Windward Vineyard Vacation Deals: Windward Vineyard, Paso Robles Vacations

Windward Vineyard vacation package deals

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

Cavalier Oceanfront Resort

Save 100% on your flight

per person

Aug 29 - Sep 1

found 11 hours ago

Roundtrip flight included

Denver (DEN) 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.

The Cayucan Bungalows by AvantStay Pet-Friendly Getaway Steps from Cayucos State Beach

Save 100% on your flight

per person

Aug 29 - Sep 1

found 10 hours ago

Roundtrip flight included

Denver (DEN) to San Luis Obispo (SBP)

Oceanpoint Ranch

per person

Sep 4 - Sep 7

found 1 day ago

Roundtrip non-stop flight included

Nashville (BNA) to San Luis Obispo (SBP)

A restaurant and an outdoor pool are featured at this hotel. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the picnic area. Guests will appreciate free perks like free self parking and WiFi in public areas.

Cambria Landing Inn & Suites

per person

Sep 4 - Sep 7

found 1 day ago

Roundtrip non-stop flight included

Nashville (BNA) to San Luis Obispo (SBP)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A fireplace in the lobby and luggage storage are also provided.

Fireside Inn on Moonstone Beach

per person

Sep 4 - Sep 7

found 1 day ago

Roundtrip non-stop flight included

Nashville (BNA) to San Luis Obispo (SBP)

An outdoor pool is featured at this hotel, along with free WiFi in public areas and concierge services.

FogCatcher Inn

per person

Sep 4 - Sep 7

found 1 day ago

Roundtrip non-stop flight included

Nashville (BNA) 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 lobby fireplace, luggage storage, and concierge services are also on offer.

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 $530 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

206 Alexa Ct, Paso Robles, CA

Free Cancellation

Reserve now, pay when you stay

$127 nightly

$145 total

Aug 10 - Aug 11

Total includes 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

2130 Arbor Road, Paso Robles, CA

Free Cancellation

Reserve now, pay when you stay

$299 nightly

$330 total

Jul 14 - Jul 15

Total includes 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

Hampton Inn & Suites Paso Robles

212 Alexa Ct, Paso Robles, CA

Free Cancellation

Reserve now, pay when you stay

$131 nightly

$150 total

Jul 15 - Jul 16

Total includes 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

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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.