Houses in Portland and cottages – Holiday Lettings - Holiday Rentals Portland

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56 Holiday homes

(38) Excellent 

1 / 24

Church Ope Studio - Portland studio sleeps 2

Isle of Portland / Portland

Studio 2 3 nights min stay

  • Studio
  • Sleeps 2
  • 3 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 0.5 km; Not suitable for children;
4 star studio on the Jurassic coast path at Church Ope Cove Portland Dorset. Spectacular view of the sea through ancient Rufus castle arch. Romantic hideaway for 2, a cosy retreat for walkers, work or leisure. Church Ope Studio is open all year. Wood burner. Wifi. Lu  …see more

from £53 / night

£325 - £395 / week

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from £53 / night

(40) Excellent 

1 / 17

Quarries Reach, rural & sea views Portland, Dorset

Isle of Portland / Portland

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Beach / lakeside relaxation; Child friendly ; Car advised;
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. Sle  …see more

from £120 / night

£900 - £1430 / week

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from £120 / night

(32) Excellent 

1 / 19

65 Fortuneswell - 180° Sea Views from Balcony

Isle of Portland / Portland

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 0 km; Child friendly ;
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, coup  …see more

from £100 / night

£760 - £1230 / week

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from £100 / night

1 / 8

Sea View - Portland cottage sleeps 6

Isle of Portland / Portland

3 6 7 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 1 km; Child friendly ;
4 Sea View offers the best of modern comforts with period character in a cottage just a short walk from the splendors of Chesil Beach & Cove on the Isle of Portland Dorset.Offering a fabulous kitchen and comfortable accommodation.A character cottage designed to slee  …see more

from £85 / night

£400 - £850 / week

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from £85 / night

1 / 14

Marina Bay View Apartment - Portland Harbour

Isle of Portland / Portland

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 1 km; Swimming pool;
Marina View Apartment is a stunning modern apartment located overlooking Portland Marina and Harbour on the Isle of Portland, Dorset. The modern accommodation on two floors is well presented and offers three spacious bedrooms. Use of indoor pool and great as a base fo  …see more

from £95 / night

£1050 / week

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from £95 / night

(4) Excellent 

1 / 17

1 The Old Police Station - Portland house sleeps 7

Isle of Portland / Portland

3 7 7 nights min stay

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 1 km; Child friendly ;
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 'alfresc  …see more

from £93 / night

£650 - £900 / week

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from £93 / night

(9) Very Good 

1 / 19

Pitt Hayes Cottage - Portland house sleeps 8

Isle of Portland / Portland

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Nearest beach 1 km; Child friendly ; Car not necessary;
This well presented holiday house has a large and sociable open plan living area with kitchen, seating and dining areas, allowing for a relaxed and inclusive holiday atmosphere.There are four bedrooms, a bathroom and a shower room. The ground floor provides two twin roo  …see more

from £75 / night

£530 - £1000 / week

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from £75 / night

1 / 10

Ted's House - Portland house sleeps 8

Isle of Portland / Portland

4 8 7 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Child friendly ; No pets allowed; Private garden;
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 p  …see more

from £93 / night

£650 - £900 / week

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from £93 / night

(6) Very Good 

1 / 22

Ocean Studio Apartments OSA11A-Southwell, Portland

Isle of Portland / Portland

Studio 2 2 nights min stay

  • Studio
  • Sleeps 2
  • 2 nights min stay
Key info: Nearest beach 3 km; Suitable for children age 5+; Car advised;
Self contained apartment base on Southwell business park , isle of Portland. A short stroll from famous Portland bill& Jurassic coastline. Come &see for yourself Towels,Linens ,Toiletries provided equipped with hair dryer,iron+board ,fridge,toaster,kettle,Microwave ov  …see more

