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, 269 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, 282 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 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, 152 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.

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, 525 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

A cozy living room features a light-colored sofa, a comfortable armchair, and a wooden coffee table. Natural light filters through windows adorned with bamboo shades, illuminating a vibrant area rug and greenery from potted plants. Colorful wall art adds a touch of personality to the space.

4.93 out of 5 average rating, 155 reviews

Valley of the Moon Vintage Guest Cottage

ASK ABOUT OUR WINTER DISCOUNT:~This Vintage 1948 home has a personality of it's own, it's original beauty shows. It is private, quiet and peaceful, perfect for a getaway with everything you need for comfortable and happy. Think ahhh when you get here.. expect to find everything you want to feel just like home. The house is clean and comfortable. You will be centrally located with great wineries and places to eat close by. Please reach out and ask questions. Thanks for looking, Rochelle

A spacious wooden cottage is framed by vibrant autumn foliage. The exterior showcases large windows and a wraparound deck with seating. A natural path leads through landscaped greenery, enhancing the serene ambiance of the surrounding environment.

4.94 out of 5 average rating, 109 reviews

Artist inspired retreat in the best part of Sonoma

Find natural beauty in the Redwood as this Cedarfield Forest home shelters you in stylish Sonoma cottage. As you open the privacy Gates you are greeted with a quintessential English garden the scent of fresh rosemary and lavender. Miles of vineyards and wineries are moments away. Sonoma is known for state parks as well as Hot Springs an abundance of eateries and the charming Glen Ellen saloon are less than 3 miles away. Just steps away from natural Sonoma warm springs open seasonally.

4.93 out of 5 average rating, 194 reviews

A scenic view captures the studio and main house nestled among greenery. A mature olive tree stands prominently in the foreground, while the surrounding landscape features gentle hills and a gravel pathway that leads to the properties.

Guesthouse in Sonoma

Cozy Sonoma Studio Nearby Wineries and Restaurants

Our super cozy Sonoma studio nestled on a twelve acre parcel has a welcoming living area, a comfortable king size bed, kitchen, and a recently refreshed bathroom. Self check in for privacy and social distancing. Home is cleaned and disinfected for 24 hours between guests, including all surfaces, sheets, towels, bedspreads, etc. This studio is a perfect wine country retreat, located about 4.4 miles from Sonoma Square, 3.7 miles to Glen Ellen, and surrounded by a multitude of wineries.

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, 217 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!

4.92 out of 5 average rating, 580 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

4.91 out of 5 average rating, 327 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, 167 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.

4.96 out of 5 average rating, 193 reviews

Vineyard Retreat • Press Pick • Walk to Wineries

WHY YOU'LL LOVE IT - Stroll your own private Sonoma vineyard - Resort-style outdoor living: pool, hot tub & bocce court with vineyard views - Prime location: minutes to top wineries, dining, spas & shops - Exclusive perk: complimentary tasting at the estate winery next door - Stylish interior with thoughtful amenities - Chef-ready, fully stocked kitchen - Ultra-fast, reliable WiFi - Attentive, responsive host

Popular amenities for Glen Ellen holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Glen Ellen

5 out of 5 average rating, 5 reviews

Home in Penngrove

Amazing views from Sonoma Mountain-top

4.93 out of 5 average rating, 40 reviews

Lovely Wine Country Creekside Stay w/ Hot Tub!

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, 34 reviews

Luxury Retreat: Fireplace, Hot Tub & Zen Garden

4.87 out of 5 average rating, 47 reviews

A cozy living space features a gray sofa and a light coffee table, positioned on a textured rug. The space is illuminated by warm lighting, showcasing a mirror against a dark wall. A soft curtain separates the living area from the bedroom in the background.

Apartment in Glen Ellen

Spacious Studio Apt. Glen Ellen

5 out of 5 average rating, 44 reviews

Oak Den - Secluded Charm in the Heart of Sonoma

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, 91 reviews

Fireside Sips & Oak Dreams in Sonoma Valley

Superhost

Home in Kenwood

5 out of 5 average rating, 4 reviews

New! Completely Brand New Home| Wineries & Dining

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.