Exclusive Windward Vineyard Vacation Deals

Windward Vineyard vacation package deals

Price found within the past 48 hours. Click for updated prices.
Beach House Inn & Suites

Beach House Inn & Suites

3 out of 5
Downtown Pismo Beach
Price was $892, price is now $705 per person
$705
per person
Oct 2 - Oct 4
found 1 day ago
Roundtrip flight included
San Diego (SAN) to San Luis Obispo (SBP)
Free WiFi in public areas is available at this hotel. Take advantage of the free self parking.
Sunset Serenity by Avantstay Rooftop w/ Hot Tub & Fire Pit, 3 Blocks to Beach!

Sunset Serenity by Avantstay Rooftop w/ Hot Tub & Fire Pit, 3 Blocks to Beach!

3 out of 5
Save 100% on your flight
Price was $2,401, price is now $1,909 per person
$1,909
per person
Oct 15 - Oct 18
found 12 hours ago
Roundtrip flight included
San Diego (SAN) to San Luis Obispo (SBP)
This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. A rooftop terrace and barbecue grills are also provided.
Casa do Sol by Avantstay Rooftop Deck w/ Ocean Views 2 Blocks to Beach!

Casa do Sol by Avantstay Rooftop Deck w/ Ocean Views 2 Blocks to Beach!

3 out of 5
Downtown Pismo Beach
Save 100% on your flight
Price was $2,080, price is now $1,675 per person
$1,675
per person
Oct 15 - Oct 18
found 12 hours ago
Roundtrip flight included
San Diego (SAN) to San Luis Obispo (SBP)
This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. A rooftop terrace and barbecue grills are also provided.
Pelican Inn & Suites

Pelican Inn & Suites

3 out of 5
Price was $1,356, price is now $1,103 per person
$1,103
per person
Oct 7 - Oct 12
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to San Luis Obispo (SBP)
This hotel features an outdoor pool and a hot tub. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A lobby fireplace, express check-out, and luggage storage are also on offer.
Blufftop Inn & Suites - Wharf/Restaurant District

Blufftop Inn & Suites - Wharf/Restaurant District

2 out of 5
Downtown Morro Bay
Price was $1,039, price is now $848 per person
$848
per person
Oct 2 - Oct 4
found 1 day ago
Roundtrip flight included
San Diego (SAN) to San Luis Obispo (SBP)
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the express check-out.
Bella Villa - Vine Cottages by Avantstay Hot Tub + Firepit + Bocce Downtown Paso Robles

Bella Villa - Vine Cottages by Avantstay Hot Tub + Firepit + Bocce Downtown Paso Robles

3 out of 5
Downtown Paso Robles
Price was $1,285, price is now $1,057 per person
$1,057
per person
Oct 15 - Oct 18
found 12 hours ago
Roundtrip flight included
San Diego (SAN) to San Luis Obispo (SBP)
This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. Barbecue grills are provided for your convenience.

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 $705 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

SummerWood Winery & Inn

SummerWood Winery & Inn

3 out of 5
2130 Arbor Road Paso Robles CA
$330 nightly
The price is $365 total per night
$365 total
Sep 1 - Sep 2
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
Oxford Suites Paso Robles

Oxford Suites Paso Robles

3.5 out of 5
800 4th Street Paso Robles CA
Free Cancellation
Reserve now, pay when you stay
$149 nightly
The price is $171 total per night
$171 total
Sep 8 - Sep 9
Total with taxes and fees
A full-service spa, a hot tub, and a restaurant are all featured at this smoke-free hotel. Business travelers can take advantage of the free WiFi in public areas. Enjoy the gym and free perks like on-the-go breakfast and free self parking.
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
$141 nightly
The price is $162 total per night
$162 total
Sep 8 - Sep 9
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
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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.