Thessaly Vacations & Trips from $1,411
Book a Hotel + Flight or Car together to unlock savings
Top destinations in Thessaly
Skiathos
Skopelos
Skiathos Town
Kalabaka
Alonissos
Volos
South Pelion
Skopelos Town
Agia
The Latest Thessaly Vacation Packages
- Milia Bay Hotel Apartments
Aug 24 - Aug 30Milia Bay Hotel Apartments + Flight
Alonissos5 nights3.0 star property8.0/10 - Very Good (3 reviews)Roundtrip • Los Angeles (LAX) - Skiathos (JSI)LAX - ATH • 1 stop ATH - LAX • 1 stop$1,612$1,411found 10 hours agoper traveler - Natura Luxury Boutique Hotel Skopelos
Aug 24 - Aug 30Natura Luxury Boutique Hotel Skopelos + Flight
Skopelos5 nights5.0 star property9.8/10 - Exceptional (42 reviews)"Amazing staff made the time there special. Will definitely be back."Reviewed July 16, 2026Roundtrip • Los Angeles (LAX) - Skiathos (JSI)LAX - ATH • 1 stop ATH - LAX • 1 stop$2,060$1,735found 10 hours agoper traveler - Skiathos Princess Resort
Aug 24 - Aug 30Skiathos Princess Resort + Flight
Skiathos5 nights5.0 star property8.6/10 - Excellent (210 reviews)"Wardrobe had a light in which kept clicking all night keeping us awake. People outside the hotel used the pool and beach seats making it difficult to get a seat. We did not get to go around the pool. Food choice was very poor if you are a vegetarian. Had the poorest food ever in Skiathos around the pool bar - tasteless chicken and cod bites. When reported to the restaurant about the limited choice we were told that is all they’ve got - no attempt to address it or improve. In the end we ate..."Reviewed June 18, 2026Roundtrip • Los Angeles (LAX) - Skiathos (JSI)LAX - ATH • 1 stop ATH - LAX • 1 stop$2,785$2,434found 10 hours agoper traveler - Anamar Skiathos Hotel
Aug 24 - Aug 30Anamar Skiathos Hotel + Flight
Skiathos5 nights4.0 star property7.2/10 - Good (32 reviews)"The room was nice. Clean and comfortable. I don't understand some negative reviews. Yes, it's not the newest, but the property is really nice, the view is stunning and location is good, just 20 minutes walking to the promenade with restaurants and 3 minutes to the airport. Breakfast in the morning is really good, with some nice bakery and hot food like eggs and bacon. Plus you can sit outdoor on the terrace, facing the pool and the airport bay while having breakfast. Overall is a good hotel.. It..."Reviewed July 11, 2026Roundtrip • Los Angeles (LAX) - Skiathos (JSI)LAX - ATH • 1 stop ATH - LAX • 1 stop$1,620$1,424found 10 hours agoper traveler - Thea Home Hotel by Booking Kottas
Aug 24 - Aug 30Thea Home Hotel by Booking Kottas + Flight
Skopelos5 nights1.0 star property9.8/10 - Exceptional (16 reviews)"Great place. Great location. Loved having the pool. The view from our balcony was amazing."Reviewed June 16, 2026Roundtrip • Los Angeles (LAX) - Skiathos (JSI)LAX - ATH • 1 stop ATH - LAX • 1 stop$1,774$1,569found 10 hours agoper traveler
Discover the most popular places to visit in Thessaly
What to do in Thessaly
Meteora Monasteries & Caves DayTrip from Athens with Greek Lunch
Majestic Sunset Meteora Tour with Local Guide
Kalabaka: Meteora Small-Group Hiking Tour w/ Monastery Visit
Thessaly Hotel Deals
Guesthouse Monastiri
Guesthouse MonastiriFrequently Asked Questions
How much does a Thessaly vacation package cost?
We make it simple to travel the world, with Thessaly packages starting from as little as $1,411. You'll have the flexibility to combine your favorite hotels, airlines and car rental. For the ultimate getaway, why not add a couple of tours and activities to your travel itinerary?
How do I get a cheap travel package to Thessaly?
Bundle your flights and hotels, throw in extras such as activities or a rental car, and save with a Thessaly vacation package. You won't just pick up awesome discounts on your trip — you'll have lots of choice at your fingertips too. When you book with Expedia, you can choose from more than 550 air carriers and 1,000,000 hotels globally. Your dream vacation starts right here, right now!
What are the top hotels in Thessaly?
When it comes to hotels in Pelion, Divani Meteora Hotel and Theatro Hotel Odysseon are two great options. If you're visiting South Pelion, Alsos House and Tsikeli Boutique Hotel Meteora - Adults Friendly are waiting to welcome you.
How far in advance should I book my Thessaly vacation?
