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Isle of Portland House Rentals

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    Travelers to Isle of Portland are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    25 Matching Rentals in Isle of PortlandView all 55 rentals
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    1 The Old Police Station1 / 17
    (9)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Spacious 3 bedroom house large balcony magnificent sea views & secure parking1 / 19
    (38)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Quarries Reach, rural & sea views Portland, Dorset1 / 17
    (58)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • Cable/satellite TV
    • Wi-Fi
    • Secure Parking
    • Central Heating
    • Washer
    • Ocean Views
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    This house was just what we needed for a get together with friends. The three storey property worked really well for us. Even thought the property is next to a road it was quiet...
    Reviewed August 1, 2018
    Perfect for our family's needs for a very enjoyable weeks stay! Plenty of room and spacious shower room, bathroom and separate toilet - not to be underestimated with a big family!
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    About this property
    Ideal for small groups, couples & families - fabulous rural and sea views. A contemporary spacious detached house with a safe, secluded and walled garden. Situated in a prime position with spectacular rural and sea views looking towards Dorset's Jurassic Coast. Sleeps up to 8 +2 comfortably in...
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    Isle of Portland, Dorset DT5 2DL
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Ted's House1 / 11
    (1)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Central Heating
    • Wi-Fi
    • Patio
    • Washer
    • Private Yard
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 2, 2018
    Just arrived home after staying for the Whitsun Week at Teds House and enjoyed our stay very much. Chesil Beach just down the road and 4 local pubs within walking distance, we...
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    About this property
    This lovely holiday home sits in the heart of Fortuneswell, Portland a short stroll from the Jurassic Coast. Sea views can be seen from the property where in the evening the rear windows provide lovely sunset viewing. The owners of the property have made this holiday property a home and offers...
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    Isle of Portland, Dorset DT5 1AG
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Cliff House1 / 8
    (4)Average
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Parking
    • Private Yard
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 21, 2018
    Large rooms basic accommodation with no frills. This is reflected in the price. Owners friendly & accommodating. Beach & parking behind property. Suited our needs for a...
    Reviewed November 10, 2016
    The whole family and dog had a great time, only thing missing for me was wifi. the pool table was in good nick, bathroom had damp walls but I was renting it not buying it so...
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    About this property
    Portland Stone detached house backing onto Chisel Beach. 3 bedrooms, gas central heating, large bathroom on the first floor, and ample parking for two cars. Ideal for sailing holidays, dog walkers, in fact anyone who wants to make use of all that Portland has to offer. The property also has a...
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    Isle of Portland, Dorset DT5 1AW
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Private Yard
    • Central Heating
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This lovely holiday home sits in the heart of Fortuneswell, Portland a short stroll from Chesil Cove. Sea views can be seen from the property where in the evening the rear windows provide lovely sunset viewing. The owners of the property have made this holiday property a home and it offers...
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    Isle of Portland, Dorset DT5 1AT
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Cliff Walk Cottage1 / 22
    (3)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Central Heating
    • DVD Player
    • Parking
    • Washer
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 12, 2018
    Really nice house has everything you need for your stay away nice quiet area good parking good base for exploring the Weymouth Portland area
    Reviewed September 6, 2018
    We were attending Weymouth and Portland sailing club for a sailing event and found this cottage perfect as only 10 min drive away and the house had everything we needed for the...
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    About this property
    Cliffwalk Cottage is a modern two bedroom house, which can sleep up to 4 people. The Property has WiFi and full gas central heating throughout. At the rear of the house there is a enclosed garden with patio and BBQ area with garden furniture and a clothesline. The lounge / diner : smart TV, Blu...
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    Isle of Portland, Dorset DT5 2LZ
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Mermaid Cottage1 / 8
    (1)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • DVD Player
    • Private Yard
    • Washer
    • Central Heating
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 21, 2017
    Our family all had a brilliant holiday, cottage comfortable, with everything we needed. Even a play room for the kids, trampoline & swings in the garden.No do's and dont's...
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    About this property
    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. A charming cottage nestled just behind Wakeham, backing on to open land. This spacious...
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    Isle of Portland, Dorset DT5 1HS
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Private Yard
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A modern spacious 2 bedroom house which formed part of the award winning Olympic Village built in 2012. There is a private garden great for barbecues. This property features an open plan kitchen & dining area and a spacious living room.Minutes away from Chesil Beach and Portland Marina. Portland...
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    Isle of Portland, Dorset DT5 1AU
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Central Heating
    • Patio
    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A sea side cottage situated a short stroll from Chesil beach and the Cove Inn, at the heart of Fortuneswell within a short distance of the Jurassic Coastline and National Sailing Academy at Portland Harbour. At the front of the property is an ideal place to relax with a cocktail under your own...
