Holiday rentals in Glen Ellen

A bright living area features a blue tufted sofa positioned opposite a wooden coffee table. A brick accent wall provides texture, while a large window allows natural light to illuminate the space. A small plant adds a touch of greenery.

4.78 out of 5 average rating, 138 reviews

2 Queen Beds • Dog Friendly • Just 3 mins to town

Welcome to your modern farmhouse Glen Ellen retreat, perfectly situated less than a mile from downtown and just minutes away from some of Sonoma County’s best wineries and restaurants. Whether you’re here to unwind, explore the local wine country, or enjoy a quiet getaway with your furry friend, this charming home offers everything you need. Book now to experience a peaceful wine country escape • open concept/no doors for the two bedrooms. • Pet Freindly! $25 flat rate, no limit to size/number

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, 260 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, 276 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.

Guest house 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

4.96 out of 5 average rating, 191 reviews

Vineyard Home • Steps to Tastings • Press Pick

WHY YOU'LL LOVE IT -Stroll through your own private vineyard -Pool, hot tub & bocce in a stunning serene setting -Minutes to top wineries, restaurants spas & towns -Complimentary tastings at the Estate Winery next door -Stylish interior with thoughtful touches -Chef-ready fully stocked kitchen -Helpful host—quick responsive communication AS FEATURED IN Condé Nast Traveler | House Beautiful | House & Garden | The Wine Daily | Esquire | Bold Italic | Refinery 29| Bon Traveler | Sunset Magazine

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, 149 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.

4.97 out of 5 average rating, 470 reviews

A round table with two chairs is positioned on lush green grass, overlooking a misty landscape at sunrise. The fog blankets the valley, enhancing views of rolling hills and distant trees. A potted plant adorns the table, creating a serene outdoor dining space.

Flat in Penngrove

Valley View-Sonoma Mountain Terrace

Take your wine country tour to a new level with a visit to Sonoma Mountain Terrace, a unique agri-tourism stay on a luxurious, non-traditional dairy farm. Nestled in the foothills of wine country, Sonoma Mountain provides a farm experience like none other, with the opportunity to feed a baby calf, observe milking our elite show cows, or just enjoy "being unplugged." Take a stroll through our extensive gardens, or enjoy million-dollar sunsets each night overlooking Petaluma & Rohnert Park.

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, 515 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

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.

4.94 out of 5 average rating, 215 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!

Guest house in Glen Ellen

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.

4.92 out of 5 average rating, 574 reviews

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

4.91 out of 5 average rating, 314 reviews

The cottage exterior is softly illuminated by string lights, enhancing its inviting atmosphere. A bicycle hangs decoratively beside the door. Lush greenery and decorative plants are present along the pathway, leading to a porch that welcomes guests into the charming space.

Cottage in Glen Ellen

Creekside Retreat Cottage – Wine Country Haven

Wake up beside the gentle creek in your own cottage escape! •Queen bed & cozy fireplace •Peaceful waterfront deck •Fully stocked kitchen & coffee bar •Fast Wi-Fi plus workspace •Backyard with creek access Minutes to Sonoma Plaza, wineries and trails, our 800-sq-ft hideaway is perfect for couples or solo travelers seeking nature and convenience. Washer/dryer, board games and parking included. Book your Wine Country Haven today!

Place to stay in Sebastopol

A spacious room features a large arched window that frames scenic views of the surrounding vineyards. A freestanding soaking tub is positioned nearby, while a private deck is accessed through sliding glass doors. A person stands on the deck, enjoying the fresh air.

4.99 out of 5 average rating, 143 reviews

The Sonoma Spyglass | Incredible Views + Sauna

The Sonoma Spyglass is a gorgeous 600 sqft retreat, designed and built by Artistree Homes, seamlessly blending sustainability with a deep connection to nature. Tucked in the heart of Sonoma’s wine country, this unique gem offers access to nearby walks and local wineries, making it perfect for couples or solo travelers. Soak in the tub with incredible views or enjoy the detached barrel sauna for a perfectly relaxing stay.

4.97 out of 5 average rating, 737 reviews

A rustic cabin interior features wooden walls and ceiling, showcasing a spacious bed with red and black plaid bedding. A cozy seating area includes a leather couch and a patterned throw pillow. A small dining table rests nearby, complemented by large windows allowing natural light.

Cabin in Glen Ellen

Wine Country Cabin in the Woods

Enjoy our family owned historic cabin and the beautiful area. Our gas fireplace, hot spa, fine bedding, and high speed wi-fi await. We're 5-10 min from wineries/dining in Kenwood and Glen Ellen in the heart of Sonoma Valley, adjacent to Napa Valley, with fantastic wineries, restaurants, breweries and 4 state parks with a free pass! We welcome friendly people of all backgrounds!

Popular amenities for Glen Ellen holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Glen Ellen

A spacious kitchen features a large island constructed from wood barrels, complemented by modern pendant lighting. Natural light floods through a skylight, illuminating the open layout that connects to the living area, where a comfortable seating arrangement is visible.

4.91 out of 5 average rating, 70 reviews

Wine Country Creekside Retreat With Hot Tub

A spacious living area features large windows that offer views of the surrounding greenery. A dark blue sofa is paired with a cozy light-colored sectional, while a round coffee table rests on a textured rug. Natural light fills the space, enhancing the inviting atmosphere.

4.91 out of 5 average rating, 35 reviews

Lovely Creekside Wine Country Home in Glen Ellen!

5 out of 5 average rating, 20 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 Near 20+ Wineries

Superhost

5 out of 5 average rating, 4 reviews

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

5 out of 5 average rating, 5 reviews

Home in Kenwood

Meadowhouse | Secluded Sonoma Wine Country Retreat

4.88 out of 5 average rating, 26 reviews

Ravenwood Wine County Retreat w/ Pool & Hot Tub!

5 out of 5 average rating, 39 reviews

Oak Den - Secluded Charm in the Heart of Sonoma