Short city breaks Isle of Wight | Holiday Lettings UK

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  • Isle of Wight

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  • Bembridge (1)
  • Brading (1)
  • Cowes (12)
  • Freshwater (2)
  • Ryde (4)
  • Sandown (2)
  • Shanklin (4)
  • St Helens (1)
  • Ventnor (3)
  • Wootton Bridge (1)

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31 Holiday homes

Filters applied: City breaks (31)

Travellers going to Isle of Wight are booking August dates now. Secure your holiday home today and have the perfect trip.

(19) Very Good 

1 / 22

Millers Rock, Ventnor - Ventnor apartment sleeps 4

England / Isle of Wight / Ventnor

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 0.1 km; Great for children of all ages ;
Millers Rock is an attractive 2 bedroom character apartment in a privileged private road location offering panoramic seaviewsLight and airy and centrally located within 2 minutes of the beach, shops, cafes, restaurant and fishing harbour , this four star rated property  …see more

from £80 / night

£350 - £784 / week

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from £80 / night

(10) Very Good 

1 / 15

Holiday Chalet in Gurnard with shared pools

England / Isle of Wight / Cowes / Gurnard Pines

2 bedroomsSleeps 5Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
We are pleased to advertise our immaculate and well maintained two bedroom Chalet in the Gurnard Pines Holiday Village that can sleep up to five persons. This Chalet comes fully equipped with all the necessary items to make your stay as close to home as possible.The mai  …see more

from £42 / night

£290 - £600 / week

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from £42 / night

(11) Very Good 

1 / 9

St Marys Road - West Cowes house sleeps 6

England / Isle of Wight / Cowes / West Cowes

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Great for children of all ages ; Car not necessary; No pets allowed;
A beautiful terraced cottage ideal for family holiday, crew let or as a corporate shore base in west Cowes. Full of character and sleeping 6 people it is equally suitable for weeks holiday, weekend getaway or a cosy Christmas and New Year break. Excellent location just  …see more

from £105 / night

£525 - £1600 / week

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from £105 / night

(25) Excellent 

1 / 22

Stable Cottage - Freshwater Bay barn sleeps 6

England / Isle of Wight / Freshwater / Freshwater Bay

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Beach / lakeside relaxation; Great for children of all ages ; Car advised;
We can book you discount Redfunnel ferry tickets. Stable Cottage, set in the grounds of Afton Farmhouse, is in an 'Area of Outstanding Natural Beauty' on the west of the Isle of Wight. Awarded a 4 star rating by visit England. Afton, on the outskirts of Freshwater, i  …see more

from £55 / night

£360 - £1080 / week

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from £55 / night

1 / 13

Yachters cottage - West Cowes townhouse sleeps 4

England / Isle of Wight / Cowes / West Cowes

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Great for children of all ages ; Car not necessary; No pets allowed;
This centrally located cottage is great for small groups or sailing crews who want to be in the heart of the action Its located just behind The Coast Bar, It has recently been refurbished to a very high standard with lovely laminate flooring & new beds. Due to its loc  …see more

from £70 / night

£250 - £1100 / week

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from £70 / night

(7) Very Good 

1 / 24

Sandlands - Appley apartment sleeps 4

England / Isle of Wight / Ryde / Appley

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 0.3 km; Great for children of all ages ;
This self catering top floor apartment in Ryde, a lovely Victorian town with lots to offer, is exceptionally well located for the Hovercraft terminal across to Portsmouth. It is a minutes walk from the lovely Appley sands beach, a boating lake, children's amusements and  …see more

from £90 / night

£365 - £690 / week

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from £90 / night

(11) Excellent 

1 / 25

Marmalade Cottage + Sea & Countryside garden Views

England / Isle of Wight / Brading

2 bedroomsSleeps 5Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 3 km; Great for children of all ages ;
Semi detached 'Marmalade Cottage' is at the top of our private gated driveway and alongside a wildflower meadow Family friendly spacious and in a Conservation Area in Brading (Gateway to the Downs) in the popular south/east of the Island, attached to our 200yr old  …see more

from £100 / night

£645 - £715 / week

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from £100 / night

(12) Excellent 

1 / 16

Apartment in Central Cowes. - West Cowes apartment sleeps 4

England / Isle of Wight / Cowes / West Cowes

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 0.5 km; Great for children of all ages ;
Lovely spacious apartment located next to Shepard's Wharf Marina. 2 bedrooms, 1 shower room, large sitting room, well equipped kitchen. TV with Freeview, Xbox 360, Chromecast, Safe for valuables, Alarm system and desk for working. Close to Cowes High Street and the Chai  …see more

