Kenwood Holiday Rentals

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Holiday Rentals in Kenwood

New Modern House in Sonoma Valley's Best Area

10.0 out of 10, Exceptional, (239)
"Loved this little get-away in an amazing location! Driving up country roads with red and gold vineyards on your right and left in autumn was amazing. And yet, so close to all the best Sonoma wineries!!! The house itself was thoughtfully decorated, with all you need for a wonderful Sonoma escape. We will definitely be back!!!"
New Modern House in Sonoma Valley's Best Area

Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N

10.0 out of 10, Exceptional, (215)
"Our stay at the Kenwood country estate was a wonderful and memorable experience! The property was private and secluded and exactly as listed. We stayed over Thanksgiving week and although our food was catered, we found all the entertaining essentials to complement our meal and make us feel right at home. The weather was warm, so we were able to join in the local Turkey Trot, play pickle ball on the well equipped courts, ride bikes on local trails, and enjoy morning yoga while taking in the...
Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N

Charming Country Home Nestled In Kenwood Village the heart of the wine country.

10.0 out of 10, Exceptional, (182)
"Well appointed comfortable small house in Kenwood. Nothing fancy, but well looked after and with a very responsive host who lives about an hour away. Nice field at a park nearby that is least free until 9 o’clock."
Charming Country Home Nestled In Kenwood Village the heart of the wine country.

Stunning retreat with private hot tub, firepit & 1 acre of country charm

9.2 out of 10, Wonderful, (71)
"4 sisters and nieces together for mini vacations in wine country. We love the location and the property."
Stunning retreat with private hot tub, firepit & 1 acre of country charm

Elegant five-acre estate with mountain view, W/D, & pond - close to wineries

8.4 out of 10, Very good, (74)
"Loved the large property. "
Elegant five-acre estate with mountain view, W/D, & pond - close to wineries

Year-Round Heated Pool | Hot Tub | Fire Pit | Lawn

10.0 out of 10, Exceptional, (31)
"We had the best stay in Kenwood—everything about the house was great for our family vacation. We loved having access to the pool and back patio, and the home was comfortable and well-appointed. Would stay here again in a heartbeat!"
The price is AU$2,813
includes taxes & fees
8 Jan - 9 Jan
Year-Round Heated Pool | Hot Tub | Fire Pit | Lawn

RiverPointe Napa Valley Resort

3.0 star property
8.6 out of 10, Excellent, (1223)
"The house is overall charming but has several issues that need attention: - There was an unpleasant smell in the bathroom. - The bathroom wasn't cleaned properly, as the tub had black hair. - The thermostat was challenging to figure out, and it was cold inside. - Equipment noises could be heard coming from the attic. - There were no power outlets near the nightstands in the bedroom to charge phones. - The TVs were outdated, making it impossible to watch YouTube. - There was no lighting above...
RiverPointe Napa Valley Resort

Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella

10.0 out of 10, Exceptional, (59)
"Villa Montebella is a wonderful place for a large group. Our families stayed at the Villa over the Thanksgiving Holiday week to celebrate our Daughter’s Napa Wedding. The pictures are accurate, but do not do the property justice. The place is Stunning! There are many comfortable and secluded bedrooms and facilities. The wine cave was amazing and we hired Chef Adair for a special rehearsal dinner there. We have an active group and took advantage of the many amenities. The media room was perfect...
Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella

Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021

10.0 out of 10, Exceptional, (221)
"Great place and good location to host 4 couples to celebrate our 50th birthdays. Thank you!"
The price is AU$3,434
includes taxes & fees
7 Jan - 8 Jan
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021

The Corner Cottage ~ Downtown out your door with Private Vineyard

10.0 out of 10, Exceptional, (212)
"We loved the corner cottage and Susan was extremely helpful, knowledgeable, and kind! This place had everything we could possibly need. We plan to be back!! "
The Corner Cottage ~ Downtown out your door with Private Vineyard

The St. Helena House

10.0 out of 10, Exceptional, (223)
"Our family stayed at the St. Helena House while attending a memorial. The house exceeded our expectations. It was beautifully decorated, comfortable, and homey with many wonderful nooks to read, views of the vineyards out of every window, and a beautiful well stocked kitchen. The beds were very comfortable. The bathrooms were fine with fluffy towels and plenty of hot water with good water pressure in the showers. The owner was very welcoming and available for any questions. It rained all...
The St. Helena House

Wine Country Harvest Vacation Home

9.8 out of 10, Exceptional, (67)
"Very niche home with plenty of space inside and out. Lots of space to gather. Convenient location close to grocery shopping and restaurants. "
Wine Country Harvest Vacation Home

Beautiful Deluxe Sonoma Retreat With Private Pool Spa Bocce & More! Sleeps 8+2

9.8 out of 10, Exceptional, (186)
"The property was as advertised with ample space for all guests. There was supposed to be a twin bed in the king bed room but otherwise, we had the beds needed/expected. There was a plumbing issue with one of the bathrooms (water leaking to ceiling below) that needs to be addressed. All else was good."
The price is AU$1,422
includes taxes & fees
2 Feb - 3 Feb
Beautiful Deluxe Sonoma Retreat With Private Pool Spa Bocce & More! Sleeps 8+2

Cozy Retreat, Studio Apartment, City Permit VR09-0038.

