
Holiday houses in Kenwood
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Top-rated holiday rentals in Kenwood
Guests agree: these stays are highly rated for location, cleanliness and more.

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.

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

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.

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

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.

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.

Spring getaway 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

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

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

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.

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!

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.
Popular amenities for Kenwood holiday rentals
Other great holiday rentals in Kenwood

Sky View: Heated Pool & Hot Tub, 5 Acres

Wine Country Farmhouse with pool & spa

Glen Ellen Wine Country Retreat/pool, hot tub +

Himmel House ~ Private Kenwood Wine Country

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

Kenwood Ranch Retreat w/ Pool (Family Friendly!)

Oak Den - Secluded Charm in the Heart of Sonoma

Jack London Inspired Luxury Wine Country Estate
When is the best time to visit Kenwood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $776 NZD | $769 NZD | $766 NZD | $780 NZD | $829 NZD | $882 NZD | $873 NZD | $855 NZD | $819 NZD | $819 NZD | $831 NZD | $781 NZD |
| Avg. temp | 10°C | 10°C | 11°C | 11°C | 12°C | 13°C | 14°C | 14°C | 15°C | 13°C | 12°C | 10°C |
Frequently Asked Questions
Are there family-friendly vacation rentals in Kenwood?
Kenwood has more than 40 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in hotel rentals in Kenwood?
Experience the best of Kenwood with our hotel rentals, starting at about $290 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in Kenwood?
Four-legged friends are welcome in Kenwood. Choose from more than 10 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Kenwood?
Yes! Work meets play with ease at over 30 vacation rentals in Kenwood featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there Kenwood vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 30 vacation homes with pools in Kenwood, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Kenwood have air conditioning?
Absolutely! We offer over 30 house rentals with air conditioning in Kenwood. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Kenwood have a kitchen?
Absolutely! We offer over 30 house rentals with a kitchen in Kenwood. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Kenwood have wifi?
Absolutely! We offer over 30 house rentals with wifi in Kenwood. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Kenwood have free parking?
Absolutely! We offer over 30 house rentals with free parking in Kenwood. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Hotel Rentals in Kenwood?
Enhance your stay in our Hotel Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Quick stats about holiday rentals in Kenwood

Total holiday rentals
Explore 60 holiday rentals in Kenwood

Nightly prices starting at
Kenwood holiday rentals start at $102 NZD per night before taxes and fees

Verified guest reviews
Over 3,330 verified reviews to help you choose

Family-friendly holiday rentals
40 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Holiday rentals with a pool
30 properties feature pools

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
60 of Kenwood holiday rentals include Wi-Fi 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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