Why should I book my Astypalaia holiday with Expedia?

Expedia has your back for all aspects of your next Astypalaia getaway. You'll always get the best deals around, but when you bundle your airfares, accommodation and/or car hire into a holiday package, you'll get even bigger savings. Looking to truly make the most of your adventure? Add some exciting tours and activities to your customised package. We offer flexible cancellation policies on almost all bookings, so you won't need to stress if your travel plans change. Head over to our Customer Service Portal link to discover more.

When is the best time of year to holiday in Astypalaia?

If you want to experience the excitement of Astypalaia in the high season, organise your escape for January, February and April. June, October and November are usually the quietest months of the year. Arrange your trip to Astypalaia based on what kind of holiday you're looking for. January is the coolest month, when average daytime temperatures are 13ºC. In August, the warmest month, you will experience temperatures of around 26ºC during the day.

What are the top hotels for my holiday in Astypalaia?

One of the most popular places to stay in Astypalaia is Pylaia Boutique Hotel & Spa , in the neighbourhood of Analipsi. Wander around the city by day and then rest up in this home away from home at night.

How do I get a cheap holiday to Astypalaia?

Booking an Astypalaia holiday with Expedia is a great way to save. We have access to more than 400 partner airlines and 321,000 hotel options around the world. With such an amazing range to choose from, you'll have no difficulty putting together your perfect adventure. Learn more about how you can save money on your next holiday when you combine your hotel and flight bookings with Expedia.

What should I do on my Astypalaia holiday?

There are lots of places to check out while enjoying your holiday in Astypalaia. Astypalaia Castle , Livadi Beach , Astipaleas Beach and Livadiou Reservoir are just a few of this city's most popular attractions.

Do I need a visa for my Astypalaia holiday?

Official government websites are the best source of information on visa requirements, application procedures and any necessary documentation. Your nationality and the purpose of your visit, whether it be for tourism or business, will determine if you need a visa for Astypalaia. Also check that your passport is up to date and has a minimum of six months validity remaining after your date of return. Finalise all your travel planning well ahead of time to avoid any last-minute surprises.

What should I wear on my Astypalaia holiday?

Do a little research into the types of things people in Astypalaia wear, and consider browsing style blogs for some fashion inspiration. You'll want to create a versatile travel wardrobe filled with pieces that suit your destination and showcase your personal style.

What does an Expedia Astypalaia holiday include?

It depends on what sort of trip you're thinking about. Astypalaia travel deals can include hotels, car hires and flights. You can mix and match to create the travel package that suits your style and budget. You can also add on experiences and activities after you've booked to score even bigger discounts. Discover a wide range of property types and select one that fits your group size and travel needs. The most in-demand rentals here are apartments and villas. With Expedia, you can easily tailor your Astypalaia retreat however you want.

Does Expedia offer Book Now, Pay Later Astypalaia holidays?

Expedia has joined forces with online lender Klarna to make booking your next trip easier on your budget. Paying by instalment means you can spread the costs of your next dream escape, leaving you with more cash to splash while you're away. Klarna has several payment plans to pick from, so you're sure to find one that falls within your budget. Browse these flexible payment options: Pay monthly holidays : Escape on that dream holiday sooner with Klarna's manageable instalment plans. If paying just a small amount each month sounds right for you, choose this option during the checkout process. No-deposit holidays : If not paying ahead of time for your getaway makes hitting that "book now" button easier, go for a no-deposit holiday plan with Klarna so you can Book Now, Pay Later!

Can I choose my airline with an Astypalaia Expedia holiday?

Yes — and it's simple too. Expedia has access to more than 400 partner airlines globally. Our packages give you the flexibility to take your pick of available flights, hotels and activities that fit your needs.

Astypalaia Holidays 2025

Top Astypalaia Flight + Hotel Deals

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

Tholaria Boutique Hotel

Save 100% on your flight

£286

per person

2 Oct - 9 Oct

found 6 hours ago

Return flight included

London (LON) to Astypalaia (JTY)

9.2/10 Wonderful! (9 reviews)

Good hotel and location.bed in a loft,local tradition but not great for older people,especially with no rail late in the night.

Reviewed on 17 Jun 2015

Pylaia Boutique Hotel & Spa

Save 100% on your flight

£301

per person

2 Oct - 9 Oct

found 2 hours ago

Return flight included

London (LGW) to Astypalaia (JTY)

8.8/10 Excellent! (23 reviews)

Amazing views and a beautiful room. We went on the boat cruise that belongs to the hotel and had a fabulous day of water activities, lunch and continuous drinks !!!

Reviewed on 12 Sep 2024

Things to do in Astypalaia

Astypalaia offers a delightful blend of beach relaxation and cultural exploration, making it an ideal destination for outdoor enthusiasts. Visitors can indulge in a variety of activities, including sailing and discovering the island's rich heritage. With its stunning landscapes and charming villages, Astypalaia promises an unforgettable holiday experience in the South Aegean.

Shopping

Astypalaia offers charming local shops and boutiques filled with handmade crafts, jewellery, and local delicacies. If you're up for a drive, consider visiting the larger Chania Shopping Centre, around 80.5km away, for a wider selection of international brands and unique gifts.