from £45 / night

£300 / week

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from £45 / night

(9) Very Good 

1 / 9

Pebble View - Portland house sleeps 6

Isle of Portland / Portland

3 6 4 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 1 km; Child friendly ;
Pebbles view is a Victorian Portland stone built mid terrace cottage in the village of Fortuneswell Portland offering stunning panoramic sea views of the Jurassic coasts Chesil beach from all floorsThe newly refurbished cottage arranged over three floors comprises of t  …see more

from £70 / night

£490 - £640 / week

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from £70 / night

(25) Very Good 

1 / 22

Rosa Cottage - Portland cottage sleeps 4

Isle of Portland / Portland

3 4 Min stay varies

  • 3 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 0.2 km; Child friendly ;
A beautiful restored Victorian terraced cottage, on a quiet street in the village of Fortuneswell on the Isle of Portland, only 5 minutes walk from the famous Chesil Beach and part of Dorset's glorious Jurassic Coast. 5 min drive from National Sailing Academy. This fo  …see more

from £75 / night

£320 - £760 / week

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from £75 / night

1 / 10

High Street - Portland private room sleeps 5

Isle of Portland / Portland

5 5 7 nights min stay

  • 5 bedrooms
  • Sleeps 5
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Not suitable for children; No pets allowed;
Well suited single occupancy rooms, possibly suitable for a couple with an additional fee providing access to communal living room, kitchen & utility room. On the ground floor there is communal living room, kitchen & one bedroom. On the first floor there are two bedro  …see more

from £20 / night

£140 / week

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from £20 / night

(1) Excellent 

1 / 10

Dory Cottage - Portland cottage sleeps 5

Isle of Portland / Portland

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 1 km; Suitable for children age 5+;
Three bedroom Portland Stone cottage over three floors with fabulous views over Chesil Beach and The Fleet. Just a short walk from Chesil Beach. Divers, sailors, walkers and families will love this cottage. WiFi and TV included but you will be busy watching the sunse  …see more

from £57 / night

£400 - £750 / week

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from £57 / night

(6) Excellent 

1 / 10

Chiswell Cottage - Portland cottage sleeps 8

Isle of Portland / Portland

4 8 7 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 1 km; Child friendly ;
A spacious, comfortable cottage in this pretty road, a short walk down to Chesil Beach and Cove, and being in a convenient position for The National Sailing Academy and Portland Harbour. A four bedroom cottage over three floors with views over Chesil Beach. There is a  …see more

from £93 / night

£450 - £950 / week

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from £93 / night

1 / 8

Mermaid Cottage - Portland house sleeps 10

Isle of Portland / Portland

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Beach / lakeside relaxation; Child friendly ; Car advised;
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  …see more

from £71 / night

£500 - £1000 / week

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from £71 / night

(8) Excellent 

1 / 32

Fishermans Cottage - Portland cottage sleeps 6

Isle of Portland / Portland

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 12 km; Child friendly ;
Fishermans Cottage is a charming detached 18th century cottage on the edge of Southwell, with excellent sea views. Recently renovated with full central heating throughout and Wi Fi. On the ground floor there is a lounge / diner with sea view, a reception room, a fully  …see more

from £85 / night

£350 - £995 / week

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from £85 / night

1 / 8

Coral Cove Cottage - Portland cottage sleeps 5

Isle of Portland / Portland

3 5 7 nights min stay

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 1 km; Suitable for children age 5+;
Charming three bedroom cottage ticked away a pebble's throw from Chesil Beach. Coral Cove is found between Sea View and Coastguard Cottages at the north end of the island. Ideal as a base for sailing, walking, diving and exploring the island and the rest of the c  …see more

from £76 / night

£530 - £750 / week

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from £76 / night

1 / 23

Pebble Watch - Portland house sleeps 5

Isle of Portland / Portland

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 1 km; Suitable for children age 5+;
This well presented holiday house has a welcoming living area with kitchen, seating and dining areas, allowing for a relaxed and inclusive holiday atmosphere. A private enclosed garden over 3 levels. There are three bedrooms, a bathroom, a shower room and WC. The ele  …see more

