
Holiday houses in Osmington
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Osmington
Guests agree: these stays are highly rated for location, cleanliness and more.

Charming Grade II listed Dorset cottage
Wintersweet Cottage (C1798) is set in the picturesque village of Osmington 3 miles from the beautiful sandy beach of Weymouth. Tucked away in a private drive with only 3 other thatched cottages it's a haven of tranquillity surrounded by stunning walks along the Jurassic Coast or up to the famous White Horse of Osmington on your doorstep. A courtyard with BBQ is the perfect place to relax on a summer's eve after a walk, a trip to Lulworth Cove or any of the other delights that Dorset offers

The Old Reading Room West Stafford, Dorset.
The Victorian Reading Room of West Stafford is of historical importance. Used before the war as a Reading Room for the villagers and estate workers, the newspapers were provided, the village shop in the late 1930s, then a workshop and a store room for the church. We have now lovingly restored, decorated and furnished this amazing building into a cosy self catering holiday retreat, "far from the madding crowd" Open plan, comfy double sofabed, wood burner, country walks and fabulous village pub.

The Beach Hytte - Stunning Sea View Penthouse
Enjoy your perfect getaway in this award winning 2 bed penthouse apartment with 180 degree sea views in the heart of the tranquil Alum Chine area of Bournemouth just a few minutes walk from the beach. The property boasts two dining areas, one of which sits on the large balcony with views across Bournemouth beach and a bespoke wood burning stove for the winter nights. The open plan kitchen leads onto a cozy living room where you can enjoy Sky Glass TV entertainment through super fast WiFi.

Private Guest Suite in Sutton Poyntz + own parking
We are a Modern Stone built cottage in beautiful village. Private secure gated parking for 2 guest cars. We love our local pub The Springhead which is 1 minute walk away, set around a duck pond with willow trees. There are numerous country and coastal walks nearby and we welcome dogs. We live upstairs but you are completely separate to us and left alone. There is 2 large bedrooms a kitchen equipped with small mini oven and microwave, bathroom inc bath and shower and comfortable lounge.

The Ringstead Suite
This unique suite with it's own private stairway from the floral garden leading to your own private balcony is a perfect base looking onto the Jurassic Coast above Ringstead Bay. Above the property is the inner coastal path and Ridgeway walks. Nearby is beach access at Ringstead Bay and Osmington Mills. The suite comprises a cosy lounge area, shower room and toilet, hallway with boot and coat cupboard and luxurious bedroom with Purbeck Stone wall overlooking the garden.

Coppice Barn, farm stay, nr Durdle Door & Lulworth
Sorry no Pets Suitable for only one infant. A barn conversion two miles from the Dorset coast. Set within its own private garden with unspoilt views of Galton Farm overlooking Moreton forest and Tadnoll Heath. Ten minutes drive to Durdle Door, Lulworth Cove and Ringstead Bay. Plenty of coastal and country walks to choose from. The barn consists of one bedroom with a superking bed. Large bathroom and open plan kitchen, dining and sitting area all delightfully decorated.

Glebe Summer House
Tidy private, serene, and peaceful setting 10-15 minute walk of Osmington Bay beach. Ideally located near many stunning coastal spots, including Weymouth, Durdle Door, and Lulworth Cove. The X54 bus, which runs hourly to these destinations stop is just a 3-2 minute walk away. Guests have access to a private full bathroom located just a few steps outside the summerhouse. Full AC. Perfect for a quiet coastal escape surrounded by nature for couples or solo travelers.

Beautiful Annex situated on the Jurrasic Coast.
Pixon Barn is situated on a working farm on the Jurassic Coastline within an easy driving distance to Weymouth, Lulworth Cove, and Abbotsbury. It is located next to numerous bridlepaths, perfect for avid walkers, cyclists and lovers of the countryside. We welcome any and all well behaved dogs. There are several pubs all within a 5 minutes distance by car, as well as our own farm cafe and shop located on the main road into Weymouth. Best ice-cream around.!

Private use of Indoor Pool available May- end Sept
Self contained detached cottage in a tranquil location close to the famous 'Jurassic Coast' ; Durdle Door, Lulworth, Corfe Castle, Weymouth and Dorchester are all a short drive away. Further attractions close by are Monkey World, Bovington Tank Museum, and Sculpture by the lakes. There is a well stocked village shop and good village pub. Dorset has so much to offer, with beautiful coastline and breathtaking scenery. Relax in the pool at your leisure!

Thatched Cottage by the Beach
The Stables is a charming thatched cottage nestled in the sort after village of Preston, Dorset. It is located a short walk to the beach and village amenities. It is perfectly located to access nearby famous Weymouth Beach, Weymouth Harbour and the beautiful Jurassic Coast. A romantic stable conversion with a recently re-designed Kitchen and Bathroom. It is perfect for an active summer beach holiday or a cozy winter holiday in front of the fire.

Quaint Thatched Coastal Cottage
Beautiful thatched cottage dating back to the 18th century in the center of the chocolate box village of Osmington. You could easily spend a relaxing break, whiling away hours in the sunny front room or garden against a backdrop of horses walking and church bells in the distance. If you want to be more active, it is the perfect setting for walkers, with easy access to the popular white horse and coastal walks on the south west coast path alike.

Luxury Coastal Bolthole · Hot Tub · Beach Access
Walk past what looks like a garage and discover a stunning coastal bolthole all your own. Perfectly formed for two, with uninterrupted sea views, an open-plan living space opening onto a sun terrace, and your own private steps down to Castle Cove beach. Soak in the hot tub, fire up the BBQ, and watch the boats drift by. All towels, toiletries, and even beach kit provided. A romantic, characterful hideaway on the Dorset coast.
Popular amenities for Osmington holiday rentals
Other great holiday rentals in Osmington

Old Dorset Cottage

Beachside Cottage with Panoramic views of the sea

Family cottage in Dorset close to Jurassic coast

Detached property, beams, hot tub big garden 166m2

No. 2 Coastguards Cottage

The Hayloft Somerset

The Arch, The Fonthill Estate, Tisbury, Wiltshire

Kingfisher - Creek Caravan Park Ringstead
Destinations to explore
- New Forest National Park
- Bournemouth Beach
- Weymouth Beach
- Paultons Park Home of Peppa Pig World
- Longleat Safari Park
- Stonehenge
- Southbourne Beach
- Boscombe Beach
- Mudeford Quay
- Lyme Regis Beach
- The Tank Museum
- Durdle Door Holiday Park
- Bournemouth International Centre
- Kimmeridge Bay
- Beer Beach
- Crealy Theme Park & Resort
- Powderham Castle
- West Bay Beach
- Highcliffe Beach
- Hoburne Naish Holiday Park
- Alum Chine Beach
- Stourhead
- Shorefield Country Park
- Mudeford Sandbank





