, producing a warm glow. Two armchairs with colorful striped blankets sit beside a small round table. A television is mounted above the mantelpiece, contributing to the inviting ambiance.

Cabin in Glen Ellen

Unique Historic Getaway w/Hot Tub and Fireplace

Hosmer House is a vintage gem, well preserved yet well appointed. Fully curated decor fills our families historic cabin. Close to wine tasting, fine dining and 3 state parks w/pass in historic Glen Ellen and Kenwood. Large always hot spa, fireplace, full kitchen, big TV, propane fire pit, screened in dining porch and 2 sets of french doors off the living room so you can enjoy nature or just curl up by the fire. Host next door for wine/food tips! We welcome people of all backgrounds!

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4.93 out of 5 average rating, 121 reviews

Modern Luxury in Sonoma's Valley of the Moon

Experience an amazing visit in this luxury vacation rental with hardwood floors, custom high end furnishings, stone counters and much more. Ideally suited for the sophisticated traveler who desires high quality modern accommodations. Relax in the private backyard overlooking a vineyard and seasonal creek. Relax and enjoy dinner on the 650 SQ. foot deck. Take a stroll through the Zinfandel & Petite Syrah vineyard and end the evening lounging by the warmth of the firepit.

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4.92 out of 5 average rating, 608 reviews

A spacious bedroom features a king bed adorned with a floral-patterned duvet. Natural light fills the room through multiple windows, with a cozy seating area visible. A flat-screen TV hangs on the wall, and a mini kitchen is positioned nearby, complemented by a small dining table.

Guesthouse in Glen Ellen

Glen Ellen Hideaway

One block to downtown Glen Ellen, with dining, shopping, & wine tasting. Hideaway is a charming, private guest house, suite-style behind our home. Spa-like bath, mini kitchen, comfy king bed! There is a large private patio for your enjoyment, great place to relax. Glen Ellen Hideaway is peaceful & private & has a separate entrance for your accommodations. Residents are Constance & Greig, and Franny, the dog, and Charm, the cat!-TOT#2398

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4.93 out of 5 average rating, 110 reviews

Family Fun in Glen Ellen: Pool, Hot Tub & Views!

Discover Glen Ellen Family Retreat, a Wine Country sanctuary perfect for families. This enchanting house features a private pool, a relaxing hot tub, and a fun bocce ball court. Enjoy the chef's kitchen, comfortable bedrooms, and a cozy fire pit for memorable evenings. Located near renowned wineries, exquisite dining, and the beautiful Jack London State Historic Park, your dream family vacation awaits.

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Popular amenities for Glen Ellen holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Glen Ellen

A beautifully landscaped garden features a pathway bordered by gravel and decorative plants. White wicker chairs surround a small table, inviting relaxation. The wooden deck and spa pool are visible in the background, complementing the modern home adorned with solar panels.

4.91 out of 5 average rating, 217 reviews

Luxury home, heated spa tub, walk to restaurants

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5 out of 5 average rating, 5 reviews

NEW! Modern Wine Country Retreat in Sonoma Valley!

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4.98 out of 5 average rating, 53 reviews

A modern single-story cottage is surrounded by lush greenery and features large windows for natural light. A small staircase leads to the front entrance, which is framed by a grassy area and ornamental plants. The exterior showcases a mix of gray siding and white accents.

Cottage in Glen Ellen

Modern Cottage on Sonoma Creek

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Guest suite in Glen Ellen

A private room features a spacious queen bed with a white comforter. Adjacent, there is a small refrigerator and a television. Natural light enters through a large window and glass doors, leading to a cozy sitting area. Light wood flooring enhances the inviting atmosphere.

4.95 out of 5 average rating, 232 reviews

Wine Country Harvest Hideaway-Private entry/space

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An outdoor living space features comfortable gray couches with soft cushions, styled with a low wooden coffee table. Stone walls and olive trees create a natural backdrop, while string lights provide gentle illumination overhead. A landscaped area with gravel completes the serene atmosphere.

5 out of 5 average rating, 69 reviews

Luxury Retreat & Zen Garden w/ Fireplace & Hot Tub

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4.96 out of 5 average rating, 26 reviews

2 Qn Beds, Fenced Yard for Pets, 1/2 mile to Town

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A welcoming home is nestled among large oak trees, featuring a spacious deck and multiple steps leading up to the entrance. Lush greenery and a variety of plants frame the path, enhancing the natural surroundings. Bright sunlight casts a warm glow on the scene.

4.89 out of 5 average rating, 549 reviews

The Oak Haven - a relaxing sanctuary w/spa!

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