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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392 Holiday homes

15

Home rental in Isle of Portland

Dorset / Isle of Portland

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden

from £70 / night

£300 - £600 / week

Book View

Responds fast!
avg. 57 minutes

from £70 / night

35

Holiday cottage in Isle of Portland

Dorset / Isle of Portland

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly

from £60 / night

£400 - £980 / week

Book View

Responds fast!
avg. 3 hours 21 minutes

from £60 / night

(3) Very Good 

14

Chalet rental in Isle of Portland

Dorset / Isle of Portland

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly

from £85 / night

£406 - £787 / week

Book View

Responds fast!
avg. 3 hours 21 minutes

from £85 / night

(18) Very Good 

9

Isle of Portland 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
“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.

from £90 / night

£650 / week

Book View

Responds fast!
avg. 3 hours 29 minutes

from £90 / night

(17) 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
“Lovely, clean, modern accommodation - close to Chesil beach” We had a wonderful holiday staying at Seagull Cottage. The house was clean, bright and modern, with good sized rooms throughout. My family of 5 slept comfortably in the 2 bedrooms, with plenty of space for our suitcases and other luggage. The living and dining area had plenty of room for playing and relaxing at the same time. Parking was fine with a free public carpark situated just across the road. The house was also near to a small supermarket and pharmacy, and the bus service around Portand and into Weymouth ran frequently. For a young family, there's not much to see/places to eat on Portland itself, but it only took us 5 or so minutes to drive into the heart of bustling Weymouth and spend the day there. Our only criticism was that the garden is located down a number of steep steps, which wasn't good for a 2 year old, however, we were blessed with good weather and spent most of our time in Weymouth on the beach! As a base for this part of the coast line, we would highly recommend Seagull Cottage. If possible, we would rate this property as 4.5 / 5.

from £90 / night

£610 - £740 / week

Book View

Responds fast!
avg. 2 hours 19 minutes

from £90 / night

(11) Very Good 

8

Holiday bungalow in Isle of Portland

Dorset / Isle of Portland

2 4 Min stay varies

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

from £75 / night

£700 / week

Book View

Responds fast!
avg. 48 minutes

from £75 / night

(2) Very Good 

18

Isle of Portland 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+

from £100 / night

£700 - £1,350 / week

Enquire View

from £100 / night

(4) Very Good 

12

Holiday cottage in Isle of Portland

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

from £79 / night

£375 - £724 / week

Book View

Responds fast!
avg. 3 hours 21 minutes

from £79 / night

(3) Excellent 

18

Holiday home letting

Dorset / Isle of Portland

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly

from £85 / night

£750 - £950 / week

Book View

from £85 / night

11

Home rental in Isle of Portland

Dorset / Isle of Portland

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Private garden

from £107 / night

£517 - £1,009 / week

Book View

Responds fast!
avg. 3 hours 21 minutes

from £107 / night

(22) Very Good 

Certificate of Excellence

43

Isle of Portland 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
“Mrs” A beautiful cottage in an ideal location. The owner seems to have her finger on what a guest would appreciate on their stay. For example a bowl of fresh fruit and a vase of flowers. Fisherman's Cottage is a must for any visitors to Portland who appreciate a home from home. I know we do and have no hesitation in booking for next year too.

Certificate of Excellence

from £95 / night

£395 - £1,020 / week

Book View

Responds fast!
avg. 57 minutes

from £95 / night

(8) Excellent 

22

Holiday studio in Isle of Portland

Dorset / Isle of Portland

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Nearest beach 3 km
  • Suitable for children age 5+

