Houses in Isle of Portland and cottages – Holiday Lettings - Holiday Rentals Isle of Portland

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Isle of Portland

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39 Holiday homes

(27) Very Good 

30

Holiday cottage letting

Dorset / Isle of Portland

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Child friendly
“Perfect trip” Outstanding all round throughout the whole process. From booking to checkout. Great house. Great vibe. Very very happy and will book again. Superbly appointed throughout.  …see more

from £60 / night

£295 - £760 / week

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from £60 / night

(42) Excellent 

17

Holiday home letting

Dorset / Isle of Portland

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly
“Perfect. Thank you.” Stayed here with friends for the weekend (5 of us in total). The house was perfect for our needs, clean and well maintained. Comfy beds with lovely bedding, good size lounge with plenty of seating and a lovely view. Large kitchen  …see more

from £120 / night

£900 - £1430 / week

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from £120 / night

(21) Very Good 

8

Holiday cottage in West Country

Dorset / Isle of Portland

3 4 7 nights min

  • 3 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Suitable for children age 5+
“Cosy but challenging cottage” Had a lovely week in fishermans cottage - small but cosy. The cottage was very clean with nice comfortable beds. Unfortunately my husband is fairly tall so had a couple of knocks to his head with the low ceilings on the  …see more

from £40 / night

£280 - £580 / week

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from £40 / night

(14) Very Good 

32

West Country holiday cottage rental

Dorset / Isle of Portland

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 12 km
  • Child friendly
“Warm, cosy cottage with lovely sea and cliff view.” We had a lovely Christmas week at Fisherman's Cottage, which was excellently equipped with central heating, fully fitted kitchen and washing machine/ tumble drier. So even when the weather was bad we  …see more

from £85 / night

£350 - £995 / week

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from £85 / night

(13) Very Good 

20

Holiday cottage in West Country

Dorset / Isle of Portland

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly
“Nice restful cottage with comfy beds” We have had a good week at pebble reef seen lots of sight we particularly enjoyed Portland Bill we have had some good weather and the Monet cafe at the water gardens  …see more

from £75 / night

£325 - £895 / week

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from £75 / night

(24) Very Good 

31

Holiday studio in West Country

Dorset / Isle of Portland

Studio 2 3 nights min

  • Studio
  • Sleeps 2
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 km
“What More Could You Ask For..?” Lovely, clean, comfortable apartment with a fantastic view of the sea and Portland Bill lighthouse. Very quiet, no traffic noise to intrude, plenty of local amenities and parking. There are lots of reasonably priced pla  …see more

from £47 / night

£295 - £365 / week

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from £47 / night

(34) Excellent 

19

Home rental in West Country

Dorset / Isle of Portland

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly
A contemporary, spacious house with private off-road parking. Situated in a central position on the lower part of the island, makes it ideal for guests visiting the Weymouth and Portland National Sailing Academy or the Jurrassic Coastline. Ideal for small groups, coup  …see more

from £100 / night

£760 - £1230 / week

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from £100 / night

(11) Very Good 

20

Holiday cottage letting

Dorset / Isle of Portland

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
“Excellent cottage for families and couples alike” We stayed in July this year as we intended to visit Weymouth and this seemed like the ideal base . David was really helpful both in the lead up and during our stay. The cottage is great , has everythin  …see more

from £64 / night

£440 - £695 / week

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from £64 / night

(13) Very Good 

9

West Country holiday home rental

Dorset / Isle of Portland

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
“Fantastic house, breathtaking views, a real seaside beauty.” The photos do not do this house justice! It is amazing, from the boat oar coat rack and the rope mirrors to the seaside theme bedrooms and breathtaking view - it is an absolute beauty!! When  …see more

from £70 / night

£520 - £650 / week

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from £70 / night

(39) Excellent 

24

Holiday studio in West Country

Dorset / Isle of Portland

Studio 2 3 nights min

  • Studio
  • Sleeps 2
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Car not necessary
“Wonderful place to stay, couldn't be better.” The studio was everything I expected it to be from the website. Everything has been provided for your comfort. The hosts are very helpful but never intrusive. The coastal path is right outsi  …see more

from £53 / night

£325 - £395 / week

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from £53 / night

(7) Very Good 

6

Cottage rental in West Country

Dorset / Isle of Portland

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Ask owner if suitable for children
  • Car not necessary
  • Air conditioning
“Mrs” Absolutely wonderful. Full of light and everything you could want for a quiet break. Near to good pub and The Bill with fantastic walks. Will definitely try to go back again.  …see more

