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Cottage holiday rentals in Osmington

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Top-rated cottage rentals in Osmington

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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...

12–19 Dec

$297 SGD per night

Guest favourite

Cottage in Dorset

4.97 out of 5 average rating, 539 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

10–17 Oct

$193 SGD per night

Guest favourite

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.

17–24 Mar

$186 SGD per night

Guest favourite

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.

4–11 Sep

$438 SGD per night

Guest favourite

Cottage in Dorset

4.98 out of 5 average rating, 155 reviews

Lovely cosy place to stay in the heart of Dorset

Oak Tree Barn is a self-catering holiday accommodation in the heart of the village of Hazelbury Bryan, Dorset. The conversion was completed in early 2012 using locally reclaimed materials and keeping many of the original features. The Barn is warm and cosy in winter and cool in summer, the detached Barn has a large open-plan lounge and kitchen with views towards the local hills. The two bedrooms (one double with bath, one twin with shower) overlook paddocks where sheep graze and chicken forage.

23–30 Oct

$170 SGD per night

Guest favourite

Cottage in Morcombelake

4.97 out of 5 average rating, 336 reviews

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.

1–8 Apr

$369 SGD per night

Guest favourite

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.

8–15 Apr

$164 SGD per night

Guest favourite

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.

7–14 Oct

$166 SGD per night

Guest favourite

Cottage in Winfrith Newburgh

4.97 out of 5 average rating, 187 reviews

17th century barn conversion with enclosed garden

Tanglewood 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.

22–29 Jun

$272 SGD per night

Guest favourite

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.

17–24 May

$270 SGD per night

Guest favourite

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.

9–16 Dec

$236 SGD per night

Guest favourite

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.

23–30 Jul

$151 SGD per night

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Popular amenities for cottage rentals in Osmington

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Air conditioning

Cottage rentals with a hot tub

Guest favourite

Cottage in Moreton

4.95 out of 5 average rating, 151 reviews

A Stunning Dorset Thatched Cottage - Dog friendly

17–24 Jun

$303 SGD per night

Guest favourite

Cottage in Dinnington

4.95 out of 5 average rating, 428 reviews

The Cottage, Parsonage Farmhouse with hot tub

25 Nov – 2 Dec

$207 SGD per night

Guest favourite

Cottage in Dorchester

4.99 out of 5 average rating, 166 reviews

Charming Brick Cottage with a Patio and Hot Tub

17–24 Feb

$383 SGD per night

Cottage in Thornicombe

4.83 out of 5 average rating, 304 reviews

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

9–16 Feb

$280 SGD per night

Guest favourite

Cottage in Chard

4.97 out of 5 average rating, 233 reviews

Abbey View Cottage - Scandi Hot Tub - EV Charging

20–27 Dec

$258 SGD per night

Guest favourite

Cottage in Devon

4.99 out of 5 average rating, 141 reviews

Romantic oasis, hot tub, Lyme Regis, ‘Retreat’

11–18 Apr

$292 SGD per night

Guest favourite

Cottage in Hampshire

4.98 out of 5 average rating, 583 reviews

Detached and romantic cottage with hot tub.

3–10 Nov

$293 SGD per night

Guest favourite

Cottage in Frogham

4.98 out of 5 average rating, 145 reviews

Luxury New Forest Cottage, with hot tub & log fire

24 Feb – 3 Mar

$498 SGD per night

Pet-friendly cottage rentals

Guest favourite

Cottage in Henley

4.92 out of 5 average rating, 277 reviews

Shepherd's Cottage

19–26 Mar

$125 SGD per night

Guest favourite

Cottage in Downton

4.96 out of 5 average rating, 438 reviews

The Coach House with walled garden

22–29 Sep

$169 SGD per night

Guest favourite

Cottage in Dorset

4.85 out of 5 average rating, 352 reviews

Character cottage close to beach

12–19 Nov

$221 SGD per night

Guest favourite

Cottage in Hooke

4.93 out of 5 average rating, 225 reviews

The Little House, Hooke, Nr Bridport, West Dorset

18–25 Jan

$215 SGD per night

Guest favourite

Cottage in Chetnole

4.9 out of 5 average rating, 146 reviews

Grove Farm Cottage-historic Cottage near Sherborne

13–20 Dec

$183 SGD per night

Guest favourite

Cottage in Bridgwater

4.93 out of 5 average rating, 236 reviews

The Granary at Pear Tree Farm

5–12 Dec

$117 SGD per night

Guest favourite

Cottage in Shaftesbury

4.99 out of 5 average rating, 125 reviews

Little Coombe

15–22 Oct

$186 SGD per night

Guest favourite

Cottage in South Somerset District

4.97 out of 5 average rating, 233 reviews

Beautiful cosy cottage in Dowlish Wake, S Somerset

21–28 Oct

$219 SGD per night

Private cottage rentals

Cottage in Portland

4.89 out of 5 average rating, 129 reviews

Number 107, Isle of Portland, Dorset

6–13 Sep

$175 SGD per night

Guest favourite

Cottage in Dorset

4.96 out of 5 average rating, 108 reviews

Harbour's Edge Cottage - Nothe Parade, Weymouth

3–10 Nov

$298 SGD per night

Guest favourite

Cottage in Fordingbridge

4.97 out of 5 average rating, 413 reviews

Wisteria Lodge

30 Oct – 6 Nov

$153 SGD per night

Guest favourite

Cottage in Okeford Fitzpaine

4.97 out of 5 average rating, 303 reviews

The Garden House Okeford Fitzpaine Dorset

30 Jun – 7 Jul

$240 SGD per night

Guest favourite

Cottage in Uplyme

4.98 out of 5 average rating, 259 reviews

Luxury cottage in Uplyme with far reaching views

11–18 Sep

$231 SGD per night

Guest favourite

Cottage in Devon

4.98 out of 5 average rating, 219 reviews

Little Roost at Uplyme: Luxury self-catering

29 Nov – 6 Dec

$209 SGD per night

Guest favourite

Cottage in Dorset

4.95 out of 5 average rating, 102 reviews

Spacious Family Cottage with Sea Views of Chesil

2–9 Oct

$334 SGD per night

Guest favourite

Cottage in Langton Matravers

4.91 out of 5 average rating, 345 reviews

Chapel Cottage

25 Nov – 2 Dec

$202 SGD per night

Destinations to explore