
House holiday rentals in Kenwood
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Top-rated house rentals in Kenwood
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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.

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!

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.

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.

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

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!

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 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!

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.

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!

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
House rentals with a pool

Luxury home, heated spa tub, walk to restaurants

Sebastopol Retreat w/ Pool, Spa, BBQ, Dog Friendly

Sonoma Country Club Wine Country w/ pool

Wine Country Villa Heated Pool Hot Tub Upper Level

Wine Country Escape: Pool & Hot Tub. Fast WiFi

Eclectic Hideaway with Backyard Pool & Hot Tub

Wine Country Retreat | Pool, Hot Tub + Vibes

Pacific Gardens Retreat
Weekly house rentals
Wine/Apple Country Cottage, Centrally Located

Sonoma Creek Haven | Creekside Hot Tub Retreat

Sonoma County Historical Ranch House on a Vineyard

Luxury Retreat & Zen Garden w/ Fireplace & Hot Tub

Amazing Santa Rosa Wine Escape Home

Sonoma Gem | VIEWS | Minutes to Dwtn | Sleeps 6

Zen House on 15 acres

Family Beach Cottage
Private house rentals

Sonoma-Napa Private Retreat by the Hills + 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

Elegant Cobb House w/ Spa | Pond | Chef Kitchen

Kenwood Vista by AvantStay | 7acres, Vineyard View

New! Completely Brand New Home| Wineries & Dining
When is the best time to visit Kenwood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| 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 |
| 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 |
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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- Rentals with a patio Kenwood
- Rentals with a hot tub Kenwood
- Rentals with outdoor seating Kenwood
- Family-friendly rentals Kenwood
- Rentals with a fireplace Kenwood
- Rentals with a washing machine and dryer Kenwood
- Rentals with pools Kenwood
- Rentals with a firepit Kenwood
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