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279 Results  |  
22 Photos

House | 2 Bedrooms | sleeps 5

Excellent 5/5 

2 Nights min stay

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from £62 /night

£430 - £620 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Stunning location with probably the best sea views on Portland. Attractive 2 bedroom house with gardens and easy parking, next to open hillside with uninterupted views of Weymouth Bay, the ocean and coastline. Close to great beaches, sailing, shops, pubs and restaurants Breath-taking panoramic views. Ideal situation for exploring Portland's natural heritage.  …see more

16 Photos

Cottage | 2 Bedrooms | sleeps 4

Excellent 5/5 

3 Nights min stay

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from £43 /night

£300 - £795 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 4 km
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Four star and M1 and M11 graded suitable for disabled. Great location with views towards Chesil Beach and Fleet Lagoon.  …see more

21 Photos

Townhouse | 2 Bedrooms | sleeps 4

Excellent 5/5 

3 Nights min stay

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from £72 /night

£500 - £900 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Modern, well equipped with great views just 100m from the beach with a traffic-free walk to Weymouth's harbour, shops and restaurants. Parking, balcony and garden. Great for families and for exploring the Dorset countryside and Jurassic coast. Last minute offers for July and August--see prices page....  …see more

Featured properties

20 Photos

Cottage | 2 Bedrooms | sleeps 4

Very Good 4.5/5 

2 Nights min stay

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from £46 /night

£320 - £695 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 4 km
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
A beautiful two bedroom cottage in Upwey, Weymouth. Ideal for family or quiet holidays. Beach and country walks near by. With 40ft garden, parking for two cars and stunning rural views down the valley. Shop 50 yards, pub ¼ mile. No smokers please. Pets welcome. The area is one of the sunniest places in Britain.  …see more

13 Photos

Cottage | 2 Bedrooms | sleeps 5

Excellent 5/5 

Short stays welcome

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from £86 /night

£600 - £750 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Suitable for over 5s only
  • Car not necessary
  • No pets allowed
  • Private garden
A cosy two bedroom cottage, with sea views. Located moments from the beach on the edge of Portland Harbour a prime location for sailing, windsurfing, fishing, walking and cycling. This two bedroom cottage is back from the main road, has off road parking and a garage. Two-bedroom cottage located moments from the beach on the edge of Portland Harbour  …see more

20 Photos

Farmhouse | 4 Bedrooms | sleeps 8

Very Good 4.5/5 

2 Nights min stay

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from £93 /night

£650 - £1050 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 6 km
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Escape to the country in this beautiful 4 bed Farmhouse with stunning views over Weymouth bay. Ideal for a relaxing in the countryside, but close enough access the town. A roaring fire, BBQ with panoramic views, or 3 good pubs within 1 mile, there's plenty on offer.  …see more

18 Photos

House | 5 Bedrooms | sleeps 12

Very Good 4.5/5 

1 night min stay

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from £122 /night

£850 - £1950 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0.8 km
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
A large garden ideal for family holidays. The house is 5 mins walk from the beach and Lodmoor park. Weymouth centre is 1/2 mile away where there are many shops, restaurants and bars. There are several pubs and shops near the house, a log fire, SKY TV, and good parking.  …see more

11 Photos

Studio | sleeps 2

3 Nights min stay

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from £46 /night

£318 - £382 / week

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Key info:

  • Beach / lakeside relaxation
  • Not suitable for children
  • Car not necessary
  • No pets allowed
The views and the privacy on this newly converted first floor studio takes some beating. The Sun streams through the large velux windows and french doors all day. Views stretch out to Lulworth cove , Kimmeridge and to the west Weymouth bay and the Isle of Portland Weymouth and Portland hosted the 2012 sailing Olympics  …see more

23 Photos

Cottage | 1 Bedroom | sleeps 2

Short stays welcome

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from £37 /night

£258 - £595 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
in Langton Herring, 200 yards from the pub, a neat semi-detached cottage, the ground floor of which has been made self-contained for your use  …see more

16 Photos

Cottage | 3 Bedrooms | sleeps 6

Short stays welcome

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from £65 /night

£449 - £948 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
 …see more

16 Photos

House | 5 Bedrooms | sleeps 10

Excellent 5/5 

3 Nights min stay

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from £190 /night

£1326 - £2993 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 4 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Summer Lodge a spacious newly built high specification property less than a mile from the coast. It is luxurious with things that most people only dream of having at home, two being a heated indoor swimming pool and games room.(perfect whatever the time of year)  …see more

