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Vacation rentals in Kenwood

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Top-rated vacation rentals in Kenwood

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Home in Glen Ellen

4.96 out of 5 average rating, 174 reviews

Stay on a Vineyard. Great Views. Great Location.

Immerse yourself in a Wine Country experience that has captured the attention of prestigious publications - Condé Nast Traveler - House Beautiful - House & Garden - Esquire - Refinery 29 - The Bold Italic - The Wine Daily - Bon Traveler - Sunset Magazine WHY YOU'LL LOVE IT - Vineyard setting and views - Minutes to award-winning wineries, restaurants & spas - Pool, hot tub, bocce ball court - Fully-stocked kitchen - Ultra high-speed Internet - Complimentary tasting at the Estate Winery next door

Guesthouse in Kenwood

4.94 out of 5 average rating, 231 reviews

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 queen size bed. TOT (Transient Occupancy Tax) included. TOT #3720N

Home in Kenwood

4.93 out of 5 average rating, 104 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.

Home in Glen Ellen

5 out of 5 average rating, 136 reviews

Tuscan Wine Country Villa sleeps 6

Picturesque and beautifully appointed villa on acreage with heated (seasonally) pool. Hot tub spa open year 'round. Gourmet kitchen, fireplace, stone work, patio and vistas. Ideal location for luxuriating in the beautiful Sonoma Valley; near wineries and quaint village of Glen Ellen. Discount for 7+nights not blocking both weekends. When requesting a reservation, please tell us about yourselves and confirm you understand our house rules: no additional visitors or parties of any kind. Thank you!

Home in Kenwood

4.97 out of 5 average rating, 127 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

Guesthouse in Sonoma

4.94 out of 5 average rating, 161 reviews

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.

Home in Kenwood

4.88 out of 5 average rating, 452 reviews

Carriage House at Hamilton Family Vineyards

Stay among the vines in our renovated Carriage House. Located on our working vineyard in the heart of Sonoma Valley, you’ll love our updated Carriage House’s vintage, wine country charm, while appreciating its modern amenities. Relax in your private outdoor space, or enjoy some friendly competition on our Bocce court. We’d also love to invite you to visit our tasting room just a few minutes away. A short walk through the vines takes you on to other world class wineries and restaurants.

Guest suite in Glen Ellen

4.96 out of 5 average rating, 243 reviews

Hummingbird Hideaway, Glen Ellen in Sonoma Valley

Hummingbird Hideaway is the perfect location to enjoy everything wine country has to offer. Located in the heart of Glen Ellen in the Sonoma Valley, you can stroll to wine tasting, restaurants, French Bakery, gourmet market and historic saloon for a night cap. Hiking the trails at the Jack London State Park is just minutes up the road. When you're ready to venture further, Sonoma is a short 15 minute drive, Kenwood is 10 minutes and just an hour to Bodega Bay on the Coast.

Home in Kenwood

4.85 out of 5 average rating, 205 reviews

Heiter House- hot tub, views, & nearby wineries

This 2 bedroom 2 bathroom jewel sleeps 4 and provides everything needed for a perfect stay in the heart of Wine Country. A well-equipped kitchen, fast Wifi SMART TV, ping pong(located in garage), 2 garages, a deck with great sunrises, AC in the bedrooms - it's all there. The lovely town of Kenwood is minutes away by car, as are some of the best vineyards in the area. Both Sonoma and Santa Rosa can be reached within 20 minutes, making this the perfect base for any trip.

Home in Kenwood

4.98 out of 5 average rating, 171 reviews

Sonoma Valley Getaway

Sonoma Valley Getaway is your perfect wine country home! Located in a quiet neighborhood in the quaint village of Kenwood, it is within walking distance to several tasting rooms, restaurants and parks. Dozens of world class wineries are just minutes away by car. For more exploring, the Napa Valley is a scenic 30 minute drive through the valley vineyards. Book now and come enjoy our contemporary 2 bed, 2 bath home with vineyard and mountain views!

Cottage in Kenwood

4.99 out of 5 average rating, 249 reviews

Sonoma Valley Sweet Spot for 2

Enjoy your stay in our charming guest cottage on a private, peaceful residential compound in Kenwood. Close to 25 wineries/tasting rooms and great restaurants w/in 5 minute drive. Bring a glass of wine to the bocce court, watch the local birdlife and the sun setting on the mountain. Hike in nearby regional and state parks. One hour from San Francisco, 12 miles to Sonoma Plaza and easy access to the coast, Napa, Russian River & Healdsburg.

Guesthouse in Glen Ellen

4.92 out of 5 average rating, 525 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

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Popular amenities for Kenwood vacation rentals

Free parking on premises

Air conditioning

Stay near Kenwood's top sights

St. Francis Winery and Vineyard96 locals recommend

Sugarloaf Ridge State Park95 locals recommend

Kunde Family Winery75 locals recommend

VJB Cellars70 locals recommend

Chateau St. Jean Winery69 locals recommend

The Kenwood Restaurant & Bar57 locals recommend

Other great vacation rentals in Kenwood

Rental unit in Santa Rosa

4.97 out of 5 average rating, 810 reviews

Private Getaway in West Santa Rosa

Home in Sonoma

4.99 out of 5 average rating, 141 reviews

Easy elegance in this wine country home

Guest suite in Sonoma

4.96 out of 5 average rating, 415 reviews

Casita de las Palmas

Guest suite in Santa Rosa

4.99 out of 5 average rating, 172 reviews

Wine Country Retreat w Pool & Spa - Near Vineyards

Home in Kenwood

4.83 out of 5 average rating, 104 reviews

Romantic Wine Country Cottage

Home in Sonoma

4.95 out of 5 average rating, 437 reviews

Zen House on 15 acres

Home in Glen Ellen

4.98 out of 5 average rating, 117 reviews

GlenEllenHaven/Petite Pets/HotTub/Yoga Yurt/EvCHGR

Guest suite in Sonoma

4.99 out of 5 average rating, 269 reviews

Sonoma Valley Terrace- Great Views!! Private Spa!!

Quick stats about vacation rentals in Kenwood

Total rentals
60 properties
Nightly prices starting at
$80 before taxes and fees
Total number of reviews
3.2K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with a pool
30 properties have a pool

Frequently Asked Questions

Do house rentals in Kenwood have a bbq area?
Absolutely! We offer over 20 house rentals with a bbq area in Kenwood. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Kenwood?
Experience the best of Kenwood with our house rentals, starting at about $140 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do hotel rentals in Kenwood have air conditioning?
Absolutely! We offer over 10 hotel rentals with air conditioning in Kenwood. Enjoy a tailored experience with all the comforts you desire.
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 hotel rentals in Kenwood have wifi?
Absolutely! We offer over 10 hotel rentals with wifi 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 wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

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