from £49 / night

£343 - £469 / week

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from £49 / night

(1) Excellent 

17

Holiday studio rental

Dorset / Isle of Portland

Studio 3 2 nights min

  • Studio
  • Sleeps 3
  • 2 nights min
  • Suitable for children age 5+
Self contained apartment base on Southwell business park , isle of Portland. A short stroll from famous Portland bill& Jurassic coastline. Come &see for yourself Towels,Linens ,Toiletries provided equipped with hair dryer,iron+board ,fridge,toaster,kettle,Microwave ov  …see more

from £79 / night

£500 / week

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from £79 / night

(2) Very Good 

18

West Country holiday home rental

Dorset / Isle of Portland

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Suitable for children age 5+
“Idyllic location, lovely cottage, very spacious” We enjoyed a beautiful week on Portland staying at 1 Bow & Arrow Cottages. The house is set over three floors with four spacious bedrooms - all the beds were very comfortable. We loved the downstairs wa  …see more

from £100 / night

£700 - £1350 / week

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from £100 / night

(9) Very Good 

8

Holiday bungalow in West Country

Dorset / Isle of Portland

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
“ecellent could not wish for anything better .” made very wellcome on arrival by the owner lesley rose,spotlasley clean .everything you could wish for even roses on the table.no problems .  …see more

from £75 / night

£500 / week

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from £75 / night

(1) Very Good 

7

Holiday home in West Country

Dorset / Isle of Portland

3 5 2 nights min

  • 3 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Ask about pets
  • Private garden
Next to the Beach House café and B&B, and less than 30 seconds walk to the Cove Inn public house.  …see more

from £150 / night

£1050 / week

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from £150 / night

(6) Very Good 

22

Holiday studio in West Country

Dorset / Isle of Portland

Studio 2 2 nights min

  • Studio
  • Sleeps 2
  • 2 nights min
  • Nearest beach 3 km
  • Suitable for children age 5+
Self contained apartment base on Southwell business park , isle of Portland. A short stroll from famous Portland bill& Jurassic coastline. Come &see for yourself Towels,Linens ,Toiletries provided equipped with hair dryer,iron+board ,fridge,toaster,kettle,Microwave ov  …see more

from £45 / night

£300 / week

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from £45 / night

(1)  

8

Holiday apartment in West Country

Dorset / Isle of Portland

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly
  • Ask about pets
Studio Apartment situated on 2nd Floor , Maritime House, Southwell Business Park, Portland .(ex mod building converted to living accommodation with kitchenette & en-suite bathroom) . Local amenities are within 5-10 mins driving distance. Approx 10 minutes walks from fa  …see more

from £49 / night

£300 / week

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from £49 / night

(16) Very Good 

14

Holiday cottage accommodation

Dorset / Isle of Portland

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Private garden
“EXCELLENT” We stayed at 'Bakers Dozen' for a week in the summer holidays with our 2 children. We absolutely loved Weymouth and Portland and found this house to be in a very quiet area of Portland with Portland Bill Lighthouse at the end of the road (a  …see more

from £90 / night

£450 - £695 / week

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from £90 / night

(1) Average 

11

West Country holiday studio accommodation

Dorset / Isle of Portland

Studio 2 2 nights min

  • Studio
  • Sleeps 2
  • 2 nights min
  • Nearest beach 3 km
  • Suitable for children age 5+
If you are looking for the perfect place for a romantic weekend break for two, a longer get-away-from-it-all holiday or fun time with a group of friends then you've found it!Every apartment combines quality overnight comfort and en-suite facilities with mod  …see more

from £59 / night

£399 / week

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from £59 / night

11

West Country holiday home accommodation

Dorset / Isle of Portland

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Child friendly
150 Year Old Portland Stone Fisherman's Cottage. Two leather sofas to seat six. Freeview T.V. Books. DVD's. C.D's. Games .Wifi. There is a wood burning stove for the winter months and barbeque and alfresco dining during the summer months. Vintage pine dining table  …see more

from £120 / night

£465 - £750 / week

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from £120 / night

19

Holiday home rental

Dorset / Isle of Portland

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
This semi detached cottage is located on the tip of Portland Bill in Dorset and can sleep four people in two bedrooms.  …see more

from £75 / night

£519 - £1104 / week

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from £75 / night

21

Holiday home accommodation

Dorset / Isle of Portland

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
This detached cottage is located on the tip of Portland Bill in Dorset and can sleep four people in two bedrooms.  …see more

from £77 / night

£536 - £1121 / week

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from £77 / night

31

Holiday cottage in West Country

Dorset / Isle of Portland

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • 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

from £48 / night

£332 - £756 / week

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from £48 / night

(1) Very Good 

34

Dorset / Isle of Portland

Studio 2 2 nights min

  • Studio
  • Sleeps 2
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 11 km
  • Suitable for children age 5+