from £100 / night

£475 - £675 / week

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from £100 / night

1 / 24

Admirals View (ADMVI) - Portland cottage sleeps 8

Isle of Portland / Portland

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Child friendly ; Car advised; No pets allowed;
Admiral's View is a unique luxurious penthouse conversion in Dorset beside the Jurassic coastline in Portland. The roof terrace enjoys wonderful views of Portland Harbour, Weymouth Bay and Lyme Bay in the distance. The layout of Admiral's View is such that it is suited  …see more

from £98 / night

£683 - £1334 / week

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from £98 / night

(11) Very Good 

1 / 20

Pebble Reef - Portland cottage sleeps 6

Isle of Portland / Portland

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 0.5 km; Child friendly ;
Pebble Reef is a traditional Quarryman's Cottage, full of character but lovingly renovated to include all the modern comforts you need. The cottage sleeps up to six people in 3 comfortable bedrooms. Upstairs there's one double with en-suite shower room, a twin  …see more

from £75 / night

£325 - £895 / week

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from £75 / night

(1) Excellent 

1 / 17

Ocean Studio Apartments OSA12- Southwell, Portland

Isle of Portland / Portland

Studio 3 2 nights min stay

  • Studio
  • Sleeps 3
  • 2 nights min stay
Key info: Suitable for children age 5+; Car essential; No pets allowed;
Self contained apartment base on Southwell business park , isle of Portland. A short stroll from famous Portland bill& Jurassic coastline. Come &see for yourself Towels,Linens ,Toiletries provided equipped with hair dryer,iron+board ,fridge,toaster,kettle,Microwave ov  …see more

from £79 / night

£500 / week

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from £79 / night

(1) Excellent 

1 / 6

10 Fortuneswell - Portland cottage sleeps 4

Isle of Portland / Portland

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 1 km; Suitable for children age 5+;
A charming Portland Stone Cottage in the heart of Fortuneswell. Tastefully decorated and furnished it offers cosy accommodation, for four people. Public parking close by and you are just a short stroll from Chesil Beach, if you turn in the other direction and head up th  …see more

from £57 / night

£400 - £675 / week

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from £57 / night

(2) Very Good 

1 / 18

1 Bow & Arrow Cottages - Portland house sleeps 8

Isle of Portland / Portland

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 0.2 km; Suitable for children age 5+;
This elegantly refurbished 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 flo  …see more

from £100 / night

£700 - £1350 / week

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from £100 / night

(13) Very Good 

1 / 14

Bakers Dozen - Three Bedroom Coastal Cottage

Isle of Portland / Portland

3 6 3 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min stay
Key info: Beach / lakeside relaxation; Child friendly ; Car advised;
A charming three bedroomed character property, situated in a quiet location on the southern part of the Isle of Portland with panoramic sea views to the rear. Beautiful coastal paths and scenery close by, ideal for a chilled out relaxing break. The house has a televisi  …see more

from £95 / night

£550 - £750 / week

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from £95 / night

(10) Very Good 

1 / 20

Seagull Cottage - Portland cottage sleeps 4

Isle of Portland / Portland

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 1 km; Child friendly ;
Seagull Cottage is a lovely holiday house ideal for sailing, beach, and outdoor activity holidays in Portland. It is located just one mile from the Weymouth and Portland National Sailing Academy (WPNSA), the 2012 Olympic Sailing venue. Chesil beach is just a few minut  …see more

from £90 / night

£595 - £695 / week

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from £90 / night

(3) Excellent 

1 / 45

Alpen Rose Cottage - Portland cottage sleeps 5

Isle of Portland / Portland

3 5 7 nights min stay

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min stay
Key info: Child friendly ; Ask about pets; Private garden;
Alpen Rose is a 200 year old 3 bedroom terraced cottage, situated in a quiet residential road in the village of Easton. The cottage is really spacious and has been totally refurbished throughout to an exceptionally high standard. It has everything you need for a very  …see more

