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Holiday houses in Thessaly

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Top-rated holiday rentals in Thessaly

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Top Guest favourite
The outdoor space features stone-paved pathways surrounded by lush olive trees. Two separate buildings are visible, connected by a serene garden area. A table with a vase of fresh flowers is positioned in the foreground, providing a welcoming atmosphere. Comfortable lounge chairs are positioned for relaxation.
Cottage in Sporades
5 out of 5 average rating, 14 reviews

Apomero Cottage - Almyra Living

Tucked away in a private 4,000 m² olive grove with views of Skopelos town and the Aegean Sea, Apomero Cottage offers peaceful seclusion just a 15-minute walk from town. Once used during olive harvest season, the cottage blends traditional Greek island architecture with modern comfort. It consists of two buildings: one with a bedroom and bathroom, and another with a living room, second bathroom, and a sheltered, fully equipped kitchen and dining area. An organic vegetable garden is also a plus.

Top Guest favourite
A two-story stone house is framed by lush greenery and a well-maintained yard. An inviting pool reflects the sky, while a cozy lounge area with a blanket and hat are arranged artfully on the deck, encouraging relaxation in the outdoor space.
Home in Ano Gatzea
5 out of 5 average rating, 13 reviews

Old Olive Villa

Στους πρόποδες του Πηλίου, εκεί όπου το βουνό των Κενταύρων συναντά το γαλάζιο του Παγασητικού αυτό το πέτρινο σπίτι προσφέρει μια εμπειρία διαμονής που ισορροπεί ανάμεσα στην αυθεντικότητα και την πολυτέλεια. Περιτριγυρισμένο από έναν αιωνόβιο ελαιώνα, το σπίτι αποπνέει ζεστασιά, άνεση και υψηλή αισθητική. Εδώ, η ηρεμία του τοπίου συναντά την ποιότητα μιας πραγματικής απόδρασης – εκεί όπου κάθε λεπτομέρεια έχει σχεδιαστεί για να προσφέρει ξεκούραση, αρμονία και μια βαθιά αίσθηση ευεξίας.

Top Guest favourite
An aerial view reveals a tranquil bay framed by lush greenery, with clear turquoise waters gently lapping at a rocky shoreline. A small boat is anchored just off the coast, while a pair of lounge chairs is set on the sandy edge, inviting peaceful relaxation.
Cabin in Magnesia
5 out of 5 average rating, 59 reviews

Magical Seafront Treehouse with breathtaking views

Happinest Treehouse is… A charming cabin for two with beguiling views. Built between ancient olive trees, overlooking the sea. You’ll sleep to the sound of rustling leaves and owls hooting. Wake up to a vision of shimmering waters then wander through a magical Mediterranean garden and dive straight into the sea. Our unique and tranquil getaway is located in undiscovered Pelion, 5km from the village of Milina, on a small bay. We're Happinest Treehouse. Curious? Let the name be your guide!

Guest favourite
A wooden deck is featured with two lounge chairs positioned near a small pool, offering views of the mountains and water. A table with refreshments is also present, inviting relaxation in a serene outdoor setting.
Home in Volos
4.95 out of 5 average rating, 131 reviews

Anna's Poolside Villa

Anna's Villa is located in the dreamlike location of a traditional settlement of Makrinitsa. Walking through the traditional cobbled streets and within the dense, evergreen vegetation of the magical mountain, you will find yourself in our beautiful setting that is ideal for both families and couples, and for those of any age. Provides all-in-one amenities, giving you unique moments of relaxation and well-being.For the house you have to walk 100 meters in the traditional cobbled streets.

Guest favourite
An aerial view of Villa Skopelita reveals its whitewashed exterior next to rocky coastline. A spacious patio with outdoor dining furniture provides a scenic spot, while the vibrant blue sea contrasts with the natural greenery surrounding the property.
Home in Skopelos
4.95 out of 5 average rating, 19 reviews

Villa Skopelita

The fully renovated three-story Villa Skopelita offers a double bedroom, a twin bedroom with two single beds, and an extra single sleeping option via a pouf bed in the living room, ideal for a child. It includes two bathrooms and a bright living area. Highlights include its unique style and a spacious patio with breathtaking, uninterrupted sea views. Due to its location and overall buety, Villa Skopelita, is one of the island’s most photographed homes!

Guest favourite
A modern wooden house is set amidst greenery, with large glass windows offering stunning views of the sea. The surrounding trees and natural landscape create a serene atmosphere. A wooden deck extends outward, complementing the house's design and inviting outdoor relaxation.
Tiny home in Nea Skioni
4.94 out of 5 average rating, 149 reviews

Wooden dream on the beach! - iHouse

A unique wooden house on the beach! All you need in 34m2! It's the iHouse and it's fully equipped with all needed amenities. The iHouse is placed on our field in Nea Skioni, right in front of the sea. If you are looking for a place to getaway, relax and enjoy the beauties of nature, then the iHouse is ideal for you! There is a self check in system allocated at the location. You will be provided with all the needed information prior to your arrival.