from £45 / night

£300 / week

Book View

Responds fast!
avg. 1 hour 3 minutes

from £45 / night

(1) Excellent 

8

Holiday home in Isle of Portland

Dorset / Isle of Portland

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Private garden

from £115 / night

£556 - £1,087 / week

Book View

Responds fast!
avg. 3 hours 21 minutes

from £115 / night

(1) Excellent 

11

Isle of Portland 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

from £106 / night

£590 - £740 / week

Book View

Responds fast!
avg. 50 minutes

from £106 / night

(1) Excellent 

15

Holiday cottage in Isle of Portland

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

from £76 / night

£362 - £699 / week

Book View

Responds fast!
avg. 3 hours 21 minutes

from £76 / night

(2) Excellent 

18

Isle of Portland holiday apartment accommodation

Dorset / Isle of Portland

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool

from £123 / night

£595 - £1,165 / week

Book View

Responds fast!
avg. 3 hours 21 minutes

from £123 / night

(1) Excellent 

10

Isle of Portland holiday cottage rental

Dorset / Isle of Portland

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly

from £88 / night

£419 - £813 / week

Book View

Responds fast!
avg. 3 hours 21 minutes

from £88 / night

(6) Excellent 

17

Holiday home in Isle of Portland

Dorset / Isle of Portland

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly

from £110 / night

£530 - £1,035 / week

Book View

Responds fast!
avg. 3 hours 21 minutes

from £110 / night

8

Isle of Portland holiday cottage rental

Dorset / Isle of Portland

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly

from £100 / night

£478 - £932 / week

Book View

Responds fast!
avg. 3 hours 21 minutes

from £100 / night

(38) Excellent 

Certificate of Excellence

19

Home rental in Isle of Portland

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
“Perfect place !” We - 6 french people and 10 others staying in the neighbourhoods - really enjoyed the warm, cosy, neat house of Deborah with its magnificent view. Everything is easy ! I definitively recommand it if you come by Portland !

Certificate of Excellence

from £120 / night

£840 - £950 / week

Book View

Responds fast!
avg. 19 minutes

from £120 / night

(3) Very Good 

22

Holiday home in Isle of Portland

Dorset / Isle of Portland

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Pet friendly

from £175 / night

£1,225 / week

Book View

Responds fast!
avg. 1 hour 41 minutes

from £175 / night

(55) Excellent 

Certificate of Excellence

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
“Wonderful” We celebrated a 60th birthday with work colleagues had a wonderful time - the place was clean tidy very bright and airy couldn't wish for anything more. Front of house overlooks fields with a sea view in the distance. Local buses easy to access and frequent

Certificate of Excellence

from £120 / night

£980 - £1,190 / week

Book View

Responds fast!
avg. 19 minutes

from £120 / night

(10) Very Good 

Certificate of Excellence

8

Cottage rental in Isle of Portland

Dorset / Isle of Portland

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Nearest beach 3 km
  • Car not necessary
  • Air conditioning

Certificate of Excellence

from £50 / night

£325 - £425 / week

Book View

Responds fast!
avg. 1 hour 39 minutes

from £50 / night

(21) Excellent 

Certificate of Excellence

21

Holiday cottage in Isle of Portland

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
“Lovely cottage, great location!” Pretty and comfortable cottage in a great location. 5 mins walk to Church Ope Cove and a quick drive to Portland Bill. We also visited Charmouth beach, Lyme Regis, Weymouth & Durdle Door. We would definitely recommend this cottage.

Certificate of Excellence

from £85 / night

£350 - £920 / week

Book View

Responds fast!
avg. 57 minutes

from £85 / night

(30) Very Good 

31

Holiday studio in Isle of Portland

Dorset / Isle of Portland

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 km
“Panoramic views of the sea in a peaceful setting.” We enjoyed the quietness, lack of passing traffic and the stunning view from the window that stretched across the width of the apartment. We would have liked a second high stool at the counter so that both occupants would be high enough to enjoy the view and to sit together at meals. On the whole the facilities and information provided were good. We appreciated the Wi-Fi. We would have liked a slightly more generous supply of basics like dish cloths, towels and toiletries - sufficient for two occupants. The bus services in the area are very frequent. We would certainly come again!

from £47 / night

£295 - £350 / week

Book View

Responds fast!
avg. 2 hours 29 minutes

from £47 / night

(2) Average 

8

Holiday home in Isle of Portland

Dorset / Isle of Portland

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 0 km
  • Child friendly
  • Pet friendly

from £80 / night

£425 - £550 / week

Book View

Responds fast!
avg. 3 hours 53 minutes

from £80 / night

(1) Average 

15

Isle of Portland 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+

from £69 / night

£399 - £525 / week

Book View

Responds fast!
avg. 1 hour 3 minutes

from £69 / night

(9) Excellent 

12

Cottage letting in Isle of Portland

Dorset / Isle of Portland

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly

from £110 / night

£530 - £1,060 / week

Book View

Responds fast!
avg. 3 hours 21 minutes

from £110 / night

(1) Excellent 

6

Penthouse rental in Isle of Portland with shared pool

Dorset / Isle of Portland

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool

from £125 / night

£600 - £1,400 / week

Book View

Responds fast!
avg. 3 hours 41 minutes

from £125 / night

11

Holiday home in Isle of Portland

Dorset / Isle of Portland

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Private garden

from £120 / night

£840 / week

Book View

Responds fast!
avg. 3 hours 21 minutes

from £120 / night

(11) Very Good 

14

Isle of Portland holiday home rental

Dorset / Isle of Portland

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 1 km
  • Child friendly
  • Car not necessary

