Portland Cottages

Your search returned 62 cottages.

REFINE SEARCH
Most relevant
  • Distance to Location
  • Most relevant
  • Price (lowest first)
  • Price (highest first)
  • Sleeps (lowest first)
  • Sleeps (highest first)
  • Rating (lowest first)
  • Rating (highest first)
  • Location (A to Z)
  • Location (Z to A)
  • Property name (A to Z)
  • Property name (Z to A)
10
  • 10
  • 20
  • 50
  • 100
Map View

    How reviews work

    A property's star rating is the average of the star ratings received from guests that wish for their review to be published
  • A balcony with glass table and chairs overlooking buildings and a body of water at Panoramic View in Castletown Portland
    Property has offers
    22
    Castletown, Portland, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      4.2★

      Good

    • Dream Cottages rating

    A well-presented, modern apartment on the rugged Isle of Portland. (Ref. 1034885)

    • Wi-fi
    • Off-road parking
    • Swimming pool
    • Dishwasher
    • Washing machine

    • 5% off - Mon 22nd Jun to 4th Sep 2026

    7 nights from From €607

    Last booked 4 hours ago
    Book now
  • Exterior view of a row of houses with bay windows a blue door and a plant in a pot at The Shambles in Fortuneswell
    25
    Fortuneswell, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      4.3★

      Good

    • Dream Cottages rating

    A well-presented two-bedroom cottage resting in Fortuneswell in Dorset. (Ref. 1082838)

    • Wi-fi
    • Dishwasher

    7 nights from From €714

    Book now
  • A brick terraced house with a green front door and front lawn at The Lookout -The House With A View in Weymouth
    29
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • Pet FriendlyYes

      4.4★

      Good

    • Dream Cottages rating

    A well-presented, mid-terrace property resting within the village of Wyke Regis. (Ref. 1006910)

    • Pets go free
    • Wi-fi
    • Dishwasher
    • Washing machine

    7 nights from From €791

    Last booked today
    Book now
  • A multi-story brick house with bay windows and greenery in front at The Lobster Pot in Weymouth
    28
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      4.6★

      Outstanding

    • Dream Cottages rating

    The Lobster Pot, a nicely-presented apartment rests in the gorgeous seaside town of Weymouth in Dorset. (Ref. 1151706)

    • Wi-fi
    • Off-road parking
    • Dishwasher

    7 nights from From €519

    Last booked 2 days ago
    Book now
  • A coastal town with houses along the shoreline and a beach at The View in Portland
    29
    Portland, Dorset
    • Sleeps6
    • Bedrooms3
    • Pet FriendlyNo

      4.8★

      Outstanding

    • Dream Cottages rating

    Bright contemporary property perfect groups of guests in the Isle of Portland. (Ref. 994754)

    • Wi-fi
    • Off-road parking
    • Ground floor bedroom
    • Washing machine

    7 nights from From €911

    Book now
  • A balcony with two chairs and a table overlooking a rocky shoreline and the sea at Sunset Lodge in Fortuneswell
    27
    Fortuneswell, Dorset
    • Sleeps6
    • Bedrooms3
    • Pet FriendlyNo

      4.9★

      Outstanding

    • Dream Cottages rating

    Sunset Lodge is a lovely retreat on Portland, moments from Chesil beach in Fortuneswell, Dorset, enjoying wonderful coastal views from the a balcony. (Ref. 1173296)

    • Wi-fi
    • Washing machine
    • Baby-friendly

    7 nights from From €753

    Last booked today
    Book now
  • A red brick residential building with multiple windows and a paved driveway near a tree at Flat 6 Thornlow Heights in Weymouth
    31
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      4.6★

      Outstanding

    • Dream Cottages rating

    A well-appointed, first-floor apartment resting in Weymouth, Dorset. (Ref. 1123245)

    • Wi-fi
    • Dishwasher
    • Washing machine
    • Baby-friendly

    7 nights from From €585

    Last booked today
    Book now
  • A view of the beach and sea with boats anchored offshore and greenery in the foreground at Castle Cove Cottage in Weymouth
    41
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • Pet FriendlyYes

      4.0★

      Good

    • Dream Cottages rating

    A coastal cottage resting in Weymouth, Dorset. (Ref. 1092544)

    • Pets go free
    • Wi-fi
    • Off-road parking
    • Dishwasher

    7 nights from From €911

    Book now
  • A backyard with a hot tub, a table with chairs, an umbrella, grass, trees, and a wooden fence at Cliffwalk Cottage in Southwell
    26
    Southwell, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyYes

      4.2★

      Good

    • Dream Cottages rating

    This contemporary holiday home rests in Portland, Dorset. (Ref. 1122555)

    • Pets go free
    • Wi-fi
    • Hot Tub
    • Dishwasher
    • Washing machine

    7 nights from From €516

    Book now
  • A row of attached houses with different exterior finishes on a street at Home From Home in Fortuneswell
    57
    Fortuneswell, Dorset
    • Sleeps8
    • Bedrooms4
    • Pet FriendlyYes

      4.5★

      Outstanding

    • Dream Cottages rating

    Home From Home is a delightful cottage nestled in the village of Fortuneswell in Dorset, Isle of Portland and is pet-friendly and near the beach. (Ref. 1158103)

    • Pets go free
    • Wi-fi
    • Washing machine

    7 nights from From €552

    Book now
Most relevant
  • Distance to Location
  • Most relevant
  • Price (lowest first)
  • Price (highest first)
  • Sleeps (lowest first)
  • Sleeps (highest first)
  • Rating (lowest first)
  • Rating (highest first)
  • Location (A to Z)
  • Location (Z to A)
  • Property name (A to Z)
  • Property name (Z to A)
10
  • 10
  • 20
  • 50
  • 100
Map View

Quick links

Popular Destinations