Thessaly holiday rentals

Search hundreds of travel sites at once for holiday home deals in Thessaly

Here is why travellers choose KAYAK

Free to useThere are no hidden charges or fees

Filter your dealsFilter by free cancellation, free breakfast and more.

Millions of reviewsCheck ratings based on millions of real guest reviews.

Recommended by KAYAK
Booking Insights
Recommended by KAYAK

Best Thessaly holiday rentals

Go to map

Search by review score

6+ Okay7+ Good8+ Great9+ Excellent

Search by price

R221 - R7 904R7 904 - R15 588R15 588 - R23 271R23 271 - R30 937R30 937+ per night

Property Types

ApartmentHomestayHouse

Search by freebies

Free cancellationFree breakfastFree parkingFree internet

Most recommended holiday rentals in Thessaly

Show all
Skyframe Apartments - Skiathos - Balcony
Skyframe Apartments
Skiathos, TS, Greece
9.1Wonderful(3)
Apartment
Parking
Free Wi-Fi
Air conditioning
R1 887+
Check availability
Asprolithos Studios - Skiathos - Living room
Asprolithos Studios
Skiathos, TS, Greece
9.1Wonderful(144)
Apartment
Parking
Free Wi-Fi
Air conditioning
R1 105+
Check availability
Villa Stratos Skiathos - Achladias - Balcony
Villa Stratos Skiathos
Achladias, TS, Greece
Villa
Free Wi-Fi
Air conditioning
R1 360+
Check availability
Villa Mitzelos - Skiathos - Pool
Villa Mitzelos
Skiathos, TS, Greece
9.6Wonderful(34)
Villa
Parking
Free Wi-Fi
Pool
Air conditioning
R3 111+
Check availability
Margio Skiathos Apartments - Skiathos - Bedroom
Margio Skiathos Apartments
Skiathos, TS, Greece
8.8Very Good(269)
Apartment
Free Wi-Fi
Air conditioning
R1 547+
Check availability
Skiathos Island Villas - Skiathos - Dining room
Skiathos Island Villas
Skiathos, TS, Greece
9.1Wonderful(13)
Villa
Parking
Airport shuttle
Free Wi-Fi
Pool
R5 882+
Check availability
Armamento Villa - Skiathos - Patio
Armamento Villa
Skiathos, TS, Greece
9.5Wonderful(5)
House
Free Wi-Fi
Air conditioning
R3 230+
Check availability
Iridanos Apartments - Skiathos - Building
Iridanos Apartments
Skiathos, TS, Greece
9.1Wonderful(111)
Apartment
Parking
Free Wi-Fi
Air conditioning
R3 621+
Check availability
Europa,2br,2bth Villa With Private Pool And Stunning Sea Views - Skiathos - Pool
Europa,2br,2bth Villa With Private Pool And Stunning Sea Views
Skiathos, TS, Greece
9.3Wonderful(3)
Villa
Air conditioning
R5 661+
Check availability
Mariza's Guest House - Skiathos
Mariza's Guest House
Skiathos, TS, Greece
9.8Wonderful(67)
Apartment
Parking
Airport shuttle
Free Wi-Fi
Air conditioning
R1 156+
Check availability
Casa Blue Sea View, Philian Collection - Skiathos
Casa Blue Sea View, Philian Collection
Skiathos, TS, Greece
8.1Very Good(237)
Apartment
Free Wi-Fi
Air conditioning
R1 207+
Check availability
Chris Rea Villa - Skiathos
Chris Rea Villa
Skiathos, TS, Greece
9.6Wonderful(34)
Villa
Parking
Airport shuttle
Free Wi-Fi
Pool
R3 077+
Check availability
Valmas village - Skiathos
Valmas village
Skiathos, TS, Greece
9.2Wonderful(27)
Apartment
Parking
Free Wi-Fi
Pool
Air conditioning
R1 037+
Check availability
Villa Anna - Skiathos
Villa Anna
Skiathos, TS, Greece
9.6Wonderful(365)
Apartment
Parking
Free Wi-Fi
Air conditioning
R1 173+
Check availability
Georgia's House Project - Skiathos
Georgia's House Project
Skiathos, TS, Greece
9.2Wonderful(11)
Apartment
Parking
Airport shuttle
Free Wi-Fi
Air conditioning
R2 023+
Check availability
Casa Blue Old Port, Philian Collection - Skiathos
Casa Blue Old Port, Philian Collection
Skiathos, TS, Greece
8.3Very Good(84)
Apartment
Free Wi-Fi
Air conditioning
R1 224+
Check availability
Booking Insights

KAYAK’s insights for holiday rentals in Thessaly

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Thessaly with confidence.

How early should you book a vacation rental in Thessaly?

Book at least 4 days before your stay begins to get the best price for your Thessaly vacation rental.

Find deals

Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

October
July
R1 745
R2 871
Cheapest month to stay with an average 58% drop in price.
Most expensive month to stay with an average 34% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

Top tips for finding the perfect Thessaly holiday rental

FAQs when booking a holiday home in Thessaly

  • What types of holiday rentals are available in Thessaly?

    There are loads of different property types that you can make your holiday home in Thessaly. You’ll find apartments, boats, campgrounds, guest houses, houses, homestays, hotels, houseboats and villas.

Where to stay in Thessaly?

Our map will help you find the perfect place to stay in Thessaly by showing you the exact location of each holiday home.

Everything you need to know for your stay in Thessaly

Complete your trip to Thessaly

Car hire in Thessaly