Cottages to rent for self-catering breaks in Portland, Dorset, England

Book a self-catering holiday in Portland and look forward to exploring some of the best of Dorset’s Jurassic Coast on your break away. Portland in Dorset is sometimes described as the ‘Isle of Portland’ but is actually a rocky limestone outcrop which is connected to the mainland by a causeway. Rich in flora and wildlife including birds, Portland is ideal for a relaxing cottage break and is home to a lighthouse on the southern tip.


Advice on Cottage Holidays in Portland

Weymouth with its beach and attractive esplanade is only around 5 miles from Portland and stunning Chesil Beach is just 9 miles away. Days out can be enjoyed discovering some of Dorset’s top attractions including the West Dorset Heritage Coast and the Purbeck Heritage Coast.  For a holiday by the seaside and time along Dorset’s UNESCO recognised Jurassic Coast, Portland has lots to recommend it. We hope you find the perfect place to stay on Country Cottages Online, as we feature an excellent collection of coastal cottages as well as rural retreats.

Book a Portland cottage and look forward to discovering some of the best of Dorset on holiday.

16 rental properties

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Pennsylvania Castle, Portland, Dorset, West Country, England

9 bedroom Castle

sleeps 10 - 20 guests
10 - 20
9 bedrooms
9
11 bathrooms
11
no dogs allowed
5 star

9 bedroom castle with stunning sea views, sleeping groups of up to 20 people on the Isle of Portland.

Special features: free internet access, pool (Indoor swimming pool in second conservatory), games room.

Weekly Price from: £11847

Branscombe Holiday Cottage at Old Higher Lighthouse, Portland, Dorset, West Country, England

2 bedroom Unique Lighthouse Cottage

sleeps 1 - 4 guests
1 - 4
2 bedrooms
2
1 bathrooms
1
no dogs allowed
4 star

For a seaside holiday how about Branscombe Holiday Cottage right next to Old Higher Lighthouse? With a stunning location perched on the cliff-side on the Jurassic Coast and with access to a shared outdoor pool in the summer months, this is a very special and unique holiday home.

Special features: free internet access, pool (Shared outdoor pool in grounds).

Weekly Price from: £599
Next availability:
from 17 December to 24 December 21 from 26 December to 31 December 21

Townbridge Apartment, Weymouth, Dorset, West Country, England

2 bedroom Holiday Apartment, Portland 4 miles away

sleeps 2 - 4 guests
2 - 4
2 bedrooms
2
2 bathrooms
2
no dogs allowed
4 star

Smartly Presented 2 Bedroom Holiday Apartment in Weymouth with Harbour Views.

Special features: free internet access.

Weekly Price from: £564
Next availability:
from 01 December to 14 May 22 from 21 May to 18 June 22

High Tide, Weymouth, Dorset, West Country, England

5 bedroom Townhouse, Portland 4 miles away

sleeps 5 - 10 guests
5 - 10
5 bedrooms
5
6 bathrooms
6
no dogs allowed
5 star

Elegant 5 bedroom holiday rental in Weymouth, all ensuite bedrooms, stunning sea views and excellent location opposite the beach.

Special features: free internet access.

Weekly Price from: £1615
Next availability:
from 01 December to 18 December 21 from 26 December to 08 April 22

Stonebank Annexe, Chickerell, Weymouth, Dorset, West Country, England

2 bedroom Cottage, Portland 6 miles away

sleeps 2 - 4 guests
2 - 4
2 bedrooms
2
1 bathrooms
1
dog-friendly cottage, 1 dog(s) welcome
1
4 star

Charming 2 bedroom, dog-friendly holiday home located near the heart of Chickerell, conveniently close to the beautiful Dorset Jurassic coast and just 3 miles from Weymouth.

Special features: free internet access.

Weekly Price from: £360
Next availability:
from 01 December to 23 April 22 from 30 April to 21 May 22

Wans Barton, Langton Herring, Dorset, West Country, England

4 bedroom Farmstay, Portland 8 miles away

sleeps 2 - 10 guests
2 - 10
4 bedrooms
4
4 bathrooms
4
no dogs allowed

Set in the grounds of Higher Farm is this fabulous large barn conversion offering high quality accommodation throughout as well as sea views, making this a very special place to holiday.

Special features: free internet access.

Weekly Price from: £1542

Stable cottage, Portesham, Dorset, West Country, England

1 bedroom Rural Retreat, Portland 9 miles away

sleeps 1 - 2 guests
1 - 2
1 bedrooms
1
1 bathrooms
1
dog-friendly cottage, 2 dog(s) welcome
2

Book a rural retreat break at this lovely Dorset romantic barn conversion, conveniently located on a working farm, close to idyllic countryside and the Jurassic Coast, this property is both dog-friendly and horse-friendly.

Weekly Price from: £325
Next availability:
from 01 May to 25 May 22

The Old Rectory, Bridport, Dorset, West Country, England

11 bedroom Mansion, Portland 13 miles away

sleeps 12 - 29 guests
12 - 29
11 bedrooms
11
9 bathrooms
9
no dogs allowed

Wonderful Georgian country house set in over an acre of gardens close to a gorgeous Dorset valley and near to the seaside, with a location and accommodation like this, this is a very special place.

Special features: free internet access, games room.

Weekly Price from: £1620

The Shooting lodge, Wrackleford Estate, Stratton, Dorset, West Country, England

4 bedroom Large Country House, Portland 14 miles away

sleeps 2 - 8 guests
2 - 8
4 bedrooms
4
4 bathrooms
4
no dogs allowed

An ideal country retreat, this holiday lodge enjoys a fantastic rural setting high within the Dorset Downs and offers characterful accommodation along with fishing on the River Frome nearby.

Special features: free internet access, games room.

Weekly Price from: £1100
Next availability:
from 11 February to 18 February 22 from 24 February to 01 April 22

The Fishing Lodge, Sydling St. Nicholas, Dorset, West Country, England

2 bedroom Holiday Lodge, Portland 15 miles away

sleeps 1 - 4 guests
1 - 4
2 bedrooms
2
1 bathrooms
1
no dogs allowed

Idyllic 2 bedroom hideaway set by Sydling Brook and Langford Lake within Dorset's Area of Outstanding Natural Beauty, relax and unwind in this tranquil setting or enjoy fishing on site.

Special features: free internet access.

Weekly Price from: £800
Next availability:
from 01 December to 24 December 21 from 26 December to 01 April 22

Langford Valley Stables, Dorchester, Dorset, West Country, England

3 bedroom Barn Conversion, Portland 15 miles away

sleeps 1 - 6 guests
1 - 6
3 bedrooms
3
3 bathrooms
3
no dogs allowed

Langford Valley Stables has recently be converted from a flint and brick barn to create a luxury 3 bed self catering property.

Special features: free internet access.

Weekly Price from: £995
Next availability:
from 01 December to 08 April 22 from 21 April to 27 May 22

Langford Valley Barn, Dorchester, Dorset, West Country, England

4 bedroom Barn Conversion, Portland 15 miles away

sleeps 1 - 8 guests
1 - 8
4 bedrooms
4
4 bathrooms
4
no dogs allowed
5 star

Newly available is this stunning 4 bedroom barn conversion set by the unspoilt Dorset Downs, enjoy a luxury country holiday, just half an hour's drive from the beautiful Jurassic coastline.

Special features: free internet access, games room, Gold Award Winning Cottage.

Weekly Price from: £1200
Next availability:
from 12 December to 22 December 21 from 04 January to 07 January 22