A lake surrounded by hills with trees and yellow wildflowers.

Oak Shores Holiday Rentals

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Our top choices for Oak Shores holiday rentals

1. 'Moe's Cabin' in the heart of Adelaida wine country and epic star gazing

'Moe's Cabin' in the heart of Adelaida wine country and epic star gazing
Adelaida District
10.0 out of 10, Exceptional, (44 reviews)
"Great location"
United States
Jaswinder S.
The price is NZ$891
includes taxes & fees
4 Oct - 5 Oct
'Moe's Cabin' in the heart of Adelaida wine country and epic star gazing

2. The Lofts at The Market

The Lofts at The Market
4.0 star property
Downtown Paso Robles
9.6 out of 10, Exceptional, (80 reviews)
"Very cute,cozy loft! Walking distance to Downtown."
United States
Michelle Rocio
The price is NZ$478
includes taxes & fees
14 Oct - 15 Oct
The Lofts at The Market

3. Phoenix Rising Villa Sauret Ste

Phoenix Rising Villa Sauret Ste
San Miguel District
10.0 out of 10, Exceptional, (12 reviews)
"Amazing stay and beautiful view "
United States
Peter N.
The price is NZ$450
includes taxes & fees
4 Oct - 5 Oct
Phoenix Rising Villa Sauret Ste

4. Phoenix Rising Villa King Suite

Phoenix Rising Villa King Suite
San Miguel District
10.0 out of 10, Exceptional, (10 reviews)
"Super welcoming and friendly! Gorgeous views, such a lovely thing to wake up to. "
United States
Lane P.
The price is NZ$452
includes taxes & fees
4 Oct - 5 Oct
Phoenix Rising Villa King Suite

5. Paso Robles - Vineyard Getaway - Video Tour

Paso Robles - Vineyard Getaway - Video Tour
San Miguel District
10.0 out of 10, Exceptional, (126 reviews)
"Beautiful property with great views. Hosts were great and the communication was swift and in detail to help make a great stay."
United States
Martin L.
The price is NZ$546
includes taxes & fees
4 Oct - 5 Oct
Paso Robles - Vineyard Getaway - Video Tour

6. Ranch style living with incredible views!

Ranch style living with incredible views!
Cambria
10.0 out of 10, Exceptional, (30 reviews)
"Great stay! "
United States
ALEXIS
The price is NZ$412
includes taxes & fees
4 Oct - 5 Oct
Ranch style living with incredible views!

7. The Redwood Hearts Cottage in Cambria

The Redwood Hearts Cottage in Cambria
Cambria
9.8 out of 10, Exceptional, (36 reviews)
"Delightful home and host!"
United States
John S.
The price is NZ$1,006
includes taxes & fees
5 Oct - 6 Oct
The Redwood Hearts Cottage in Cambria

8. Coastal Retreat Big Sur Style • King Beds • EV+Pet

Coastal Retreat Big Sur Style • King Beds • EV+Pet
Cambria
10.0 out of 10, Exceptional, (71 reviews)
"We were delighted with the hospitality, cleanliness, and location."
United States
David H.
The price is NZ$1,479
includes taxes & fees
9 Oct - 10 Oct
Coastal Retreat Big Sur Style • King Beds • EV+Pet

9. Charming Remodeled Single Level. HotTub. Fenced backyard. Porch view!

Charming Remodeled Single Level. HotTub. Fenced backyard. Porch view!
Cambria
10.0 out of 10, Exceptional, (213 reviews)
"We keep returning to the Squirrel's Cottage because of how clean, comfortable and cheerful it is. We also love being just 2 short blocks to the Fiscalini Preserve."
United States
Beatrice D.
The price is NZ$895
includes taxes & fees
7 Oct - 8 Oct
Charming Remodeled Single Level. HotTub. Fenced backyard. Porch view!

10. The Vineyard House - Paso Robles

The Vineyard House - Paso Robles
San Miguel District
The price is NZ$2,358
includes taxes & fees
4 Oct - 5 Oct
The Vineyard House - Paso Robles

11. Traveler’s Dream! Lux Wine Country Escape

Traveler’s Dream! Lux Wine Country Escape
Adelaida District
10.0 out of 10, Exceptional, (11 reviews)
"Loved the house and awesome views. "
United States
Sue Ann R.
The price is NZ$1,353
includes taxes & fees
15 Oct - 16 Oct
Traveler’s Dream! Lux Wine Country Escape

12. Hilltop Vineyard Estate | Infinity Pool + Views

Hilltop Vineyard Estate | Infinity Pool + Views
Adelaida District
10.0 out of 10, Exceptional, (1 review)
"Great place"
United States
Arrow G.
The price is NZ$1,996
includes taxes & fees
6 Oct - 7 Oct
Hilltop Vineyard Estate | Infinity Pool + Views

13. Cabin in the Oaks, Paso Robles. Private hot tub! We sleep 4! AC Works!

Cabin in the Oaks, Paso Robles. Private hot tub! We sleep 4! AC Works!
Willow Creek District
9.4 out of 10, Exceptional, (23 reviews)
"Fantastic stay."
United States
Michael A.
The price is NZ$663
includes taxes & fees
13 Oct - 14 Oct
Cabin in the Oaks, Paso Robles. Private hot tub! We sleep 4! AC Works!

