Chalkhill View.

A dog-friendly holiday home in Weymouth, just 5 minutes from Portland

The perfect blend of comfort, price-point, and frankly incredible location. It’s no wonder so many watersports and climbing enthusiasts re-visit this property year-after-year.

At a glance

Sleeps 4; one double with sea views, one twin.
Perfect base for a watersports or climbing holiday.
Walking distance into Weymouth and just a 5 minute drive from Portland
Dog friendly with an enclosed garden
One free parking space, plus more on the road if you need
Gorgeous sea views across Weymouth Bay to the cliffs of Portland

The Experience

The car doors clunk shut behind you, and the smell of lavender meets you from the flowerbed.

A tug on your sleeve, “Hey look, we can see the sea!”

You turn around. A beaming smile of white cliffs, a scattering of sails on the deep blue ocean. Portland’s silhouette like the hump of a whale.

You leave the bags and head inside. The dog sprints ahead on pitter-patter paws, the kids go tumbling after. It’s cosy, warm, and welcoming. Coffee and tea are waiting for you; there’s milk in the fridge. You fill up the kettle at the kitchen sink, smiling through the window at the glittering sea.

In the afternoon, you take a stroll together along the Rodwell Trail and into Weymouth. You treat yourselves to ice cream in the harbour, but manage to resist the fish and chips (for now). That evening you play board games with the kids, snuggle into the comfy sofa and eat more chocolate than you should.

The next few days are exhausting in the best possible way. You climb- maybe the beginners’ walls with the kids; maybe The Cuttings and the Blacknor Crags. You swim in the ocean, cycle, and sail. You kitesurf, and paddleboard. Some days you simply sprawl out on the beach and bury each other in sand.

In the evenings you eat dinner as a family, content in your cosy little home. You relive each day blow-by-blow, smile with tan-lined faces, and promise to come every year.

The Practicalities

Chalkhill View is the perfect Weymouth holiday home for a family of four (or five with a dog!)

More than anything, Chalkhill View’s incredible location is what sets it apart. It’s right on the Jurassic Coast, walking distance into Weymouth along the Rodwell Trail, and just a 5 minute drive from the “sporty Mecca” of Portland. If you love cycling, hiking, climbing or watersports, Chalkhill View has it all on its doorstep.
Your furry family members are most definitely welcome! The garden is enclosed and secure, so they’re safe and free to run around to their heart’s content. The owners have gone above and beyond for dogs, with leads, beds, and blankets all supplied. If you are bringing your dog with you, let me know and I’ll leave them some welcome biscuits (I want them to feel at home too!)
The Weymouth holiday home has two bedrooms. One is a spacious single room, ideal for two children. The other is a cosy double. If you need a travel cot, let me know in advance and I’ll make sure it’s all set up and waiting for you when you arrive.
You’ll find a welcome pack when you arrive with nice tea, coffee, sugar & local biscuits, so you can have a nice hot drink as you settle in.
The light and modern bathroom consists of a bath with an overhead shower, a toilet and sink, with a cabinet for you to store your toiletries during your stay. Soft towels are supplied for your stay along with one eco-friendly toilet roll.

For every holiday booked at Chalkhill View, I plant a tree.

The location was great near to Portland and Weymouth and right next to the coastal path. We found plenty to do around the area even though the weather wasn't the best. The house was clean, nicely decorated and the beds very comfy. Towels were provided. Georgina messaged us during our stay to ask if she could help in any way. We would definitely stay here again if we were visiting the area in the future.

Claire, 5*
This place was faultless I cannot add any anything less than positive.

Dave, 5*
Georgina was very responsive to messages. The house was in a small close and overlooked the sea (upstairs views). It felt like a home from home. Great location for exploring South Dorset and Portland.

Gemma, 5*
Have just spent a wonderful long weekend at Chalkhill View. Lovely clean and uncluttered home with everything we needed for our stay and dog friendly. Great views from bedroom towards Portland. Lots to do in the area and Chesil Beach is a short walk away.

Amy*