Exclusive Windward Vineyard Vacation Deals

Windward Vineyard vacation package deals

Price found within the past 48 hours. Click for updated prices.
Avila Village Inn

Avila Village Inn

3.5 out of 5
Price was $919, price is now $707 per person
$707
per person
May 28 - May 31
found 23 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to San Luis Obispo (SBP)
This hotel features free WiFi in public areas, a fireplace in the lobby, and concierge services. Staff at the 24-hour front desk can provide around-the-clock assistance.
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 $2,525, price is now $1,879 per person
$1,879
per person
May 28 - May 31
found 23 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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.
Pismo Beach Club

Pismo Beach Club

3 out of 5
Downtown Pismo Beach
Price was $1,678, price is now $1,286 per person
$1,286
per person
May 28 - May 31
found 23 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to San Luis Obispo (SBP)
This hotel features free WiFi in public areas, laundry facilities, and self parking. Express check-out, concierge services, and a virtual front desk are also on offer.
Beach House Inn & Suites

Beach House Inn & Suites

3 out of 5
Downtown Pismo Beach
Price was $965, price is now $749 per person
$749
per person
May 15 - May 18
found 1 day ago
Roundtrip non-stop flight included
Tulsa (TUL) to San Luis Obispo (SBP)
Free WiFi in public areas is available at this hotel. Take advantage of the free self parking.
Spyglass Inn

Spyglass Inn

3 out of 5
Price was $938, price is now $740 per person
$740
per person
May 28 - May 31
found 23 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to San Luis Obispo (SBP)
This motel features an outdoor pool and a hot tub. WiFi in public areas is free. Self parking, a garden, and a lobby fireplace are also offered.
Blue Seal Inn

Blue Seal Inn

2 out of 5
Downtown Pismo Beach
Price was $1,073, price is now $867 per person
$867
per person
May 28 - May 31
found 23 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to San Luis Obispo (SBP)
Free self parking is available and the motel's front desk is staffed around-the-clock. WiFi in public areas is free. Limo/town car service is 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 $707 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

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
$140 nightly
The price is $161 total per night
$161 total
Apr 28 - Apr 29
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
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
$122 nightly
The price is $140 total per night
$140 total
Apr 13 - Apr 14
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
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
Apr 13 - Apr 14
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
Don't see what you're looking for?
See all available properties in Windward Vineyard
View all properties
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.