Chalet vacation rentals in Weymouth and Portland District

We stayed here for my husband’s birthday as a family of two adults, three children, our small dog and my mother in law. It was a lovely clean spacious caravan with an amazing view. We had gorgeous weather which really was the icing on the cake. When we arrived it was easy to find and there were biscuits and cakes left for us by Caroline. We also went to Haven reception and they gave us free entertainment passes which meant we could visit the entertainment in the evenings with the children. We’d definitely love to stay again! Ashleigh

We had a lovely family stay on the farm. Lots of space outside for the kids (and parents) to run around, get to know the cows (and hares) as well as explore the area. Quiet and peaceful, so bear in mind if you are looking for lots of things to do. Great spot and lovely spaces - inside and out.

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!

We had a superb 4 night stay at The Victorian Barns, staying in the lovely Lodge. The property was set in beautiful private grounds with its own larger indoor heated swimming pool, huge activity barn (complete with table tennis and badminton court) and plenty of land and lakes to walk our two Springer Spaniels around! Our host Claire gave us lots of information before our stay and also answered any questions that we had during our time there. Their on site EV charger was a god send allowed us to to-up our car at the end of the day after trips out. All in all we loved our stay and we hope to visit again soon!

Really nice place, will go again!

Kirsty and Gary’s caravan was lovely. Very cosy and clean, loved the patio! The duvet covers were super soft and comfy as well. The park is not even a 5 minute walk from Bowleaze Cove, and you can get into town in about 30 minutes walking, or 15 minutes by car. Guest passes are included so you can use the on site club which is lovely. The hosts were very professional and friendly, and responded quickly whenever necessary! Definite recommend and will stay again if we have the opportunity!

Well, what can I say, I have lived and worked all over Dorset and this little bit of Upwey just on the outskirts of Weymouth, a busy bustling town is so peaceful and calming. It truly is a little oasis, feels like a country village but you are next to major bus routes, shops, pubs & amenities. The little complex is private, tranquil and makes you feel at ease straight away. The lodge is perfect if you have a dog as it has a separate fenced garden or you can sit on the decking other side through the patio doors which gets the sun all afternoon. Great kitchen, comfy sofas, nice big beds, gas boiler for instant hot water, we didn't use the heating as our home is draughty and this place kept its heat and no noise from the road, heaven. You have footpaths just down the lane that opens up the jubilee trail, local circular walks. I walked to hardy's monument from the door step and Hells bottom which has a Neolithic dolmen hidden in the corner of the field. This place is bless!

We have stayed at the shack several times and have always loved it. It is always so clean and comfortable and the chalet park is quiet, convenient for lots of locations and shopping. Veronica is always helpful and responsive to messages. We thoroughly recommend it. Thank you Veronica.

This is our second time to book this cabin and it never disappoints! Very comfortable, peaceful surroundings and the private sauna was a bonus! Would love to book again with friends as a yearly cabin trip 🥰

Such a nice place for us to stay. we had a family gathering and it was relaxing and cosy despite the size of the place! Thanks!

The chalet is so spacious and stocked with everything you need. The location was perfect to visit lulworth cove and durdle door. Stephen was responsive, via messaging, and although we didn’t get to meet him, we checked in via the reception desk with no trouble at all, friendly staff. There was 8 of us, 4 adults and 4 children. The fact 3 of the rooms were en suite and a main bathroom was so handy, plus how big the chalet was you don’t feel on top of each other at all! We stayed only 2 nights due to no other availability, but would 100% stay again.

Our stay at The Dorset Resort Chalet (called Sand Banks) was exceptionally good. Had most enjoyable comfortable stay. Chalet had just about everything you could need or wish for. Stayed July 2024. Beds super comfy. Best AirB&B’s we’ve stayed in – exceptionally comfortable, roomy, clean and just perfect. We would have absolutely no hesitation in recommending this Chalet as a great place to stay. We travelled to The Boat on the Bay Kimmeridge & had fresh lobster and scampi with salad and the best chips ever…! Fresh Crab and other fish available. This really is worth a visit as food incredible & prepared in professional food van served outside on picnic benches – all very comfortable. The Dorset Resort Chalet complex is connected to The Dorset Golf Resort and because of that, we had use of the Golf Bar, Club and Dining room for drinks, breakfast, sandwiches & Dinner. Our particular chalet also had a Sauna and 3 bathrooms. Top spec highly recommend.

We had such a lovely stay at Kate’s place. It was just what we needed…. Relaxing, peaceful with beautiful surroundings and views. The Chalet has been nicely decorated and has everything you’d need for a comfortable stay. There are activities onsite and lots to do locally. We especially loved our visits to Portland Bill. We’d definitely come back another time. Thanks for a wonderful stay. :-)

Sam’s place is exactly as described, spotlessly clean and extremely comfortable. Sam is a brilliant host, very responsive and a delight to deal with. I would highly recommend both the home and the host.

The chalet location is beautiful Private, peaceful,the sound of waves crashing on the shore - for us particularly this was so poignant. The chalet is bigger inside than expected and as my husband said, ‘well appointed’. It has everything you need. Walks, fishing, friendly locals, good restaurants, nearby farm shops. I so wish I could stay again, for me, for my husband, the chalet, and West Bexington, will remain in my memory forever as somewhere painfully beautiful. Maybe one day in the future I can come here again. Please enjoy your time here, the host is so genuinely kind. This will become your most favourite Air BnB in the area.

We had a great stay at Rachael and Stephen’s caravan. The communication was great and as no-one was in the caravan the night before they said we could get to the caravan much earlier than usual (motorway traffic had other ideas but the thought was appreciated). The caravan was very clean, we took our own sleeping bags but all the pillows and duvets looked extremely clean and new. That’s about it really, we were hardly in the caravan as we were out early and in late to enjoy our long weekend but it was lovely to come back to a clean and comfortable caravan :) we all had a lovely time!