Vacation Rentals with Self Check-in in Helmsley

Osmund's Firewood

• 8 guests

• 4 bedrooms

Osmotherley, Northallerton

Set within the North York Moors National Park, the village of Osmotherley is a quaint resting spot for hikers and history fans. As this fantastic home is located just a four-minute drive from the Mount Grace Priory House and Gardens, you might fancy spending the day roaming the ruins of a medieval monastery.

Pat-a-Cake

• 2 guests

• 1 bedrooms

Pickering, North Yorkshire

This elegant cottage in the ancient town of Pickering had us on the private outdoor terrace alone. But step inside, and this home keeps on surprising.

Beehive Cottage

• 5 guests

• 3 bedrooms

Whitby, North Yorkshire

Modern, stylish and in the heart of charming Whitby, this home ticks all the boxes for a memorable stay on the North Yorkshire coast. Honeycomb print livens up licks of trendy grey and we particularly loved the subtle nods to Whitby’s history and maritime identity in the living space and bedroom.