List your home
Apply filters
£ to

15 Holiday homes in Portland

Reset search

Show results on map

Filter your search

Price per day

£ to

Bedrooms

Location

  • England Clear
  • West Country Clear
  • Dorset Clear
  • Weymouth Clear
  • Portland Clear
  • All locations

more +

less -

Property type

more +

less -

Also consider

Cornwall
2,983 properties
Greater London
941 properties
Cumbria / Lake District
940 properties
Devon
2,810 properties
Central England / Cotswolds
940 properties
Dorset
819 properties
Isle of Wight
507 properties
Peak District / Derbyshire
460 properties
Somerset
610 properties
Kent
557 properties
Sussex
770 properties
Norfolk
1,023 properties
Isle of Man
11 properties
Northumberland
640 properties
Yorkshire / Yorkshire Dales
1,496 properties
Coastal Cottages
222 properties
Central London/Zone 1
2,334 properties
Central London/Zone 2
1,198 properties
Newquay
610 properties
Bideford
487 properties

Filters applied: Nightlife (15)

To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more
15 Results  |  
20 Photos

House | 3 Bedrooms | sleeps 6

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £61 /night

£425 - £800 / week

View

Key info:

  • Nearest beach 0 km
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Within sound of the breaking surf, take breakfast on the balcony and enjoy stunning views of Chesil Beach. Situated in a quiet area of Fortuneswell yet only a short walk from Shops, Restaurants, Pubs and Beach and 5 minutes from the Olympic Sailing Venue.  …see more

22 Photos

House | 2 Bedrooms | sleeps 5

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £89 /night

£620 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Stunning location with probably the best sea views on Portland. Attractive 2 bedroom house with gardens and easy parking, next to open hillside with uninterupted views of Weymouth Bay, the ocean and coastline. Close to great beaches, sailing, shops, pubs and restaurants Only 5 minutes from the National Sailing Academy. Ideal situation for exploring Portland's natural heritage.  …see more

20 Photos

House | 2 Bedrooms | sleeps 4

3 Nights min stay

Add to shortlist

from £53 /night

£371 - £1095 / week

View

Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Car advised
  • No pets allowed
Ocean Views is a new luxury seafront development of apartments on the Isle of Portland in Dorset, situated on the Jurassic coast beside Chesil Beach, a location guaranteed to inspire.101 Ocean Views is a stylishly furnished apartment locate  …see more

Featured properties

17 Photos

House | 1 Bedroom | sleeps 4

Good 3/5 

3 Nights min stay

Add to shortlist

from £42 /night

£288 - £723 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
Ocean Views is a new luxury seafront development of apartments on the Isle of Portland in Dorset, situated on the Jurassic coast beside Chesil Beach, in a location guaranteed to inspire.  …see more

24 Photos

House | 3 Bedrooms | sleeps 6

Very Good 4/5 

3 Nights min stay

Add to shortlist

from £67 /night

£464 - £1312 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
A stylish apartment with fantastic on-site health facilities, situated on the Jurassic coast beside Chesil Beach  …see more

18 Photos

House | 3 Bedrooms | sleeps 6

3 Nights min stay

Add to shortlist

from £53 /night

£371 - £1095 / week

View

Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Car advised
  • No pets allowed
Sea Pinks Cottage was built around 1860 and is a fine example of a traditional fisherman's cottage built with Portland stone.  …see more

20 Photos

House | 2 Bedrooms | sleeps 4

Very Good 4/5 

3 Nights min stay

Add to shortlist

from £58 /night

£402 - £1149 / week

View

Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Car advised
  • No pets allowed
Ocean Views is a new luxury seafront development of apartments on the Isle of Portland in Dorset, situated on the Jurassic coast beside Chesil Beach, in a location guaranteed to inspire.  …see more

8 Photos

House | 4 Bedrooms | sleeps 10

Short stays welcome

Add to shortlist

from £72 /night

£500 - £900 / week

View

Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Whether you are looking for that relaxing break, or here to sail or just time with the family this charming cottage would suit your needs. Nestled off Wakeham, you will agree this cottage is a real find. This deceptive very comfortable house offers home from home facilities with everything to entertain a family  …see more

8 Photos

Cottage | 3 Bedrooms | sleeps 4

Very Good 4/5 

Short stays welcome

Add to shortlist

from £58 /night

£400 - £550 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Suitable for children over
  • Car advised
  • No pets allowed
  • Private garden
A charming cottage in this pretty road, a short walk down to Chesil Beach and Cove and easy going of the National Sailing Academy at Portland Harbour.  …see more

11 Photos

Apartment | 2 Bedrooms | sleeps 4

Short stays welcome

Add to shortlist

from £65 /night

£450 - £625 / week

View

Key info:

  • Nearest beach 1 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
A two bedroom holiday apartment, close to Portland Harbour, Portland Castle and the National Sailing Academy.  …see more

8 Photos

Cottage | 3 Bedrooms | sleeps 7

7 Nights min stay

Add to shortlist

from £58 /night

£400 - £550 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Character cottage over three floors, sleeps seven comfortably. A short walk from Chesil Beach and the local amenities, the National Sailing Academy and Portland Harbour. The harbour is found within a short drive or leisurely walk from the property. At the centre of the Jurassic Coast, Portland is an ideal base for water sports, walking & exploring Dorset.  …see more

8 Photos

Cottage | 4 Bedrooms | sleeps 8

Very Good 4/5 

7 Nights min stay

Add to shortlist

from £65 /night

£450 - £625 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Mallams Cottage is a beautifully finished period cottage, well located for Chesil Beach, Portland Harbour and the National Sailing Academy. Close to the best sailing waters in Europe.  …see more

10 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £65 /night

£450 - £625 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
Frigate Apartment is a stunning holiday apartment with sea views situated in the eye-catching Ocean Views development, close to Portland Harbour and the National Sailing Academy. The development boasts a state-of-the-art health and fitness centre complete with an indoor swimming pool.  …see more

8 Photos

Cottage | 3 Bedrooms | sleeps 6

7 Nights min stay

Add to shortlist

from £58 /night

£400 - £550 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
4 Sea View offers the best of modern comforts with period character in a cottage just a short walk from the splendors of Chesil Beach & Cove on the Isle of Portland Dorset. Offering a fabulous kitchen and comfortable accommodation.  …see more

11 Photos

House | 4 Bedrooms | sleeps 8

Very Good 4.5/5 

Short stays welcome

Add to shortlist

from £72 /night

£500 - £675 / week

View

Key info:

  • Nearest beach 1 km
  • Great for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
This well presented holiday house has a large and sociable open plan living area with kitchen, seating and dining areas, allowing for a relaxed and inclusive holiday atmosphere.  …see more