House holiday rentals in Kenwood

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Top-rated house rentals in Kenwood

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Top guest favourite
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.
Home in Glen Ellen
4.94 out of 5 average rating, 113 reviews

Artist retreat/Hot Tub/2B/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, a 5 person private hot tub. Miles of vineyards and wineries are moments away. Sonoma is known for state parks as well as Hot Springs an abundance of eateries a lovely 3 miles to Glen Ellen town center. Just steps away from natural Sonoma warm springs open seasonally.

Guest favourite
A comfortable living room is presented, featuring a dark leather sofa, two armchairs, and a coffee table. Natural light enters through window coverings, and a decorative fireplace adds warmth. A simple artwork adorns the wall, complemented by a small welcome sign on a shelf.
Home in Santa Rosa
4.96 out of 5 average rating, 223 reviews

Cozy, Convenient, Central Wine Country Home

Quaint home located in a convenient location less than 20 minutes from Kenwood. Enjoy the fire pit in the backyard, the ping pong table, and the fireplace in the cozy living room. This home is less than a mile and a half to Howarth Park and Spring Lake, featuring renowned hiking and biking trails, tennis courts and a park. Just a short drive to both Montgomery Village and downtown Santa Rosa, where you will find shopping and superb restaurants, including the famous Russian River Brewing Company!

Top guest favourite
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.
Home in Glen Ellen
4.99 out of 5 average rating, 284 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

Guest favourite
Home in Kenwood
4.96 out of 5 average rating, 99 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.

Top guest favourite
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.
Home in Glen Ellen
4.97 out of 5 average rating, 104 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.

Top guest favourite
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.
Home in Kenwood
4.97 out of 5 average rating, 141 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

Guest favourite
A modern living area features a large dark green sofa complemented by a cozy white chair and a stylish coffee table. Natural light streams through multiple windows, illuminating a patterned area rug. A dining area and kitchen are visible in the background.
Home in Calistoga
4.96 out of 5 average rating, 114 reviews

Calistoga Tejas Trails

Welcome to Tejas Trails, your country getaway nestled in Calistoga's mountain vistas, just 10 minutes from downtown. This new home (2023) is easy to share with friends or family. Enjoy refreshing mountain sunrises, dinners on the huge deck, watch sunsets sipping wine by the firepit, swing under a large oak tree, and take tranquil walks on the country road. This is the perfect place to leave the hustle and bustle behind, while still minutes from Napa Valley’s finest restaurants and wineries!

Top guest favourite
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.
Home in Glen Ellen
4.89 out of 5 average rating, 535 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

Top guest favourite
An open living space is presented with vaulted ceilings and skylights that allow natural light to fill the room. A cozy dining table is surrounded by chairs, while a white sofa and dark seating option create a welcoming area. Shelves display dishware and decorative items.
Home in Sonoma
4.96 out of 5 average rating, 531 reviews

A sophisticated Wine Country Cottage with Hot tub

Escape to Thornsberry Cottage, a luxe wine country retreat 5 mins from Sonoma Square. This unique property features two separate cottages, each with a private bed/bath, perfect for guests seeking privacy and togetherness. Enjoy vaulted ceilings, a large deck, a private hot tub, and a fire pit under ancient oaks. 5 minutes from the Sonoma Square, 3 minutes to the oldest wineries in California, or walk or bike to Gundlach Bundschu at the end of our road. Your serene getaway awaits!

Guest favourite
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
4.93 out of 5 average rating, 116 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.

Top guest favourite
A hot tub is positioned on a grassy area, offering a view of rows of grapevines against a serene sunset. Colorful flowers are visible nearby, complementing the natural surroundings.
Home in Healdsburg
5 out of 5 average rating, 232 reviews

10-Acre Vineyard Cottage w/Hot Tub + Bocce Court

Escape to a private and peaceful retreat surrounded by Russian River Valley Chardonnay and olive trees. Set on 10 acres of producing vines, our cottage offers vineyard views, a bocce court, fire pit, garden, cruiser bikes, and a sparkling hot tub. Immerse yourself in world-class food, wine, cycling, and nature. Guests staying 3+ nights will receive a complimentary bottle of Chardonnay crafted from our vines. Your perfect wine country escape awaits!

Top guest favourite
A spacious bedroom features a comfortable bed dressed in crisp white linens with a decorative blanket. Natural light streams in through sliding glass doors leading to an outdoor area. Two nightstands with lamps flank the bed, and a wooden dresser completes the room's decor.
Home in Glen Ellen
4.94 out of 5 average rating, 185 reviews

Glen Ellen Retreats Coastal Cottage

Charming wine country retreat in the heart of Glen Ellen, one of Sonoma Valley's best-kept secrets. Steps from acclaimed restaurants, tasting rooms, and markets. Two bedrooms with king beds, and the living room sofa pulls out for additional guests. Full kitchen, private hot tub, and a back patio perfect for outdoor dining. Wi-Fi, Netflix, coffee, and tea included. Come fall in love with this magical little town.

Popular amenities for house rentals in Kenwood

When is the best time to visit Kenwood?

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Avg. price$609 SGD$642 SGD$654 SGD$558 SGD$665 SGD$725 SGD$746 SGD$694 SGD$687 SGD$705 SGD$618 SGD$609 SGD
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Quick stats about house rentals in Kenwood

  • Total holiday rentals

    Explore 30 holiday rentals in Kenwood

  • Nightly prices starting at

    Kenwood holiday rentals start at $152 SGD per night before taxes and fees

  • Verified guest reviews

    Over 2,560 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    30 of Kenwood holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Kenwood rentals

  • 4.9 Average rating

    Kenwood stays are highly rated by guests – averaging 4.9 out of 5!

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