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.

Pilgrims Cottage-Luxury Grade 1 Listed cottage

Take it easy at this unique and tranquil getaway. Come and unwind in our Grade 1 listed cottage set in the most beautiful street in gorgeous Cerne Abbas. Steeped in history you won’t want to leave this hidden gem. Out the front door are walks for miles and a visit to the Giant is a must! Then either cook up a storm in the well equipped kitchen , enjoy the garden with Big Green Egg bbq or wander down to the choice of three local pubs. The Sea is just a short 30 mins drive. Parking free opposite

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.

Authentic, cosy, thatched cottage, mins from coast

Cosy Carters Cottage nestles in the peaceful Dorset hamlet of North Chideock, adjacent to 16th century Home Farm Cottage. A fab 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 smugglers hollow-way, Colmers Hill & Symondsbury Estate Cafe. 15 mins drive to Lyme Regis. The cottage is simply furnished - 2 bedrooms, (second at top of stairs) WC, kitchen & lounge. Guest parking with private, walled garden.

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.

Strawberry Cottage

Lovingly restored and modernised by Harry in 2011, Strawberry Cottage is nestled by the river Wey in the village of Upwey, Dorset. This quaint property is close to the famous Jurassic Coast, within 4 miles of the seaside town of Weymouth and Dorchester town.Durdle Door / Lulworth Cove is an approximate 29 minute drive,and the main supermarket is 8 minutes away by car. Upwey has two pubs a busy tearoom,garden nursery and Tesco Express all within 5 to 10 minutes walk. Relax inside or out.

Luxury Interior Designed Retreat w/Tennis Court

This 17th Century Grade II Listed Cottage, nestled in the beautiful Cranborne Chase AONB, is a luxurious, interior designed haven perfect for a tranquil getaway. The design and decor offers a blended creation of contemporary and period accents, combining original rustic features with an architecturally-crafted state of the art extension for spacious dining and lounging. This is an ideal spot to kick back and relax in a calm, stylish space, whilst only being a short drive from civilization.

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.

Cosy ecolodge with free parking near town & beach

Asker Lodge is an eco-friendly lodge, seconds from the Old Railway Track for a lovely 2.4 mile stroll or cycle to the Jurassic Coast at West Bay. Or walk 15 mins in the opposite direction and you're in Bridport's bustling town centre Downstairs, there's an inviting open plan kitchen & living room opening onto a sunny patio garden. There's also a log burner & sofa bed, plus bathroom with electric shower. Upstairs are 2 cosy bedrooms (1 double & 1 single). Free parking for 2 cars