Astypalaia Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Your Astypalaia Vacation

The stress-free way to experience this interesting city is with a customized Astypalaia vacation package. Stay in the neighborhood of Analipsi, which is good for families, views and watersports or go someplace else — our package deals are all about you. You'll want to go sightseeing during your trip to Astypalaia. Don't miss major attractions such as Livadi Beach, Astypalaia Castle and Livadiou Reservoir. Browse Expedia's wide range of travel options and book your ideal vacation to Astypalaia now.

Stay near popular Astypalaia attractions

Astypalea Windmills

9.8/5 (8 reviews)
You can learn about the history of Astypalaia with a visit to Astypalea Windmills. Wander the marina and gardens while you're in the area.
See properties

Astypalaia Hotel Deals

Kallichoron Art Boutique Hotel

Kallichoron Art Boutique Hotel

Chora Astypalaia Astypalaia Island
$173 nightly
The price is $192 total per night from Jun 30 to Jul 1
$192 total
Jun 30 - Jul 1
Total with taxes and fees
9.8/10 Exceptional! (18 reviews)
"Centrally located"

Reviewed on Sep 12, 2025

Kallichoron Art Boutique Hotel
Pylaia Boutique Hotel & Spa

Pylaia Boutique Hotel & Spa

3 out of 5
Chora Astypalaia Astypalaia Island
$131 nightly
The price is $149 total per night from Jun 28 to Jun 29
$149 total
Jun 28 - Jun 29
Total with taxes and fees
8.8/10 Excellent! (24 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 Aug 1, 2025

Pylaia Boutique Hotel & Spa
Chrysalis Boutique Hotel

Chrysalis Boutique Hotel

3 out of 5
Eparchiaki Odos Livadia-Vathis Astypalaia
10/10 Exceptional! (20 reviews)
"I had a wonderful stay at Hotel Chrysalis in Astypalaia. The staff were absolutely amazing—warm, welcoming, and always ready to help. My room was beautiful, and the view from the balcony was nothing short of magical!! One thing to keep in mind: if you book extra services like car rental or a massage, ..."

Reviewed on Sep 28, 2025

Get rates
Chrysalis Boutique Hotel
See all 92 properties in Astypalaia
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.

Find the Best Astypalaia Vacation Packages

Astypalaia Beach Vacation

Get ready to live out those beachy daydreams on your upcoming Astypalaia vacation. Enjoy a relaxing stroll, savor the spectacular coastal views and collect unique seashells on your trip to Astypalaia. Located just 0.6 miles (1.0 km) from the town center, Livadi Beach is the place to be for many sun-seeking visitors. Have a look through our Astypalaia packages and watch your travel budget go further!

Things You Should Know About Astypalaia

  • If waking to the sounds of the ocean is your idea of getaway bliss, see what's available among our Astypalaia beach hotels. You're sure to find something that has everything you need for an ideal beachside stay.
  • A vacation in Astypalaia means staying in apartments for many visitors. Astypalea Villas and Viva Mare Studios are a few of the top options here.
  • The population of Astypalaia is roughly 1,150. If you'd like a few great travel tips, there are lots of locals who'll be happy to give you advice. Our Astypalaia things to do page is also a wealth of useful information.
  • One sight to put on your itinerary is Astypalaia Castle. But there are many other fantastic things to discover around this area. Tick off more of them with our bargain Astypalaia vacation deals.

Astypalaia Essential Information

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
60ºF
Max Temp Summer
80ºF
Top Sights
Livadi Beach, Astypalaia Castle and Panormos

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does an Astypalaia vacation package cost?
Offering great value package deals on Expedia, you'll be thrilled with how little a vacation to Astypalaia costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Astypalaia?
If you'd like to book a cheap Astypalaia vacation package, consider visiting in June, October and November. You'll generally find lower rates on hotels and airfares during these months — perfect for a budget-friendly getaway.
How many days is enough for Astypalaia?
For your Astypalaia vacation, a few days will be enough to explore the highlights. Make sure to check out Panormos — it's one of the major sights in this destination. If you're after more activities, think about basing yourself here and setting off on some trips from Astypalaia.
Is it worth booking a vacation package to Astypalaia?
It's easy to see why an Astypalaia vacation is on the must-do list of many travelers. Top attractions like Astypalaia Castle are just the start of what you can explore here.
How to find the best Astypalaia package deals?
Bagging a cheap Astypalaia package deal is a breeze with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your budget range, add a couple of filters and browse what's available. You can tweak your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most economical Astypalaia package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are usually lower.
Is it cheaper to book an Astypalaia vacation as a package?
An Expedia vacation package could score you significant savings when compared to arranging accommodations and flights separately. Better still, you can personalize your Astypalaia trip to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Astypalaia?
Secure incredible discounts by booking your flights ahead of time with Expedia. If spontaneity is more your style, grab one of our last-minute deals for an impromptu Astypalaia trip.
How to plan a trip to Astypalaia?

  1. Choose your dates: What you plan to do in Astypalaia and your preferred season will help you decide when to go.
  2. Set your budget: Consider expenses such as flights, food and transportation when working out how much to put aside for your trip to Astypalaia. Then, pick a hotel that works with your budget, whether that's a wallet-friendly stay or a deluxe retreat.
  3. Use Expedia's trip planning tool to discover Astypalaia: Research every part of your trip to Astypalaia with this handy planner. Invite your friends and family to collaborate on a group getaway, search for hotels or things to do and make bookings.
  4. Work out your trip length: Consider how long you want to spend discovering Astypalaia. Plan your days so you can get to all the attractions and experiences you're interested in at a comfortable pace.
  5. Bundle your accommodations and airfare: After you've settled on your dates and duration, book the right Astypalaia vacation package for you.
  6. Book experiences or activities ahead of time: Whether it's a ticket to a major attraction or a walking tour, you won't have to worry about missing out on the highlights of Astypalaia. Find all the incredible things to do in Astypalaia in Astypalaia with our dedicated travel guide.

Does Expedia offer Book Now, Pay Later Astypalaia vacation packages?
Your Astypalaia break should be a relaxing escape from your busy life, not a reason for money-related stress. So to give you extra flexibility, we've partnered with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the total cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.