A large brick mansion with a central fountain surrounded by white and red flowers.

Kenwood Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Kenwood holiday rentals

A spacious living room with a large sectional sofa, a wooden coffee table, and a dining area with a round table and chairs.

1. Modern Organic 3BR Oasis w/ Creek&Near State Park

Modern Organic 3BR Oasis w/ Creek&Near State Park
Kenwood
9.6 out of 10, Exceptional, (8 reviews)
"Beautiful home and a great location!"
United States
Samantha S.
Modern Organic 3BR Oasis w/ Creek&Near State Park
Lounge poolside under umbrellas with wine, games, and playful floats for a sun soaked afternoon with friends.

2. Base Camp

Base Camp
Kenwood
The price is HK$9,353
HK$28,512 total
includes taxes & fees
10 Nov - 11 Nov
Base Camp
An outdoor patio area with stone flooring, wooden furniture, and string lights.

3. Casa Bella Estate in Wine Country w/ New Pool!

Casa Bella Estate in Wine Country w/ New Pool!
Kenwood
9.6 out of 10, Exceptional, (153 reviews)
"Our stay was fantastic! The room was incredibly clean, the host was welcoming and helpful. The kitchen was also well-equipped and convenient."
United States
Maitrayee s.
The price is HK$19,110
HK$32,926 total
includes taxes & fees
28 Nov - 29 Nov
Casa Bella Estate in Wine Country w/ New Pool!
A wooden deck with potted plants, a bench, and a building with large windows and a door.

4. The Oak Haven! Private, Nature Retreat w/ Hot Tub in Wine Country!

The Oak Haven! Private, Nature Retreat w/ Hot Tub in Wine Country!
Glen Ellen
9.8 out of 10, Exceptional, (139 reviews)
"Great home, hosts, and area. We loved everything about the trip and will be back in the fall. Thank you for the wonderful experience."
United States
Robert K.
The price is HK$2,079
HK$4,280 total
includes taxes & fees
19 Nov - 20 Nov
The Oak Haven! Private, Nature Retreat w/ Hot Tub in Wine Country!
A sliding glass door leading to an outdoor deck with a wooden bench, a table, and a chair.

5. Fireside Sips & Oak Dreams in Sonoma Valley

Fireside Sips & Oak Dreams in Sonoma Valley
Glen Ellen
10.0 out of 10, Exceptional, (11 reviews)
"We had a really pleasant stay here. Lots of personal touches and amenities provided which are very thoughtful. Nice location away from Sonoma and accessible to the more Northern areas of Sonoma County as well."
United States
Steve M.
The price is HK$2,393
HK$4,275 total
includes taxes & fees
24 Nov - 25 Nov
Fireside Sips & Oak Dreams in Sonoma Valley
A backyard with a barbecue grill, wooden deck, and a view of a tree-lined area.

6. Glen Ellen Retreats Coastal Cottage

Glen Ellen Retreats Coastal Cottage
Glen Ellen
10.0 out of 10, Exceptional, (180 reviews)
"Awesome place to stay! "
United States
Amanda D.
The price is HK$2,236
HK$4,381 total
includes taxes & fees
11 Nov - 12 Nov
Glen Ellen Retreats Coastal Cottage
A bedroom with a bed, nightstands, a ceiling fan, a window with curtains, and a wall painting.

7. Glen Ellen Retreats Sunset Cottage

Glen Ellen Retreats Sunset Cottage
Glen Ellen
10.0 out of 10, Exceptional, (89 reviews)
"Great house and location. Very clean and comfortable. Perfect location as a base for visiting wineries. Highly recommend"
United States
patrick s.
The price is HK$2,236
HK$4,412 total
includes taxes & fees
9 Nov - 10 Nov
Glen Ellen Retreats Sunset Cottage
A house with a hot tub in the backyard, a wooden deck, and a covered patio area.