Top Guest favourite
An outdoor area is showcased with elegant wooden pergolas and soft curtains. A hot tub is positioned on a stone patio, surrounded by garden elements. Scenic Meteora rocks provide a dramatic backdrop, illuminated by subtle outdoor lighting that highlights the tranquil space.
Villa in Kalabaka
4.98 out of 5 average rating, 320 reviews

Meteora boutique Villa E

Το Meteora boutique Villas βρίσκεται στο κέντρο της πόλης της Καλαμπάκας, σε έναν ήσυχο δρόμο. Προσφέρει έναν περιποιημένο κήπο ,δυο κομψά διακοσμημένες βίλες, και ένα εξωτερικό τζακούζι. Κάθε βίλα έχει ξύλινη οροφή και μοναδικό ντιζάιν. Όλα τα υπνοδωμάτια περιλαμβάνουν κρεβάτια της εταιρείας Coco-mat, τηλεόραση επίπεδης οθόνης, ιδιωτικό μπάνιο με ντους και δωρεάν προϊόντα περιποίησης. Παρέχεται δωρεάν Wi-Fi.

Top Guest favourite
A serene outdoor space features a rustic stone wall and a wooden table adorned with a striped tablecloth. Two blue chairs are positioned around the table, while a large tree provides shade. In the background, a hammock hangs gently, inviting relaxation.
Home in Trikala
5 out of 5 average rating, 110 reviews

Like a Fairytale

Located just 15 min from the city of Trikala, this property, straight out of a fairytale, nested among lush greenery, is awaiting you for an escape from reality! Perfect for a family or a group of friends, it has been decorated with respect to tradition and nature! Do not miss on a unique opportunity for a getaway! Free Wifi and parking on the street are available to our guests!

Top Guest favourite
A grassy outdoor area is highlighted by a wooden support and vine-covered trees. Soft, oversized cushions provide seating options, while a decorative lantern is positioned on the ground, adding charm to the natural setting.
Holiday home in Kastraki
4.94 out of 5 average rating, 120 reviews

Avli Luxurious House

Renovated ground floor apartment with unrestricted views of the Meteora. It is located at the Kastraki Village just 150m from the central square. The area is full of life with many small cafe, tavernas, restaurants etc. everything you need is within walking distance. It is only 500 meters from Meteora Rocks formation and 200meters to the point of interest.

Superhost
A cozy studio space is shown, featuring a stone wall and high ceilings. A fireplace is located in the corner, complemented by a chandelier. Two built-in sofas, a dining table with four chairs, and a spacious bed are visible, creating an inviting atmosphere.
Chalet in Leptokarya
4.86 out of 5 average rating, 107 reviews

Stone cottage by the coast of Olympus

A large studio that benefits from high ceilings, fireplace, a full- fitted kitchen, and WC with shower. It has a double bed and 2 build-in sofas that turn into beds. The cottage is at the back of a larger house but has its own private garden. Ενιαίος χώρος με μεγάλη κουζίνα, μπάνιο, διπλό κρεβάτι και καναπέδες που γίνονται κρεβάτια.

Top Guest favourite
A serene outdoor seating area includes a gently swaying hammock suspended from a wooden pergola. Lush greenery surrounds the space, and a vibrant sunset casts warm hues across the sky, creating a peaceful ambiance overlooking the landscape.
Apartment in Tsagkarada
4.97 out of 5 average rating, 119 reviews

Petit Stonehouse

A country stone house gives you the opportunity of privacy and relaxation. Surrounded by olive trees and a breathtaking view of Aegean sea. Petit Stonehouse is five minutes drive from Mulopotanos Beach and five mins from Tsagarada village. Also available BBQ-Air cooler - fireplace-Tv-Hot water

Top Guest favourite
A charming bedroom is characterized by a stone wall and wooden beams overhead. A plush bed with a dark tufted headboard is adorned with neatly arranged blankets. Soft lighting highlights a nature-themed mural behind the bed, while a cozy seating area is positioned to the side.
Home in Trikala
5 out of 5 average rating, 13 reviews

Archontiko Theofanous 1915

Αυτός ο μοναδικός χώρος έχει το δικό του στιλ. Εγώ κι ο σύζυγός μου, μετά από 9 χρόνια εμπειρίας, έχοντας το Traditional Guesthouse, αποφασίσαμε το 2025, από μονοι μας, να ανακαινισουμε και να δώσουμε ξανά ζωη σ' ένα παλιό πετρινο σπίτι που ήταν ακριβώς δίπλα μας.

Popular amenities for Thessaly holiday rentals

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