Beginning of main content
Due to coronavirus (COVID-19) travel advisories, some destinations may be unavailable for certain dates. Find out more.

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

This weekend
Jul 10 - Jul 12
Next weekend
Jul 17 - Jul 19

Featured St. Augustine Winery Hotels

The Cozy Inn
The Cozy Inn
2.0 out of 5.0 202 San Marco Ave, St. Augustine, FL
Free Cancellation
4.9/5 (25 reviews)

We stayed in one of the townhouses. I loved that we could hang out downstairs and watch TV before heading upstairs to bed. The only drawback at all was the size of the shower. Overall an awesome room!

Reviewed on Dec 8, 2019
The Cozy Inn features free WiFi in public areas and a garden. You can put free parking to good use if you drive. Front-desk staff can help with tours or tickets, ...
WineryParkingFree Wifi
TRYP by Wyndham Sebastian Saint Augustine
TRYP by Wyndham Sebastian Saint Augustine
3.5 out of 5.0 333 S. Ponce De Leon Blvd, St. Augustine, FL
Free Cancellation
4.6/5 (43 reviews)

One of the pillow case has a blood stain and no breakfast. Other than that the hotel is nice.

Reviewed on Jun 25, 2020
Built in 2016, the brand new TRYP by Wyndham Sebastian Saint Augustine offers an outdoor pool, a 24-hour fitness center, and free WiFi in public areas. There's ...
WineryFamily FriendlyMicrowave
Casa Monica Resort & Spa, Autograph Collection
Casa Monica Resort & Spa, Autograph Collection
4.0 out of 5.0 95 Cordova St, St. Augustine, FL
Free Cancellation
4.5/5 (41 reviews)

We were only staying in St Augustine for one night so we decided to go all out and stay in the nicest hotel. The hotel has lots of old world charm and the staff was very accommodating. The room itself was run of the mill. Nothing special. Average. The bathroom was older and even had a chunk missing ...

Reviewed on Oct 13, 2019
At Casa Monica Resort & Spa, Autograph Collection, guests enjoy a full-service spa, an outdoor pool, and a children's pool. Valet parking is offered for USD ...

St. Augustine wineries with lodging

A good night’s sleep and a glass of wine is the perfect recipe for relaxation. If your idea of recharging involves the pop of a cork and the cool feel of fresh bedlinens, a winery hotel is the vacation you need. Luckily, many of the most beautiful wineries in St. Augustine double as hotels or inns. No designated driver required when you’re staying just steps away!

St. Augustine wineries make great getaways
St. Augustine winery hotels have clear benefits: You never have to worry about how you’ll get home, and the wine keeps coming. Plus, winery vacations are perfect for all types of trips.

• Family: Get together your adult siblings and parents to make new memories. The greatest family reunions are the ones that feature group activities and plenty of wine.
• Friends: Girls’ trip? College reunion? Whatever the occasion, grab a few friends and get sipping. It’s sure to be a party to remember.
• Romance: Nothing is more romantic than sharing a bottle of bubbly with your sweetheart on a trip out of town.

You know you need to spend more than a day in St. Augustine to really see it all—and to drink all the wine. Some of the best wineries to visit in St. Augustine rent rooms to guests, who are happy for an excuse to stay longer. Take in the scenery along with that crisp local vintage: Picturesque rows of grapevines invite you to stop, unwind, and enjoy life.

Reward yourself with Orbitz
What could be better than a weekend winery getaway? How about earning points for it? Orbitz Rewards gives you an Orbuck for every dollar spent, and points are redeemable at over 350,000 hotels worldwide, with no blackout dates. We’ll drink to that.

Recent Winery Hotels Reviews

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.