Cottage vacation rentals in Osmington

Cute, Cosy & Stylish Bothy Cottage, near Sherborne

Stylish, Comfortable & Quirky - “Top 10 Dorset Airbnb” (Conde Nast Traveller) in a “Top 50 UK Village” (Sunday Times). The Bothy is a detached stone cottage where you can share some free Prosecco on your private terrace. It is in the rural historic Yetminster Conservation Area with a thatched pub, café & shop. It is next door to a quintessential "Chocolate Box" thatched cottage. You are on the edge of the Dorset Area of Outstanding Natural Beauty with good access to the sea & Jurassic Coast.

The Coach House, Duntish Mill Farm, EV Charging

Whether you're exploring Dorset's countryside and coastline or simply looking to switch off for a few days The Coach House offers a peaceful escape for two. Beautifully renovated it combines exposed beams, a cosy wood-burning stove and a luxurious walk-in rainfall shower with plenty of space to relax and unwind Set within Duntish Mill Farm between Sherborne and Dorchester and within easy reach of the Jurassic Coast, it's the perfect base for discovering some of Dorset's most beautiful landscapes

Stylish Country Cottage, Popular Village, sleeps 6

A stylish cosy village cottage, centrally located in the popular, sought after Somerset village of Curry Rivel is perfect for group trips, family get togethers, sophisticated stag or hen do's, suitable for walkers, cyclists, weekends away with friends and we’re dog friendly. Modern, quirky interiors give the cosy cottage a feeling of space and light. The cottage has all amenities within a minutes walk including popular The Firehouse Somerset pub, One Stop Convenience Store, Petrol Station & PO.

Honeysuckle Cottage: Lulworth Cove & Durdle Door

A beautifully restored 300-year-old thatched retreat in the heart of West Lulworth. Tucked among the historic thatched cottages Honeysuckle Cottage is a romantic one-bedroom retreat a short stroll from Lulworth Cove, Durdle Door and the Coast Path. Lovingly restored over two years with quality craftsmanship and carefully chosen finishes, the cottage blends historic character with modern comfort, offering a peaceful, luxurious base to explore the Jurassic Coast. Arrive, unpack, and slow down.

Beautiful 2 bedroom cottage in glorious Dorset

Nestled in the picturesque Dorset countryside, this charming Portland stone cottage offers a quintessential English retreat. Set within the grounds of a historic Old Rectory, the property is surrounded by rolling hills, lush meadows, and the tranquil River Frome, providing an idyllic spot for a holiday. It is all on one level,we are able to rent out the whole cottage also which creates an additional 2 bedrooms for extended family - we rarely rent this out to another party and is mostly empty.

Romantic hillside hideaway with outstanding views

A unique and romantic hideaway, Quarryman's Cottage is dinner on the roof terrace watching the sunset over Lyme Bay & Charmouth, stargazing from the luxury freestanding bath, epic views from the double shower, reading under the old oak tree, BBQ's & firepits, leisurely walks to The Anchor at Seatown via Golden Cap or the coastal path, the sound of birdsong, the glimpse of a deer, curling up in front of the wood burner in winter. It is a tranquil & heavenly escape from the bustle of daily life.

The Hollies, Dorset A countryside~coastal ‘gem’

Close to the coast, ‘The Hollies, Dorset’. Relaxing, quiet ‘getaway’ for you and family in a pretty village 5 mins stroll from a super pub. Mid-terrace single story with dogs welcome (please enquire). Access to SW Coast Path, towns, beaches & visitor attractions inc Lulworth Cove & Castle, Durdle Door, Monkey World & The Tank Museum. 3 beds (2 double, 1 single) *fold-out bed for extra child. Big well-equipped kitchen. Cosy lounge. Enc rear garden, 2 parking spaces. Peruse our 5* reviews!

Cobb Cottage - Harbourside, permit parking

Cobb Cottage is a stylish hideaway, tucked down a cobbled side street in the heart of Weymouth's historic harbour. The cottage has been lovingly converted from a former bookshop into a contemporary, centrally located holiday home with easy access to Weymouth harbour. Perfectly suited for two couples or a family, with three bedrooms and two bathrooms. There is a parking permit to for one car which provides free parking on street outside the cottage, or in a nearby car park. Dog friendly!

Stunning Barn conversion with heated swimming pool

Courage Cottage is a two bedroom detached barn conversion in a Georgian farmyard.The barn was converted in 2013 so has all modern conveniences including underfloor heating. It is very individual and situated in a quiet , rural setting. It has two bedrooms with en-suite bathrooms. The village of Martinstown has an excellent pub and shop. Dorchester is 2 miles away and has every facility including good rail connections in all directions.Swimming pool (shared ) open May 15th-Sept 15th

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.

Berry Farm Cottage

Berry Farm Cottage nestles in a private area of the grounds of Berry Farm, which dates back to the 16th century. It is located in the charming Conservation Village of Walditch, within walking distance of Bridport. The Cottage itself has 2 bedrooms and two bathrooms with an open-plan living space and is set away from the main house in its own private grounds, with 1,200sqm (0.3acres) of orchard garden, as well as an outside patio with table and chairs, with country views.

Secluded Woodland Cottage with Private Hot Tub

Escape to Meadow Cottage, a peaceful countryside retreat perfect for couples. This modern studio features a private hot tub, a dedicated workspace with super-fast fiber optic internet, and a fully fenced yard. Enjoy access to 40 acres of private woodland. Watch wildlife from your window in this cozy, pet-friendly getaway. Comfortably fits 2 guests. • King Size Bed • Private Hottub • Dog Friendly • Fully Equipped Kitchen • Private Garden • Smart TV • Super Fast WiFi