Holiday houses in Osmington

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Top-rated holiday rentals in Osmington

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Guest favourite
The cozy living room features a historical stone fireplace with an inglenook, complemented by exposed beamed ceilings. A colorful area rug covers the wooden floor, and a green sofa is positioned opposite a wooden television stand. Soft cushions are arranged on the seating for comfort.
Cottage in Osmington
4.89 out of 5 average rating, 38 reviews

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

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, 292 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.

Superhost
A cozy living room is furnished with a spacious sectional sofa facing a wall-mounted TV. Large glass doors offer sweeping views of the sky and surrounding area. Green plants add a natural touch, while a sleek wood-burning stove creates a focal point in the inviting space.
Condo in Westbourne
4.84 out of 5 average rating, 193 reviews

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.

Top Guest favourite
The exterior of a modern stone cottage is shown, featuring a gravel driveway and landscaped areas with shrubs and plants. A large garage is visible, and the structure's red roof contrasts with the stone walls. A blue water barrel is positioned near the entrance.
Guest suite in Weymouth
4.92 out of 5 average rating, 200 reviews

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.

Top 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, 143 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, 148 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
4.87 out of 5 average rating, 79 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, 314 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.!

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, 395 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, 126 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.

Guest favourite
Cottage in Osmington
4.76 out of 5 average rating, 89 reviews

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.

Top Guest favourite
Home in Weymouth
5 out of 5 average rating, 8 reviews

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