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Isle of Portland House Rentals

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    Travellers to Isle of Portland are booking July dates now. Secure your holiday rental today, and have the perfect trip.
    30 Matching Rentals in Isle of PortlandView all 58 rentals
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    Pitt Hayes Cottage1 / 14
    (11)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pebble View1 / 9
    (18)Very good
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
    • Wi-Fi
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cliffwalk Cottage is a modern two bedroom house, which can sleep up to 4 people. The Property has 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 : Double leather sofa...
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    DT5 2LZ, Isle of Portland, Dorset
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    65 Fortuneswell - 180° Sea Views from Balcony1 / 19
    (38)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Central Heating
    • Ocean Views
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Parking
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 July 2017
    This holiday house is lovely. On the isle of portland with beautiful views over the sea from a large balcony which can be accessed from the master bedroom or a door on the...
    Reviewed 6 June 2017
    We stayed as a family (3 couples and a teen) and there was plenty of space. The location is great. Beach is a good 'walk the dinner off' distance away. Pubs and shops nearby...
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    About this property
    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, couples and families - with...
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    DT5 1LX, Isle of Portland, Dorset
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    1 The Old Police Station1 / 17
    (6)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Private Garden
    • Wi-Fi
    • Ocean Views
    • Grill
    • DVD Player
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 September 2017
    Lovely holiday home, really well equipped and very spacious. Only thing missing was a washing machine. Location close to the beach, Weymouth and many places to visit.
    Reviewed 1 January 2017
    The property was as described and larger than anticipated. Although there is a designated car parking space behind the property, we managed to park on the road outside the...
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    About this property
    A beautifully presented character house with views over Chesil Beach and Portland Harbour. This holiday home has many character features and really is a home from home. The property has a single parking space, there is also ample on road parking and a covered 'alfresco dining' seating area. A...
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    DT5 1AU, Isle of Portland, Dorset
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    Quarries Reach, rural & sea views Portland, Dorset1 / 85
    (55)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • Central Heating
    • DVD Player
    • Ocean Views
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    We loved our stay at Quarries Reach! From the minute we arrive, we were all settled and felt at home. It’s fully equipped for a stay. The garden is fully enclosed meaning the...
    Reviewed 4 weeks ago
    This property is ideal for a family stay with a gated garden and lovely lounge with great views. The house has a well equipped kitchen and is generously supplied with towels etc...
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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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    DT5 2DL, Isle of Portland, Dorset
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Mermaid Cottage1 / 8
    (1)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Grill
    • DVD Player
    • Private Garden
    • Washer
    • Central Heating
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 August 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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    DT5 1HS, Isle of Portland, Dorset
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Private Garden
    • 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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    DT5 1AT, Isle of Portland, Dorset
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    The Gift House, a historic Seaman's Chaplaincy1 / 44
    (3)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Cable/satellite TV
    • Private Garden
    • Central Heating
    • Ocean Views
    • Wi-Fi
    • Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 January 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 28 September 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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    DT5 1AQ, Isle of Portland, Dorset
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lyndhurst is a four bedroomed house opposite Victoria Gardens and a short walk from Chesil Beach. Downstairs you will find two family rooms, one with a TV and the other for quiet moments. The kitchen, which overlooks the outside decking area, is spacious and sports a large dining table - ideal...
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    DT5 1AH, Isle of Portland, Dorset
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 7
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    'Stones throw'1 / 18
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Garden
    • Parking
    • Central Heating
    • Ocean Views
    • Patio
    • DVD Player
    • Washer
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 July 2016
    Great weekend spent down in Portland staying at Windmill's, tucked away in a quiet area with a very short walk to the shops.Very modern & clean, all the mod-cons you could...
    Reviewed 1 June 2016
    House is stunning... feels brand new. All mod cons - TVs in every room - and very effective heating even for my filipina wife. Lovely sailing themed decor throughout.Very...
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    About this property
    Modern 3 bedroom house located in a quite cul de sac in Easton on the Isle of Portland at the centre of the Jurassic coast three double bedrooms, 1 ensuite, 3 toilets secure storage for bikes etc. 2 private parking spaces. Ground floor consists of a hallway, a large utility room with sink. washing...
