Thessaly Vacations & Trips 2026 from CA $2,125

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Your Thessaly Vacation

With a Thessaly vacation package, you can forget about the hassle of planning and instead focus on experiencing all this interesting destination has on offer. Your trip to Thessaly wouldn't be complete without getting to some of its most renowned cities, starting with Kastraki. Some of the most popular attractions here include Meteora and Theopetra Cave. Volos should also be on the itineraries of all Thessaly travellers. Visitors to this destination enjoy Pelion Ski Centre and Path of the Centaurs. Expedia has everything you need when it comes to organizing your Thessaly vacation. From hotels and flights, to activities and more, we're here to help you create a travel experience like no other.

Top vacation destinations in Thessaly

A coastal town with a turquoise bay, surrounded by lush green hills and a clear blue sky.

A coastal cliff with ruins and a metal staircase.

A coastal landscape with a clear blue sea, a sandy beach, and rocky cliffs.

Top Thessaly Vacation Deals

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

4 Epoches hotel

CA $2,125

per person

Sep 30 - Oct 8

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Skiathos (JSI)

9.8/10 Exceptional! (66 reviews)

A beautiful hotel, with attractive calming decor and fabulous facilities and a lovely cooling swimming pool although the beach is only a short walk The staff are all very friendly and helpful and the beds are the most comfortable I’ve ever slept on in Greece!! Breakfast was included and was great every morning with a huge choice of fresh tasty produce Definitely recommend

Reviewed on Jun 6, 2026

Mythos Luxury Villa-Skiathos

CA $3,810

per person

Sep 19 - Sep 29

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Skiathos (JSI)

9/10 Wonderful! (2 reviews)

Mandraki Village Boutique Hotel

CA $2,541

per person

Sep 30 - Oct 8

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Skiathos (JSI)

9.2/10 Wonderful! (58 reviews)

It was pricy, but ok. It was hard to find a trasfer to airport. Even if the lady at the reception called a taxi, the taxi was very late and we

Reviewed on Jul 23, 2026

Mato Hotel

CA $2,274

per person

Sep 30 - Oct 8

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Skiathos (JSI)

9/10 Wonderful! (66 reviews)

Perfect spot ... 300 yards from the old port .... if you dont like cats its not for you ... we had 11 days and loved it

Reviewed on Jul 20, 2026

Natura Luxury Boutique Hotel Skopelos

CA $2,605

per person

Sep 30 - Oct 8

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Skiathos (JSI)

9.8/10 Exceptional! (44 reviews)

Our stay was fabulous 5 Star. Amazing place to relax and unwind. Breakfast was full of delicious foods and desserts. Staff were very friendly and helpful making your stay very enjoyable. Place is very clean and the pool view is a spectacular. Definitely will be returning.

Reviewed on Jul 30, 2026

Where to stay in Thessaly

Find the best Thessaly areas and neighborhoods for the activities you enjoy most.Learn more about Thessaly

A yellow building with a green roof and palm trees in front.

A waterfront with a historic building featuring a tall tower, a paved walkway, and a calm sea.

A harbor with a sailboat, buildings, and a mountainous backdrop.

A marina with boats docked along a waterfront promenade.

A coastal cityscape with a marina, dense urban buildings, and mountains in the background.

Volos City Centre

Waterfront views, beaches, and bars are some highlights of Volos City Centre. Make a stop by Volos Port or Archaeological Museum of Volos while you're exploring.

Find hotel + flight trips in Volos City Centre

Aerial panoramic view over Chora the beautiful old Village of Alonnisos island, Sporades, Greece

Alonnisos Old Town

While there might not be top attractions in Alonnisos Old Town, you can explore the larger area and discover places like Patitiri Harbour and Port of Alonissos.

Find hotel + flight trips in Alonnisos Old Town

Varousi

You'll enjoy the mountain views and spas in Varousi. You might want to make time for a stop at Trikala Castle or Asclepieion of Triki Archaeological Site.

Find hotel + flight trips in Varousi

Xanemos

Though Xanemos might not have many top sights, you can venture to the surrounding area to see attractions like Xanemos Beach and Port of Skianthos.

Find hotel + flight trips in Xanemos

Thessaly Hotel Deals

Divani Meteora Hotel

National Rd, Trikala - Ioannina Kalabaka Thessalia

Fully refundable

CA $183

CA $224 total

Aug 28 - Aug 29

includes taxes & fees

Grecotel Larissa Imperial

182, Farsalon Str Larissa Thessalia

Fully refundableReserve now, pay when you stay

CA $134

CA $177 total

Aug 9 - Aug 10

includes taxes & fees

8.8/10 Excellent! (209 reviews)

"The Imperial was a great place to stay for our week long visit! From check in, to the morning breakfast staff and everyone else we encountered, they were all polite, helpful and very accommodating! The breakfast buffet was so nice every morning, a great way to start the day! I hope to return to the ..."

Reviewed on Aug 3, 2026

Nostalgia

Riga Fereou 5 kai Papadiamanti Skiathos thessalia

CA $77

CA $90 total

Sep 7 - Sep 8

includes taxes & fees

See all 2,477 properties in Thessaly

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.

Frequently asked questions

How much does a Thessaly vacation package cost?

Be ready to book, because a trip to Thessaly starts from an enticing CA $2,125. When you combine your flights, hotels and car rentals into a vacation package, you'll pick up the best deals.

How do I get a cheap travel package to Thessaly?

Just think of all the fun things you could do in Thessaly with a pile of extra cash in your wallet. Watch your savings stack up when you bundle your hotel and airfare bookings into a Thessaly vacation package. You have plenty of choice when you book your trip with Expedia too. In fact, you can pick from more than 550 airlines and 1,000,000 hotels around the globe. Whether you're heading away with the whole family or traveling on your own, exploring Thessaly is better with a package.

What are the top hotels in Thessaly?

Check out Divani Meteora Hotel and Theatro Hotel Odysseon. They're the first choice for many travelers headed to Pelion. If South Pelion features on your itinerary, Tsikeli Boutique Hotel Meteora - Adults Friendly and Hotel Aegli are a couple of top-notch options.

How far in advance should I book my Thessaly vacation?

It can be difficult to know when is the perfect time to book your trip to Thessaly. But generally the earlier you book, the more affordable the prices. In some cases, you can book your flights and hotels up to a year before departure. If you're hoping for a last-minute getaway, no need to worry! There are fabulous bargains announced on Expedia all the time.

What does an Expedia Thessaly travel package include?

From hotels and airfares to car rentals, Expedia can help you put together a Thessaly package that's ideal for you. Vacationing for a week or longer? Consider a rental car, flight and hotel bundle. If you're taking a short break, an airfare and hotel deal could be more your style. Experiences can also be added after you've booked. Our packages make it easy to plan and save.

What should I know before booking a Thessaly travel package?

Locking in all the parts of your trip together is a simple way to save. Combine car rentals, airfares and hotels into one package. But you're not restricted to hotels. Expedia offers all kinds of properties, including vacation rentals like beach villas and short-term homes. You've got choices galore!

Can I choose my airline with a Thessaly Expedia vacation package?

With a vacation package, you're the one in charge. Whether you're looking to fly to Thessaly in coach or business class, simply pick from the available airline options. Expedia has access to over 550 partner airlines all over the world.

If I'm not able to travel, can I cancel my Thessaly vacation package?

Whether it's your flight or hotel, you can cancel and rebook it. Booked your Thessaly vacation package in the last 24 hours? You may be able to make any changes for free. For older bookings, you may incur a charge from your airline, hotel or car rental company. For more details, check out our Customer Service Portal. We'll help you each step of the way.