We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Kenwood Holiday Rentals

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Price
    per night
    £423 Average
    |||
    |||
    £0£1,000+
    Suitability
    More filters
    Travellers to Kenwood are booking March dates now. Secure your holiday rental today, and have the perfect trip.
    All 24 Rentals in Kenwood
    Sort by:
    Default
    Relaxing, Private Poolside Cottage for 2 in Sonoma Valley Wine Country1 / 18
    (18)Excellent
    Kenwood
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other travellers have booked this property
    Certificate of Excellence
    Check in Check out
    Show Prices
    Payment Protection
    Heiter House - the perfect getaway in Wine Country1 / 25
    (6)Excellent
    Kenwood
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Kenwood
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Modern 3br Home W/Pool & Seasonal Creek in Sonoma.1 / 31
    (9)Excellent
    Kenwood
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Patio
    • Grill
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Washer
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 July 2015
    I live locally and wanted to find a rental that my family could gather at and decided on this Kenwood property mainly as the pool looked like the perfect place to relax and...
    Reviewed 27 March 2015
    Wow this place was so tranquil and beautiful. It was exactly what I needed to recharge my batteries. The drive up there was so relaxing and beautiful. It's in the perfect area...
    See all reviews
    About this property
    Escape to this 2 acre, 3-bedroom retreat in the heart of Sonoma Wine Country, nestled among Oak and Fir trees along a calming seasonal creek. Located in Adobe Canyon, off the Valley of the Moon Highway, the quintessential Wine Country Hamlet of Kenwood is just a short 5-minute drive as is the...
    View all property information
    Location Information
    Kenwood, Sonoma County 95452
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    WALK to Wineries from this Gorgeous Designer Home!1 / 23
    (4)Excellent
    Kenwood
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • DVD Player
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 May 2017
    The house is perfectly located in the middle of wine country - between Sonoma Valley & Napa Valley and just down the road from Anderson Valley - three amazing areas for...
    Reviewed 6 August 2015
    This home was truly amazing!! Our friends and I truly enjoyed its beauty, both inside and out. We laughed, ate, reminisced and drank wine with such joy here. The kitchen was...
    See all reviews
    About this property
    Sonoma Valley is the epicenter of food and wine culture, but sometimes no one wants to have to be the 'D.D.' on vacation. With our perfect location in the heart of Sonoma Valley, you can walk to 9 wineries within 5 blocks, and still feel like you're 'getting away from it all' in our quiet...
    View all property information
    Location Information
    Kenwood, Sonoma County 95452
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    Spa, Bocce, Bbq Kitchen, Walk or Bike to Wineries1 / 24
    (1)Excellent
    Kenwood
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Wi-Fi
    • Hot Tub
    • Central Heating
    • Cable/satellite TV
    • Grill
    • Patio
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 September 2016
    I booked this property for 4 adults. We ended up with a Newborn as our 5th!!! This house has been transformed by the Owner Peter into a great oasis in the middle of an old...
    See all reviews
    About this property
    Hello and welcome to Casa Orinda, our newly renovated wine country home in Kenwood, in the heart of the Valley of the Moon. Our 2 bedroom, 2 bathroom home features an open kitchen-living floor plan perfect for enjoying a good time with family and friends. The kitchen is fully equipped and...
    View all property information
    Location Information
    Kenwood, Sonoma County 95452
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    Kenwood
    4 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Amenities & Details
    • Wi-Fi
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Panoramic vineyard views anchor this expansive 4-bed, 3.5-bath rental with a main house and separate guest house. This place has it all: an ideal location in the center of wine country, a gorgeous outdoor space with pool and patio, and a light-washed, modern interior. Ready for relaxation? Drive...
    View all property information
    Location Information
    Kenwood, Sonoma County 95452
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 6
    Make Enquiry
    Kenwood Cottage - Canyon Setting on Sonoma Creek1 / 17
    (3)Excellent
    Kenwood
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Waterfront
    • Washer
    • Hot Tub
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 September 2012
    Stayed here with 2 friends....all middle-aged ladies enjoying Northern California. The Cottage was spotlessly clean, well maintained, restfull, and centrally located. From...