20 Photos

House | 4 Bedrooms | sleeps 10

Excellent 5/5 

3 Nights min stay

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from £69 /night

£480 - £1150 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Suitable 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 is suited to outdoors enthusiasts and families. A perfect retreat with modern luxuries.  …see more

8 Photos

House | 3 Bedrooms | sleeps 6

Short stays welcome

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from £58 /night

£402 / week

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Key info:

  • Suitable for children of all ages
  • Pets welcome
  • Private garden
Country views/Four poster bed Situated in a semi-rural location beside a country road with extensive views across the downs towards Hardys Monument is this cosy cottage, the middle one of three  …see more

19 Photos

House | 2 Bedrooms | sleeps 4

Short stays welcome

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from £71 /night

£492 - £1150 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for over 5s only
  • Car advised
  • No pets allowed
  • Private garden
This semi detached cottage is located on the tip of Portland Bill in Dorset and can sleep four people in two bedrooms.  …see more

18 Photos

House | 4 Bedrooms | sleeps 8

Very Good 4.5/5 

3 Nights min stay

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from £83 /night

£578 - £1645 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
A newly built four bedroom house, just minutes from the attractions of Weymouth and Portland. A newly built 4 bedroom house, sleeps 8. Fully furnished patio and garden area with access to the Rodwell Trail coastal path.  …see more

9 Photos

House | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £70 /night

£485 - £1251 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0.08 km
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
A modern 3 bedroom split level house, sleeps 6. Passive House Eco-Home with triple glazing. Furnished to a high standard throughout. Private furnished patio ideal for al fresco dining. Off-street parking for 2 cars.  …see more

14 Photos

House | 4 Bedrooms | sleeps 8

Excellent 5/5 

3 Nights min stay

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from £62 /night

£433 - £1096 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
A large Victorian house boasting original, period features and close proximity to Chesil Beach. A 4 bedroom house set over three floors, sleeps 8. Furnished to a high standard throughout with period features. Close to Chesil Beach and the 2012 Olympic Sailing venue.  …see more

16 Photos

House | 3 Bedrooms | sleeps 6

Good 3.5/5 

Short stays welcome

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from £46 /night

£320 - £800 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable for over 5s only
  • Car advised
  • Pets welcome
  • Private garden
Sleeping up to six people in three bedrooms, this detached holiday home is just over a mile from the sea front, on the edge of Weymouth.  …see more

10 Photos

House | 3 Bedrooms | sleeps 6

Short stays welcome

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from £80 /night

£560 - £675 / week

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Key info:

  • Suitable for children of all ages
  • Pets welcome
Close to the seafront at Chiswell near the southern end of the famous Chesil Beach, this charming refurbished, 200 year old holiday cottage retains period features, offering stylish and comfortable accommodation  …see more

17 Photos

House | 4 Bedrooms | sleeps 8

Very Good 4/5 

3 Nights min stay

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from £83 /night

£578 - £1645 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
Cormorant View is a spacious house situated in a gated cul-de-sac within walking distance of the shops, restaurants, attractions and sandy beaches of Weymouth.Internally this spacious accommodation is furnished to a high standard and offers fan  …see more

8 Photos

House | 3 Bedrooms | sleeps 6

Excellent 5/5 

Short stays welcome

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from £64 /night

£447 / week

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Key info:

  • Suitable for children of all ages
  • Pets welcome
Sea views from rear of cottage Set at the southern point of Portland with great coastline views  …see more

17 Photos

House | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £65 /night

£454 - £1044 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
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.  …see more

18 Photos

Cottage | 3 Bedrooms | sleeps 6

Good 3/5 

3 Nights min stay

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from £65 /night

£454 - £1251 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
Sea Shell Cottage offers spacious accommodation in the heart of the highly desirable Brewers Quay area of Weymouth.  …see more

18 Photos

Apartment | 2 Bedrooms | sleeps 4

Excellent 5/5 

3 Nights min stay

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from £70 /night

£485 - £1251 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
Ocean View is a fifth floor apartment in a landmark building benefiting from level access and stunning views over the 2012 Olympic sailing venue.  …see more