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    DT5 2AD, Isle of Portland, Dorset
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Hot Tub
    • Grill
    • Washer
    • Central Heating
    • DVD Player
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Set in a stunning location with magnificent views over Portland Bill and the lighthouse, this detatched cottage for 4 with decked patio, offers a great holiday location where one can watch time go by with the passing ships and boating activity around Portland Bill. There is superb scenic coastal...
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    DT5 2JT, Isle of Portland, Dorset
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Hot Tub
    • DVD Player
    • Washer
    • Grill
    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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    DT5 1BS, Isle of Portland, Dorset
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Central Heating
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This centuries-old cottage is in Easton, a village at the heart of the peaceful island of Portland. Easton has a good selection of shops, friendly pubs, cafes and a children's play area. Dunsubbin is a short walk from the atmospheric Church Ope Cove with its 'smuggler's' graveyard. Portland is...
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    DT5 1HG, Isle of Portland, Dorset
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Central Heating
    • Patio
    • Parking
    Suitability
    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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    DT5 1NJ, Isle of Portland, Dorset
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Cliff House1 / 8
    (2)Average
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Parking
    • Private Garden
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 November 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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    DT5 1AW, Isle of Portland, Dorset
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    Shearwater located in Portland, Dorset1 / 16
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 January 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...
    Reviewed 12 May 2013
    Found the property to be very clean and beautifully decorated. The kitchen had everything you needed down to washing up liquid to tin foil and cling film. There was a brochure...
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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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    DT5 1FJ, Isle of Portland, Dorset
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Casita del mar1 / 11
    (1)Excellent
    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 6 August 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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    DT5 1NJ, Isle of Portland, Dorset
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    9 Sidon Mews located in Portland, Dorset1 / 24
    (1)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 January 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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    DT5 1FG, Isle of Portland, Dorset
    Holiday Rental House - 4 Bedrooms, 2 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 10 August 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 29 May 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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    DT5 1HE, Isle of Portland, Dorset
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Terrace
    • Grill
    • Patio
    • Housekeeping Included
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our house will be a perfect place for you to linger with family and friends on the amazing Jurassic Coast. Whether you want to relax by the sea, enjoy sailing, diving, climbing or fishing or simply want to explore this fascinating and beautiful part of England you can have it all. Our Grade II...
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    DT51LU, Isle of Portland, Dorset
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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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 are...
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    DT5 1AU, Isle of Portland, Dorset
    Holiday Rental House - 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 25 August 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 17 January 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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    DT5 1JY, Isle of Portland, Dorset
    Holiday Rental House - 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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    DT5 1LX, Isle of Portland, Dorset
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    9 Bedrooms, 10 Bathrooms, Sleeps 20 Quick View
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    • Grill
    • Balcony
    • Parking
    • Washer
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Opulence reigns at this modernized castle in Dorset. Chandeliers swing above you, and the blue English Channel beckons below. Though it was built 200 years ago of Portland stone, this castle is far from old school. The furnishings exhibit classic lines in sophisticated neutral colors, full of...
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    DT5 1AA, Isle of Portland, Dorset
    Holiday Rental House - 9 Bedrooms, 10 Bathrooms, Sleeps 20
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    Elizabethan House located in Portland, Dorset1 / 24
    (3)Average
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 October 2017
    The house was perfect for our visit, everything we needed. Close to the beach and also local pub. The dogs enjoyed it too!
    Reviewed 6 August 2015
    This is a pleasant property with plenty of space. The lounge/dining room was welcoming and comfortable and it has possibly the best equipped kitchen I have had in a rented...
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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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    DT5 1AP, Isle of Portland, Dorset
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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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 12 March 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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    DT5 2JT, Isle of Portland, Dorset
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1 Bow & Arrow Cottages1 / 36
    (2)Very good
    4 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Grill
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • Private Garden
    • DVD Player
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 June 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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    DT5 1JA, Isle of Portland, Dorset
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 8
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    OLD HIGHER LIGHTHOUSE STOPES COTTAGE, family friendly, character holiday cottage1 / 16
    (6)Average
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Washer
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 April 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...
    Reviewed 15 October 2017
    Branscombe Cottage The positive side. A great location. Quiet and with everything you needed there . The decor downstairs is rather tired and the carpets dingy but actually...
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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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    Location Information
    DT5 2JT, Isle of Portland, Dorset
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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