Holiday houses in Kenwood

4.9 out of 5 average rating, 114 reviews

Two turquoise chairs are positioned near a serene creek, surrounded by lush greenery. The water reflects the surrounding trees, creating a calm and tranquil atmosphere. A wooden deck of a nearby cabin is visible above, adding to the natural setting.

Cottage in Glen Ellen

Cozy Sonoma Creekside Escape: Couples Retreat

Peaceful retreat in Glen Ellen, right on Sonoma Creek. Sleep to the sound of bubbling water! 1BR/1BA with a full kitchen, smart TV, washer/dryer, big office, and fast Wi-Fi. Relax on the deck with creek views, BBQ, and loungers. Pet-friendly, self check-in and great restaurants. Close to wineries and hiking. Perfect for couples, digital nomads, and nature lovers. You're just minutes from wineries, scenic hikes, and the charm of Glen Ellen — but you might find it hard to leave this peaceful spot.

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.

4.94 out of 5 average rating, 113 reviews

Modern Luxury in Sonoma's Valley of the Moon

Go for a long visit in this luxury vacation rental with hardwood floors, custom high end furnishings, stone counter tops and much more. Ideally suited for the sophisticated traveler who desires high quality modern accommodations. Relax in a private backyard with a deck overlooking our vineyard and seasonal creek. Enjoy dinner at the large grapevine covered picnic table. Stroll through the Zinfandel & Petite Syrah vineyard. Every detail is taken into consideration to insure your maximum comfort.

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, 259 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.

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

4.92 out of 5 average rating, 167 reviews

A cozy treehouse retreat is surrounded by towering redwoods, resting on stilts above the forest floor. Large windows illuminate the structure, allowing natural light to flood the interior. A wooden deck extends outdoors, providing a relaxing space to enjoy the serene woodland environment.

Treehouse in Camp Meeker

Redwood Treehouse Retreat - Hot tub, fire pit

Welcome to our Redwood Treehouse Retreat, where cozy meets luxury in the heart of nature. Nestled in the ancient trees, this romantic escape offers privacy and indulgence. Relax in the hot tub, cozy up by the fire, recharge your EV, and explore. We’re centrally located: 5 min from Occidental, 10 min to Russian River/Monte Rio beach, 20 min to coast/Sebastopol, and 30 min to Healdsburg. A perfect base to discover all the wonders of this captivating region. Your dreamy, secluded getaway awaits.

4.99 out of 5 average rating, 267 reviews

Cottage in Kenwood

Enjoy autumn and beyond in beautiful Sonoma Valley

Escape to your home-away-from-home on a private residential compound: the perfect getaway spot in the heart of beautiful Sonoma Valley! 🏡 Why You’ll Love It: ✔️ Minutes to 25+ wineries & great restaurants ✔️ Easy drives to Sonoma, Calistoga, Healdsburg, Napa & the Coast ✔️ Great hiking in nearby parks ✔️ Birdwatching in the garden ✔️ Saltwater pool & bocce court ✔️ Stunning Mountain views ✔️ Private patio with gas grill & outdoor dining ✔️ Full kitchen, separate bedroom with ensuite bath

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.

Apartment 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 serene backyard setting features a stone patio with four wooden Adirondack chairs arranged around a central fire pit. Lush greenery, including ferns and flowering plants, surrounds the area, creating a cozy atmosphere for relaxation.

4.97 out of 5 average rating, 137 reviews

The Kenwood House, A Place to Stay

The Kenwood House, is a newly renovated turn of the century craftsman cottage, one of the most charming in Kenwood! Walking distance to wineries, vineyards and restaurants! You’ll love our cozy farmhouse style, relax on the front porch with views of the Kenwood Plaza Park. Enjoy the HOT TUB and fire pit under the stars in the magical backyard! Wine country serenity reminiscent of a New England landscape. Tesla Battery protection. $30 per extra guest over 4 per night. Sonoma County TOT #373

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

4.96 out of 5 average rating, 190 reviews

Vineyard Retreat • 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 and quick communication AS FEATURED IN Condé Nast Traveler | House Beautiful | House & Garden | The Wine Daily | Esquire | The Bold Italic | Refinery 29| Bon Traveler | Sunset Magazine

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, 141 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.

Guest suite in Santa Rosa

A private patio area is depicted, featuring wooden decking and surrounding foliage. A small metal chair is positioned on the patio, providing a peaceful spot to enjoy the outdoor scenery. In the background, a green landscape with distant hills is visible under a cloudy sky.

4.9 out of 5 average rating, 743 reviews

Wine Country guest house

This large private studio apartment is modern and cozy. You are next to beautiful country side while you are in the city. There is a large patio for you to relax and enjoy the beautiful wine country view. You can drive or ride your bike to Sonoma Wine Country at HWY 12 or to Russian River Brewery. The Listing excludes Tax. The unit has short term permit form Santa Rosa SVR24-056.

Popular amenities for Kenwood holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Kenwood

5 out of 5 average rating, 23 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

Superhost

5 out of 5 average rating, 4 reviews

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

An aerial view captures a hillside property featuring a spacious house with solar panels, surrounded by lush greenery. A solar-heated lap pool is nestled amongst landscaped gardens, while multiple outdoor seating areas are visible, ensuring ample space for outdoor relaxation.

4.89 out of 5 average rating, 47 reviews

Himmel House ~ A tranquil Wine Country retreat

A heated pool is surrounded by a well-maintained yard, featuring a gray water slide. Four wooden lounge chairs are positioned near the pool, offering a comfortable seating area. Lush greenery and a small building are visible in the background, providing a serene outdoor space.

5 out of 5 average rating, 40 reviews

[Egg Farm Ranch] Heated Pool-Water Slide-Hot Tub

4.96 out of 5 average rating, 83 reviews

Vineyard Haven: Pool, Hot Tub & Wine Country Charm

5 out of 5 average rating, 14 reviews

A sparkling, unheated swimming pool is framed by natural stone decking, offering panoramic views of the rolling hills at sunset. The peaceful scene is complemented by lounge chairs and a large, bright yellow umbrella, creating a serene atmosphere for relaxation.

Villa in Glen Ellen

When in Glen Sonoma Panoramic Views 3bed 3bath

A spacious living area is showcased with high wooden beams and large windows providing natural light. An inviting seating arrangement includes a soft couch and two lamps. A rustic wooden dining table contrasts with the modern television, enhancing the overall warmth of the space.

5 out of 5 average rating, 13 reviews

Jack London Inspired Luxury Wine Country Estate

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.