List your home
Apply filters
£ to

Holiday homes 12

Reset search

Show results on map

Filter your search

Price per night

Price per night

£ to per night

Bedrooms

Location

  • England Clear
  • Dorset Clear
  • Isle of Portland Clear
  • Portland Clear

Location

  • 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

Filters applied: High chair (12)

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
12 Results   |  

Very Good 4.5/5 

20 Photos

Isle of Portland / Portland

Cottage / 3 Bedrooms / sleeps 6

Very Good 4.5/5 

3 Nights min stay

Add to shortlist

from £50 / night

£350 - £950 / 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  …see more


20 Jul 2015

5/5

"Lovely clean spacious cottage with sea views"

We all loved Fishermans Cottage. It is light, airy and spotlessly clean! The cottage is in a quiet position set in a pretty garden with raised decking to give you a lovely sea view. The position o… More


16 Dec 2014

5/5

"Beautiful"

Me & my partner stayed at the end of November for a week & loved every minute... Recently having talks of coming back due to loving the house so much. We have loved every minute. Thank you for lending… More


17 Nov 2014

5/5

"Excellent place to stay"

This is a beautiful cottage and has very quiet and peaceful surroundings. Perfect for visiting Portland. The cottage is clean and has all the necessary amenities. We had a wonderful time there. All ma… More

See all reviews Continue

Excellent 5/5 

17 Photos

Isle of Portland / Portland

House / 2 Bedrooms / sleeps 6

Excellent 5/5 

2 Nights min stay

Add to shortlist

from £43 / night

£300 - £690 / 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. Wha  …see more


1 May 2014

5/5

"A true home from home - a true gem of a property"

Hillside is a beautiful well restored property in Fortuneswell, Portland, just off Weymouth. The area is lovely and very good for those who like to go on some nice walks. I've been to HIllside 2 years… More


24 Apr 2014

5/5

"Fantastic house everything you need"

Well kitted out, comfortable, clean, well decorated. We were down with our daughter at sailing event and would highly recommend Hillside.… More


1 Apr 2014

5/5

"Beautifully furnished property perfect holiday home."

We booked in the morning and arrived late on Friday night for a two night stay. Beautiful property. With a lovely seated area outside with views of the bay. Only issue would be to practice your parall… More

See all reviews Continue

Very Good 4.5/5 

20 Photos

Isle of Portland / Portland

Cottage / 3 Bedrooms / sleeps 6

Very Good 4.5/5 

3 Nights min stay

Add to shortlist

from £47 / night

£325 - £850 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0.5 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


4 Jun 2015

5/5

"Great"

We had a great time , very clean , nice size for a cottage rooms larger than expected . Lots of places to walk or drive to , great views all over the isle , great beach , weymouth not far away ,lots … More


30 Jul 2015

5/5

"Pebble Reef is a real home from home"

Stayed here for 2 weeks with my husband, daughter, son in law and grandsons. It is a lovely old cottage, extended at the back to give a spacious kitchen diner and a second bathroom. As I am disabled,… More

Thank you for your wonderful review, we are sorry to hear that the TV was faulty will get that checked out and repaired as soon as possible. Regards Mandy


18 Mar 2015

5/5

"Good location"

A lovely cottage, in a good location for the village and the coastal walks, shopping really close, lots of places to explore on the island. Nice and clean accommodation at a good price, I hope to sta… More

See all reviews Continue

Featured properties

Excellent 5/5 

19 Photos

Isle of Portland / Portland

House / 3 Bedrooms / sleeps 8

Excellent 5/5 

2 Nights min stay

Add to shortlist

from £72 / night

£500 - £1190 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Great for children of all ages
  • Car not necessary
  • No pets allowed
50% DISCOUNT FOR JUST 2 PEOPLE STAYING, SEND ENQUIRY TO GET DISCOUNT. Ideal for small groups, couples and families - extensive sea views. Sleeps up to 6 +2 people comfortably. 3 bedrooms with either twin or king-size beds & sofa bed in lounge. Off road parking. Si  …see more


8 Sep 2010

5/5

"A Holiday to Remember"

My family and I stayed at 65 Fortuneswell while on Portland this summer and it was perfect. Such a beautiful holiday cottage set in just the perfect location. It had great views out of every window!… More


19 May 2015

5/5

"Comes up trumps again!!"

We live in Spain and came over to the UK on this trip (May 2015) for my mums birthday, as a surprise for her. We stayed, in the run-up to Christmas 2014 at Deborah's other property, Quarries Reach, … More

Thank you Lorraine for such a great review, I am so glad you enjoyed both of our houses. We look forward to welcoming you again soon. Deborah


21 Apr 2015

5/5

"Great place to stay, fabulous view"

We I stayed at 65 Fortuneswell for a week in mid April. We chose it on the basis of the reviews and photos on TripAdvisor. We were not disappointed. The property is excellent, modern but in keeping… More