8. Glen Ellen Retreats Hot Tub Cottage

Glen Ellen Retreats Hot Tub Cottage
Glen Ellen
10.0 out of 10, Exceptional, (101 reviews)
"Enjoyed our stay! Walkable to restaurants, groceries, hiking trails. Well stocked kitchen for cooking. Beds and pillows extremely comfortable. The place was spotless and well maintained. Would stay here again and highly recommend!"
United States
Amy
The price is HK$2,459
HK$4,694 total
includes taxes & fees
9 Nov - 10 Nov
Glen Ellen Retreats Hot Tub Cottage
A swimming pool with a slide, a barbecue area, and a wooden deck.

9. 2 Hidden Wine Country Gem Upstairs Unit

2 Hidden Wine Country Gem Upstairs Unit
Scenic Brush Creek
9.8 out of 10, Exceptional, (32 reviews)
"We enjoyed our stay and would certainly use this rental again if we're ever in the area. "
United States
Glen M.
The price is HK$981
HK$2,102 total
includes taxes & fees
16 Nov - 17 Nov
2 Hidden Wine Country Gem Upstairs Unit
A modern living room with a fireplace, comfortable seating, a glass coffee table, and large windows offering a view of a mountainous landscape.

10. Cloud 9 - A Retreat for Bliss and Happiness

Cloud 9 - A Retreat for Bliss and Happiness
Glen Ellen
10.0 out of 10, Exceptional, (23 reviews)
"We loved our stay here, the spacious living space, gorgeous decor and lovely pool were the highlights. Can't wait to be back!"
United States
Amy M.
The price is HK$6,613
HK$13,297 total
includes taxes & fees
29 Nov - 30 Nov
Cloud 9 - A Retreat for Bliss and Happiness
A wooden deck with two rocking chairs and a small table with a bottle and glasses.

11. Romantic Sonoma Creek Cottage With Pool & Spa

Romantic Sonoma Creek Cottage With Pool & Spa
Glen Ellen
10.0 out of 10, Exceptional, (54 reviews)
"Charming cottage. It really is a gem! It’s very private and the grounds are beautiful.We enjoyed the pool, hot tub and decks. The home was spotless and the kitchen well stocked. We appreciated the snacks and drinks that were provided. We had a very smooth check in and the hosts are very responsive. Highly recommend this rental. We’ll be back!"
United States
una m.
Romantic Sonoma Creek Cottage With Pool & Spa
A modern, open-plan living space with a large sliding door, a sofa set, and a dining area with a table and benches.

12. Modern Farmhouse on Vineyard w/ Deck, Bocce & Wine Country Views

Modern Farmhouse on Vineyard w/ Deck, Bocce & Wine Country Views
Sonoma
10.0 out of 10, Exceptional, (7 reviews)
"Had a wonderful stay, right next to a vinyard. Area was nice and quiet. Would definitely recommend. "
United States
David B.
The price is HK$1,789
HK$3,000 total
includes taxes & fees
30 Nov - 1 Dec
Modern Farmhouse on Vineyard w/ Deck, Bocce & Wine Country Views
A row of colorful, single-story houses with numbered windows, white picket fences, and well-maintained lawns.

13. RiverPointe Napa Valley Resort

RiverPointe Napa Valley Resort
3.0 star property
Stonehouse
8.8 out of 10, Excellent, (1,551 reviews)
"Great place to stay"
United States
Waldemar.
The price is HK$817
HK$1,210 total
includes taxes & fees
9 Nov - 10 Nov
RiverPointe Napa Valley Resort
An outdoor dining area with a central fountain, surrounded by trees and illuminated by chandeliers.

14. The Napa Residences

The Napa Residences
4.5 star property
Napa
8.8 out of 10, Excellent, (44 reviews)
"A very comfortable bed and beautiful pool setting in Napa Valley!"
United States
David
The price is HK$342
HK$3,866 total
includes taxes & fees
4 Nov - 5 Nov
The Napa Residences
A spacious living room with a fireplace, wooden flooring, and a cozy seating area.

