Vacation rentals in Chalandriani

4.95 out of 5 average rating, 40 reviews

An outdoor seating area is visible, featuring a stone table surrounded by a shaded vine-covered trellis. Two wooden chairs are positioned nearby, complemented by a few plants in pots. The natural stone flooring extends throughout the space, enhancing the rural charm.

Cottage in Ano Syros

Yianni's house

Παραδοσιακό αγροτόσπιτο στην περιοχή Μύτακας. Ήσυχο χωρίο σε μεγάλο υψόμετρο, με λίγους μόνιμους κάτοικους, δροσερό το καλοκαίρι με καθαρό αέρα. Άνετο σπίτι με δική του μεγάλη αυλή και χωραφάκι. Ιδανικό για όσους θέλουν ησυχία και ξεκούραση, περπάτημα στο βουνό και στα μονοπάτια που οδηγούν στις μαγευτικές παραλίες της Απάνω Μεριάς. Οι φίλοι της πεζοπορίας μπορούν να απολαύσουν την άγρια ομορφιά της περιοχής και να μαζέψουν άγρια βότανα την κατάλληλη εποχή (θυμάρι, φασκόμηλο, καρύδα, κάπαρη κλπ)

Superhost

A compact bathroom is observed featuring a wall-mounted sink and a toilet. The walls are adorned with light-colored tiles, contributing to a clean look. Essential fixtures, including a faucet and toiletries, are present, with a small cleaning brush positioned nearby.

4.81 out of 5 average rating, 159 reviews

Irene Guest House-Syros

Στη περιοχή Ψαριανά κοντά στον Ναό της Κοίμησης και στην αφετηρία λεωφορείων, ενα πλήρως αυτόνομο διαμέρισμα-μεζονέτα ενός υπνοδωματίου με εσωτερική σκάλα.Έχει πλήρως εξοπλισμένη κουζίνα και δυνατότητα φιλοξενίας τριών ατόμων. Πλήρως εξοπλισμένο για διαμονή καλοκαίρι και χειμώνα. Μόνο 250 μέτρα από λιμάνι και 350 μέτρα από την κεντρική πλατεία Μιαούλη (Δημαρχείο). Δεν χρειάζεται αμάξι για να γνωρίσεις την Ερμούπολη αφού περπατώντας μπορείς να απολαύσεις το μπάνιο σου στην παραλία «Αστέρια».

A doorway opens to reveal a view of the Aegean Sea, with gentle waves lapping at the shore. Sunlight illuminates the water, highlighting the distant silhouette of a lighthouse on the horizon. The entrance features a large arched top with glass panes and a set of double doors.

4.97 out of 5 average rating, 119 reviews

Nelly's Dream

A beautiful traditional house in the heart of Syros town, at the exclusive picturesque 'Vaporia' neighbourhood. The house is built on the rocks, with a unique view of the Aegean sea. It is built on four levels (many steps!) with private access to the seaside and a private open terrace. The two advertised, private rooms, are located on levels 3 and 4 and are accessible through the main entrance through level 1 (street level). The host family of two and a small dog and cat, live on levels 1 & 2.

Cycladic home in Chalandriani

A shaded outdoor area featuring a wooden table and stone seating is located beneath a pergola. A door opens to the interior, framed by whitewashed walls. Coastal views extend beyond, showcasing the blue sea and distant landforms.

4.9 out of 5 average rating, 31 reviews

Crumble-2

The newly built, stone-built house is hooked on the fertile terraces of Ano Meria, the last authentic area on the island.At a distance of just 7 KM from Ermoupolis,each dawn the sun is projecting directly opposite,behind Delos.The area is far from the city's turbulence, without at the same time being far from it,while in the background the lights of Tinos, Mykonos, Ikaria are shining. Cool springs, fiery dry stone walls, juicy arid seeds mark the retreat of the traveler.

4.88 out of 5 average rating, 111 reviews

A private terrace features a wooden table with chairs and a pair of sun loungers, set against a backdrop of stone walls. The tranquil sea is visible just a few steps away, surrounded by a rocky shoreline and a soft, cloudy sky.

Condo in Ermoupoli

Oasea Apartment II Syros

Fully equipped one-bedroom apartment with frontal sea view. One double bed in the bedroom, and 1 sofa bed in the living room, fully equipped kitchen (oven, fridge-freezer, dishwasher, 4-pits), bathroom with shower , washing machine, private terrace with chairs and table. Access to a shared patio with direct access to the sea (rocks) where the guests can take a morning swim. Frontal sea view from living and bedroom. A few steps from the center of Ermoupolis.

4.97 out of 5 average rating, 98 reviews

A window adorned with white shutters opens to a panoramic view of Ermoupolis and the Aegean Sea. A green plant is positioned in a ceramic pot on the windowsill, while a simple lamp and a book are placed on the surface beneath the window.