14. Casa Caballo: Vineyard views and close to downtown

Casa Caballo: Vineyard views and close to downtown
Adelaida District
10.0 out of 10, Exceptional, (16 reviews)
"Excellent place to stay... What a nice setting"
United States
Ariane T.
The price is NZ$1,211
includes taxes & fees
4 Oct - 5 Oct
Casa Caballo: Vineyard views and close to downtown

15. Views, King bed, EV charger, 5 min to Downtown

Views, King bed, EV charger, 5 min to Downtown
Adelaida District
10.0 out of 10, Exceptional, (8 reviews)
"Wonderful cozy room and location. Hosts go out of their way to make guests feel welcome and comfortable. We’ll be back!"
United States
Alina
The price is NZ$573
includes taxes & fees
5 Oct - 6 Oct
Views, King bed, EV charger, 5 min to Downtown

16. Paso Wine Country Farmhouse | Pool, Spa, Game Room

Paso Wine Country Farmhouse | Pool, Spa, Game Room
Adelaida District
10.0 out of 10, Exceptional, (29 reviews)
"We had the best stay! The house was amazing! Great location for wine tasting and Mitch was super responsive!! "
United States
Natalie J.
The price is NZ$2,055
includes taxes & fees
2 Nov - 3 Nov
Paso Wine Country Farmhouse | Pool, Spa, Game Room

17. Vino On Vineyard by LUX Retreats Paso

Vino On Vineyard by LUX Retreats Paso
Willow Creek District
10.0 out of 10, Exceptional, (31 reviews)
"Perfect location, accommodations and view!"
United States
Catherine O.
The price is NZ$1,626
includes taxes & fees
4 Oct - 5 Oct
Vino On Vineyard by LUX Retreats Paso

18. Paso Robles Wine Country Stay, Pool and Views

Paso Robles Wine Country Stay, Pool and Views
Adelaida District
8.0 out of 10, Very good, (1 review)
"The stay was nice. We would have appreciated a later check-out time especially because it was day light savings time and we lost an hour... We had to rush, rush, rush the morning to check out and that was a bummer... Otherwise, the property was nice, clean with great views from the front yard. "
United States
Pamela L.
The price is NZ$1,994
includes taxes & fees
4 Oct - 5 Oct
Paso Robles Wine Country Stay, Pool and Views

19. Bella Vista- Paso Wine Country with Vineyard Views

Bella Vista- Paso Wine Country with Vineyard Views
Adelaida District
10.0 out of 10, Exceptional, (29 reviews)
"Lovely with a beautiful view."
United States
Maureen C.
The price is NZ$1,195
includes taxes & fees
27 Oct - 28 Oct
Bella Vista- Paso Wine Country with Vineyard Views

20. FarmStay HillTop wine country views 4BR/4BA

FarmStay HillTop wine country views 4BR/4BA
Adelaida District
10.0 out of 10, Exceptional, (1 review)
"Wild Rose did not disappoint! Great location and property, just as advertised. We had a group of 12 adults and there was plenty of room for everyone. Courtney was extremely responsive and awesome to work with. We will be back. Highly recommend."
United States
Lance H.
The price is NZ$1,497
includes taxes & fees
6 Oct - 7 Oct
FarmStay HillTop wine country views 4BR/4BA
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 Oak Shores Hotel Reviews

Find out more about Oak Shores

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Oak Shores holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Oak Shores. 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 Oak Shores. Seeing all the best attractions is bound to make you fall in love with Oak Shores. Who knows, you may even be tempted to extend your 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 holiday 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 Oak Shores short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Oak Shores?

Yes, there are holiday rentals close to the most popular sights in Oak Shores, or you can select a more secluded option if you're looking for a relaxing stay. Oak Shores is known for its beaches and restaurants.

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

Cottage By The Sea And Trails. Blocks from the Fiscalini Preserve.: This holiday home rental outside of Oak Shores offers a balcony, a BBQ and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals are there in Oak Shores?

Choose from 12 Expedia holiday rentals in Oak Shores for a memorable holiday.

What’s there to see and do in Oak Shores?

While exploring the area, visit family-friendly sights like Coastal Discovery Center at San Simeon Bay, or get outside and enjoy nature at Lake Nacimiento. In the wider area, you’ll find Justin Vineyards and Winery and Hearst Castle.

What’s a holiday rental in Oak Shores like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Oak Shores. Holiday rentals provide amenities like kitchens and laundry facilities so you'll feel right at home. If you're concerned about cleanliness, holiday rentals can offer a sense of safety away from shared hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for a family trip.