Thank you for the great review, I am so glad you enjoyed your stay. Deborah

See all reviews Continue

Very Good 4.5/5 

17 Photos

Isle of Portland / Portland

House / 4 Bedrooms / sleeps 10

Very Good 4.5/5 

2 Nights min stay

Add to shortlist

from £86 / night

£600 - £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
50% DISCOUNT FOR JUST 2 PEOPLE STAYING, SEND ENQUIRY TO GET DISCOUNT. Ideal for small groups, couples and families - fabulous sea views. Sleeps up to 8 +2 people comfortably. 4 bedrooms - 3 double/twin, bunk bedroom & sofa bed. Secure gated parking for several cars.  …see more


1 Nov 2014

5/5

"Excellent house dan pleasant stay"

We (7 family members) arrived to a great house, with ample parking space for our large MPV, clean and comfortable bedrooms, excellent bath and shower rooms as well as a spotless and well-equipped kitc… More

I am so glad you enjoyed the house and the area, thank you for the review. Deborah


30 Oct 2014

5/5

"A perfect base"

We have just returned from a short break in Portland, staying at Qaurries Reach. We loved the house. It had everything we could possibly need. It was the perfect base for us to explore the local are… More

Thank you for the review I am glad you enjoyed your stay. Deborah


20 Oct 2014

5/5

"Brilliant everything you cBrilliant"

Quarries reach is a beautiful house with everything you could wish for from cleanliness to lovely comfortable beds, plenty of places to eat and also to visit, we will definitely be going back… More

Thank you for the review I am so glad you enjoyed your stay and look forward to welcoming you back. Deborah

See all reviews Continue

20 Photos

Isle of Portland / Portland

Cottage / 3 Bedrooms / sleeps 6

1 night min stay

Add to shortlist

from £50 / night

£350 - £850 / week

View

Key info:

  • Nearest beach 2 km
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
there are many beaches around Portland and only a short drive away you can enjoy Weymouth beach with its golden sands,there is a lot of history around Portland, lots of places to explore, perfect for walking and dog friendly, we are 10 mins away from the sailing academy  …see more

11 Photos

Isle of Portland / Portland

House / 3 Bedrooms / sleeps 6

3 Nights min stay

Add to shortlist

from £71 / night

£495 - £750 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
'Casita del mar' is suited to families and Yachtsmen. Home of Weymouth and Portland Sailing Academy  …see more

Excellent 5/5 

22 Photos

Isle of Portland / Portland

House / 2 Bedrooms / sleeps 5

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £89 / night

£620 - £632 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0.5 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 uninterrupted sea views on Portland. Attractive 2 bedroom house with gardens and easy parking.Close to shops, pubs, restaurants and beaches but right on the edge of open hillside. Only 5 minutes from the National Sailing Academy.  …see more


29 Aug 2013

5/5

"Home From Home"

Considering the weather was not too kind to us we had a great time, plenty to see and do no matter what the weather was like. Without repeating other traveller’s reviews too much, the views have to … More


7 Feb 2013

5/5

"Highly recommend this lovely house, very well equipped with the most fantastic views."

Really enjoyed our stay in this lovely house. It was spacious, very clean & comfortable and was extremely well equipped for a self catering property. The views from the house of Portland Harbour, Weym… More


14 Jan 2013

5/5

"Ideal quiet family holiday cottage"

Bayview is tucked in the nice residential area of Portland. The view of Chesil beach and the harbour are really awesome. This cottage is well equipped, spotlessly clean, well furnished with a comfo… More

See all reviews Continue

Excellent 5/5 

20 Photos

from £69 / night

£480 - £1150 / week

View

View

Holiday home rental

Isle of Portland / Portland

House / 4 Bedrooms / sleeps 10

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £69 / night

£480 - £1150 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0.3 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  …see more


8 Sep 2014

5/5

"brilliant"

what a lovely house warm welcoming,fully equipped kitchen all the mod cons would highly recommend have just spent long weekend with family lovely place to visit, pubs restaurants all on your doorstep … More


8 Sep 2014

5/5

"cant wait to book again......."

We stayed at the gift house for a long weekend with extended family, the house is beautiful, very spacious, immaculately clean, everything you would need its there in the house, the finishing touc… More


5 Sep 2014

5/5

"Super house in a beautiful location"

This is a lovely house with all you could need for a great holiday. It is close to Chesil Beach with wonderful views of the sea, and the amenities which were used for the 2012 Olympics. There is easy … More

See all reviews Continue

12 Photos

Isle of Portland / Portland

Lodge / 3 Bedrooms / sleeps 6

3 Nights min stay

Add to shortlist

from £91 / night

£631 - £1485 / week

View

Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • No pets allowed
A perfect choice for those wishing to relax in a peaceful setting after a day out in the fresh sea air  …see more

23 Photos

Isle of Portland / Portland

Castle / 9 Bedrooms / sleeps 20

3 Nights min stay

Add to shortlist

from £1715 / night

£12000 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
Nestled on the Isle of Portland, the peaceful castle welcomes you to live your very own fairytale  …see more

31 Photos

Isle of Portland / Portland

Cottage / 3 Bedrooms / sleeps 5

Short stays welcome

Add to shortlist

from £46 / night

£320 - £823 / 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

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