9.6 out of 10, Exceptional, (267)
"Great location, well appointed and host was responsive to requests. "
Cozy Retreat, Studio Apartment, City Permit VR09-0038.

Cottage home near the Russian River; county parks; numerous wineries

10.0 out of 10, Exceptional, (92)
"Property was perfect for me while I was taking care of my grandchildren"
Cottage home near the Russian River; county parks; numerous wineries

Relaxing & Romantic 1 bedroom Condo, in the Heart of Wine Country

9.6 out of 10, Exceptional, (82)
"We loved everything about this condo!! Very charming, "
The price is AU$652
includes taxes & fees
19 Jan - 20 Jan
Relaxing & Romantic 1 bedroom Condo, in the Heart of Wine Country

Beautiful Napa Valley Home on Golf Course - Perfect Wine Country Retreat

9.8 out of 10, Exceptional, (172)
"We had the most amazing and memorable stay! The house was fantastic for our family, so much room and a perfect location- easy to head into town for a bite or go wine tasting. The check in process was beyond smooth and I can’t thank owners Lisa and Jack enough for their hospitality- they knew we had 2 kiddos under 2 and made sure the house was baby proofed for us. Lisa also called to let us know that Santa and his train ride were at the clubhouse, it was definitely a highlight :) we can’t wait to...
Beautiful Napa Valley Home on Golf Course - Perfect Wine Country Retreat

Beautiful Home in Northwest Napa

10.0 out of 10, Exceptional, (25)
"Great location in a quiet neighborhood. Host was super responsive throughout the visit. Perfect house for our family vacation to Napa Valley! "
Beautiful Home in Northwest Napa

'De Mar House'- Historic Victorian Residence "Stroll Downtown Napa!"

10.0 out of 10, Exceptional, (175)
"We took a family trip to Napa to visit our oldest son and spend some time in the valley. There was no doubt that we were going to stay in the damar house again and it was perfect just like the last time. Beautiful home, perfect location, and great host. Highly recommended."
'De Mar House'- Historic Victorian Residence "Stroll Downtown Napa!"

Charming Napa Valley Retreat w/ Pool Near Wineries

8.6 out of 10, Excellent, (14)
"Great location to downtown Napa and Silverado resort was fantastic for coffee drinks and dinner. "
The price is AU$543
includes taxes & fees
5 Jan - 6 Jan
Charming Napa Valley Retreat w/ Pool Near Wineries
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other types of properties in Kenwood you may be interested in

The Sandman Hotel

3.0 star property
8.2 out of 10, Very good, (1999)
"Awesome Hotel "
The price is AU$150
includes taxes & fees
7 Jan - 8 Jan
The Sandman Hotel

Silverado Resort

4.0 star property
8.6 out of 10, Excellent, (1004)
"Beautiful property, great amenities, very clean."
The price is AU$421
includes taxes & fees
26 Jan - 27 Jan
Silverado Resort

Napa Valley Marriott Hotel & Spa

4.0 star property
8.2 out of 10, Very good, (1001)
"Thank you!"
The price is AU$403
includes taxes & fees
30 Jan - 31 Jan
Napa Valley Marriott Hotel & Spa
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Can I find holiday rentals in Kenwood?

Yes, there are holiday rentals in Kenwood close to Robert Ferguson Observatory, or you can select a more secluded option if you're looking for a relaxing stay. The spas and wineries are several reasons why visitors like Kenwood. Make sure you have time to check out the gardens while you're in the area.

What are some of the best holiday rentals that Kenwood has to offer?

New Modern House in Sonoma Valley's Best Area: This highly rated holiday home rental in Kenwood is located in a rural location, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Kenwood?

With 40 Expedia holiday rentals, you're guaranteed to find just the right place for your Kenwood stay.

What can I see and do in Kenwood?

Sugarloaf Ridge State Park and Trione-Annadel State Park are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Robert Ferguson Observatory. Other places in town to visit include Chateau St. Jean Winery and St. Anne's Crossing Winery.

What are holiday rentals like in Kenwood?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Kenwood. Holiday rentals feature amenities like kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a sanitised environment, a holiday rental can provide a sense of privacy away from public hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for family trips or small group gatherings.