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, 282 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

4.95 out of 5 average rating, 287 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

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, 100 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.

The exterior of the home features a welcoming entrance with a wooden front door surrounded by lush greenery. The two-story building is complemented by large windows, allowing natural light to fill the interior. A stone pathway leads up to the entrance.

5 out of 5 average rating, 116 reviews

Sonoma Valley, Glen Ellen Retreat - Wolf Glen

Wolf Glen is on a private road nestled in trees on Sonoma Creek, just a 2 - 3 minute walk to Glen Ellen village restaurants and Sonoma Valley wineries. Wolf Glen offers all the amenities of wine county living at its finest! This newly furnished, elegant 3,000 square foot home, designed for entertaining, offers lavish accommodations for 8 - 10 guests, featuring a gourmet kitchen, fireplace and new Samsung 65' flat screen Smart TV, private outdoor entertaining & eating area and new gas grill.

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, 532 reviews

The Oak Haven - a relaxing sanctuary w/spa!

Welcome to The Valley Of The Moon! Glen Ellen, a hidden gem in the heart of the rolling hills of wine country, is only 20 minutes from downtown Sonoma and prides itself on offering something amazing for everyone. Many beautiful state parks and famous vineyards are just a few minutes away. Enjoy wilderness and fine wine at your doorstep in a beautiful, private home away from home at The Oak Haven. Relax, take a load off, you deserve it! License Number: LIC24-0319 TOT Certificate No: 1387N

4.96 out of 5 average rating, 200 reviews

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

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.

4.99 out of 5 average rating, 234 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!

Guest suite in Glen Ellen

A spacious sleeping area features a large bed with a dark patterned duvet and matching pillows. Natural light filters through two windows, illuminating the room's neutral walls and wooden floor. A bedside table holds a reading lamp, and an en suite bathroom is visible in the background.

4.95 out of 5 average rating, 291 reviews

Hummingbird Hideaway, Glen Ellen in Sonoma Valley

Hummingbird Hideaway is the perfect location to enjoy everything wine country has to offer. Located in the heart of Glen Ellen in the Sonoma Valley, you can stroll to wine tasting, restaurants, French Bakery, gourmet market and historic saloon for a night cap. Hiking the trails at the Jack London State Park is just minutes up the road. When you're ready to venture further, Sonoma is a short 15 minute drive, Kenwood is 10 minutes and just an hour to Bodega Bay on the Coast.

4.93 out of 5 average rating, 116 reviews

The exterior of a charming single-story home is featured, with a covered porch framed by white columns. A well-maintained garden surrounds the house, showcasing colorful flowers and neatly arranged stepping stones leading to the entrance.

Home in Kenwood

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 square foot deck. Take a stroll through the Zinfandel & Petite Syrah vineyard and end the evening lounging by the warmth of the firepit.

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, 222 reviews

Wine Country Harvest Hideaway-Private entry/space

Welcome to our Harvest Hideaway! We’re centrally located in the heart of Sonoma Valley, right in downtown Glen Ellen. We are walking distance to restaurants, tasting rooms, and the great Glen Ellen Village Market. With dozens of wineries nearby, we are a 10 minute drive to Kenwood, and 15 minutes to the Sonoma Square. Within an hour, you can be on the coast in Bodega Bay or on the Golden Gate Bridge entering San Francisco. We are sure you'll have a fantastic stay!

4.91 out of 5 average rating, 586 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

A wooden deck extends from the cottage, featuring a comfortable seating area with cushions. String lights are hung overhead, offering a warm glow as the sun sets. Surrounding trees provide a natural backdrop, creating a peaceful outdoor space.

4.93 out of 5 average rating, 166 reviews

Creekside Sonoma Cottage • Patio, Hot Tub & BBQ

Wake up beside the creek in our bright 2-bedroom Sonoma cottage just minutes from world-class wineries. Unwind in the private hot tub, grill local produce on the patio BBQ, or sip coffee while oaks sway overhead. Fast Wi-Fi, full kitchen, king & queen bed, and self-check-in keep stays hassle-free. Book your relaxing wine-country escape today! Permit# ZPE15-0779

Popular amenities for Glen Ellen holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Glen Ellen

5 out of 5 average rating, 39 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

5 out of 5 average rating, 40 reviews

The home is set amidst lush greenery beside a tranquil creek, with a spacious deck inviting relaxation. Sunset rays stream through trees, creating a warm ambiance. The gentle flow of water enhances the serene environment, offering a picturesque backdrop for outdoor gatherings.

Home in Kenwood

Sonoma Creek Haven | Creekside Hot Tub Retreat

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, 48 reviews

Luxury Retreat & Zen Garden w/ Fireplace & Hot Tub

4.93 out of 5 average rating, 14 reviews

Oak & Vine: Pool | Hot Tub | Fire Table | BBQ | EV

4.89 out of 5 average rating, 38 reviews

Ravenwood Wine County Retreat w/ Pool & Hot Tub!

The outdoor area features a circular brick patio surrounded by lush greenery and a large tree. A pathway leads to the home, which has a mix of wood and metal siding. A covered seating area is visible in the background, providing additional outdoor space.

5 out of 5 average rating, 45 reviews

Oak Den - Secluded Charm in the Heart of Sonoma

5 out of 5 average rating, 27 reviews

The outdoor pool area features a spacious swimming pool surrounded by lounge chairs and umbrellas. Views of rolling vineyards and lush greenery are visible in the background, enhancing the tranquil setting under a clear blue sky.

Home in Kenwood

Kenwood Vista by AvantStay | 7acres, Vineyard View

A modern living area features a cozy sofa paired with two armchairs and a glass coffee table. A textured area rug adds warmth beneath the seating. The open-plan layout connects to a sleek kitchen, where natural light floods the space through large windows.