List your home
Apply filters
£ to

30 Holiday homes in Portland

Reset search

Show results on map

Filter your search

Price per night

£ to

Bedrooms

Location

  • England Clear
  • Dorset Clear
  • Isle of Portland 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
London
4,584 properties
Brighton
287 properties
St Ives
255 properties
Bournemouth
254 properties

Filters applied: Private garden (30)

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
30 Results  |  
14 Photos

Cottage | 2 Bedrooms | sleeps 5

Very Good 4.5/5 

3 Nights min stay

Add to shortlist

from £50 /night

£350 - £690 / week

View

Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Situated in a quiet location at the southern end of the island with stunning sea views just a stone's throw away from beautiful coastal walks and scenery - near Portland Bill lighthouse and the Lobster Pot restaurant.  …see more

20 Photos

Cottage | 3 Bedrooms | sleeps 6

Very Good 4.5/5 

3 Nights min stay

Add to shortlist

from £47 /night

£325 - £795 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Pebble Reef is a traditional Quarryman's Cottage, full of character but lovingly renovated to include all the modern comforts you need. Now has WiFi.  …see more

17 Photos

House | 4 Bedrooms | sleeps 10

Very Good 4.5/5 

2 Nights min stay

Add to shortlist

from £43 /night

£300 - £1365 / week

View

Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Car not necessary
  • Some pets are welcome - please contact the owner
  • Private garden
Ideal for small groups, couples and families - fabulous sea & rural views. Sleeps up to 8 +2 people comfortably. 4 bedrooms - 3 double/twin, bunk bedroom & sofa bed. Secure gated parking for several cars. There is a generous 50% discount for just 2 people staying. Situated very near to Weymouth & Portland National Sailing Academy & in centre of Dorset's Jurassic Coast  …see more

Featured properties

9 Photos

House | 3 Bedrooms | sleeps 6

Very Good 4/5 

4 Nights min stay

Add to shortlist

from £65 /night

£450 - £600 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Great for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Pebbles view cottages is the perfect holiday destination whether you just want to get away from it all exploring the Isle of Portland or beaches of Weymouth or a more active holiday with fantastic sailing,diving rock climbing cycling and walking, portland has it all.  …see more

21 Photos

Cottage | 2 Bedrooms | sleeps 5

Very Good 4.5/5 

3 Nights min stay

Add to shortlist

from £60 /night

£415 - £775 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Great for children of all ages
  • No pets allowed
  • Private garden
Seagull Cottage is a lovely holiday house ideal for sailing, beach, and outdoor activity holidays in Portland. It is located a mile from the WPNSA National Sailing Academy, the 2012 Olympic Sailing venue, and just a few minutes walk from the world famous Chesil Beach. The well-equpped cottage offers comfortable, superior two bedroom accommodation in a convenient location.  …see more

28 Photos

House | 3 Bedrooms | sleeps 7

Very Good 4.5/5 

3 Nights min stay

Add to shortlist

from £62 /night

£433 - £1414 / 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
Seagull House in Portland Chesil Beach  …see more

17 Photos

House | 2 Bedrooms | sleeps 6

Excellent 5/5 

2 Nights min stay

Add to shortlist

from £43 /night

£300 - £660 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Great for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Hillside is a stunning fully refurbished Victorian house with views from a southwest facing garden overlooking Portland Harbour and WPNSA.Only five minutes walk from Chesil beach, Hillside was refurbished to be our home which we have chosen to allow others to enjoy. What other property on Portland has chandeliers ,roll top bath and feature wallpaper?  …see more

45 Photos

Cottage | 3 Bedrooms | sleeps 5

Excellent 5/5 

4 Nights min stay

Add to shortlist

from £47 /night

£325 - £795 / week

View

Key info:

  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Portland is a unique place to visit. It sits 40 feet above sea level at the highest point and made up of limestone rock. Portland is part of the Jurassic Coastline. There is so much to explore and see during your stay. Leisure facilities include Sailing, fishing, diving, windsurfing, swimming, bird watching, walking etc  …see more

20 Photos

Cottage | 3 Bedrooms | sleeps 6

Very Good 4.5/5 

3 Nights min stay

Add to shortlist

from £50 /night

£350 - £895 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 12 km
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Fishermans Cottage is a charming detached 18th century cottage on the edge of Southwell, with excellent sea views. Ideal for Sailing academy, bird watching or just a quiet getaway. The ideal location for the 2012 Olympic Sailing whether supporting, taking part or just for the atmosphere.  …see more

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

24 Photos

Apartment | 1 Bedroom | sleeps 2

3 Nights min stay

Add to shortlist

from £35 /night

£239 - £369 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • Pets welcome
  • Private garden
Very spacious self catering “studio style” apartment close to Portland Bill & Jurassic coastal scenery. Sleeps 2+ cot. Flexible living area. Large enclosed sun-trap patio with safe parking. Very well equipped with 32” Flat screen Sat. TV & WiFi Broadband. Pets welcome. Ideal for young/mature couples. Seating for four plus. Car unnecessary, close to walks/sailing/sports  …see more