    See all reviews
    About this property
    Kenwood Cottage is located in the heart of Sonoma's wine country and the charming town of Kenwood. This two bedroom home (over 1300 square feet of living space) is walking or biking distance to Sugarloaf Ridge State Park and major wineries. This idyllic cottage rests on a year round creek in the...
    View all property information
    Location Information
    Kenwood, Sonoma County 95452
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Kenwood
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • Patio
    • Central Heating
    • DVD Player
    • Grill
    • Balcony
    • Hot Tub
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This one of a kind stone lodge is located in a secluded location at the very heart of the Sonoma Valley, all 5 bedrooms are large and have a private, ensuite bath. We have a caretaker who lives just down the lane, so you can be assured of superior oversight and assistance. We now have access to a...
    View all property information
    Location Information
    Kenwood, Sonoma County 95452
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    Make Enquiry
    Kenwood
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    » Ideal location in Kenwood, close to many of the top wineries » 2 acres of meticulously maintained grounds, including a tennis court and pool » Separate carriage house sleeps 4-6, perfect for larger families » Stunning views of Sugarloaf Ridge and Hood Mountain » Ample outdoor entertaining space...
    View all property information
    Location Information
    Kenwood, Sonoma County 95409
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
    Make Enquiry
    Save time - get the best Kenwood rentals sent straight to your email!
    Get the List
    Kenwood
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Hot Tub
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Balcony
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This secluded home is nestled on the hillside on over 7 acres of century old oak trees in Sonoma wine country. The sweeping driveway takes you up the property to the house and 2 car garage. Along the way, you may be greeted by a family of deer resting under the large fig tree in the field. Before...
    View all property information
    Location Information
    Kenwood, Sonoma County 95452
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Kenwood
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Pinot Blanc Cottage is cute little home located in the heart of Sonoma Valley on a quiet, tree lined street with easy walking access to the local market and numerous wineries and tasting rooms. There are two full bedrooms - one with a queen bed and one with a king bed. The sofa in the living room...
    View all property information
    Location Information
    Kenwood, Sonoma County 95452
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Poolside 3BR in Wine Country w/ Cabana, Hot Tub, Bocce Court & Fruit Trees1 / 24
    (1)Excellent
    Kenwood
    3 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Hot Tub
    • Washer
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 October 2017
    Been traveling to wine country for over 25 years. Of course when we are accompanied by friends, they always want to visit Napa. Who doesn't like Disneyland? On this most recent...
    See all reviews
    About this property
    Surrounded by wineries in the darling area of Kenwood, this elegant 3BR/4.5BA home offers an upscale stay central to Napa and Sonoma. Enjoy the sweeping backyard, where a pool, spa, bocce court, dining patio and fire pit offer an extraordinary outdoor experience. Modern décor intermingles with...
    View all property information
    Location Information
    Kenwood, Sonoma County 95452
    Holiday Rental House - 3 Bedrooms, 5 Bathrooms, Sleeps 8
    Make Enquiry
    The following rentals are within 10 kilometres of Kenwood.
    Charming Wine Country Cottage in Serene Setting1 / 17
    (7)Excellent
    Glen Ellen
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
    Certificate of Excellence
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Cable/satellite TV
    • Patio
    • Washer
    • Central Heating
    • Internet Access
    • Balcony
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 July 2017
    The place has everything we were looking to have a relaxed and peaceful short vacation. The house is very clean and I like that it is surrounded by tall trees. The seating area...
    Reviewed 29 October 2016
    Better than we could have thought. Wonderful home base for exploring Sonoma. High end kitchen made meals easy and fun. Napa is a bit of a drive either over a winding road or...
    See all reviews
    About this property
    This wine country cottage sits in a sunny spot on a private lane just off Warm Springs Road. Your experience here will be peaceful and private, with only a few deer crossing the property occasionally. The two bedroom home provides you with a cozy atmosphere, closeness to Glen Ellen with a large,...
    View all property information
    Location Information
    Glen Ellen, Sonoma County 95442
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Glen Ellen
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Air Conditioning
    • Wi-Fi
    • Balcony
    • Grill
    • Washer
    • Mountain Views
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to The Valley Of The Moon! Nestled among giant Oaks, hugging a sprawling forest and across from Morton's Warm Springs, our lovely sanctuary offers the blissful relaxation of a welcome retreat. Come and see the deer, turkey, fox and other wildlife that wander among the native trees and...
