Holiday rentals in Osmington

4.91 out of 5 average rating, 458 reviews

Apartment in Dorset

1 Bed home near Sailing academy Portland, Weymouth

The home is located in Portland near to a Port and 5 miles to Weymouth also 10 min walk to sailing academy The area is noted for diving,windsurfing,fishing,sailing,extensive coastal walks,rock climming, cycle routes It is a one bedroom apartment.There is a small Beach and it’s a short walk to shops,cafe's and restaurants.Includes an open plan kitchen,living room and en-suite bathroom with electric showerThere is a sofa bed on request Parking is nearby but free parking is available in the street

4.88 out of 5 average rating, 275 reviews

Hut in Owermoigne

Woodland Retreat Log Cabin nr Durdle Door Weymouth

Come stay in our secluded woodland glade in your own log cabin! Bring your own bed linen. Snuggle by the outdoor fire pit. Enjoy the views across picturesque dorset countryside. Super cosy and surrounded by nature! Only 10 minutes drive to the World Heritage Jurrasic coast, Dorset's famous beaches Durdle Door and Lulworth Cove. Parking 50 metres away with compost toilet and basic outside off grid shower. Check out our Magic, Bus, Yummy Yurt, and Homely Horsebox for more luxurious accommodation.

5 out of 5 average rating, 223 reviews

Barn in Dorset

Galton Barn, farm stay nr Durdle Door and Lulworth

Strictly no Pets Bright and spacious three bedroom self-contained newly converted dairy barn, nestled down private a track on Galton Organic Farm. Conveniently located that it is of an easy driving distance to Durdle Door and Lulworth Cove, Weymouth, the Jurassic Coastline and the Purbeck’s. And close enough to take a hearty walk to soak in the breathtaking views over Ringstead Bay. The Barn comfortably sleeps 5 persons please contact us prior to booking if you intend to book for more than 5.

Superhost

4.86 out of 5 average rating, 129 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.

4.91 out of 5 average rating, 219 reviews

Guest suite in Dorset

Discover Little Drey: Your Perfect Getaway

At Little Drey, you'll find comfort, and warm hospitality, all while being conveniently close to Dorchester. A variety of restaurants, cafes, and shops are all within walking distance. Close to some of the best places to visit in Dorset, and within easy reach of famous beauty spots and amazing places to visit. Parking on property along with self-check-in, makes it super easy to have a relaxing, enjoyable break. Your host lives next door and is on hand to make your stay the best possible.

4.94 out of 5 average rating, 282 reviews

Cottage in Lewell

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.

4.83 out of 5 average rating, 240 reviews

Guest house in Southhill

Bright & Snug annexe with Parking in Weymouth

Welcome to our one bedroom self contained private accommodation with parking space in Weymouth. Consisting of a double bed, two seater sofa, mini kitchen unit with sink, kettle & toaster, fridge, smart TV, chest of drawers, shower room. Weymouth town Centre, train station and Weymouth’s popular beach is a 20 minute walk through the RSPB nature reserve, where you will see swans, ducks & plenty of bird species. Pub, pharmacy & shop is only a 5 min stroll down the road.

Superhost

Guest suite in Osmington

4.78 out of 5 average rating, 116 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.

4.98 out of 5 average rating, 356 reviews

Cottage in Dorset

The Condo (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!

4.98 out of 5 average rating, 128 reviews

Home in Dorset

Cheerful one bedroom home in the heart of Dorset

A great base for exploring Dorset and centrally-located. This newly decorated self contained 1 bedroom annexe has a fully equipped kitchen & in the county town of Dorchester, the birth place of Thomas Hardy. It is a perfect base to explore the beautiful countryside and Jurassic coast! The town’s amenities are only a short walk away including the new Brewery Square development. Complimentary tea and coffee also provided.

4.93 out of 5 average rating, 244 reviews

Farm stay in Osmington

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 three pubs all within walking distance, aswell as a farm cafe and shop located 5 minutes away. Best ice-cream around!

4.91 out of 5 average rating, 404 reviews

Flat in Weymouth

(Upper Deck) Beachside studio Weymouth

A stones throw from the waters edge this studio has 270 degrees of coastal views from an elevated position (The 'crows nest' balcony! ) The windows and Private balcony have outstanding panoramic views across the Jurassic coast and Weymouth, catching beautiful sunrise and sunsets. NO NEED FOR A CAR- ITS ALL HERE! ...(NEW : ‘Beryl bikes’ nearby!) Great vibe at the famous Oasis Cafe nearby.

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Pool

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Other great holiday rentals in Osmington

5 out of 5 average rating, 7 reviews

1 Bed in Osmington (82098)

NeilRating, 5 stars3 months ago

We had a lovely stay here in March 25 The accommodation was spotless and lovely The added bonus of a hot tub was great Overall can't think of any major issues Only tiny one was maybe a black out blind in the bedroom to block out the light as the blinds there let a lot of light in but didn't detract from our stay Would definitely book here next year

5 out of 5 average rating, 13 reviews

Home in Osmington

Old Dorset Cottage

BenRating, 5 stars1 week ago

My family & I had a lovely 2 night stay at Richard & Lizzie’s cottage. They were both very responsive when I had a question about the bunkbeds (plenty of room for a tall chap like myself!) The cottage was easy to find & to get inside. It is very spacious & decorated very nicely - the garden is particularly lovely & great for when the sun’s out! My family (5 of us) had plenty of room and had a relaxing time away. Thanks so much Richard & Lizzie!

Tiny home in Preston

5 out of 5 average rating, 4 reviews

Cosy Cabin Near The Coast

KarthikRating, 5 stars2 weeks ago

The place was a bit small unlike the photos , but everything else was just perfect. Good location,just 20 mins drive to Durdle door. Host is very responsive and the place was clean and cosy.

4.97 out of 5 average rating, 108 reviews

Private room in Preston

Private Room in small cul-de-sac close to Weymouth

KyraRating, 5 stars1 day ago

Laura and Dave’s place was absolutely fantastic. Exactly what we needed for a short stay after a strenuous hot hike! The small touches wee everything. Cannot recommend enough.

4.7 out of 5 average rating, 50 reviews

Old Post Office Thatched Cottage

AnnaRating, 5 stars1 month ago

We had such a lovely peaceful stay in this beautiful cottage. Absolutely stunning house, so spacious and bigger than the photos online. Kate was friendly and super responsive, offering advice and tips for local places and answering any questions we had really quickly. She offered us a late check out which was really kind and considerate too. The area is so stunning, chocolate box village with beautiful beaches and walks nearby. Would definitely recommend and can’t wait to return.

Guest suite in Broadmayne

5 out of 5 average rating, 75 reviews

Stunning and luxurious Manor House holiday home

LucyRating, 5 stars3 days ago

The Orangery is absolutely lovely and exactly as the photos show. Excellent location for exploring the jurassic coast and surrounding areas. We would stay in this location again when we come back to this area.

Cottage in Osmington Mills

4.74 out of 5 average rating, 19 reviews

The Boathouse Osmington Mills

WarrenRating, 5 stars1 week ago

Wonderful cottage for a short stay for our small family in the beautiful Osmington Mills.