Cottage holiday rentals in Osmington

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Top-rated cottage rentals in Osmington

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Guest favourite
Cottage in Portland
4.92 out of 5 average rating, 213 reviews

1888 Portland stone cottage

1888 Portland stone cottage, with many original features. Stone fireplace with log burner. Cosy 2 bedroom, 3 storey cottage located within easy walking distance of Easton Square, which has local amenities, including grocery stores, chemist, pubs and cafes. Small sunny aspect courtyard with bistro table and chairs. A perfect holiday location all year round, for either sun and relaxation, or enjoy activities like windsurfing, sailing, diving, rock climbing, fishing, walking and bird watching.

Top Guest favourite
The charming exterior of Carter's Cottage is showcased, featuring traditional stone walls and a thatched roof. Lush greenery surrounds the property, while the gravel pathway leads to a welcoming entrance framed by potted plants.
Cottage in Chideock
4.87 out of 5 average rating, 102 reviews

Authentic thatched cottage, mins from coast

Thatched Carters Cottage nestles in the peaceful Dorset hamlet of North Chideock, adjacent to 16th century Home Farm Cottage. A fabulous rambler's location, with EV charger, 40 mins walk from the Jurassic coastline, 3 thatched pubs, Spar shop, Felicity's Farm Shop, Hell's Lane fab hollow-way, Colmers Hill & Symondsbury Estate Cafe. 15 mins drive to Lyme Regis. The cosy Cottage is simply furnished - 2 bedrooms, bathroom, kitchen & TV lounge. Guest parking with private garden and bike storage.

Superhost
The exterior view of the converted barn is presented, showcasing the stone structure surrounded by lush greenery. A gravel driveway leads to the property, with an outdoor seating area visible. Neat hedges outline the garden, offering a sense of privacy amid the scenic countryside.
Cottage in Portesham
4.93 out of 5 average rating, 263 reviews

Little Barn is a cosy dwelling in a remote valley

Little Barn is located in a remote valley between Upwey and Portesham near Weymouth in Dorset A converted Barn with a modern open plan interior. An adequate garden with Outdoor furniture and BBQ with an external secure store for bicycles etc. The area is good for walking (dogs welcome), many footpaths line the surrounding countryside. Hardy's monument is situated a few miles away. The area offers good cycling both on and off road. Good access to the Dorset coastline which is a short drive away.

Top Guest favourite
A bright living area features a comfortable sofa with navy blue and plaid cushions, complemented by a rustic coffee table. A flat-screen TV is mounted on the wall, and natural light floods in through large windows, illuminating the stone wall and wooden furniture.
Cottage in Weymouth
4.97 out of 5 average rating, 176 reviews

Cottage close to Beach & Old Harbour with Parking

Sydenham Cottage is an attractive cottage with designated parking, refurbished to a high standard; designed to make you feel at home. The cottage is located in the heart of Weymouth just 2 minutes walk from restaurants, cafes, the old harbour, and award winning blue flag beach. The house is perfect for families or couples wanting a cosy retreat. You can walk from the house to the sandy beaches, craggy cliffs off the Jurassic Coast with the Dorset Downs nearby, so walkers will love it too.

Guest favourite
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
4.86 out of 5 average rating, 169 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
A bright and inviting bedroom features a spacious king-sized bed dressed in soft linens with decorative cushions. A rustic chest of drawers complements the decor. Natural light filters through a window adorned with delicate curtains, enhancing the warm atmosphere.
Cottage in Stourpaine
4.96 out of 5 average rating, 158 reviews

Tudor Rose Luxury thatched cottage Dorset.

A boutique and chic thatched cottage for 2 nestled within the beautiful village of Stourpaine in an AONB. Escape to this romantic couples hideaway for the ultimate luxury getaway. Finished and equipped to a high standard including king size bed with designer linens, roll-top bath and separate shower, cosy lounge, separate dining room, fully equipped kitchen and lovely sunny courtyard. Great walks and the superb village pub are just a short stroll away. 1 small dog is welcome to join you!

