We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Airbnb your place

Cottage vacation rentals in Osmington

Find and book unique cottages on Airbnb

Top-rated cottage rentals in Osmington

Guests agree: these cottages are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

1 of 3 pages

Cottage in Dorset

4.88 out of 5 average rating, 308 reviews

18th Century Coastal Cottage

This historic home features original stone floors, rustic wood beam ceilings, a wood-burning fireplace, modern finishes, a sauna, and a private back patio overlooking the beach. Breathe in the refreshing ocean air from this hillside retreat. I’m sorry I have a no pets policy at the cottage. This cottage has steep stairs, low ceilings, a very low rise bed and a low sofa as seen in the pictures. 60 Mallams was built in approximately 1760 and still has many rustic features throughout. The cottage has two levels, ground floor consists of open plan lounge leading to the kitchen then conservatory with shower room. Which opens out into courtyard garden with a terrace and sea views. 1st floor has the main bedroom with a super king size bed and separate bathroom with a free standing bath with room for two.. Private parking on driveway 24hr key access safe by the front door I can be contacted at any time throughout your stay. The property is located just a five minute walk from Chesil Beach. It is also close to a number of the town's local shops and cosy pubs. There’s plenty of coastal walks all around Portland The sailing club is close offering various water sports There is bus services to and from Weymouth. There are amazing coastal walks around Portland. Please be mindful of the rubbish I have food waste bins , glass only tubs and the larger of the wheelie bins (green) are recycling only ( cans paper and plastic) and the black bins are general rubbish.. please be careful with the rubbish because if it's all mixed up the bin men won't take it away...

Sep 1 – 8

R4,037 ZAR per night

Cottage in Dorset

4.98 out of 5 average rating, 281 reviews

The Old Apple Store, Bridport and Jurassic Coast

Our cottage is nestled in the heart of the Bride Valley close to the Jurassic Coast. This converted barn has views over our orchard. The cottage is 20 minutes drive from Dorchester and Bridport. 40 minutes to Durdle Door. Upstairs kitchen area with cooker, fridge, washing machine, lounge area with lots of books, DVD ‘s. Dining area and balcony with seating. Downstairs Large bedroom with King Size bed. Bathroom with shower. Outside pretty walled garden with seating. Min 2 night stay.

Oct 11 – 18

R2,501 ZAR per night

Cottage in Dorset

4.97 out of 5 average rating, 540 reviews

Cute & Cosy Bothy Cottage, near Sherborne & Yeovil

The Bothy is a stylish detached cottage where you can share some Prosecco on your terrace or snuggle up beside a log fire Dating from the 1700's, our recently restored "boutique" stone cottage is in the rural historic Yetminster Conservation Area with a thatched pub, lovely local cafe & shop. It is next door to a quintessential English Heritage listed thatched cottage You are on the edge of the Dorset Area of Outstanding Natural Beauty and you have great access to the sea on the Jurassic Coast

Sep 28 – Oct 5

R2,622 ZAR per night

Cottage in Dorset

4.94 out of 5 average rating, 210 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.

Sep 6 – 13

R5,959 ZAR per night

Cottage in Langton Matravers

4.92 out of 5 average rating, 133 reviews

Cosy Cottage in Rural Hamlet on the Jurassic Coast

Quirky, Cozy Cottage. Perfect for a romantic winter/summer break. Mutli -Fuel burner and a Super-King Size Bed. Located in Acton, A small tranquil hamlet, The cottage is surrounded by fields and located right on the South West Coast Path. Incorporating breath-taking views from all around. Everything is on your doorstep! Walkable is the Square and Compass, The Kings Arms in Langton, Dancing Ledge, Seacombe, Chapmans Pool, Dinosaur Footprints, The South West Coast Path and Swanage Beaches.

Feb 2 – 9

R2,229 ZAR per night

Cottage in Easton

4.92 out of 5 average rating, 167 reviews

Milly Moll Cottage, next to Church Ope Cove.