Home in Ermoupoli

Sunny suite in a neoclassical 1870 town house

The 1870 listed neoclassical town house lies in the heart of Ermoupolis. The entire second floor, saved for our guests, is a spacious and sunny suite with a spectacular view over the city and the Aegean sea. It consists of 2 bedrooms, 1 bathroom, a living room with access to a balcony and a kitchen. On the third floor is a huge terrace. The space is perfect for families, couples or a group of friends and everything is at a very short walking distance.

4.95 out of 5 average rating, 19 reviews

The spacious living area features a light-filled atmosphere with whitewashed stone walls. A wooden dining table is accompanied by chairs, while a cozy sofa is positioned nearby. Potted plants add a touch of greenery, and a glimpse of the Aegean Sea can be observed through the window.

Home in Ermoupoli

Nysea

Welcome to my tranquil home in Ermoupoli, Syros. Situated directly behind Kyveli Institute in the historic center, the property offers serenity amidst a bustling city. Tucked away on a quiet street, the neoclassical building blends modern comfort with timeless elegance. The property is on the upper floor of a renovated 19th century mansion and enjoys glimpses of the Aegean Sea from select windows and the rooftop garden.

4.96 out of 5 average rating, 27 reviews

A fishing boat is moored in calm waters, with its reflection visible on the surface. Surrounding rocky shoreline and distant white buildings create a serene coastal scene, while two additional boats are anchored nearby. The setting offers a peaceful view of the local maritime environment.

Apartment in Kini

Apartment 1 of "Markos Rooms" by the sea

Rent apartment just 20 meters from the beach of picturesque Kini, a minute from the restaurants and cafes of the village. Quiet and family-friendly in a blooming backyard. The apartment is located on the ground floor of the complex and has a double bed, air conditioning, kettle, kitchenette and a small terrace. There is also public parking outside the property. A place perfect for a carefree vacation.

4.95 out of 5 average rating, 39 reviews

An open terrace is featured, framed by natural stone walls. Large views of mountains and a shimmering water body are visible beyond. Cushioned seating with patterned pillows offers a comfortable space for relaxation, inviting the surrounding landscape into the living area.

Cycladic home in Tinos

Apigania house

Amazing house on the beach of Apigania, unique sunset, clear waters, you can feel the nature, feel the wind of Cyclades as on a sailing ship, smell the thyme and the sage. Μinimal decoration with touches of authentic traditional objects. Big terrasse in front of the see, private acces to the see, private parking. Providing breakfast with local products. Personalized services on request.

4.93 out of 5 average rating, 125 reviews

A bright corner room features large windows framed by exposed stone walls, offering views of the sea and waterfront. A glass table with modern chairs is adorned with fresh fruit, while colorful flowers on the table add a touch of vibrancy to the space.

Townhouse in Ermoupoli

Vaporia seaview suites - Mini suite

Νεοκλασικό αρχοντικό του 1852. Μέσα στο Ιστορικό κέντρο της Ερμούπολης. Η Μίνι Σουίτα, διαμορφώθηκε με αγάπη, στον πιο φωτεινό χώρο του κτιρίου με τις πιο σύγχρονες ανέσεις για να προσφέρει μία αξέχαστη διαμονή. Μέσα από τα τέσσερα παράθυρά της ο επισκέπτης έχει την δυνατότητα να απολαύσει την μαγευτική θέα της θάλασσας και τον παλαιότερο εν λειτουργία και μέγεθος φάρο της Μεσογείου.

A private balcony features a small wooden table and two chairs, offering a view of the charming pedestrian street below. A potted yellow flowering plant adds a touch of color, while the surrounding buildings reflect the architectural style of the area.

4.95 out of 5 average rating, 129 reviews

2L - Beautiful 2 level apartment in Ermoupoli

Wake up in this charming, contemporary bright apartment located in the heart of Ermoupolis. This newly renovated, luxurious flat is well-equipped and situated in the vibrant center of Ermoupolis, Syros. Just 100 meters from amazing restaurants, cafes, and bars, it’s also a short walk from Miaouli Square, the Ermoupolis harbor, and the waterfront.

Superhost

A blue door with a decorative lattice design is framed by white walls. A shelf planted with small potted plants is attached adjacent to the door, adorned with blooming pink bougainvillea, adding color and depth to the entrance.

Apartment in Ano Syros

4.83 out of 5 average rating, 120 reviews

By the bougainvillea!

The traditional stone building house is located only 200 m. from the entrance of Ano Syros (where all the vehicles stopped). Few metres from the house at the area "Piatsa", you will find many cafes, bistros, restaurants and shops for your buys. The stone building keep the house cold even the most high temperatures of the summer days!

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Popular amenities for Chalandriani vacation rentals

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Other great vacation rentals in Chalandriani

Cycladic home in Kardiani

A comfortable living area features natural stone walls and wooden beams. A neutral-colored sofa and chairs surround a wooden coffee table, complemented by decorative elements on a nearby shelf. Light filters through blue-framed windows, enhancing the room's inviting ambiance.

