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

Asprolithos Studios - Skiathos - Living room
Asprolithos Studios
Skiathos, TS, Greece
9.1Wonderful(144)
Apartment
Parking
Free Wi-Fi
Air conditioning
R982+
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 759+
Check availability
Armamento Villa - Skiathos - Patio
Armamento Villa
Skiathos, TS, Greece
9.5Wonderful(5)
House
Free Wi-Fi
Air conditioning
R3 162+
Check availability
Villa Mitzelos - Skiathos - Pool
Villa Mitzelos
Skiathos, TS, Greece
9.6Wonderful(34)
Villa
Parking
Free Wi-Fi
Pool
Air conditioning
R3 046+
Check availability
Iridanos Apartments - Skiathos - Building
Iridanos Apartments
Skiathos, TS, Greece
9.1Wonderful(111)
Apartment
Parking
Free Wi-Fi
Air conditioning
R3 545+
Check availability
Ps House Old Port - Skiathos - Bedroom
Ps House Old Port
Skiathos, TS, Greece
9.1Wonderful(17)
Apartment
Air conditioning
R2 896+
Check availability
Mariza's Guest House - Skiathos
Mariza's Guest House
Skiathos, TS, Greece
9.9Wonderful(67)
Apartment
Parking
Airport shuttle
Free Wi-Fi
Air conditioning
R1 148+
Check availability
Antelia Homes - Skiathos
Antelia Homes
Skiathos, TS, Greece
9.7Wonderful(42)
Apartment
Parking
Free Wi-Fi
Air conditioning
R1 465+
Check availability
Chris Rea Villa - Skiathos
Chris Rea Villa
Skiathos, TS, Greece
9.6Wonderful(34)
Villa
Parking
Airport shuttle
Free Wi-Fi
Pool
R3 012+
Check availability
Saint George Villas & Apartments - Skiathos
Saint George Villas & Apartments
Skiathos, TS, Greece
9.0Wonderful(307)
Apartment
Parking
Free Wi-Fi
Air conditioning
R1 515+
Check availability
villa axiothea - Skiathos
villa axiothea
Skiathos, TS, Greece
9.4Wonderful(9)
House
Parking
Free Wi-Fi
Air conditioning
R3 395+
Check availability
Valmas village - Skiathos
Valmas village
Skiathos, TS, Greece
9.2Wonderful(27)
Apartment
Parking
Free Wi-Fi
Pool
Air conditioning
R1 015+
Check availability
Villa Anna - Skiathos
Villa Anna
Skiathos, TS, Greece
9.6Wonderful(366)
Apartment
Parking
Free Wi-Fi
Air conditioning
R1 148+
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 198+
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
R1 981+
Check availability
Angelos House Deluxe Apartments - Skiathos
Angelos House Deluxe Apartments
Skiathos, TS, Greece
9.6Wonderful(39)
Apartment
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
R1 598+
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 49 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 709
R2 811
Cheapest month to stay with an average 55% drop in price.
Most expensive month to stay with an average 41% 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.

  • Are there any pet-friendly holiday rentals in Thessaly?

    There are a number of dog and pet-friendly Thessaly holiday rentals, with around 7% allowing you to bring your pet along with you.

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