8 Photos

Cottage | 3 Bedrooms | sleeps 8

3 Nights min stay

Add to shortlist

from £65 /night

£450 - £860 / week

View

Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
The perfect base for a beach side holiday. We are close to the National Sailing Academy and a short walk to the Castletown diving centre. The Cove House Inn is a 300 yard walk along the beach and has a lovely atmosphere and good food.  …see more

18 Photos

House | 4 Bedrooms | sleeps 8

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £100 /night

£700 - £1350 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Suitable for children over 5
  • Car not necessary
  • Some pets are welcome - please contact the owner
  • Private garden
Beautifully renovated family house situated down a quiet lane, minutes from a picturesque cove and lovely cliff top walks.  …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 5
  • 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

10 Photos

Cottage | 4 Bedrooms | sleeps 8

Excellent 5/5 

1 night min stay

Add to shortlist

from £65 /night

£450 - £850 / week

View

Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Great location and close to The National Sailing Academy home of British sailing. Beautifully restored stone cottage over three floors, so close to Chesil Beach you hear the pebbles roar.  …see more

20 Photos

House | 4 Bedrooms | sleeps 10

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £69 /night

£480 - £900 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Great for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
The Gift House is a beautiful fully renovated and refurbished 4 bedroom house situated 2 minutes walk from the beach, with stunning panoramic sea views from all reception rooms and bedrooms stretching across Chesil Beach to the Olympic Sailing Village. The property is suited to outdoors enthusiasts and families. A perfect retreat with modern luxuries.  …see more

11 Photos

House | 4 Bedrooms | sleeps 8

Very Good 4.5/5 

Short stays welcome

Add to shortlist

from £72 /night

£500 - £900 / 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

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

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

24 Photos

Cottage | 3 Bedrooms | sleeps 6

3 Nights min stay

Add to shortlist

from £54 /night

£377 - £803 / week

View

Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
A traditional Portland stone property  …see more

31 Photos

Cottage | 3 Bedrooms | sleeps 5

Short stays welcome

Add to shortlist

from £45 /night

£314 - £785 / week

View

Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • No pets allowed
  • Private garden
This charming detached cottage sits in a quiet cul-de-sac in Easton on the Isle of Portland, sleeping five people in three bedrooms.  …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 5

Short stays welcome

Add to shortlist

from £46 /night

£320 - £450 / week

View

Key info:

  • Beach / lakeside relaxation
  • Not suitable for children
  • No pets allowed
  • Private garden
The cottage offers a cosy living area with farmhouse style kitchen leading to the courtyard garden to the rear. Two further floos accommodate two double bedrooms and a single bedroom which is to be found on the top floor Character seaside cottage close to Chesil Beach and the National Sailing Academy.  …see more

20 Photos

Cottage | 3 Bedrooms | sleeps 5

3 Nights min stay

Add to shortlist

from £57 /night

£397 - £837 / week

View

Key info:

  • Great for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
An original terraced fisherman's cottage which has been delightfully restored.  …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

19 Photos

House | 2 Bedrooms | sleeps 4

Short stays welcome

Add to shortlist

from £71 /night

£492 - £1150 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children over 5
  • Car advised
  • No pets allowed
  • Private garden
This semi detached cottage is located on the tip of Portland Bill in Dorset and can sleep four people in two bedrooms.  …see more

21 Photos

House | 2 Bedrooms | sleeps 4

Short stays welcome

Add to shortlist

from £73 /night

£508 - £1165 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children over 5
  • Car advised
  • No pets allowed
  • Private garden
This detached cottage is located on the tip of Portland Bill in Dorset and can sleep four people in two bedrooms.  …see more

24 Photos

Cottage | 2 Bedrooms | sleeps 4

3 Nights min stay

Add to shortlist

from £57 /night

£397 - £837 / week

View

Key info:

  • Great for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
National Sailing Academy a few minutes walk  …see more

10 Photos

Cottage | 3 Bedrooms | sleeps 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 5
  • Car advised
  • No pets allowed
  • Private garden
Fabulous sea views from this cottage just a few minutes from Chesil Beach.  …see more

5 Photos

Cottage | 2 Bedrooms | sleeps 4

1 night min stay

Add to shortlist

from £65 /night

£450 - £550 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Suitable for children over 5
  • Car not necessary
  • Some pets are welcome - please contact the owner
  • Private garden
If you were much closer you would be in the sea!!  …see more

Don’t let an old browser slow down your holiday

Your browser is out of date and might not work well with our website. Download the latest version to speed up your hunt for the perfect holiday home.

Just click on the icons to get to the download page