Oia Vacations from $2,170
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The Latest Oia Vacation Packages
- Art Maisons Aspaki Exclusive Suites
Oct 9 - Oct 14Art Maisons Aspaki Exclusive Suites + Flight
Santorini4 nights5.0 star property9.8/10 - Exceptional (141 reviews)Roundtrip • Boston (BOS) - Santorini (JTR)BOS - JTR • 1 stop JTR - BOS • 1 stop - Grand Ambassador Santorini Hotel
Sep 5 - Sep 11Grand Ambassador Santorini Hotel + Flight
Santorini5 nights5.0 star property9.4/10 - Exceptional (255 reviews)Roundtrip • Boston (BOS) - Santorini (JTR)BOS - JTR • 1 stop JTR - BOS • 1 stop - Aria Suites
Sep 24 - Sep 28Aria Suites + Flight
Santorini3 nights4.0 star property10/10 - Exceptional (313 reviews)Roundtrip • Boston (BOS) - Santorini (JTR)BOS - JTR • 1 stop JTR - BOS • 2 stops - West East Suites
Aug 26 - Sep 1West East Suites + Flight
Santorini5 nights5.0 star property9.8/10 - Exceptional (203 reviews)Roundtrip • New York (EWR) - Santorini (JTR)EWR - JTR • 1 stop JTR - EWR • 1 stop - Art Maisons Oia Castle
Oct 4 - Oct 9Art Maisons Oia Castle + Flight
Santorini4 nights5.0 star property9.6/10 - Exceptional (122 reviews)"This was a pinch-me, I must be dreaming hotel. We had the suite with little pool that overlooked the caldera which gave us the most beautiful experience with the Santorini sunset! The staff was extremely friendly and helpful when we requested extra towels, or ice when I sprained my ankle. This may have been one of the best and unique hotel experiences I have ever had. 10/10 would recommend!"Reviewed June 27, 2026Roundtrip • Philadelphia (PHL) - Santorini (JTR)PHL - JTR • 1 stop JTR - PHL • 2 stops
Discover the most popular places to visit in Oia
Castle of Oia
What to do in Oia
Santorini: Top Sights Day Trip, Wine Tasting, & Oia Sunset
Traditional Greek Night live Music & Dinner Show in Santorini
From Fira: Santorini Highlights Minibus Tour with Oia Sunset
Oia Hotel Deals
Vogue Suites
Vogue Suites
Caldera Premium Villas - Adults Only
Caldera Premium Villas - Adults Only
Just Blue
Just Blue
Diamond Luxury Suites Collection
Diamond Luxury Suites Collection
Filomare Suites
Filomare Suites
White Pearl Villas
White Pearl Villas
Terra Verde Oia by K&K
Terra Verde Oia by K&K
Elea Resort - Adults Only
Elea Resort - Adults OnlyFrequently Asked Questions
How much does an Oia vacation package cost?
Offering excellent value package deals from $2,170 on Expedia, you'll be surprised at how little a vacation to Oia costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Oia?
You're likely to find reduced prices and greater availability in October, November and December. Check out our cheap Oia vacation packages and you could land some great off-season deals.
How many days is enough for Oia?
The ideal duration of your Oia vacation depends on what you'd like to see and do. Typically, a few days to a week will give you time to hit all the major sights and explore some hidden gems along the way.
Is it worth booking a vacation package to Oia?
Whether you're looking to explore key attractions such as Oia Blue Dome Church Viewpoint and Oia Castle on your Oia vacation, or coming for its great culture, gift and craft shops and views, there's something for everyone here. With so much to do, you'll soon find out why so many families think Oia is a good vacation destination.
How to find the best Oia package deals?
Landing a cheap Oia package deal is a breeze with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget, apply some filters and browse what's available. You can tweak your search by "Amenities," "Property type," "Traveler experience" and more. Order the results by "Price: low to high" to view the most pocket-friendly Oia package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are often lower.
Is it cheaper to book an Oia vacation as a package?
You can enjoy significant savings on your Oia escape by booking a customized vacation package. Check the "Package" heading, then select your travel dates and destination to view some great flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Oia?
If you have your Oia travel dates confirmed, book as early as you can to snap up some awesome deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for jetting off on a whim.
How to plan a trip to Oia?
- Pick the perfect time to travel: Your schedule, favorite season and the type of weather you enjoy can all impact your decision on when to travel to Oia.