from £125 / night

£400 / week

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from £125 / night

(3) Excellent 

1 / 20

1 Bars Mews, Bars Hill, Cowes - West Cowes cottage sleeps 4

England / Isle of Wight / Cowes / West Cowes

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 0.5 km; Not suitable for children;
Beautiful, totally refurbished town cottage tucked away in the heart of the old town in West Cowes, complete with private parking and two lovely, separate, fully enclosed gardens. Tastefully decorated with a light, neutral colour scheme and with a fully equipped kitchen  …see more

from £150 / night

£1050 - £2000 / week

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from £150 / night

1 / 14

Martindale - St Helens - Bembridge house sleeps 8

England / Isle of Wight / Bembridge / St Helens, Bembridge

3 bedroomsSleeps 8Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 1 km; Great for children of all ages ;
This charming detached two / three bedroom house is situated in a quiet residential area of the village of Bembridge. It makes an ideal holiday home being within easy walking distance of the beach at Forelands and the village shops, restaurants, cafes and public houses.  …see more

from £100 / night

£500 - £950 / week

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from £100 / night

(2) Excellent 

1 / 10

Red squirrels Grange Farm - Wootton Bridge lodge sleeps 6

England / Isle of Wight / Wootton Bridge

3 bedroomsSleeps 67 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Great for children of all ages ; Some pets are welcome - please contact the owner; Private garden;
This is a barrier free brand new build. Suitable for wheel chair users. Sleeps 5 to 6. All on one level with car parking and garden. The Lodge comprises of a Large wet room, en-suite double room and two twin rooms, Large kitchen / diner lounge. A veranda to the front  …see more

from £75 / night

£525 - £750 / week

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from £75 / night

(20) Excellent 

1 / 18

42a, Cowes Town Centre Home - West Cowes apartment sleeps 4

England / Isle of Wight / Cowes / West Cowes

2 bedroomsSleeps 44 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 2 km; Suitable for children age 5+;
Welcome to 42a, our beautiful apartment located right in the heart of the charming old town of Cowes. 42a is situated just moments from the sea and famous yacht haven. Bright and spacious with high ceilings, the apartment has been kitted-out to a very high standard wit  …see more

from £95 / night

£525 - £1410 / week

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from £95 / night

1 / 16

Gurnard Cottage - Niton - Isle of Wight cottage sleeps 5

England / Isle of Wight / Ventnor / Niton, Isle of Wight

3 bedroomsSleeps 5Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Great for children of all ages ; No pets allowed; Private garden;
In association with Trinity House, Rural Retreats are pleased to present St Catherine's Lighthouse. Situated just outside the hamlet of Niton, approximately 10 minutes' drive from the popular coastal resort of Ventnor, the southern most point of the Isle of Wi  …see more

from £175 / night

£715 - £1421 / week

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from £175 / night

(7) Excellent 

1 / 24

The LOFT Holiday Apartment Cowes - Cowes apartment sleeps 3

England / Isle of Wight / Cowes

1 bedroomSleeps 31 night min stay

  • 1 bedroom
  • Sleeps 3
  • 1 night min stay
Key info: Beach / lakeside relaxation; Great for children of all ages ; Car not necessary;
The Loft Cowes.is situated in the heart of the historical seaside town of Cowes on the beautiful Isle of Wight accessed by steps and your own private front door leading up to the Kitchen/Lounge which has far reaching views overlooking the Solent to the mainland beyon  …see more

from £95 / night

£665 / week

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from £95 / night

1 / 22

Luxury Yurt - Newchurch yurt sleeps 5

England / Isle of Wight / Sandown / Newchurch

1 bedroomSleeps 5Min stay varies

  • 1 bedroom
  • Sleeps 5
  • Min stay varies
Key info: Nearest beach 8 km; Great for children of all ages ; Car essential;
Located in a private field on The Garlic Farm on the Isle of Wight. This beautiful yurt is spacious and comfortable with king size double bed, and mezzanine deck with two single mattresses. It has a fully equipped kitchen and ensuite shower with flushing toilet. It sits  …see more

from £100 / night

£575 - £675 / week

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from £100 / night

(10) Excellent 

1 / 22

Tower House - Freshwater Bay house sleeps 11

England / Isle of Wight / Freshwater / Freshwater Bay

5 bedroomsSleeps 11Min stay varies

  • 5 bedrooms
  • Sleeps 11
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 1 km; Great for children of all ages ;
Tower House Is A Beautifully Restored 150 Year Old Victorian Property. A Peaceful Location With Walks Across The Downs And Beaches Just Minutes Away. Sleeps 11 (5 Bedrooms) and with 4 bathrooms (2 ensuite) there is ample room and amenities for everyone. With spacious r  …see more