Julie and Matt welcome you to Milly Moll Cottage. A quirky C18th, grade 2 listed property full of character and charm, just next door to the Portland museum. Built of Portland stone with original fireplaces and a cozy lounge with a log burner, from here you can explore the Jurassic coast. It’s a 2 minute walk to Church Ope Cove, either passing under Rufus Castle arch or via the ruins of St Andrews church and is ideally placed for numerous outdoor pursuits. We hope you will enjoy your stay.

Oct 12 – 19

R2,262 ZAR per night

Cottage in Sutton Poyntz Weymouth

4.85 out of 5 average rating, 160 reviews

A peaceful retreat to rest, recharge and explore.

A cosy self-contained Annex with open plan living area, log burner and character wood floor and stone walls. A spiral staircase leads up to a very comfortable double bedroom with a king-size bed. The bedroom on the ground floor contains a double bed and enjoys patio doors leading onto a small private garden with patio table and chairs. The property is hidden away in a very quiet, peaceful setting and is entered from the gravel drive through the front door into the light airy kitchen.

May 17 – 24

R3,668 ZAR per night

Cottage in Winfrith Newburgh

4.98 out of 5 average rating, 252 reviews

Bramble - 17th Century Barn Conv -enclosed garden

Bramble Barn is a beautiful 17th-century barn conversion situated down a private road just 4 miles from Lulworth Cove, Durdle Door and the Jurrasic Coast World Heritage Site. This large splendid brick barn has been converted into two identical properties creating accommodation of the highest standards. Each barn has its own enclosed garden and a south-facing terrace, ideal for eating out. Tadnoll Heath, a Dorset Wildlife Trust Reserve, lies just to the north. Ample off-road parking.

Mar 10 – 17

R3,072 ZAR per night

Cottage in Dorset

5.0 out of 5 average rating, 109 reviews

Rocket Cottage with sea views

Rocket Cottage is a perfect getaway from the crowds . It is a detached self contained cottage set in the garden of the main house with breathtaking countryside & sea views. Situated off a quiet country lane, 8 mins walk to village pub & farm shop. Large open plan living/dining/kitchen. The kitchen is fully equipped. Bedroom with super king bed and en-suite. Perfect for couples. Excellent for walkers/cyclists to explore the Jurassic Coast. Woodburner and CH for all year round booking.

May 18 – 25

R5,214 ZAR per night

Cottage in Lewell

4.94 out of 5 average rating, 245 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.

Jan 27 – Feb 3

R3,209 ZAR per night

Cottage in Dorset

4.92 out of 5 average rating, 135 reviews

Chesil Cove Holiday Cottage

A Grade II listed traditional characterful fisherman's cottage located adjacent to the iconic Chesil Cove on the island of Portland, part of the Jurassic Coast. The cottage is small and cosy with two bedrooms, small upstairs wetroom and modernised kitchen with solid wood breakfast bar. The wooden stairs are very steep and narrow so the property is not suitable for young children. An enclosed south-facing backyard is a suntrap for private sunbathing, drying swimming/diving gear etc.

May 11 – 18

R2,098 ZAR per night

Cottage in Fortuneswell

4.98 out of 5 average rating, 186 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, 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.

Nov 8 – 15

R2,930 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Osmington cottage rentals

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

Cottage in Dinnington

4.95 out of 5 average rating, 429 reviews

The Cottage, Parsonage Farmhouse with hot tub

Nov 8 – 15

R2,814 ZAR per night

Cottage in Moreton

4.95 out of 5 average rating, 151 reviews

A Stunning Dorset Thatched Cottage - Dog friendly

Mar 1 – 8

R4,312 ZAR per night

Cottage in Dorchester

4.99 out of 5 average rating, 166 reviews

Charming Brick Cottage with a Patio and Hot Tub

Mar 31 – Apr 7

R5,213 ZAR per night

Cottage in Thornicombe

4.83 out of 5 average rating, 304 reviews

Ranmoor Estate - Owl Lodge - Hot Tub & A/C

Oct 15 – 22

R3,930 ZAR per night

Cottage in Cotford Saint Luke

4.99 out of 5 average rating, 116 reviews

stylish barn conversion with hot tub and lake view

Feb 15 – 22

R3,780 ZAR per night

Cottage in Hampshire

4.98 out of 5 average rating, 583 reviews

Detached and romantic cottage with hot tub.

