Skopelos Winter Rentals & Holiday Homes

There are a lot of options in Skopelos. If you plan on staying in the Skopelos area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Skopelos:

• Villa Natura, Stunning Sea Views across the Aegean,Infinity Pool, trees around.
• Villa Pasifika Glossa with Swimming Pool And Extraordinary Views
• Villa Myli - Skopelos
• State-of-the-Art Villa has Infinity Pool, Jacuzzi, Comfort Cooling, Sunset View
• Pasithea Skopelos Retreat
• villa Avaton near Skopelos town
• Sunshine Pool Villa
• Villa Antigone Luxury Retreat
• Villa Politimi Luxury Retreat
• Villa Kamperis Skopelos island

The average cost for winter rentals in Skopelos is $377 per night. Estiavillas has a wide list of great winter places to stay near Skopelos that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.

Yes, here are the top cottage/chalet rentals in Skopelos that allow you to bring your pet or dog:

• Traditional Villa Maria O with fantastic view between mountain forest and sea
• VILLA ESMERALDA
• Villa Katerina Private Pool Sea Views A C Wifi - 2179
• Villa Elaion Private Pool- Sea Views -sleeps 4+3 KIDS (bunk bed +cot+baby chair

See all pet-friendly vacation rentals in Skopelos on Estiavillas

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Skopelos to find what works for you.

As of 2026, the data from Estiavillas shows that there are over 246 private swimming pools or indoor pools accommodations near Skopelos along with other great amenities.