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.

14 rental properties

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Price from £420
Next available 30/05 to 08/06/22
sleeps 1 - 2 guests 1 - 2
1 bedrooms 1
1 bathrooms 1
dog-friendly cottage, 2 dog(s) welcome2

1 bedroom Rural Retreat

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.

Facilities & Features: TV
Price from £360
Next available 10/09 to 01/10/22
sleeps 2 - 4 guests 2 - 4
2 bedrooms 2
1 bathrooms 1
dog-friendly cottage, 1 dog(s) welcome1
4 star

2 bedroom Cottage

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.

Facilities & Features: TVFree Wifi
Price from £1200
Next available 16/06 to 24/06/22
sleeps 1 - 8 guests 1 - 8
4 bedrooms 4
4 bathrooms 4
no dogs allowed
5 star

4 bedroom Barn Conversion

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.

Facilities & Features: Gold Award Winning CottageTVFree WifiGames room
Price from £995
Next available 02/06 to 10/06/22
sleeps 1 - 6 guests 1 - 6
3 bedrooms 3
3 bathrooms 3
no dogs allowed

3 bedroom Barn Conversion

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

Facilities & Features: TVFree Wifi
Price from £610
Next available 28/10 to 04/11/22
sleeps 1 - 4 guests 1 - 4
2 bedrooms 2
1 bathrooms 1
no dogs allowed
4 star

2 bedroom Unique Lighthouse Cottage

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.

Facilities & Features: TVHeated pool
Price from £479
Next available 03/09 to 10/09/22
sleeps 2 - 4 guests 2 - 4
2 bedrooms 2
1 bathrooms 1
no dogs allowed
3 star

2 bedroom Chalet

Tucked away on the Eypes Mouth Chalet Park in Eype, Dorset is this wonderful, two-bedroom chalet, Beside the Sea.

Facilities & Features: TV
Price from £1596
Next available 03/06 to 08/07/22
sleeps 5 - 10 guests 5 - 10
5 bedrooms 5
6 bathrooms 6
no dogs allowed
5 star

5 bedroom Townhouse

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

Facilities & Features: TV
Price from £527
Next available 19/06 to 24/06/22
sleeps 2 - 6 guests 2 - 6
3 bedrooms 3
2 bathrooms 2
dog-friendly cottage, 2 dog(s) welcome2
5 star

3 bedroom Holiday Barn

Want to stay somewhere with tranquil rural views over fields and pastures where you can relax and unwind in Dorset? This 3 bedroom family-friendly and dog-friendly ban could be perfect, close to Thomas Hardy's Country and within reach of Dorset's Jurassic Coast for day trips.

Facilities & Features: TV
Price from £574
Next available 06/06 to 11/06/22
sleeps 2 - 4 guests 2 - 4
2 bedrooms 2
2 bathrooms 2
no dogs allowed
4 star

2 bedroom Holiday Apartment

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

Facilities & Features: TV
Price from £710
Next available 04/06 to 02/07/22
sleeps 4 - 8 guests 4 - 8
4 bedrooms 4
2 bathrooms 2
no dogs allowed
3 star

4 bedroom Cottage

Positioned in the heart of the popular seaside resort of Weymouth rests this remarkable whitewashed holiday home, Picardy Cottage.

Facilities & Features: TV
This owner/agency is showing availability but has not provided full pricing information.
Price from £800
Next available 27/06 to 01/07/22
sleeps 1 - 4 guests 1 - 4
2 bedrooms 2
1 bathrooms 1
no dogs allowed

2 bedroom Holiday Lodge

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.

Facilities & Features: TVFree Wifi
This owner/agency is showing availability but has not provided full pricing information.
Price from £1100
Next available 14/06 to 24/06/22
sleeps 2 - 8 guests 2 - 8
4 bedrooms 4
4 bathrooms 4
no dogs allowed

4 bedroom Large Country House

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.

Facilities & Features: TVFree WifiGames room
Sorry, this owner/agency has not provided availability and full price information.
Price from £1890
sleeps 10 - 18 guests 10 - 18
9 bedrooms 9
4 bathrooms 4
no dogs allowed

9 bedroom Large Country House

Very special holiday cottage with an outstanding location and fantastic sea views right by the pebble beach at Chesil Bank in Dorset.

Facilities & Features: TVFree Wifi
Sorry, this owner/agency has not provided availability and full price information.
Price from £1620
sleeps 12 - 29 guests 12 - 29
11 bedrooms 11
9 bathrooms 9
no dogs allowed

11 bedroom Mansion

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.

Facilities & Features: TVFree WifiGames room
* Price quoted is not inclusive of any applicable booking fees or local charges.