Chalet holiday rentals in West Dorset District

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!

My partner and I loved it THAT much, we are STILL there! We requested to extend our stay and despite having to move some bookings around, Alan and Lynne managed to make it possible for us! I had 3 nights of blissful sleep thanks to their fabulous pillows and now I get 3 more! 😁

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 loved it so much the first time we visited back in 2020, that we came back. And just like then, it was fantastic. The cottage is absolutely lovely, the whole farm is amazing, and it is just so nice to walk around, see the cows, absorb the nature. Topping it all: Ailse and "Farmer Phillip", as our kids kept calling him. they just make you feel so welcomed, like you're part of the family. Our boys had a great time, and have to say their favourite part was undoubtedly playing with Effie. Thank you again for welcoming us to your place, and being so loving and accommodating.

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.

Absolutely stunning lodge, very spacious with lovely views of the ocean. Very comfortable and homely feel. Hot tub was private and very clean. Would highly recommend and would definitely go back. Thank you Lorraine

Great place, great location, perfect for a big group

Great accommodation in the perfect location for our needs. Helpful instruction received, thank you.

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.

The caravan was extremely clean and well equipped. Reg always responded to my emails and texts straight away which was so reassuring. Our 2 year old grandchild was with us and a travel cot was installed in the bedroom. The South West walkway was just a short distance from the caravan and Chisel beach can be seen from the caravan's balcony. We had a chill out weekend but there is so much to see in the surrounding area. We had a most enjoyable stay.

Nice quiet hottub get away! Right on a lake fishing isnt the greatest but trout can be caught on the stream!

The cabin at Hunters Lodge was an ideal place for a romantic weekend. The cabin was spacious and well appointed with all kitchen amenities available. Upon arrival we only had to go to the cabin, the key was inside, so check in couldn't be easier. The lakeside surroundings were even more beautiful than it appeared the photos. The staff helpfully furnished us with extra towels after we took full advantage of the hot tub. An idyllic stay, would highly recommend!

Detailed but simple instructions provided for self check in. Easy to find and a lovely peaceful location. The four poster bed was very comfy and the hot tub was lush on a drizzly evening. Loads of attractions nearby and nice to return to the peaceful cabin.

awsome place very clean . hot tube spotless . deffo return

Great vibes, lovely stay, would go again.

We will be back!!! Great stay! Thank you ☺️

We celebrated first anniversary and I paid extra for a decoration, but honestly they made much more then I expected. We would love to go back. Everything was so clean, the house was warm, hot tub was on and ready for us. I recommend that beautiful peaceful place 100%. Don’t think twice is worth every penny we paid! We didn’t wanna leave! 10/10!