While not all air carriers advertise tickets early, customers are usually able to look up international flights on Expedia up to 12 months in advance. This is the time when you can score some fantastic bargains. If you're booking last minute, you might still be in luck. Low prices occasionally emerge only weeks prior to departure.
What does an Expedia Thessaly travel package include?
That depends on you. You can select from a range of Thessaly bundles, such as a hotel, rental car and flight. You can also book a flight and a hotel, or a rental car with a flight. Once you've made your booking, you can add the fun stuff like experiences and tours. Whatever your ideal Thessaly vacation looks like, get ready to save!
What should I know before booking a Thessaly travel package?
When you book your hotels, flights and car rentals together, you'll nab awesome discounts. Whether you're planning an outdoor getaway in a chalet or want to stay in a convenient hotel in the city, Expedia will help make it happen.
Can I choose my airline with a Thessaly Expedia vacation package?
With a vacation package, you're the boss. Whether you're eager to fly to Thessaly in coach or business class, simply pick from the available airline options. Expedia has access to more than 550 partner airlines around the world.
Does Expedia offer Book Now, Pay Later Thessaly vacation packages?
Pay the total cost of your package booking when you lock it in or split the cost over a number of installments — the choice is yours. Each wanderer has their own unique financial circumstances. It's for that reason Expedia has joined forces with online lender Affirm to offer a Book Now, Pay Later option for all package bookings.
If I'm not able to travel, can I cancel my Thessaly vacation package?
You can. We totally understand that life doesn't always go to plan, so we're here to help if you have to make changes to your Thessaly vacation package. You may be able to amend or cancel your itinerary for free if you've booked within 24 hours. Your airline, hotel or car rental company may charge you a fee if you booked more than 24 hours ago. Take a look at our Customer Service Portal for further information. Also, be sure to check your itinerary for the nitty-gritty on change fees.
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Things to do in Thessaly
Thessaly offers an exciting mix of outdoor and adventure activities perfect for your vacation. You can explore scenic spots, embark on sightseeing tours, and enjoy spa treatments. Don't miss the chance to visit the breathtaking Meteora and delve into archaeology tours. For skiing enthusiasts, the region also features ski options as well as the beautiful island of Skiathos to explore, ensuring a memorable getaway filled with diverse experiences.
Shopping
In Thessaly, discover the vibrant Market of Larissa, perfect for unique souvenirs. For a more modern experience, visit the Volos Mall, which offers a variety of shops featuring local crafts and fashion. These spots provide a delightful mix of local culture and shopping convenience.
Recreation
Experience the vibrant atmosphere at Alkazar Stadium, where you can soak in the sports energy and enjoy various athletic events. For a cultural escape, the Theatre of Larissa and Volos Municipal Theatre offer captivating performances, perfect for family outings or a romantic evening filled with entertainment.
Adventure
Experience thrilling skiing at Pelion Ski Centre, where the slopes invite you to carve your way through fresh powder. Hike the scenic Path of the Centaurs, immersing yourself in nature's beauty. At Pertouli Ski Center, enjoy a blend of sports and adventure amidst breathtaking mountain landscapes.
Nightlife
Thessaly's nightlife is vibrant and diverse. Visit the trendy La Bottega in Larissa for creative cocktails and a lively atmosphere. For a taste of local music, check out Café Bar Kentrikon, where you can enjoy live performances and socialize with friendly locals in a cozy setting.
Find the best attractions in Thessaly
Thessaly, Greece offers a perfect blend of outdoor adventures and stunning scenery, making it an ideal vacation spot for tourists. Visitors can explore beautiful beaches, breathtaking monasteries, and even nudist beaches. With a variety of attractions, including the famous Meteora, Thessaly caters to those seeking culture and outdoor experiences. Whether you're looking for top tourist destinations or unique local spots, Thessaly promises a memorable getaway filled with diverse activities and sights.
- Meteora: Experience the breathtaking beauty of Meteora, where towering rock formations host ancient monasteries perched high above the horizon. This UNESCO World Heritage site offers a serene atmosphere, rich history, and stunning views that blend spirituality and nature seamlessly.
- Koukounaries Beach: Relax on the golden sands of Koukounaries Beach, known for its crystal-clear waters and lush pine surroundings. Ideal for sunbathing, swimming, and enjoying beachside cafes, this picturesque location is perfect for unwinding under the Greek sun.
- Theopetra Cave: Explore the fascinating Theopetra Cave, one of the oldest archaeological sites in the world. With its impressive stalactites and stalagmites, this cave promises an adventurous journey through ancient history and stunning natural formations.
Best time to go to Thessaly
The best time to visit Thessaly can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Thessaly falls in July, when visitor numbers are high and weather is sunny with no rain. The coolest average temperature in Thessaly falls in January, visitor numbers are low and weather is mostly sunny with light rain.
Tips to save on your trip to Thessaly
- Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
- Consider traveling to Thessaly during the low season (February and October to November) 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.