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

Kenwood Vacation Rentals

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Our top choices for Kenwood vacation rentals

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

2. Base Camp

Base Camp
Kenwood
The price is CA $1,666
CA $5,271 total
includes taxes & fees
Nov 10 - Nov 11
Base Camp

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 CA $3,404
CA $5,781 total
includes taxes & fees
Nov 28 - Nov 29
Casa Bella Estate in Wine Country w/ New Pool!

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 CA $350
CA $741 total
includes taxes & fees
Nov 8 - Nov 9
The Oak Haven! Private, Nature Retreat w/ Hot Tub in Wine Country!

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 CA $446
CA $817 total
includes taxes & fees
Nov 24 - Nov 25
Fireside Sips & Oak Dreams in Sonoma Valley

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 CA $398
CA $782 total
includes taxes & fees
Nov 11 - Nov 12
Glen Ellen Retreats Coastal Cottage

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 CA $398
CA $782 total
includes taxes & fees
Nov 4 - Nov 5
Glen Ellen Retreats Sunset Cottage

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 CA $438
CA $832 total
includes taxes & fees
Nov 3 - Nov 4
Glen Ellen Retreats Hot Tub Cottage

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 CA $194
CA $401 total
includes taxes & fees
Nov 16 - Nov 17
2 Hidden Wine Country Gem Upstairs Unit

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 CA $548
CA $1,537 total
includes taxes & fees
Nov 3 - Nov 4
Cloud 9 - A Retreat for Bliss and Happiness

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

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 CA $319
CA $551 total
includes taxes & fees
Nov 3 - Nov 4
Modern Farmhouse on Vineyard w/ Deck, Bocce & Wine Country Views

13. RiverPointe Napa Valley Resort

RiverPointe Napa Valley Resort
3.0 star property
Stonehouse
8.8 out of 10, Excellent, (1,549 reviews)
"Great place to stay"
United States
Waldemar.
The price is CA $142
CA $211 total
includes taxes & fees
Nov 8 - Nov 9
RiverPointe Napa Valley Resort

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 CA $49
CA $664 total
includes taxes & fees
Nov 4 - Nov 5
The Napa Residences

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 CA $266
CA $543 total
includes taxes & fees
Nov 3 - Nov 4
Wine Country Cottage in downtown Santa Rosa, CA

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 CA $326
CA $641 total
includes taxes & fees
Nov 3 - Nov 4
Wine Country Farmhouse on a Horse Ranch w/ Hot Tub

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 CA $475
CA $1,258 total
includes taxes & fees
Nov 3 - Nov 4
Spacious 5BR/3BA Group Getaway, Pool & EV Charger

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 CA $440
CA $477 total
includes taxes & fees
Nov 3 - Nov 4
Cozy Wine Country Guesthouse with Private Pool & Yard

19. Hideaway Cottages

Hideaway Cottages
2.0 star property
Calistoga
The price is CA $307
CA $354 total
includes taxes & fees
Nov 10 - Nov 11
Hideaway Cottages

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 CA $488
CA $641 total
includes taxes & fees
Nov 4 - Nov 5
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.
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Top Kenwood Hotel Reviews

Find out more about Kenwood

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Kenwood. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Kenwood?

Yes, we offer vacation rentals in Kenwood close to Robert Ferguson Observatory, or you can go with a secluded option if you want 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 vacation rentals in Kenwood?

Casa Bella Estate in Wine Country w/ New Pool!: Visitors like this Kenwood vacation home rental. It offers a balcony, a garden, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub.

How many vacation rentals are there in Kenwood?

With 52 Expedia vacation rentals, you're sure 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 vacation rentals like in Kenwood?

Vacation rentals are private accommodations you can reserve for several days or longer in Kenwood. Vacation rentals offer extras such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of privacy away from public hotel elevators and lobbies packed with people while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great option for a family trip or a small group gathering.