Holiday houses in Osmington

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Top-rated holiday rentals in Osmington

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Top Guest favourite
A cozy sitting area features a plush olive green velvet sofa adorned with patterned and solid cushions. A stylish wooden chair complements the vintage aesthetic, while large artworks decorate the walls. Exposed wooden beams add character, and a patterned rug enhances the inviting ambiance.
Barn in Dorset
5.0 out of 5 average rating, 136 reviews

Artist’s Creative Hideaway & Sauna

Beautiful, inspiring, and peaceful, Arthouse is a place to escape. This converted art studio in West Dorset is close to Chesil Beach and the Jurassic Coast. It is surrounded by wildflowers and features contemporary art and sculptures by artists Rouwen and Reeve. The space is complemented by mid-century modern furnishings, high ceilings, and exposed beams. All doors open to a private patio and a naturalistic garden. The Sauna, located in the gravel garden looks out onto sculptures and plants.

Guest favourite
The exterior of the Victorian Reading Room is presented, showcasing a charming brick facade with light moss present on the roof. A welcoming entry door, framed by two chimneys, is complemented by modern windows. A vintage-style post box is positioned beside the entrance.
Tiny home in West Stafford
4.92 out of 5 average rating, 295 reviews

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.

Top Guest favourite
Barn in Dorset
5.0 out of 5 average rating, 231 reviews

Jurassic Coast Boutique Retreat with Views

Set amid the rolling Dorset countryside with far reaching breathtaking views The Hayloft is a stylish but relaxed retreat designed for slow, restorative stays. Part of Grandview Farm The Hayloft is a self contained annex offering a secluded, peaceful haven just moments from the Jurassic Coast. Thoughtfully styled with natural textures and luxurious touches throughout, it is the perfect base for a couple or two friends who enjoy coastal walks, cosy mornings and drinks under the stars.

Top Guest favourite
A charming stone cottage is depicted, featuring a well-maintained entrance with a decorative white railing. Lush greenery surrounds the doorway, complemented by flowering plants. The two-story structure exhibits traditional architectural elements, including a sloping roof and chimney, under a backdrop of a bright blue sky with scattered clouds.
Home in Osmington
4.96 out of 5 average rating, 50 reviews

Old Dorset Cottage

Relax with the whole family in this peaceful traditional Dorset Cottage. Set in the tranquil village of Osmington, this Cottage has all the traditional features with the exposed stonework, beams and large inglenook fireplace. It has been tastefully modernised to make it fit for a family get away. With a new kitchen, large farmhouse dining room and all facilities to help you feel right at home. Outside enjoy the gardens, bbq and patio and easy access to country walks and beaches.

Guest favourite
A well-maintained garden is framed by a charming stone house with dark-framed windows. An inviting grassy area features various flowering plants and a seating chair, while a wooden garden structure adds character. The image conveys a serene outdoor environment with a hint of nature.
Guest suite in Osmington
4.82 out of 5 average rating, 147 reviews

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.

Top Guest favourite
The exterior of the barn features a heart-shaped wooden accent on the entrance, surrounded by two planters with neatly trimmed shrubs. A pathway of stone slabs leads through a grassy area adorned with round stones and blooming flowers, set against a backdrop of large windows.
Barn in Dorset
4.99 out of 5 average rating, 150 reviews

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.

Guest favourite
A cozy bedroom features wooden paneling and natural light filtering through multiple windows. A double bed with floral bedding is positioned beside a nightstand and a chest of drawers. A plant and a television are also included, enhancing the tranquil ambiance.
Cabin in Osmington
4.89 out of 5 average rating, 87 reviews

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.

Top Guest favourite
A cozy sleeping area features a spacious bed with soft gray bedding and a decorative throw pillow. A wooden bookshelf displays various items, while a glass door opens to a view of the outside. Warm lighting highlights the room's inviting design.
Farm stay in Osmington
4.93 out of 5 average rating, 318 reviews

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.!

Top Guest favourite
An indoor swimming pool is featured, surrounded by large windows allowing natural light. The ceiling beams reveal a spacious, airy atmosphere. Two red chairs are positioned nearby, and a shallow end is visible with steps leading into the water. A blue cover rests along one side of the pool.
Cottage in Dorset
4.97 out of 5 average rating, 396 reviews

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!

Guest favourite
The exterior of the cottage features a charming stone façade with a thatched roof. A wooden door is surrounded by multiple windows. Lush greenery is present in the garden, along with a small patio area furnished with a dining set.
Cottage in Weymouth
4.95 out of 5 average rating, 129 reviews

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.

Top Guest favourite
Cottage in Osmington
5.0 out of 5 average rating, 12 reviews

Cosy Cottage with Hot Tub and Pub

Beautifully restored three-bedroom Dorset cottage sleeping up to six guests, perfectly located near Weymouth and the Jurassic Coast. Combining original character with modern comforts, the cottage features a cosy wood-burning stove, private garden and a traditional wood-fired hot tub. Ideal for families and friends, with a children's play area and the welcoming Sunray pub on-site. Dog friendly, with private parking for two cars included.

Top Guest favourite
A spacious patio area features a circular dining table surrounded by six chairs, complemented by a large umbrella. Decorative planters with green plants add a touch of nature. Full height glass doors provide a view of the surroundings while inviting natural light.
Apartment in Weymouth
5.0 out of 5 average rating, 554 reviews

Apartment with panoramic sea views

We are situated 600 yards, through the nature reserve, from the beach and at the top of the hill with panoramic views over Weymouth bay, beach and nature reserve. 3 miles from the town With loads of parking available outside .You’ll love my place because of the location, the views. good for couples, solo adventurers, business travellers and small, well behaved dogs.

Popular amenities for Osmington holiday rentals