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
4.88 out of 5 average rating, 33 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

Top 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, 285 reviews

The Old Reading Room West Stafford

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
4.85 out of 5 average rating, 189 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.

Superhost
An indoor pool is surrounded by sleek gray tiling and illuminated by recessed lighting. The pool's inviting turquoise water reflects the ceiling lights. A cozy seating area with cushions is visible in the corner, providing a relaxed atmosphere.
Cottage in Osmington
4.85 out of 5 average rating, 189 reviews

A luxury unique home spa - White Stones Retreats.

Set in a prime position amidst a quintessential village of thatched cottages. Where wildflower paths and trickling streams amble down the the beautiful Osmington Bay. Toe dipping in the shallows, coastal walks under flaring sunsets, hibernating in our home spa while storms crash outside. Our unique holiday home offers a sanctuary in all weathers. With a collated & collected vibe, this light filled cottage is perfect for families looking for a beach escape, only a 5 minute drive to the sea.

Top Guest favourite
An open living area features a modern, plush sectional sofa facing a large glass wall that connects to the outdoor space. Two small, round tables, one with a decorative tray, are positioned in front. Natural light fills the room, highlighting the simple decor.
Bungalow in Somerset
4.99 out of 5 average rating, 280 reviews

Modern & spacious house in the countryside.

The Pavilion is a modern, purpose built holiday house in the quiet Somerset village of Yarlington. It has all the conveniences: Wood burning stove, underfloor heating, Washer & tumble dryer, Iron & ironing board, fast fibre optic broadband and a charging station for an electric or plug in hybrid car, but sadly the mobile phone signal is very poor. The house is next to the pub and a stones throw from the church. The Newt and Hauser Wirth Gallery in Bruton are within a 15 minute drive.

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
5 out of 5 average rating, 39 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
Apartment in Weymouth
4.87 out of 5 average rating, 15 reviews

Spacious Beachfront Apartment, Sea Views, Parking

Just a 10-second walk from the beach, our spacious ground floor sea view apartment offers stunning beach and sea views. Relax in a large front room with comfortable armchairs, dining table, TV, and fiber internet. Includes a separate bedroom, a well-appointed kitchen with a cooker, microwave, toaster, and kettle, and a bathroom with a large bath and shower mixer. Large Victorian ceilings add character. Private off-road parking at the rear. Your perfect coastal retreat awaits!

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
4.81 out of 5 average rating, 139 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.

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, 71 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
An exterior view of the annex presents a combination of a stone and wooden facade. A seating area with four black chairs is surrounded by a gravel space, complemented by a decorative planter. The sky is clear and blue, enhancing the outdoor ambiance.
Farm stay in Osmington
4.93 out of 5 average rating, 302 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
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
4.96 out of 5 average rating, 119 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
A stone exterior of the home is visible, framed by lush greenery. A glimpse of the sea is seen in the background, with gentle light illuminating the setting. A pathway leads through the garden, enhancing the natural charm of the location.
Place to stay in Osmington
4.99 out of 5 average rating, 74 reviews

Delightful one bed property on the Jurassic Coast

This unique single storey home has been refurbished to a high standard and makes comfortable accommodation for two people. Situated in the garden of the owners' thatched thirteenth century cottage it offers plenty of character, and is well screened from main house. It sits in a delightful garden with table and chairs for your use. It is situated within yards of the beautiful Jurassic coastal path.

Popular amenities for Osmington holiday rentals

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  4. Dorset
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