 …see more

from £79 / night

£550 / week

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from £79 / night

(2) Very Good 

32

Dorset / Isle of Portland

Studio 2 3 nights min

  • Studio
  • Sleeps 2
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 11 km
  • Child friendly

 …see more

from £45 / night

£315 / week

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from £45 / night

18

Dorset / Isle of Portland

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly

 …see more

from £67 / night

£464 - £1157 / week

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from £67 / night

17

Dorset / Isle of Portland

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Suitable for children age 5+

 …see more

from £90 / night

£630 - £1888 / week

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from £90 / night

20

Dorset / Isle of Portland

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Suitable for children age 5+

 …see more

from £90 / night

£630 - £1888 / week

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from £90 / night

(2) Excellent 

43

Dorset / Isle of Portland

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Suitable for children age 5+

 …see more

from £98 / night

£681 - £2187 / week

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from £98 / night

(1) Average 

6

Dorset / Isle of Portland

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly

 …see more

from £49 / night

£320 / week

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from £49 / night

52

Dorset / Isle of Portland

9 20 3 nights min

  • 9 bedrooms
  • Sleeps 20
  • 3 nights min
  • Swimming pool
  • Suitable for children age 5+

 …see more

from £1715 / night

£12000 - £16000 / week

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from £1715 / night

(1) Very Good 

24

Dorset / Isle of Portland

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+

 …see more

from £53 / night

£371 - £1103 / week

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from £53 / night

24

Dorset / Isle of Portland

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Suitable for children age 5+

 …see more

from £90 / night

£630 - £1738 / week

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from £90 / night

14

Dorset / Isle of Portland

Studio 2 2 nights min

  • Studio
  • Sleeps 2
  • 2 nights min
  • Nearest beach 11 km
  • Ask owner if suitable for children

 …see more

from £59 / night

£350 / week

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from £59 / night

39

Dorset / Isle of Portland

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly

 …see more

from £618 / night

£4320 / week

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from £618 / night

44

Dorset / Isle of Portland

6 12 3 nights min

  • 6 bedrooms
  • Sleeps 12
  • 3 nights min
  • Swimming pool
  • Child friendly

 …see more

from £1235 / night

£8640 / week

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from £1235 / night

39

Dorset / Isle of Portland

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly

 …see more

from £823 / night

£5760 / week

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from £823 / night

41

Dorset / Isle of Portland

5 10 3 nights min

  • 5 bedrooms
  • Sleeps 10
  • 3 nights min
  • Swimming pool
  • Child friendly

 …see more

from £1029 / night

£7200 / week

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from £1029 / night

43

Dorset / Isle of Portland

7 14 3 nights min

  • 7 bedrooms
  • Sleeps 14
  • 3 nights min
  • Swimming pool
  • Child friendly

 …see more

from £1372 / night

£9600 - £10080 / week

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from £1372 / night

Top Destination reviews

Rosa Cottage
Wonderful holiday home

We stayed at Rosa Cottage for a week in March, and had a wonderful stay. The cottage is furnished to a high standard with a tasteful and original look. The kitchen is well equipped, and we had some wonderful evenings around the large dining room … see more
Church Ope Studio
Lovely homely place & great location

The studio has all the things you need for a short break, we took Ruby our West highland terrier and she loved it just as much as we did. The location is great and as you leave the studio to the left is the lane that leads to the coastal path an … see more
fishermans view
Fantastic Cottage

Spent a week at Fisherman's View with my wife and dog, my daughter joined us for a few days. The cottage is in an ideal spot to explore Portland, Weymouth and all surrounding coast. Fishermans View was spotlessly clean and very welcoming and comfor … see more
Bakers Dozen - Three Bedroom Coastal Cottage
Quirky Little Find

We stayed at Bakers Dozen for a week whilst visiting family that live on Portland, so we know the area well. A brilliant quirky little find much bigger than you think. A real peaceful suntrap in the back garden, with amazing views. Definitely looki … see more
Pebble View
Beautiful house in a beautiful place

Very well presented house with great sea views from 2 of the 3 bedrooms. Small park, local shop and beach all within 5 minute walk. … see more
Pebble Reef
Nice restful cottage with comfy beds

We have had a good week at pebble reef seen lots of sight we particularly enjoyed Portland Bill we have had some good weather and the Monet cafe at the water gardens … see more

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