5 out of 5 average rating, 7 reviews

Peftasteri Villa | Tinos Island

LucRating, 5 stars4 weeks ago

We fell totally in love with this place and house. It is located in a unique village accessible through a number of stairs. The places to sit outside are unique, there is even a three providing shadow. The house is decorated with love and passion, attention has been paid to every single detail. We a kind of felt sad when we had to leave. The island is “mineral” , rocky but a kind of poetic and super quiet. We would love to go back. We also discovered nice little villages and beaches. A perfect spot with nice restaurants and smiling people

5 out of 5 average rating, 36 reviews

A shaded outdoor seating area overlooks the sea, with a wooden bench and two chairs positioned for relaxation. A table in the foreground displays a bowl of fresh vegetables, including tomatoes and zucchini, alongside a basket of bread.

Farm stay in Ermoupoli

Traditional stone house 1bedroom, sea view, Syros

TomRating, 5 stars3 weeks ago

Thank you so much for a lovely stay on your wonderful farm. The setting was beautiful and the views to the sea as the sun set were truly magnificent. We loved the isolated, quiet, peace and the simplicity of the accommodation. We had plenty of hot water and the the property is self suffecient in electricity which was great on one night when the whole island had a power cut. Kostas was very helpful and informative on the first day, showing us all he has achieved in just a few short years and he checked in with us a couple of times during the week but was respectful of the fact we were on holiday. We would recommend ear plugs as the cockerels start crowing very early and at night there is the sound of the large wind turbines on the opposite hill. We enjoyed the hikes to the deserted beaches and although many restaurants were closed as it was early in the season we found Plakostroto served great food with amazing views of the sunset. Thank you for a great stay.

Cottage in Chalandriani

5 out of 5 average rating, 3 reviews

Casa Natura summer nest overlooking the Aegean Sea

ZoeRating, 5 stars9 months ago

Welcoming space, spotless and tidy traditional little house in the countryside. Unique magnificent views of the sea, the islands and the nature of Apano Meria. Very good communication with a host, helpful, took care of our every need. Tranquility, quiet , walks in the pristine serene countryside. A different summer vacation experience in touch with tradition & simple lifestyle, we are lucky to have experienced it.

4.92 out of 5 average rating, 25 reviews

A small wooden table sits on a stone patio, overlooking clear blue waters. A glass of water and a book are placed on the table, while comfortable seating options are positioned around it. The balcony railing features a geometric design, enhancing the scenic view.

Townhouse in Ermoupoli

Townhouse in "Vaporia" of Syros

MeredithRating, 5 stars3 weeks ago

Syros was the absolute highlight of our trip to Greece, and staying at this Airbnb made it even more special. The view from the house is truly unforgettable - sunrises, sailboats, and neoclassical rooftops all right outside your window. It felt like a dream. The location couldn’t have been better. We were able to walk to everything—cafés, restaurants, shops, even the beach—while still feeling tucked away in a peaceful, elegant part of town. It was the perfect home base for exploring Ermoupoli and beyond. Highly recommend to anyone looking for a stay that’s equal parts charming, convenient, and breathtaking.

The entrance shows a neutral-colored wall with a decorative door framed by a classic architectural detail. A white planter containing green shrubs sits beside a marble step, which leads up to the door.

4.91 out of 5 average rating, 142 reviews

Esperance Corner

AnnwennRating, 5 stars2 weeks ago

The apartment was very clean and in a great location, a 2-minute walk from the port, on a relatively quiet street. Kostas's directions were clear and detailed, everything went very well for me :) The only two things I could point out are the narrow entrance and the rather steep stairs, as well as the fridge that tends to make a lot of noise at times.

Cycladic home in Ai Michalis

A traditional Cycladic stone house is surrounded by a natural landscape. The exterior features whitewashed walls and crimson shutters. A pergola adorned with vibrant bougainvillea provides shade over a front porch. A stone pathway leads to the house, enhancing its rustic charm.

4.95 out of 5 average rating, 84 reviews

Syros - Cycladic stone house

WendyRating, 5 stars1 week ago

Mario’s place is beyond stunning - the sunsets are incredible and the surroundings peaceful and pretty idyllic. Walks are a bit problematic from the house as you are on top of steep hill and all paths to beaches go down and the. Very steeply up but the location is fabulous for an away from it all escape.

A private balcony features a decorative wrought iron railing overlooking the Aegean Sea. A small round table holds an open book, inviting leisurely reading, while a comfortable chair provides a serene spot to enjoy the expansive sea views and distant islands.

5 out of 5 average rating, 6 reviews

Salty suites

PanosRating, 5 stars3 days ago

Absolutely loved our stay in Syros! The accommodation was impeccably clean and extremely well decorated, making it feel like a cozy home away from home. The attention to detail in the decor truly enhanced our experience. Our host was fantastic—friendly, helpful, and always available for any questions we had. We couldn't have asked for a better place to relax and enjoy our time on the island. Highly recommend!