Exclusive Windward Vineyard Vacation Deals

Windward Vineyard vacation package deals

Price found within the past 48 hours. Click for updated prices.
Cavalier Oceanfront Resort

Cavalier Oceanfront Resort

3.5 out of 5
Price was $638, price is now $533 per person
$533
per person
Apr 30 - May 3
found 11 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to San Luis Obispo (SBP)
This smoke-free hotel features 2 outdoor pools, 2 hot tubs, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
Sea Otter Inn

Sea Otter Inn

3 out of 5
Price was $681, price is now $563 per person
$563
per person
Apr 30 - May 3
found 11 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to San Luis Obispo (SBP)
This hotel features an outdoor pool and a hot tub. Guests will appreciate free perks like free self parking and WiFi in public areas. A garden, concierge services, and free newspapers are also on offer.
CaliPaso Winery

CaliPaso Winery

4.5 out of 5
Price was $1,034, price is now $872 per person
$872
per person
May 11 - May 14
found 18 hours ago
Roundtrip flight included
Dallas (DFW) to San Luis Obispo (SBP)
An attached winery and a restaurant are featured at this smoke-free bed & breakfast. Guests will appreciate freebies like continental breakfast and free self parking. A business center, a terrace, and a garden are also on offer.
Garden Street Inn, A Kirkwood Collection Hotel

Garden Street Inn, A Kirkwood Collection Hotel

4 out of 5
Downtown San Luis Obispo
Price was $832, price is now $707 per person
$707
per person
May 11 - May 14
found 18 hours ago
Roundtrip flight included
Dallas (DFW) to San Luis Obispo (SBP)
Free WiFi in public areas, a terrace, and a garden are available at this bed & breakfast. Enjoy the free cooked-to-order breakfast each morning. A lobby fireplace, a library, and luggage storage are also on offer.
Cambria Landing Inn & Suites

Cambria Landing Inn & Suites

3 out of 5
Price was $737, price is now $628 per person
$628
per person
Apr 30 - May 3
found 11 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to San Luis Obispo (SBP)
This hotel features free self parking and free WiFi in public areas. Enjoy the 2 hot tubs and free continental breakfast each morning. A fireplace in the lobby and luggage storage are also provided.
White Water

White Water

3 out of 5
Price was $1,048, price is now $897 per person
$897
per person
Apr 30 - May 3
found 11 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to San Luis Obispo (SBP)
This guesthouse doesn't skimp on freebies - guests receive free continental breakfast and free WiFi. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. There's a bar/lounge on site, and a 24-hour front desk and concierge services are also provided.

Frequently asked questions

How much are vacation packages to Windward Vineyard?
Save on your Windward Vineyard adventure by combining your hotel and return flights into a $533 package deal. With all that extra money in your pocket, why not stay for a couple more nights and discover even more?
Where can I get the best vacation package deals for Windward Vineyard?
Travelocity has countless ways to score a great Windward Vineyard package deal. Take your pick of 400 air carriers and 1,000,000 properties all over the world and craft a travel itinerary that's suited to you. With so many options at hand, you'll have plenty of inspiration for your next great adventure.
Why should I purchase my Windward Vineyard vacation bundle via Travelocity?
Because life is one amazing journey, and we offer everything you need to get you on your way. With our superb service and Price Match Guarantee, you can organize your trip with confidence. What's more, you can rest easy while you're away knowing we're always available to chat via our round-the-clock support.

Top Windward Vineyard hotel deals

Hampton Inn & Suites Paso Robles

Hampton Inn & Suites Paso Robles

3 out of 5
212 Alexa Ct Paso Robles CA
Free Cancellation
Reserve now, pay when you stay
$102 nightly
The price is $117 total per night
$117 total
Feb 23 - Feb 24
Total with taxes and fees
This hotel features an outdoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free buffet breakfast each morning.
Pool
Hot Tub
Bellasera Hotel & Suites Paso Robles, Tapestry by Hilton

Bellasera Hotel & Suites Paso Robles, Tapestry by Hilton

4 out of 5
206 Alexa Ct Paso Robles CA
Free Cancellation
Reserve now, pay when you stay
$127 nightly
The price is $145 total per night
$145 total
Mar 1 - Mar 2
Total with taxes and fees
This resort features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the seasonal outdoor pool and conveniences like a terrace and laundry facilities.
Pool
Pet friendly
SummerWood Winery & Inn

SummerWood Winery & Inn

3 out of 5
2130 Arbor Road Paso Robles CA
Free Cancellation
Reserve now, pay when you stay
$279 nightly
The price is $308 total per night
$308 total
Feb 22 - Feb 23
Total with taxes and fees
This guesthouse features free WiFi in public areas, concierge services, and free self parking. Enjoy the free cooked-to-order breakfast each morning. A garden, luggage storage, and free newspapers are also on offer.
Breakfast included
Parking included
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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.