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

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!

The place was perfect for three of us and our dog. Located right in the town centre and short walk to two great beaches. You park in the driveway right next to the chalet which is a major bonus in Portland.

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!

This lodge was just perfect for a relaxing week away, which was just what we needed. It was immaculately clean, well set out and well equipped. We loved the fact that our children and dog could explore and play freely and safely, and the lodge was well fenced and very dog friendly. We would definitely recommend, and would love to visit again ourselves.

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.

Christina was a fantastic host. The chalet was beautiful, clean and peaceful. The little extra touches were a nice surprise when we arrived. The kids loved the cows, hot tub and games room and Christina and her farm team were always so friendly answering all our questions and allowing the kids to see the calves. A very enjoyable stay.

We LOVED our stay at The Dolphins. It was spotlessly clean with everything you could need. All the rooms are large and the garden is a great space. Perfect for a large family or 2 families. The distance to the centre of Swanage and the beach was excellent. We will definitely stay again

Great place, great location, perfect for a big group

The home was spacious and easily accommodated my family of 8. There was a crib provided for my youngest. Each room had an joined bath which was really appreciated. The location is perfect for exploring the Jurassic coast. If I visit the area again, I would gladly choose the same location.

Fantastic location, very peaceful. Lovely setup within the lodge and great additional feature with the private sauna. All round very good and everyone was excited to stay over.

Beautiful location well connected to some stunning parts of the Dorset county including Lulworth Cove and the Jurassic Coast. The chalet was really well equipped and the kids loved it especially and are keen to go back. It definitely felt like a home from home. Stephen was great at communicating too.

Joe was a great host and provided all information requested. Arrival was straightforward plenty of space. House was clean and welcoming. Photos need updating as property has been extended further. Shepherd hut in Garden was a great addition however it is cited at the bottom of a steep incline. The hot tub was a great addition and used well journey to the beach was about 15 minutes and parking was difficult but manageable. Shops et cetera were a short drive from the house. There were not many places to eat locally but plenty of takeaways if you needed them. A very enjoyable week in a lovely area about 30 minute drive to New Forest. Definitely worth considering.

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 loved it, back to nature but very comfortable, had everything we needed and more. Loved the closeness to the sea. We walked all around the location, didn’t move our car for 4 days! We want to go back, that probably says it all. Thank you Beth

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. :-)

We stayed for 3 nights. The holiday house was spacious enough to fit family of 4. Plenty of room to play for little ones. Very clean and well organised. The only improvement I could suggest would be to install slim dishwasher but it was perfect anyway. I would recommend and come back.

Immaculate place in a perfect location. The holiday park was very quiet and spotless, with great access to the coastal footpath. We explored so much of the Jurassic Coast & it was great to come back to our base. We found lots of great pubs close by and several different walking routes into Lulworth Cove. A super place to stay - we would highly recommend!

quick response time , clean and comfortable caravan in a great location. will be back again . even posted back our left behind iPad

I had a wonderful 3 days at Chalet 31. Lyme Regis is a very special place for me and was just what I needed. I felt like I was in a little cocoon, all cosy and warm. Being by the sea is so good for the soul. The chalet was exceptional, beautiful flowers, yummy biscuits, tea and milk, such a thoughtful gesture. Didn't want to leave! Just right and you need 3 days to wind down and appreciate it. Will be back again for sure. Thank you Irene xx

The Beach house was just perfect for our weekend away. It is situated in a peaceful location with beautiful views and within walking distance of two restaurants. For me it provided an ideal space to relax and read. From the lounge or the bench in the front garden I had views of the sea or I could enjoy sitting in the shrub lined garden at the back. I was also able to walk some of the coastal path, although very slowly with our 15 year old Jack Russell! For Andy it was just a 2 min walk down the path to the sea to go fishing. He's been fishing at West Bexington over the past 15 years and it was an absolute bonus to find this fab beach house. Sadly no fish this time! The Beach house is tastefully decorated and had absolutely everything we could possibly have needed for our stay. We also appreciated the eggs, milk and biscuits which were there for us on our arrival. We'll definitely be back! Many thanks Rosie and Andy

Stayed for a few days in May 25. The place is stunning, with excellent views. Is exactly as described and has been a pleasure to stay at! Great communication and excellent hosts. Cheryl & Mark