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    Location Information
    Isle of Portland, Dorset DT5 1NJ
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Grill
    • Wi-Fi
    • Private Yard
    • Patio
    • Washer
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Guillemot Cottage is a three storey terraced cottage in the heart of the small village of Easton and is a wonderful base for exploring Portland, Weymouth and the scenic Chesil Beach. The Cottage is newly refurbished over three floors. On entering the cottage you will find yourself in a cosy...
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    Isle of Portland, Dorset DT5 1BS
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    The Gift House, a historic Seaman's Chaplaincy1 / 22
    (3)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Washer
    • Cable/satellite TV
    • Private Yard
    • Central Heating
    • Ocean Views
    • Wi-Fi
    • Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 2, 2018
    We stayed at the Gift House over Christmas / New Year and enjoyed staying, the accommodation was well equipped and generally well maintained.Our party consisted of two...
    Reviewed September 28, 2017
    We stayed at The Gift House for 4 nights last week and loved the house so much! It has everything you could need and is really nicely decorated with lots of quirky additions...
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    About this property
    The house is a late Georgian stone house located in the middle of island village, facing the sea. All 4 double bedrooms, the lounge and dining room are having panoramic sea view. The house is fully equipped self catering and has everything you need for an unforgettable holiday. The house has...
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    Isle of Portland, Dorset DT5 1AQ
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Bayview1 / 22
    (5)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Wi-Fi
    • Balcony
    • Cable/satellite TV
    • Central Heating
    • Washer
    • Patio
    • DVD Player
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 10, 2015
    We loved our stay at Bayview. The back garden was definitely the best part of this property, the views were breathtaking! Lovely views from most windows too. House had lovely...
    Reviewed May 29, 2014
    My partner and I stayed here while visiting our nieces and needed a close place to stay. She was pregnant at the time and so proximity to our nieces and cleanliness were very...
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    About this property
    Bayview has beautiful sea and coastal views in all directions. There are extensive coast and country walks from the door and a number of local coves and beaches with safe swimming, in particular Weymouth. Portland Harbour is famed for its water sports and was the venue for the last Sailing...
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    Isle of Portland, Dorset DT5 1HE
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Shearwater located in Portland, Dorset1 / 36
    (4)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    The house was lovely with everything you needed down to cling film, take away menus, local interests and a beach hut. The area was great with a Tesco’s, small coop and great...
    Reviewed January 5, 2014
    We rented this house for a family holiday in October 2013, and couldn't of been happier with the accommodation.The house was clean, well laid out and had everything you could...
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    About this property
    Shearwater is a newly built three bedroom house, set over three floors, designed by an award-winning team and located on the east coast of Portland. It offers superb views of Pennsylvania Castle and out to the sea. The property is a highly energy efficient ‘Passivhaus' eco-home, operating on a low...
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    Isle of Portland, Dorset DT5 1FJ
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Jurassica House is part of our Olympic legacy, home to the Swedish sailing team during the sailing events in 2012. A great location for water sports enthusiasts, walkers, cyclists, rock climbing, bird watching and of course, perfect for simply for relaxing. Internally, the spacious living areas...
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    Isle of Portland, Dorset DT5 1AU
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You'll be sure to enjoy your time whilst staying at Cornerstone. This well-appointed home from home, complete with period features, offers ample accommodation for up to six guests, looking to enjoy a holiday in coastal Dorset. The modern kitchen is fully-equipped with a breakfast bar, which makes...
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    Castletown, Isle of Portland DT5 1LD
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    OLD HIGHER LIGHTHOUSE STOPES COTTAGE, family friendly, character holiday cottage1 / 16
    (7)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 13, 2018
    We stayed for a few days at the old lighthouse in May. Great cottage with everything we needed. Fantastic solar heated pool which we had use of, the kids swam every day! We...
    Reviewed April 19, 2018
    Having read all the details carefully and inspected photos thoroughly we thought we had found a real gem for what was for us, an expensive holiday rental at over £900 for a...
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    About this property
    This semi detached cottage is located on the tip of Portland Bill in Dorset and can sleep four people in two bedrooms.Stopes Cottage is a semi detached cottage next to a lighthouse on the tip of Portland Bill near to Weymouth in Dorset. The cottagesleeps four people in one double bedroom, one twin...