- Calculate your budget: Make sure you have enough money to cover everything from transportation and dining out to airfares and activities. Your hotel will probably be the biggest expense during your trip to Oia.
- Use Expedia's trip planning tool to explore Oia: Research every aspect of your trip to Oia with this handy planner. Invite your family and friends to collaborate on a group getaway, search for stays or things to do and make bookings.
- Decide how many days away: Start by making a list of all the sights and activities you'd like to experience in Oia. Then, estimate how long you'll need at each, along with any travel time.
- Bundle your bookings: With your travel dates in place, you can combine your car rental, hotels, flights and more into a customized Oia vacation package.
- Book any activities or excursions: Here's the fun part — locking in everything you want to see and do. Explore some of the best things to do in Oia and book your tickets early to save time (and maybe some dollars too!).
Does Expedia offer Book Now, Pay Later Oia vacation packages?
Secure your ideal getaway to Oia with our Book Now, Pay Later vacations. No need to save up or hold off until your next paycheck — we've joined forces with online lender Affirm to offer you flexibility and choice. Our vacation packages with payment plans mean you can spread the total cost across 3, 6 or 12 months. With no hidden charges or late payment fees, it's a breeze to stay on budget and snap up bargains while they last.
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Things to do near Oia
Oia, Santorini is perfect for a romantic and culturally rich vacation, offering stunning hiking trails and charming shopping areas. Popular activities include scenic sightseeing tours, roundtrip transport for the famous Oia sunset, relaxing visits to hot springs, and boat tours around the island. Discover the beauty and allure of this picturesque village while enjoying its outdoor adventures and vibrant atmosphere.
Shopping
In Oia, wander through charming shops that offer unique handmade jewelry, local art, and beautiful textiles. If you're up for a drive, visit Fira's Koutsoyannopoulos Wine Museum, 10 miles away, for local wines, or the nearby Santorini Caldera for stunning views and souvenirs.
Recreation
Catch a film under the stars at Open Air Cinema Kamari, just 8 miles from Oia, where family-friendly and romantic vibes meet. For a cultural experience, visit Odysseas Elytis Theatre, located 19 miles away, offering a blend of entertainment and romance in a stunning setting.
Adventure
The Fira to Oia Walk is a breathtaking hiking trail located 3 miles from Oia, offering stunning views of the caldera. This scenic route features rugged cliffs and vibrant landscapes, making it perfect for adventurers seeking outdoor thrills and picturesque moments along the way.
Nightlife
Oia's nightlife is enchanting, with stunning sunset views at the iconic Oia Castle. Enjoy a cocktail at the lively 1800-Floga or savor local wines at the tranquil Santorini Wine Bar. For a romantic evening, consider a seaside dinner at Amoudi Bay, where the atmosphere is magical under the stars.
Find the best attractions in Oia
Oia, located on the stunning island of Santorini, Greece, is an ideal destination for romantic and culture-themed vacations. Visitors can explore beautiful beaches, breathtaking crater views, and charming churches. Key attractions include the iconic Oia sunset, the historic Oia Castle, and the picturesque surroundings that enhance the scenic experience. This enchanting village offers a perfect blend of outdoor adventures and cultural richness for every traveler.
- Oia Castle: Perched high above the village, Oia Castle offers breathtaking sunset views and a romantic atmosphere steeped in history. This ancient fortress showcases the rich culture of the area, making it a perfect spot for couples and history enthusiasts alike.
- Oia Blue Dome Church Viewpoint: A quintessential symbol of Santorini, this viewpoint features iconic blue-domed churches against a backdrop of stunning sea views. It's a cultural landmark that captures the essence of Greek architecture, attracting photographers and visitors seeking to experience authentic beauty.
- Amoudi Bay: Nestled below Oia, Amoudi Bay is a picturesque spot known for its crystal-clear waters and charming waterfront tavernas. Ideal for swimming and enjoying fresh seafood, it offers a laid-back atmosphere surrounded by stunning coastal scenery.
Best time to go to Oia
The best time to visit Oia can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Oia falls in August, when visitor numbers are average and weather is sunny with no rain. The coolest average temperature in Oia falls in January, visitor numbers are average and weather is mostly sunny with light rain.
Tips to save on your trip to Oia
- Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Oia.
- Consider traveling to Oia during the low season (December to February) for more affordable options.
- Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
- Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.