Nov 28 – Dec 5

R4,075 ZAR per night

Cottage in Chard

4.97 out of 5 average rating, 233 reviews

Abbey View Cottage - Scandi Hot Tub - EV Charging

Mar 7 – 14

R3,515 ZAR per night

Cottage in Spaxton

4.98 out of 5 average rating, 110 reviews

Stay in the AONB with Own Hot Tub, Dogs Welcome

Mar 22 – 29

R3,506 ZAR per night

Pet-friendly cottage rentals

Cottage in Morcombelake

4.97 out of 5 average rating, 336 reviews

Romantic hillside hideaway with outstanding views

Mar 2 – 9

R5,022 ZAR per night

Cottage in Corfe Castle

4.99 out of 5 average rating, 202 reviews

Cottage by the Common, Corfe Castle

Oct 7 – 14

R3,635 ZAR per night

Cottage in Downton

4.96 out of 5 average rating, 438 reviews

The Coach House with walled garden

Sep 16 – 23

R2,299 ZAR per night

Cottage in Hooke

4.93 out of 5 average rating, 225 reviews

The Little House, Hooke, Nr Bridport, West Dorset

Oct 22 – 29

R2,923 ZAR per night

Cottage in Freshwater

5.0 out of 5 average rating, 387 reviews

A beautiful country cottage, close to the sea

Nov 29 – Dec 6

R3,122 ZAR per night

Cottage in Somerset

4.94 out of 5 average rating, 262 reviews

Cottage in the heart of Montacute

Jan 5 – 12

R2,520 ZAR per night

Cottage in Dorset

4.85 out of 5 average rating, 352 reviews

Character cottage close to beach

Oct 17 – 24

R3,115 ZAR per night

Cottage in Chetnole

4.9 out of 5 average rating, 146 reviews

Grove Farm Cottage-historic Cottage near Sherborne

Oct 30 – Nov 6

R2,493 ZAR per night

Private cottage rentals

Cottage in Dorset

4.97 out of 5 average rating, 156 reviews

Lovely cosy place to stay in the heart of Dorset

Oct 23 – 30

R2,316 ZAR per night

Cottage in Portland

4.89 out of 5 average rating, 129 reviews

Number 107, Isle of Portland, Dorset

Dec 11 – 18

R2,424 ZAR per night

Cottage in Dorset

4.96 out of 5 average rating, 108 reviews

Harbour's Edge Cottage - Nothe Parade, Weymouth

Jan 6 – 13

R4,040 ZAR per night

Cottage in Okeford Fitzpaine

4.97 out of 5 average rating, 303 reviews

The Garden House Okeford Fitzpaine Dorset

Jun 30 – Jul 7

R3,262 ZAR per night

Cottage in Waytown

4.97 out of 5 average rating, 215 reviews

Gorgeous rural cottage nr Jurassic Coast

Feb 28 – Mar 7

R2,649 ZAR per night

Cottage in Langton Matravers

4.91 out of 5 average rating, 345 reviews

Chapel Cottage

Apr 24 – May 1

R2,743 ZAR per night

Cottage in Axminster

4.98 out of 5 average rating, 116 reviews

The Nest, thatched barn conversion near Lyme Regis

Feb 10 – 17

R2,913 ZAR per night

Cottage in Dorset

4.95 out of 5 average rating, 102 reviews

Spacious Family Cottage with Sea Views of Chesil

Sep 30 – Oct 7

R4,552 ZAR per night

Destinations to explore