Guest favourite
A private garden features a round table surrounded by four chairs, set on a stone patio. Lush greenery and flowering plants border a well-maintained lawn, while a rustic shed is visible in the background under a clear blue sky dotted with clouds.
Cottage in West Knighton
4.94 out of 5 average rating, 303 reviews

Jasmine Cottage

Jasmine Cottage is a characterful, compact barn conversion, that sits next to the 400 year old farm house. It sleeps up to four people (including infants), with a double and a twin room. We are one mile away from The Wise Man Inn - an award-winning pub; 6 miles from Dorset's stunning Jurassic coast and 3 miles from the county town of Dorchester. You will, however, need a car- or bikes! Sorry, no pets and no smoking. No EV charging, yet, but there are many fast charging points nearby.

Guest favourite
The exterior features a quaint stone facade complemented by a black front door and window boxes filled with greenery. The entrance is framed by a cobblestone pathway, with a visible sign indicating 'The Old Stable.' Natural light illuminates the inviting entrance.
Cottage in Corfe Castle
4.91 out of 5 average rating, 223 reviews

The Old Stable central & OSP, 2 bed/2 ensuite

The Old Stable , situated in the centre of the historical village of Corfe Castle, Dorset overlooking the Castle Ruins with OSP Recently converted with original features, open plan lounge, Purbeck stone wall, wood flooring, leading to a bespoke hand painted Kitchen providing all mod cons & dining table Upstairs 2 bedrooms (1 small double & 1 twin room) 2 en-suites, A picturesque Idyllic location, perfect to rest & enjoy Tea rooms, Jurassic coastline, local beaches. & pubs

Top Guest favourite
The exterior of the Artist's Studio is highlighted by soft lighting that outlines the balcony and windows, creating an inviting ambiance. Lush gardens surround the stone structure, showcasing a variety of plants and flowers against the evening sky.
Cottage in Widworthy
5 out of 5 average rating, 102 reviews

Luxurious studio for two with spectacular views

  Situated in the East Devon National Landscape at the end of a magical winding country lane is the stunningly located Artist’s Studio - luxury accommodation nestling in a south facing hillside and boasting far-reaching uninterrupted views across the spectacular Devon countryside. The Studio, originally a barn, is now a spacious self catering rural retreat, comfortably accommodating 2 adults, with huge vaulted ceilings and where your every whim and desire is catered for.

Top Guest favourite
A view of Maidenwell Cottage from the garden, showcasing a landscaped area with palm trees and vibrant flowers. The cottage's exterior features a blue door and a stone wall, framed by greenery that enhances the inviting outdoor space.
Cottage in Portland
4.99 out of 5 average rating, 303 reviews

Maidenwell Cottage. Near Chesil Beach, Portland

Maidenwell Cottage is a Grade II listed period property on Portland, the southernmost point of the Jurassic Coast that has been refurbished to a high standard and designed to make you feel at home. Chesil Beach, local shops, cafes and pubs are all a within a short walking distance. Maidenwell Cottage is perfect for families and couples looking for a cosy seaside retreat and those looking for a place to relax following a day of walking, climbing and water sports.

Guest favourite
The exterior of The Parlour cottage is depicted, featuring a brick façade with large windows that allow natural light to fill the interior. A spacious gravel area surrounds the cottage, providing convenient access. The tranquil countryside can be glimpsed in the background under a clear blue sky.
Cottage in Buckland Newton
4.95 out of 5 average rating, 175 reviews

The Parlour, Duntish Mill Farm, EV Charging

The Parlour is a 3 double bedroom cottage which is part of Duntish Mill Farm that has recently been lovingly renovated. There is open plan living with vaulted ceilings and a cosy log burner. French doors that lead onto a large private patio area. Located in an AONB of Dorset, we are surrounded by plenty of stunning countryside centrally located between the historic towns of Sherbourne and Dorchester, which is also only a short drive away from the Jurassic Coast.

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 Warmwell
4.98 out of 5 average rating, 375 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!

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