Recreation

Discover the tranquil Astypalaia Wellness Retreat, where you can indulge in rejuvenating spa treatments and yoga sessions overlooking the Aegean Sea. For outdoor activities, explore the island's picturesque hiking trails that lead to stunning vistas and secluded beaches, perfect for relaxation and reflection.

Adventure

Explore the stunning beaches of Agios Konstantinos for sunbathing and swimming in crystal-clear waters. Hike to the scenic Chora, where you can enjoy breathtaking views and traditional Greek architecture. For a unique experience, consider a boat trip to nearby secluded coves, perfect for snorkelling and relaxation.

Nightlife

Astypalaia offers a charming nightlife with vibrant bars and tavernas. Head to Chora, where you can find lively spots like the beach bars and local taverns, perfect for enjoying cocktails and traditional Greek music under the stars, creating a relaxed yet festive atmosphere.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in Astypalaia

Astypalaia offers a delightful mix of beachside relaxation and cultural exploration, making it ideal for outdoor vacations. Key attractions include the charming Astypalea windmills, the picturesque town, the historic Astypalaia Castle, and the stunning Astipaleas Beach. Whether you're seeking beautiful scenery or a taste of local heritage, this enchanting island has something for every traveller.

Astypalaia Castle: Perched atop a hill, Astypalaia Castle offers a romantic atmosphere steeped in history. Its ancient walls and stunning panoramic views of the Aegean Sea create a perfect backdrop for exploration and quiet reflection, allowing visitors to immerse themselves in the island's rich cultural heritage.
Astypalea Windmills: These iconic windmills, with their charming architecture, stand as a testament to the island’s agricultural past. Their picturesque setting enhances the cultural vibes, making it a delightful spot for photography and appreciating local craftsmanship.
Central Square: The heart of Astypalaia, Central Square is a serene gathering place ideal for leisurely strolls and enjoying local cafés. This vibrant area invites visitors to unwind and soak in the island's relaxed pace and friendly atmosphere, perfect for excursions.

Best time to go to Astypalaia

The best time to visit Astypalaia is dependant on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are moderately high and weather is sunny with no rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	56.1°F (13.4°C)	Light Rain	Mostly Sunny	Average
February	56.5°F (13.6°C)	Light Rain	Mostly Sunny	Average	Average
March	57.7°F (14.3°C)	Light Rain	Mostly Sunny	Average	Average
April	61.7°F (16.5°C)	No Rain	Sunny	Average	Average
May	67.5°F (19.7°C)	No Rain	Sunny	Average	Average
June	73.8°F (23.2°C)	No Rain	Sunny	Moderately High	Moderately High
July	78.1°F (25.6°C)	No Rain	Sunny	Moderately High	Moderately High
August	78.8°F (26.0°C)	No Rain	Sunny	Moderately High	Moderately High
September	75.4°F (24.1°C)	No Rain	Sunny	Average	Average
October	70.2°F (21.2°C)	No Rain	Sunny	Moderately Low	Average
November	65.1°F (18.4°C)	Light Rain	Mostly Sunny	Moderately Low
December	59.5°F (15.3°C)	Light Rain	Mostly Sunny	Moderately Low

Tips to save on your trip to Astypalaia

Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
Consider traveling during the off-peak season (typically ) for more affordable package holidays to Astypalaia.
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.

Language	Greek
Currency	Euros
Local Welcome	Ya su
Local Goodbye	Yiá sou
Closest Airport	Astypalaia Island National Airport (JTY)
Population	1,150
Max Temp Winter	16ºC
Max Temp Summer	27ºC
Top Sights	Livadi Beach, Astypalaia Castle and Panormos

Language

Greek

Currency

Euros

Local Welcome

Ya su

Local Goodbye

Yiá sou

Closest Airport

Astypalaia Island National Airport (JTY)

Population

1,150

Max Temp Winter

16ºC

Max Temp Summer

27ºC

Top Sights

Livadi Beach, Astypalaia Castle and Panormos

Top hotels in Astypalaia

Caldera Studios

Pera Yialos, Astypalaia

£49

20 Sept - 21 Sept

includes taxes & fees

9.4/10 Exceptional! (26 reviews)

"Unbelievable experience!"

Reviewed on 12 May 2025

Fildisi Boutique Hotel

Livadi, Astypalaia, Astypalaia Island

10/10 Exceptional! (7 reviews)

"From the moment we arrived at Fildisi Boutique Hotel, we were welcomed with warmth, elegance, and a breathtaking view of the Aegean that immediately set the tone for a perfect stay. Nestled on the hillside with panoramic views of Chora and the sea, the location alone is worth the visit, but what ..."

Reviewed on 8 Jul 2025

Get rates

Pylaia Boutique Hotel & Spa

Chora, Astypalaia, Astypalaia Island

£85

22 Sept - 23 Sept

includes taxes & fees

8.8/10 Excellent! (22 reviews)

Excellent boutique hotel

"Room are modern updated and chic Bed was fine Food was excellent. They make omelets on request and specialty coffees without charge Baked good are from a nearby bakery and were excellent. We even went to the bakery to buy items"

Reviewed on 1 Aug 2025

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.