from £43 / night

£295 - £850 / week

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from £43 / night

1 / 24

Bowman's Cottage (BOWMA) - Portland cottage sleeps 4

Isle of Portland / Portland

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Child friendly ; Car advised; No pets allowed;
Situated on the rugged and beautiful isle of Portland, Bowman's is a character, terraced Dorset holiday cottage located on the wide avenue which is Wakeham. Internally, the owners have sympathetically updated the decor in a contemporary style, whilst maintaining the ori  …see more

from £51 / night

£355 - £685 / week

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from £51 / night

1 / 11

Casita del mar - Portland house sleeps 6

Isle of Portland / Portland

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 5 km; Child friendly ;
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  …see more

from £120 / night

£465 - £750 / week

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from £120 / night

(22) Very Good 

1 / 31

BEAUTIFUL STUDIO APARTMENT - OCEAN VIEWS,PORTLAND

Isle of Portland / Portland

Studio 2 3 nights min stay

  • Studio
  • Sleeps 2
  • 3 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 2 km; Not suitable for children;
A VERY MODERN HOLIDAY LET STUDIO APARTMENT LOCATED IN A QUIET POSITION ON THE ISLE OF PORTLAND NEAR WEYMOUTH IN THE HEART OF DORSET, ON THE COAST OF SOUTH WEST ENGLAND. SUITABLE FOR SINGLE OR DOUBLE OCCUPANCY. FACILITIES INCLUDE FLAT SCREEN TV, DVD PLAYER, MICROWAVE,  …see more

from £47 / night

£295 - £365 / week

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from £47 / night

(8) Very Good 

1 / 8

Two bedroom holiday bungalow - Portland bungalow sleeps 4

Isle of Portland / Portland

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Child friendly ; No pets allowed;
A comfortable terraced bungalow with lounge/diner, kitchen and patio area in grounds near to Pennsylvania Castle so ideal for anyone attending functions there. Portland is a nature lovers paradise particularly of interest to birdwatching enthusiasts also to sailors as t  …see more

from £75 / night

£500 - £700 / week

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from £75 / night

(20) Very Good 

1 / 8

fishermans view - Portland cottage sleeps 4

Isle of Portland / Portland

3 4 7 nights min stay

  • 3 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 0.2 km; Suitable for children age 5+;
Cottage with sea views over beautiful famous Chesil Beach. South facing patio with sea view. Accommodates up to four . Weekly change over Saturday. Dogs welcome and most places are dog friendly. Nearest beach approximately 200 metres. Minutes from excellent bus servic  …see more

from £40 / night

£280 - £580 / week

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from £40 / night

(1) Good 

1 / 11

Ocean Studio Apartments OSA9- Portland Dorset

Isle of Portland / Portland

Studio 2 2 nights min stay

  • Studio
  • Sleeps 2
  • 2 nights min stay
Key info: Nearest beach 3 km; Suitable for children age 5+; Car advised;
If you are looking for the perfect place for a romantic weekend break for two, a longer get-away-from-it-all holiday or fun time with a group of friends then you've found it!Every apartment combines quality overnight comfort and en-suite facilities with modern self  …see more

from £59 / night

£399 / week

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from £59 / night

(2) Very Good 

1 / 6

Portland Hideaway - Portland cottage sleeps 2

Isle of Portland / Portland

1 2 3 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 3 nights min stay
Key info: Ask owner if suitable for children; Car not necessary; Air conditioning;
The Portland Hideaway is a 4* self contained self catering unit with open plan living space.It benefits from a fully equipped kitchen,separate shower room with wc & sink,open plan bedroom/lounge area with ample seating on the reclining leather sofa's & air  …see more