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    Isle of Portland, Dorset DT5 2JT
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Casita del mar1 / 11
    (2)Very good
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Ocean Views
    • Grill
    • Balcony
    • Washer
    • DVD Player
    • Terrace
    • Central Heating
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 6, 2017
    This cottage suited our family needs perfectly as we were able to bring our very well behaved dog with us! Susan was so helpful and ensured we were well informed about the...
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    About this property
    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 and chairs to seat six. A...
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    Isle of Portland, Dorset DT5 1NJ
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Central Heating
    • Ocean Views
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wavecrest is in the village of Fortuneswell, overlooking Chesil Beach and close to the Weymouth and Portland Sailing Academy and Windsurfing Centre. Perfectly located for sailors, windsurfers, divers, walkers and cyclists with storage for boards, sails, bikes and wetsuits as well as a 72 hour free...
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    Isle of Portland, Dorset DT5 1LX
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    1 Bow & Arrow Cottages1 / 18
    (3)Very good
    4 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Amenities & Details
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • Private Yard
    • DVD Player
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 23, 2018
    The house is very well presented and equipped. Lovely modern kitchen and bathroom, just a joy to use! The decor is smart and contemporary but the house retains great character...
    Reviewed June 9, 2016
    Spacious family house with loads of character and big rooms and comfy beds! Fantastic, well equipped kitchen and all amenities. Owners very helpful and neighbours friendly...
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    About this property
    This lovely family house is located in a perfect spot to offer the best of both worlds, a semi detached Edwardian cottage down a quiet lane leading to the beach and cliffs and just 10 minutes walk away from shops, cafes and other amenities. The ground floor offers comfortable, spacious open plan...
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    Isle of Portland, Dorset DT5 1JA
    Rental Home - 4 Bedrooms, 1 Bathroom, Sleeps 8
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    OLD HIGHER LIGHTHOUSE BRANSCOMBE LODGE, family friendly, character holiday cotta1 / 20
    (3)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 12, 2017
    Firstly I have to say that the location of Branscombe cottage is absolutely brilliant with views from the first floor sitting room area down to the current lighthouse,the old...
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    About this property
    This detached cottage is located on the tip of Portland Bill in Dorset and can sleep four people in two bedrooms.Brancombe Lodge is a detached cottage next to a lighthouse on the tip of Portland Bill near to Weymouth in Dorset. The cottage sleeps four people in one double bedroom, one twin room and...
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    Isle of Portland, Dorset DT5 2JT
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    9 Sidon Mews located in Portland, Dorset1 / 24
    (2)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 6, 2018
    We booked Sidon Mews for our summer holiday this year with my mother and father in law, my sister in law, her partner and their 7 month old as well as my husband and our...
    Reviewed January 6, 2018
    Fantastic location in easy walking distance to the beach. Had a great NY break and would certainly return to this property if staying in Portland again. House is very...
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    About this property
    When you're looking for an escape with the beauty of Portland Harbour on your doorstep, look no further that 9 Sidon Mews. With stylish and modern interiors and a bright and sunny garden, you will find plenty of space for everybody to unwind. This contemporary house is especially well suited to...
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    Isle of Portland, Dorset DT5 1FG
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Chesil View House located in Portland, Dorset1 / 15
    (2)Very good
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 25, 2017
    Just back from a lovely week here. The house is beautiful and the views from the top floor are amazing. Yes it's on a steep hill but so are most houses on Portland! Parking...
    Reviewed January 17, 2017
    The little house on St Martins Road is very sweet. It is on a tremendous hill and parking can be a problem but once inside it is very well appointed. The living/dining room is a...
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    About this property
    Chesil View House offers stylish accommodation that was originally a fisherman's cottage in the beautiful village of Fortuneswell, nestled amongst the hills of Portland. Internally the property is furnished to a high standard with spectacular views from the top of the house of Chesil Beach, Lyme...
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    Isle of Portland, Dorset DT5 1JY
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Elizabethan House located in Portland, Dorset1 / 24
    (4)Average
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 16, 2018
    Lovely old house, walls very thick so nice and cool in the hot weather. Typical stairs for an old property loved it. The free car park opposite does get busy as is the road that...
    Reviewed October 3, 2017
    The house was perfect for our visit, everything we needed. Close to the beach and also local pub. The dogs enjoyed it too!
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    About this property
    Elizabethan House is 17th Century Grade II listed property located in Portland, situated just 500 yards from Chesil Beach and within a short walk from the National Sailing Academy. Internally, the property has been refurbished whilst retaining a character style with exposed stone walls, stripped...
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    Location Information
    Isle of Portland, Dorset DT5 1AP
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    • Exchange rate: 1 British Pounds = 1.29 U.S. Dollars
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