    View all property information
    Location Information
    Glen Ellen, Sonoma County 95442
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Glen Ellen
    2 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The charming house has two bedrooms: a very generous master bedroom suite with a private deck and a second bedroom with two beds that can be coverted into one queen size bed. Additionally, the living room has a comfortable pull-out couch suitable for sleeping two. The gourmet kitchen is fully...
    View all property information
    Location Information
    Glen Ellen, Sonoma County 95442
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 7
    Make Enquiry
    Glen Ellen
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Hot Tub
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A View from the Top is a luxury villa situated in the lush Glen Ellen area of California. Enter a magical landscape where pastoral life, fine dining and magnificent spa treatments seamlessly coexist, where natural fragrances permeate the air and where rest and rejuvenation never felt so good....
    View all property information
    Location Information
    Glen Ellen, Sonoma County 95442
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    Glen Ellen
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Outdoor Dining Area
    • Internet Access
    • Washer
    • Parking
    • Mountain Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Studio cottage, attached to main house. Located in beautiful wine country, close to downtown Glen Ellen. Furnished, very clean. Across the street from Jack London Village, wine, port & chocolate tasting, and fine dining. Full bath, fridge, cable, and wi-fi available. Country setting with views....
    View all property information
    Location Information
    Glen Ellen, Sonoma County 95442
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Glen Ellen
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • Hot Tub
    • Grill
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Breathtaking views of the Sonoma Valley steal the show at this magnificent California ranch-style home, nestled in the heart of Glen Ellen’s wine country. Featured on ABC's 'The Bachelor', this 6BR/4BA private estate overlooks its own vineyard and features both a main house and guest house with...
    View all property information
    Location Information
    Glen Ellen, Sonoma County 95442
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
    Make Enquiry
    Glen Ellen
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Grill
    • Terrace
    • Central Heating
    • Balcony
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spectacular 4500 sq. ft. wine country estate on a 10 acres has expansive views of Sonoma Valley and colorful vineyards. On a private gated road, this 3-story sunny Chateau-style home has an open floor plan with 5 bedrooms, 4 full baths and 2 half bathrooms. Hardwood, granite, marble and stone...
    View all property information
    Location Information
    Glen Ellen, Sonoma County 95442
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    Glen Ellen
    2 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The charming house has two bedrooms: a very generous master bedroom suite with a private deck and a second bedroom with two beds that can be coverted into one queen size bed. Additionally, the living room has a comfortable pull-out couch suitable for sleeping two. The gourmet kitchen is fully...
    View all property information
    Location Information
    Glen Ellen, Sonoma County 95442
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 7
    Make Enquiry
    Glen Ellen
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Grill
    • Balcony
    • Mountain Views
    • Patio
    • DVD Player
    • Housekeeping Included
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Olive Glen is a vacation rental in beautiful Glen Ellen, California, minutes from the world-famous wineries of Sonoma Valley and Napa. This beautiful, private home was recently completed by a premium local builder. It is sited on nearly an acre of land with views of treetops, Sonoma Mountain, and...
    View all property information
    Location Information
    Glen Ellen, Sonoma County 95442
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Glen Ellen
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Amenities & Details
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Terrace
    • Balcony
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Get swept away in the romance of this 3BR, 3BA modern mountain home between Napa and Sonoma valleys Resplendent, spacious rooms with contemporary touches. Expansive deck overlooking 4 picturesque acres, nestled in the Mayacamas Mountains. Sleeps 8. ABOUT THE HOUSE Surrounded by mountains and...
    View all property information
    Location Information
    Glen Ellen, Sonoma County 95442
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    Glen Ellen
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    • Hot Tub
    • Patio
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Vista is a one-of-kind, completely private estate in the heart of Sonoma wine country. Beautifully furnished, this 2BR/2BA compound sits behind a gated entry on a verdant hillside. The home’s abundant windows showcase the stunning views. Swim in the solar-heated pool and enjoy relaxing soaks...
    View all property information
    Location Information
    Glen Ellen, Sonoma County 95442
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    List your property
    Owner log in