from £210 / night

£995 - £1670 / week

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from £210 / night

(1) Excellent 

1 / 15

3 Victoria Mews, Cowes - West Cowes house sleeps 6

England / Isle of Wight / Cowes / West Cowes

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 2 km; Great for children of all ages ;
Charming modern cottage in a secluded development close to the centre of Cowes. Three bedrooms, a double and two rooms with a double and an additional single. Two bathrooms and comfortable lounge and well equipped kitchen. Patio area outdoors with table, chairs and B  …see more

from £150 / night

£446 - £3150 / week

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from £150 / night

(5) Very Good 

1 / 17

76 York Street - West Cowes house sleeps 12

England / Isle of Wight / Cowes / West Cowes

5 bedroomsSleeps 12Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 2 km; Great for children of all ages ;
This welcoming home provides all mod cons and is a two minute walk from the heart of Cowes - the home of world yachting. Can either be let with the 'Boat House' annexe (total 5 bedrooms, 4 bathrooms) or without it (4 bedrooms 3 bathrooms). Unusually for this area is  …see more

from £325 / night

£850 - £6650 / week

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from £325 / night

(1) Excellent 

1 / 23

Sun Hill Retreat - Cowes house sleeps 6

England / Isle of Wight / Cowes

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 1 km; Great for children of all ages ; No pets allowed;
This cosy cottage dating back to 1700 is situated at the top of Sun Hill .Within a minutes walk of all the amenities and yacht havens. Private parking for one guest car exists and the use of a small private garden equipped with BBQ & seating. The rear bedrooms share vi  …see more

from £150 / night

£900 - £2400 / week

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from £150 / night

1 / 5

Wooden Cabin for 2, with private hot tub

England / Isle of Wight / Shanklin

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Swimming pool; Ask owner if suitable for children; No pets allowed;
Lyon Court is a beautiful country house in a lovely countryside setting, tastefully converted into individual apartments. It overlooks Shanklin Down, yet is close to bus & train routes, and only 10 minutes walk to the town centre or Shanklin Old Village. The beach is  …see more

from £135 / night

£640 - £700 / week

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from £135 / night

1 / 12

Luxury caravan thorness bay,isle of Wight

England / Isle of Wight / Cowes

3 bedroomsSleeps 81 night min stay

  • 3 bedrooms
  • Sleeps 8
  • 1 night min stay
Key info: Beach / lakeside relaxation; Great for children of all ages ; Some pets are welcome - please contact the owner;
Welcome to our page for the rental of a Vogue caravan with double glazing throughout and full central heating to make your stay more comfortable. Our caravan has 40inch TV , wifi,free veiw & DVD player It comprises of a kitchen/diner,3 bedrooms(1double en-suite with fit  …see more

from £100 / night

£475 / week

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from £100 / night

(2) Excellent 

1 / 8

Pink Beach Cottage - St Helens cottage sleeps 4

England / Isle of Wight / St Helens

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Beach / lakeside relaxation; Great for children of all ages ; Some pets are welcome - please contact the owner;
Pink Beach Cottage is a detached cottage situated in a quiet little road just off the St Helens village green. The well presented accommodation includes two bedrooms being a double & a twin room. In addition, swell fitted modern kitchen, a separate dining room, char  …see more

from £43 / night

£295 - £680 / week

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from £43 / night

1 / 6

Airy 2 Bedroom Apartment with pool and sauna

England / Isle of Wight / Shanklin

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Great for children of all ages ; No pets allowed;
Lyon Court is a beautiful country house in a lovely countryside setting, tastefully converted into individual apartments. It overlooks Shanklin Down, yet is close to bus & train routes, and only 10 minutes walk to the town centre or Shanklin Old Village. The beach is  …see more

from £170 / night

£675 - £900 / week

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from £170 / night

(2) Excellent 

1 / 22

65 York St - West Cowes townhouse sleeps 10

England / Isle of Wight / Cowes / West Cowes

3 bedroomsSleeps 10Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Great for children of all ages ; No pets allowed; Private garden;
This Cowes Holiday homes listing is a 3 storey townhouse in the very popular York St which is a 2 minute walk from the Marinas & town so with its 10 singles in 3 bedrooms & 1 main bathroom & 2 shower rooms this property makes a fantastic crew house for sailing events or  …see more

from £100 / night

£395 - £2800 / week

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from £100 / night

(2) Excellent 

1 / 16

Isle Of Wight 2 bed Apartment in woods with wifi

England / Isle of Wight / Ryde

2 bedroomsSleeps 67 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 0.5 km; Great for children of all ages ;
The Garden Apartment is a cosy yet spacious and bright space to be in, located in the lower part of a Swiz style wooden house. The lodge has been newly decorated with a modern feel. There are two rooms bedrooms, one double and one twin room which can also be a king.  …see more

from £86 / night

£600 / week

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from £86 / night

1 / 10

DORANES LUXURY VICTORIAN FLAT - Ryde apartment sleeps 2

England / Isle of Wight / Ryde

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 1 km; Not suitable for children;
Doranes luxury Victorian flat: plush self-catering apartment on ground floor level for discerning couple; part of an 1844 Victorian Grade 2 Listed building.It is a six minute walk to the High Street in Ryde, boasting pubs, restaurants, Chemist, Supermarket, clothing and  …see more

