Monthly Rentals in Upwey

I stayed at Shepherd Oak from February to March during my 6 week placement as a student at the hospital in Dorchester and loved having such a lovely, quiet place to retreat to in the evenings after busy weekdays. The cottage and its surroundings were very clean and tidy and its location is beautiful and very peaceful. The town of Upwey in general is also lovely and I spent my weekends discovering the walks around the area and frequenting the most gorgeous tearoom I've ever been in (the Wishing Well tearoom just down the road!) so for me the cottage couldn't have been in a more perfect location! The host and co-host, Helen and Gemma, were very friendly and communicative throughout my stay and overall I thoroughly enjoyed my time at Shepherd Oak and would wholly recommend to anyone. Thanks Helen and Gemma for a wonderful stay!

It was a complicated start due to my arrival time, but even so, Helen was always attentive. Helen and Steve are incredible hosts and made me feel at home. I highly recommend this accommodation.

I had an outstanding experience at Joy’s property. From the moment I arrived, it was evident that exceptional care had been taken to ensure a welcoming and pristine environment. The accommodation was impeccably clean, well-maintained, and thoughtfully designed for comfort and convenience. Every amenity worked flawlessly, and the attention to detail—from fresh linens to the well-equipped kitchen—made it feel like a home away from home. Joy was a responsive and gracious host, offering clear communication throughout and helpful local insights. Her commitment to guest satisfaction was evident in every interaction. Highly recommended for anyone seeking a reliable, serene, and well-appointed stay. I wouldn’t hesitate to return.

Fantastic stay at The Tack Room and amazing hosts! The accommodation is absolutely spotless and well equipped with everything you need. I must say the shortbread biscuits were a hit all round! You can tell the hosts take great pride in looking after their property. We had a few questions on a Sunday morning and the host was over to help us straight away, you can’t get better service than that. Great location with Weymouth only a 10 minute drive away. Will certainly be booking again when we next visit Weymouth! Would highly recommend!