9 Photos

House | 2 Bedrooms | sleeps 4

Short stays welcome

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from £57 /night

£394 - £756 / week

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Key info:

  • Suitable for children of all ages
  • Pets welcome
  • Private garden
Ground floor: Living/dining room  …see more

17 Photos

House | 2 Bedrooms | sleeps 4

Excellent 5/5 

3 Nights min stay

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from £50 /night

£350 - £899 / week

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Key info:

  • Nearest beach 5 km
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Stylish open plan 2 bedroom house, sleeping 4. Enclosed, furnished garden with seating for 4 and barbeque. Offers low energy, low carbon living in a sustainably built home. Just a short walk away from Chesil Beach and the National Sailing Academy.  …see more

13 Photos

House | 3 Bedrooms | sleeps 7

Excellent 5/5 

3 Nights min stay

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from £65 /night

£454 - £1251 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
A three bedroom grade 2 listed house, sleeps 6/7. South facing private courtyard. Short walk to the beach. Great location for exploring the Jurassic coast. Parking permit provided.  …see more

21 Photos

Apartment | 2 Bedrooms | sleeps 4

Good 3/5 

3 Nights min stay

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from £96 /night

£671 - £1769 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
Spectacular views from the penthouse of Portland's premier development. A seventh floor triplex apartment with 2 bedrooms, sleeps 4. High quality finish throughout. Panoramic views over the 2012 Olympic sailing venue and out to sea.  …see more

19 Photos

Apartment | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £62 /night

£433 - £1096 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 4 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
Ocean Views is a new luxury seafront development of apartments on the Isle of Portland in Dorset, situated on the Jurassic coast beside Chesil Beach, in a location guaranteed to inspire. 106 Ocean Views is a fifth floor apartment benefiting from superb sea views  …see more

13 Photos

House | 3 Bedrooms | sleeps 6

Very Good 4/5 

3 Nights min stay

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from £70 /night

£485 - £1251 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0.75 km
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
A 3 bedroom house, sleeping 6. Pionerring Passivhaus Eco-Home with triple glazing. Pennsylvania Heights includes a dedicated nature reserve offering large open space free to enjoy for all. Far reaching sea views of Pennsylvania Castle and Portland Bill.  …see more

12 Photos

House | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £58 /night

£401 - £836 / week

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Key info:

  • Suitable for children of all ages
  • No pets allowed
This terraced holiday home sits in a quiet area between Weymouth and Portland overlooking Portland harbour with sea views  …see more

16 Photos

House | 2 Bedrooms | sleeps 4

Short stays welcome

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from £48 /night

£332 - £728 / week

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Key info:

  • Suitable for over 5s only
  • Pets welcome
  • Private garden
This is a wonderful Grade II listed, 18th century, thatched cottage, nestling opposite the village church in the picturesque Dorset village of Upwey, just four miles from Weymouth and can sleep four people in two bedrooms.  …see more

5 Photos

House | 1 Bedroom | sleeps 2

Short stays welcome

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from £41 /night

£284 - £316 / week

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Key info:

  • Suitable for children of all ages
  • Pets welcome
  • Private garden
This 17th century cottage, originally the village bake-house, adjoins the owners home 1/2 mile from the village and within a stone's throw of the famous Abbotsbury Swannery  …see more

15 Photos

Cottage | 3 Bedrooms | sleeps 5

Short stays welcome

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from £45 /night

£314 - £785 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable 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

6 Photos

House | 1 Bedroom | sleeps 2

Very Good 4/5 

Short stays welcome

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from £49 /night

£340 - £703 / week

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Key info:

  • Suitable for children of all ages
  • No pets allowed
Ground floor: Living/raised dining area with wooden floors/kitchen with tiled floor  …see more

17 Photos

House | 1 Bedroom | sleeps 4

Good 3/5 

3 Nights min stay

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from £43 /night

£298 - £723 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
Ocean Views is a new luxury seafront development of apartments on the Isle of Portland in Dorset, situated on the Jurassic coast beside Chesil Beach, in a location guaranteed to inspire.  …see more

16 Photos

House | 4 Bedrooms | sleeps 8

Excellent 5/5 

3 Nights min stay

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from £96 /night

£671 - £1769 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable for children of all ages
  • No pets allowed
A stylish 3 storey house situated in the popular Brewers Quay area of Weymouth  …see more

