Chiswell On Portland Holiday Cottages

REFINE SEARCH

Your Portland, Dorset search returned 338 cottages

Most relevant
  • Distance to Location
  • Most relevant
  • Price (lowest first)
  • Price (highest first)
  • Sleeps (lowest first)
  • Sleeps (highest first)
  • Tick Rating (lowest first)
  • Tick Rating (highest first)
20
  • 10
  • 20
  • 50
  • 100
Map View
A house with stone and wooden exterior at Everdene Upwey near Weymouth
46
Upwey near Weymouth, Dorset, DT3
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.7★

    Outstanding

  • Sykes rating

A quality semi-detached holiday home, one of five in a courtyard location, close to Weymouth. En-suite, modern features. Shop and pub within walking distance. Weymouth 3.5 miles. (Ref. 932160)

  • Wi-fi
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from $900

See more details
A brick terraced house with bay windows and a front door numbered 7 with adjacent houses at Seahorse Cottage in Weymouth
21
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.4★

    Good

  • Sykes rating

Delightful stone terraced cottage close to Old Harbour in Weymouth, Dorset. Conservatory and garden. Pet-friendly. Beach 1 mile, shop and pub 0.3 miles. Dorchester 7 miles. (Ref. 1000703)

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

7 nights from $768

See more details
A front view of a house with windows and door at Guinea Cottage Brewers Quay Harbour
30
Brewers Quay Harbour, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.2★

    Good

  • Sykes rating

Two bedroom cottage close to Weymouth harbour. Dog friendly. Close to all amenities. (Ref. 994236)

  • Wi-fi
  • Washing machine
  • Baby-friendly

7 nights from $569

See more details
A narrow street with houses and a view of the water at Blanche Cottage Brewers Quay Harbour
45
Brewers Quay Harbour, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

A fabulous, three-storey home resting near Weymouth's Old Harbour in Dorset. Close to amenities, beach and attractions. Near AONB. Open-plan living. Stylish. Dorchester 8.8 miles; West Lulworth 15.8 miles. (Ref. 1092575)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from $900

See more details
Exterior view of a brick terraced house with blue door white window and small hedge at Leo's Place in Weymouth
33
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

A well-presented property nestled in the heart of Weymouth, Dorset. Roadside parking. Enclosed patio. Dorchester 8.5 miles; Bridport 19.2 miles. (Ref. 1134491)

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

7 nights from $794

See more details
A house with a front door and gravel driveway at Coastguard Lookout in Wyke Regis
43
Wyke Regis, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

  • Sykes rating

Coastguard Lookout is a modern, reverse-level house near a beach in Wyke Regis, Dorset, with off-road parking, Juliet balcony, and underfloor heating. Weymouth 2.5 miles; Dorchester 9.6 miles. (Ref. 1169223)

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

7 nights from $645

Last booked 2 hours ago
See more details
A white three-story residential building with a black and white tiled walkway leading to a black door at 66 3 Compass Point in Weymouth
22
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

3 Compass Point is a stylish, ground-floor apartment resting in Weymouth, Dorset. Near beach and amenities. Contemporary. Open-plan. Private parking. Dorchester 6.7 miles; Bridport 20.5 miles. (Ref. 1129014)

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

7 nights from $860

See more details
Exterior view of a white house with flower pots near the door and a tree in the foreground at The Little Cottage in Weymouth
27
Weymouth, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7★

    Outstanding

  • Sykes rating

A quaint, white-washed cottage resting in Weymouth, Dorset. Off-road parking. Smart TV. Open-plan living. Xbox. Close to beach. Dorchester 5.2 miles; Bridport 17 miles; Lyme Regis 26.3 miles. (Ref. 1113457)

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

7 nights from $717

See more details
A street view of row houses with brick walls and bay windows with plants in front at Sandsfoot Rest in Weymouth
26
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.6★

    Outstanding

  • Sykes rating

An attractive, Edwardian terraced house situated in Weymouth, Dorset. Woodburner. WiFi. Pet-friendly. Dorchester 7 miles; Bridport 17 miles. (Ref. 1001484)

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

7 nights from $754

Last booked 2 days ago
See more details
A living room with sofas a coffee table a fireplace a television and wall art at Victorian Town House in Weymouth
36
Weymouth, Dorset, DT4
  • Sleeps8
  • Bedrooms5
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

Victorian Town House is a large, coastal property resting in the seaside town of Weymouth, Dorset. Close to a shop, a pub, and a beach. Large property. Dorchester 7.5 miles; West Bay 17.5 miles. (Ref. 1035186)

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

7 nights from $950

See more details
A living room with a brown sectional sofa armchair and round coffee table near a sliding door at Waterston Cottage in West Lulworth
42
West Lulworth, Dorset, BH20
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.6★

    Outstanding

  • Sykes rating

This beautiful three-bedroom property resides in West Lulworth, Dorset. Off-road parking. In an AONB. En-suite bedrooms. Close to amenities and a beach. Wareham 8.8 miles; Weymouth 15.3 miles. (Ref. 1126738)