from £123 / night

£595 - £1,191 / week

Book View

Responds fast!
avg. 3 hours 21 minutes

from £123 / night

8

Isle of Portland holiday cottage rental

Dorset / Isle of Portland

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly

from £87 / night

£414 - £802 / week

Book View

Responds fast!
avg. 3 hours 21 minutes

from £87 / night

5

Holiday home in Isle of Portland

Dorset / Isle of Portland

4 7 7 nights min

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min
  • Child friendly
  • Pet friendly

from £150 / night

£1,100 / week

Book View

Responds fast!
avg. 3 hours 21 minutes

from £150 / night

(34) Very Good 

Certificate of Excellence

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
“Lovely cottage on Portland” We stayed at Rosa Cottage for a week in July, and had a wonderful time. The cottage is spacious and beautifully furnished, and in an ideal location to explore Portland. Only a couple of minutes walk to Chesil Beach and a short drive to the National Sailing Academy. The cottage was spotlessly clean and very well equipped for self catering . Beds were comfortable and we very much enjoyed the spacious dining room for long lingering suppers. Having 2 children the separate lounge was also very handy for them to watch TV in the evenings. Parking was easy right outside the cottage most of the time, a couple of times we had to park in the road above, but only as minute walk from the property. We really enjoyed our stay and hope to return sometime later this year.

Certificate of Excellence

from £85 / night

£560 - £880 / week

Book View

Responds fast!
avg. 2 hours 39 minutes

from £85 / night

(5) Excellent 

22

Holiday home in Isle of Portland

Dorset / Isle of Portland

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly

from £86 / night

£600 / week

Book View

from £86 / night

(2)  

8

Holiday apartment in Isle of Portland

Dorset / Isle of Portland

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Ask about pets

from £49 / night

£300 / week

Book View

Responds fast!
avg. 1 hour 3 minutes

from £49 / night

10

Home rental in Isle of Portland

Dorset / Isle of Portland

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly

from £103 / night

£416 - £807 / week

Book View

Responds fast!
avg. 3 hours 21 minutes

from £103 / night

8

Holiday home rental

Dorset / Isle of Portland

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly

from £92 / night

£440 - £854 / week

Book View

Responds fast!
avg. 3 hours 21 minutes

from £92 / night

37

Holiday home in Isle of Portland

Dorset / Isle of Portland

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 3 km
  • Child friendly

from £90 / night

£374 - £1,020 / week

Book View

Responds fast!
avg. 57 minutes

from £90 / night

29

Holiday home in Isle of Portland

Dorset / Isle of Portland

2 4 Min stay varies

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

from £85 / night

£350 - £600 / week

Book View

Responds fast!
avg. 57 minutes

from £85 / night

Top Destination reviews

Shearwater located in Portland, Dorset
Special birthday

My partner & our dog the house was beautiful we would recomend it ever one made our holiday perfect … see more
Quarries Reach, rural & sea views Portland, Dorset
Mrs

Had a fantastic stay in this beautiful property. Equipped with everything you need. Clean and comfortable. It's a brilliant base to explore the surrounding area. This was our first visit to Portland as we normally stay in a hotel on Weymouth seafront when visiting family whom live in the area. So glad we decided to stay here instead. Beautiful sea views throughout the house. Couldn't fault it and we're already planning our next stay.see more
Pitt Hayes Cottage
Lovely accomodation, great location

This is a great choice for a break in Portland. The cottage is well situated (although quite hard to find the first time) and is in a great location, so no where is too far. The cottage was fully stocked and there was even milk tea and biscuits which were appreciated after our journey. Will definitely be returning.see more
Fishermans Cottage
,Great place, many extras, comfy beds, nice hot tub.

Conveniently located property of good size, nice walking areas nearby, good sea view. Plenty of good food and drink venues to walk or drive to. loved the hot tub. So many extras provided, even milk and flowers. Good value for money. … see more
Rosa Cottage
Lovely well equipped cottage

Rosa cottage is a warm, spacious character cottage within easy walking distance of Chesil Beach and the coast path. It was very clean and tidy and the welcome items left were appreciated. We returned to the house at various times and found parking right outside on all occasions. Karin also made the booking process very easy. A lovely few days away.see more
Pebble Reef
Great Cottage would rent again

Fully met with our expectations, would rent again, all info and details sent in advance and everything explained well. … see more