from £49 / night

£343 - £469 / week

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from £49 / night

(3) Excellent 

1 / 18

Windmills - Portland house sleeps 6

Isle of Portland / Portland

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Beach / lakeside relaxation; Child friendly ; Ask about pets;
New 3 bedroom house located in a quite cul de sac in Easton on the Isle of Portland at the centre of the Jurassic coast two double bedrooms one twin 3 toilets secure storage for bikes etc. 2 private parking spaces. Ground floor consists of a hallway, a large utility ro  …see more

from £80 / night

£650 - £800 / week

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from £80 / night

(1) Good 

1 / 14

Artist Cottage - Portland cottage sleeps 4

Isle of Portland / Portland

2 4 7 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 1 km; Child friendly ;
Built in the 1800's, this sweet little original Portland stone Fisherman's cottage promises a lovely holiday experience.Artist Cottage sleeps four people in two bedrooms and has been delightfully restored.The cottage is found in Fortuneswell just five minutes from the N  …see more

from £68 / night

£475 - £675 / week

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from £68 / night

(1) Poor 

1 / 8

Portland house with a view - Portland house sleeps 5

Isle of Portland / Portland

3 5 3 nights min stay

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min stay
Key info: Child friendly ; Pet friendly; Private garden;
Detached house on small development of similar properties. Lovely views from rear windows. Good quiet location, property is in a small cul-de-sac so no through traffic. Chisel beach is just a few minutes walk along with beautiful nearby walks through Portlands disused  …see more

from £100 / night

£595 / week

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from £100 / night

1 / 31

Delimara - Portland cottage sleeps 5

Isle of Portland / Portland

3 5 7 nights min stay

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Child friendly ; No pets allowed;
Delimara is a charming, detached cottage set in a quiet cul-de-sac in Easton on the Isle of Portland near Weymouth. With one ground floor king-size double, plus one twin and one single set in the eaves, this cottage can sleep five people. Delimara also offers a kitchen,  …see more

from £48 / night

£332 - £756 / week

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from £48 / night

1 / 19

Stopes Cottage - Portland house sleeps 4

Isle of Portland / Portland

2 4 7 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Swimming pool; Suitable for children age 5+;
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 room and a family bathroom. Also in the cottage is a fitted kitchen with a dining area an  …see more

from £75 / night

£519 - £1104 / week

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from £75 / night

1 / 21

Branscombe Lodge - Portland house sleeps 4

Isle of Portland / Portland

2 4 7 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Swimming pool; Suitable for children age 5+;
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 a family bathroom. Also in the cottage are a fitted kitchen and a sitting room with  …see more

from £77 / night

£536 - £1121 / week

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from £77 / night

1 / 14

Isle of Portland / Portland

Studio 2 2 nights min stay

  • Studio
  • Sleeps 2
  • 2 nights min stay
Key info: Nearest beach 11 km; Ask owner if suitable for children; Car advised;
 …see more

from £59 / night

£350 - £399 / week

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from £59 / night

Top Destination reviews

Church Ope Studio
Lovely homely place & great location

The studio has all the things you need for a short break, we took Ruby our West highland terrier and she loved it just as much as we did. The location is great and as you leave the studio to the left is the lane that leads to the coastal path an … see more
Quarries Reach, rural & sea views Portland, Dorset
Perfect for a short break with friends

Nice sized house, close to the sea and shops. Good shower and easy to find. Perfect amount of bathrooms for 6 people. Small but cozy living room area. Great stay! … see more
fishermans view
Fantastic Cottage

Spent a week at Fisherman's View with my wife and dog, my daughter joined us for a few days. The cottage is in an ideal spot to explore Portland, Weymouth and all surrounding coast. Fishermans View was spotlessly clean and very welcoming and comfor … see more
Rosa Cottage
Wonderful holiday home

We stayed at Rosa Cottage for a week in March, and had a wonderful stay. The cottage is furnished to a high standard with a tasteful and original look. The kitchen is well equipped, and we had some wonderful evenings around the large dining room … see more

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