13 Photos

Apartment | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £56 /night

£391 - £961 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
A stylish apartment complete with furnished balcony, just a short walk from the attractions of Weymouth. A 2 bedroom, first floor apartment, sleeps 4. Furnished to a high standard throughout. Balcony complete with two chairs. Off-street parking for 1 car.  …see more

18 Photos

House | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £53 /night

£371 - £1095 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
Sea Pinks Cottage was built around 1860 and is a fine example of a traditional fisherman's cottage built with Portland stone.  …see more

9 Photos

House | 1 Bedroom | sleeps 2

7 Nights min stay

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from £90 /night

£625 / week

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Key info:

  • Suitable for children of all ages
  • No pets allowed
Set in the heart of the picture postcard village of Osmington, this single storey holiday cottage offers comfortable accommodation in a peaceful location, opposite the church and attached to the owners home  …see more

17 Photos

Apartment | 2 Bedrooms | sleeps 4

rentals_reviews_rating_1 

3 Nights min stay

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from £65 /night

£454 - £961 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
A modern apartment with fantastic on-site health facilities, near the 2012 Olympic Sailing venue.  …see more

14 Photos

Apartment | 3 Bedrooms | sleeps 5

3 Nights min stay

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from £65 /night

£454 - £1251 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable for children of all ages
  • No pets allowed
A stylish penthouse set over two floors with views over Weymouth Harbour  …see more

17 Photos

House | 4 Bedrooms | sleeps 8

Excellent 5/5 

3 Nights min stay

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from £96 /night

£671 - £1894 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Nothe View is spacious four bedroom townhouse set over three storeys. Situated within the Admirals Quarter development, Nothe View perfectly combines contemporary comfort and design with environmental sensitivity.  …see more

23 Photos

House | 3 Bedrooms | sleeps 6

Very Good 4.5/5 

3 Nights min stay

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from £70 /night

£485 - £1355 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 11 km
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
A period stone house full of character in a peaceful location close to Weymouth. A charming 3 bedroom house, sleeps 6. Furnished to a high standard throughout with open fires. Pretty courtyard garden with furniture.  …see more

11 Photos

Apartment | 1 Bedroom | sleeps 2

3 Nights min stay

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from £43 /night

£298 - £775 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
Well-appointed, contemporary and centrally located in the heart of Weymouth  …see more

21 Photos

House | 2 Bedrooms | sleeps 4

Short stays welcome

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from £73 /night

£508 - £1165 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for over 5s only
  • Car advised
  • No pets allowed
  • Private garden
This detached cottage is located on the tip of Portland Bill in Dorset and can sleep four people in two bedrooms.  …see more

16 Photos

House | 4 Bedrooms | sleeps 6

3 Nights min stay

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from £74 /night

£516 - £1475 / week

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Key info:

  • Suitable for children of all ages
  • Car advised
  • No pets allowed
A newly refurbished country house set in a beautiful rural position. A 4 bedroom house sleeping 6. Set in a rural position with 1/3 acre garden. Newly refurbished to a high standard. Short distance to coastal walks along sea cliff edge. Off-street parking for 2 cars.  …see more

13 Photos

House | 3 Bedrooms | sleeps 6

Excellent 5/5 

3 Nights min stay

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from £65 /night

£454 - £1251 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
Wessex Ho is a three bedroom property, sleeping up to six people.  It is situated a short drive or a 20 minute walk away from the town centre and beach.  …see more

20 Photos

Apartment | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £90 /night

£630 - £1645 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
Spectacular, unrivalled balcony views from the penthouse of Portland’s premier development. 2 bedroom luxury penthouse apartment, sleeping 4. High quality and stylish finish throughout. Breathtaking views from each room over the 2012 Olympic sailing venue and out to sea  …see more

9 Photos

House | 3 Bedrooms | sleeps 7

Short stays welcome

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from £74 /night

£512 - £1038 / week

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Key info:

  • Suitable for children of all ages
  • Pets welcome
  • Private garden
Situated in a secluded valley on the edge of the 'picture postcard' village of Osmington, this comfortable and sympathetically converted holiday cottage lies just a mile from the Heritage coastline of Dorset  …see more