15. Wine Country Cottage in downtown Santa Rosa, CA

Wine Country Cottage in downtown Santa Rosa, CA
Santa Rosa
9.8 out of 10, Exceptional, (82 reviews)
"Our stay was pleasant, the place was exceptionally clean and the owners were very helpful."
United States
joanne h.
The price is HK$1,647
HK$3,241 total
includes taxes & fees
27 Nov - 28 Nov
Wine Country Cottage in downtown Santa Rosa, CA
An outdoor patio with a wooden deck, a table with chairs, and a door with a hanging light fixture.

16. Wine Country Farmhouse on a Horse Ranch w/ Hot Tub

Wine Country Farmhouse on a Horse Ranch w/ Hot Tub
Santa Rosa
10.0 out of 10, Exceptional, (75 reviews)
"The property was beautiful and the beds were so comfy! The property manager was very friendly and responsive. "
United States
Abigail M.
The price is HK$1,828
HK$3,600 total
includes taxes & fees
4 Nov - 5 Nov
Wine Country Farmhouse on a Horse Ranch w/ Hot Tub
A modern kitchen with a central island, dining area with chairs, and a view of the outdoors.

17. Spacious 5BR/3BA Group Getaway, Pool & EV Charger

Spacious 5BR/3BA Group Getaway, Pool & EV Charger
Santa Rosa
10.0 out of 10, Exceptional, (13 reviews)
"This was a perfect place for our group. The home is beyond beautiful and felt very clean and homey. I would absolutely recommend this stay!"
United States
shea o.
The price is HK$2,666
HK$7,110 total
includes taxes & fees
9 Nov - 10 Nov
Spacious 5BR/3BA Group Getaway, Pool & EV Charger
A house with a swimming pool surrounded by lush greenery and a small waterfall feature.

18. Cozy Wine Country Guesthouse with Private Pool & Yard

Cozy Wine Country Guesthouse with Private Pool & Yard
Santa Rosa
10.0 out of 10, Exceptional, (39 reviews)
"Wonderful stay!"
United States
Adam C.
The price is HK$2,471
HK$2,667 total
includes taxes & fees
6 Nov - 7 Nov
Cozy Wine Country Guesthouse with Private Pool & Yard
A room with a brown sofa, two wicker chairs, a small table, and a lamp.

19. Hideaway Cottages

Hideaway Cottages
2.0 star property
Calistoga
The price is HK$1,961
HK$2,255 total
includes taxes & fees
4 Nov - 5 Nov
Hideaway Cottages
A small, single-story house with a front porch, a chimney, and a door with a window above it.

20. Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown

Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown
Calistoga
9.6 out of 10, Exceptional, (49 reviews)
"We stayed here 15 years ago , same bedspreads and no new updates . We love it for its cozy feeling , and love the peacefulness of staying in Calistoga. We walked across the street for an awesome dinner at Sam’s Social club , walked down the street to shop and cruise around this quaint town . It’s a high price point , but we always enjoy our time there . I worry that if they ever remodel this place , the price point will be more than what it’s worth a night , for which I don’t believe would be...
United States
William
The price is HK$2,738
HK$3,597 total
includes taxes & fees
9 Nov - 10 Nov
Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Kenwood Hotel Reviews

Archer Hotel Napa

Archer Hotel Napa

10/10 Excellent
"Nice hotel. Close to everything"
Sadie 3-night trip
Posted 4 hours ago
Archer Hotel Napa

Find out more about Kenwood

Search for holiday rentals in Kenwood on Expedia! You can easily find your home rentals, villas, holiday apartments in Kenwood using one of the methods below:

  • View our selection of featured holiday rentals in Kenwood
  • Use the map to find apartments and other holiday homes in the Kenwood neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Kenwood while they last

Look no further and take a look at our great range of rental properties in Kenwood!

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?

Casa Bella Estate in Wine Country w/ New Pool!: This highly rated holiday home rental in Kenwood offers a balcony, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 10 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

How many holiday rentals are there in Kenwood?

With 52 Expedia holiday rentals, you're guaranteed to find just the right place for your Kenwood stay.

What can I see and do in Kenwood?

While exploring the area, visit family-friendly sights like Robert Ferguson Observatory, or get outside and enjoy nature at Jack London State Historic Park. Other places in town to visit include VJB Vineyard & Cellars and Chateau St. Jean 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.