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(1) Excellent 

1 / 10

Spacious 1 bedroom apartment with pool and sauna

England / Isle of Wight / Shanklin

1 bedroomSleeps 3Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
Key info: Nearest beach 2 km; Great for children of all ages ; Car not necessary;
Lyon Court is a beautiful country house in a lovely countryside setting, tastefully converted into individual apartments. It overlooks Shanklin Down, yet is close to bus & train routes, and only 10 minutes walk to the town centre or Shanklin Old Village. The beach is  …see more

from £135 / night

£525 - £700 / week

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from £135 / night

1 / 22

Clarendon Villa Holiday Apartment Ventnor

England / Isle of Wight / Ventnor

3 bedroomsSleeps 67 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Suitable for children age 5+; Some pets are welcome - please contact the owner;
This Victorian-era, top-floor penthouse apartment gives some of the most spectacular, panoramic sea views on the Isle of Wight.Wake-up in the morning to enjoy the view of the sun rising, with no land to interrupt the marriage of the clear blue sky and the sea. The perfe  …see more

from £86 / night

£600 / week

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from £86 / night

1 / 8

Stylish 2 bedroom apartment with pool and sauna

England / Isle of Wight / Shanklin

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Great for children of all ages ; No pets allowed;
Lyon Court is a beautiful country house in a lovely countryside setting, tastefully converted into 5 individual apartments. It overlooks Shanklin Down, yet is close to bus & train routes, and only 10 minutes walk to the town centre or Shanklin Old Village. Flat 1 is a  …see more

from £170 / night

£675 - £900 / week

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from £170 / night

(6) Excellent 

1 / 24

SPACIOUS VICTORIAN RESIDENCE - Ryde house sleeps 8

England / Isle of Wight / Ryde

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 0.6 km; Suitable for children age 5+;
This very comfortable Grade 2 Listed, four-bedroom holiday home has been lovingly restored and refurbished. It is beautifully presented throughout, making extensive use of Victorian and other antique furniture, together with six charming fire-places. Set in the heart of  …see more

from £128 / night

£896 - £1367 / week

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from £128 / night

1 / 6

Rookery Nook, Holiday Chalet - Sandown chalet sleeps 5

England / Isle of Wight / Sandown

2 bedroomsSleeps 5Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Beach / lakeside relaxation; Great for children of all ages ; Pets welcome;
A light and airy, comfortable and homely, holiday chalet, very close to the Sandown beaches, Red Cliffs and the National Trust owned Culver Down. It has a fully equipped kitchen with cooker, microwave, fridge, toaster and a host of utensils and crockery. It also has a s  …see more

from £70 / night

£450 - £550 / week

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from £70 / night

Top Destination reviews

The Salisbury
Ideal location for family break

Well equipped and comfortable caravan, nice location with views of the solent. Central site location with good vehicle access. Close to shop, bar, pool, and entertainment. We were a group of five with a 90 and 87 year old both in wheel chairs all ove … see more
Worsley Apartment
Excellent accomodation with great facilties

A great set of apartments, with high quality apartments, fantastic staff and great views. The apartment block is in a great location with ample parking for the apartments. … see more
Yachtman's Rest
What a find !

We had a fantastic week on the IoW, seven of us in total with extended family, and Yachtsman's Rest easily accommodated us all in comfort. Plenty of bathrooms, all well placed next to bedrooms or en-suite, no kids squabbling about whose turn it is … see more
Plum Cottage
Highly recommended

Lovely, spotlessly clean accommodation situated in a quiet central location. We all enjoyed our stay at Plum Cottage and would definitely recommend.. … see more
Woodland Cottage, Fort Victoria
Amazing - everything you could want and more ......

A fab property minutes from Yarmouth and the ferry terminal, but tucked away in the haven called Fort Victoria Country Park. Woodland Cottage is great - big enough not to feel on top of each other but cosy at the same time, there were 8 of us. The pr … see more
Gills Cliff House
Comfortable beautiful house

The perfect stay 3 generation family trip all had fun Well equipped house , perfect location great views , everything spot on … see more

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