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

7 nights from $1066

See more details
A living room with a sofa and armchair at Apartment 1 in Weymouth
29
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

  • Sykes rating

Vista Mare 1 is a pleasant apartment located in the heart of Weymouth in Dorset, enjoying close proximity to a beach and pub, as well as a warm welcome to pets. Dorchester 7.5 miles; Bridport 21.1 miles. (Ref. 1164685)

    7 nights from $1787

    See more details
    An entrance area with a door and window at Durbyfield in Nottington near Weymouth
    58
    Nottington near Weymouth, Dorset, DT3
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.8★

      Outstanding

    • Sykes rating

    Durbyfield is a tasteful property resting in Nottington near Weymouth, Dorset. Dog-friendly. Off-road parking. Garden. Barbecue. Family-friendly. Weymouth 3.4 miles; Dorchester 6.4 miles; Fortuneswell 7.1 miles. (Ref. 1105446)

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

    7 nights from $900

    See more details
    A dining area with a long table set with plates glasses and bread surrounded by blue chairs and a kitchen with appliances and plants at Beachaven in Weymouth
    48
    Weymouth, Dorset, DT4
    • Sleeps15
    • Bedrooms7
    • PetsNo

    • Sykes rating

    Beachaven is a charming holiday home, set over three floors, located in the popular resort of Weymouth in Dorset resting near the beach and amenities. Dorchester 7.6 miles; Bridport 19.2 miles. (Ref. 1151664)

    • Wi-fi
    • Ground floor bedroom
    • Dishwasher
    • Washing machine
    • Baby-friendly

    7 nights from $1880

    See more details
    A blue building with bay windows and two white doors behind a black metal fence at Brewers Quay Harbour
    23
    Brewers Quay Harbour, Dorset, DT4
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.5★

      Outstanding

    • Sykes rating

    All second floor. Two bedrooms: 1 x double bed with en-suite shower, basin and WC, 1 x twin single. Bathroom with bath, basin and WC. Open plan living area with kitchen, dining area and sitting area. (Ref. 994293)

    • Wi-fi

    7 nights from $830

    See more details
    A beachfront with kayaks lined up near houses and water at Fairways in Wyke Regis
    22
    Wyke Regis, Dorset, DT4
    • Sleeps5
    • Bedrooms3
    • PetsNo

      4.5★

      Outstanding

    • Sykes rating

    Fairways is a delightful house situated less than 2 mins walk to Smallmouth beach in Wyke Regis, Dorset, boasting an enclosed garden, Smart TV, and private driveway parking. Weymouth 2.5 miles; Dorchester 10.2 miles; Poole 34.1 miles. (Ref. 1047698)

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

    7 nights from $689

    See more details
    A living room with blue sofas a wooden coffee table and red rug by large windows overlooking the sea at Weymouth Bay in Weymouth
    22
    Weymouth, Dorset, DT4
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.5★

      Outstanding

    • Sykes rating

    A well-appointed apartment resting in Weymouth, Dorset. Stunning sea views. Open-plan living. Isle of Portland 7miles. Dorchester 7.8 miles. Bridport 21.5 miles. (Ref. 1003082)

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

    7 nights from $890

    See more details
    A beachfront with a stone barrier green garden and a small gate at Weymouth Bay Apartment C in Greenhill
    19
    Greenhill, Dorset, DT4
    • Sleeps7
    • Bedrooms3
    • PetsYes

      4.9★

      Outstanding

    • Sykes rating

    Second floor comfy apartment sleeping 7 guests close to the sea in Weymouth. Welcomes two dogs. Garden. Beach 2 min. Shop 10 min. Pub 5 min. Dorchester 7.6 miles. (Ref. 994773)

    • Wi-fi
    • Off-road parking
    • Washing machine
    • Baby-friendly

    7 nights from $785

    See more details
    A large apartment building with green-tinted glass balconies and cylindrical glass elevator shafts along a street at Manhattan Beach in Castletown Portland
    27
    Castletown, Portland, Dorset, DT5
    • Sleeps4
    • Bedrooms2
    • PetsNo

    • Sykes rating

    Manhattan Beach is an apartment with a balcony with sunning sea and marina vistas, on the edge of the village of Castletown, Isle of Portland, in Dorset. Portland 2.2 miles; Weymouth 5.5 miles; Dorchester 12.5 miles. (Ref. 1161472)

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

    7 nights from $771

    See more details
    Exterior view of a stone and brick house with a thatched roof and gravel courtyard at Little Forge in West Lulworth
    29
    West Lulworth, Dorset, BH20
    • Sleeps5
    • Bedrooms2
    • PetsNo

      4.4★

      Good

    • Sykes rating

    Modern, beautiful thatched cottage. Inglenook fireplace. Local activities only a short drive away. Nearby pubs and restaurants. Ensuite bedrooms. (Ref. 994342)

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

    7 nights from $832

    See more details
    Map View

    Quick links

    Popular Destinations