Chiswell On Portland Holiday Cottages

Your Portland, Dorset search returned 361 cottages

REFINE SEARCH
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

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
Stone row houses with front doors, windows, grass lawn, and a stone sign reading Chestnut Court in West Lulworth
Offer
21
West Lulworth, Dorset, BH20
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.6★

    Outstanding

  • Sykes rating

A pleasant, first-floor apartment located in West Lulworth, Dorset. Close to beach. Dog-friendly. Washing machine. Wareham 8.8 miles; Weymouth 15.4 miles. (Ref. 1102852)

  • Wi-fi
  • Dishwasher
  • Washing machine

  • 10% off - Sat 13th Jun to 30th Jun 2026


for 7 nights £522

Last booked 2 days ago
See more details
A red brick building with blue doors and white framed windows at Old Malthouse Apartment in Weymouth
18
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.3★

    Good

  • Sykes rating

Old Malthouse Apartment, a practical apartment in the town of Weymouth, Dorset, with a Smart TV and is a short stroll to the beach, harbour, pub and shop. Dorchester 8.1 miles; Bridport 19.3 miles. (Ref. 1175711)

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


for 7 nights £679

See more details
A corner with two purple chairs and a round glass table by windows with shutters overlooking the beach at High Tide in Weymouth
31
Weymouth, Dorset, DT4
  • Sleeps10
  • Bedrooms5
  • PetsNo

    3.7★

    Good

  • Sykes rating

Beautiful, Georgian seafront house, nestled in the lively town of Weymouth. Sea views. En-suite bedrooms. WiFi. Beach less than 50 metres away. (Ref. 1006583)

  • Wi-fi
  • Dishwasher
  • Baby-friendly


for 7 nights £1550

See more details
A mobile home with a deck and stairs at The Hideaway in Portesham
37
Portesham, Dorset, DT3
  • Sleeps4
  • Bedrooms3
  • PetsNo

    4.5★

    Outstanding

  • Sykes rating

A wonderful holiday home resting on the outskirts of Portesham, Dorset. Countryside views. Open-plan living. Barbecue. Decking. Weymouth 8 miles; Dorchester 8 miles. (Ref. 1127855)

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


for 7 nights £420

See more details
A house with a garage and plants in front at Millmead House Annex Portesham
New property
27
Portesham, Dorset, DT3
  • Sleeps2
  • Bedrooms1
  • PetsNo

  • Sykes rating

Millmead House Annex is a welcoming holiday annex in Portesham, Dorset, featuring open‑plan living, a woodburning stove and an enclosed garden. Weymouth 7.8 miles; Dorchester 7.8 miles (Ref. 1201417)

  • Wi-fi
  • Off-road parking


for 7 nights £398

Last booked 2 days ago
See more details
An aerial view of a building with a gravel driveway a parked car a fenced garden area and pathways surrounded by trees at Casterbridge Upwey near Weymouth
33
Upwey near Weymouth, Dorset, DT3
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.5★

    Outstanding

  • Sykes rating

Superb, modern semi-detached holiday cottage, one of five on-site, on the edge of the Dorset village of Upwey, near Weymouth. Tastefully furnished. En-suite, Smart TVs. Dog-friendly. Short drive to Weymouth beach. Weymouth 3.5 miles. (Ref. 932161)

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


for 7 nights £673

See more details
A house with garage and pathway at Millmead House in Portesham
New property
61
Portesham, Dorset, DT3
  • Sleeps8
  • Bedrooms4
  • PetsYes

  • Sykes rating

Millmead House is a welcoming house in Portesham, Dorset, within the Dorset National Landscape, featuring a toasty woodburning stove and a garden. Weymouth 7.8 miles; Dorchester 8.1 miles (Ref. 1200773)

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


for 7 nights £942

Last booked 2 days ago
See more details
A brick house exterior with two white garage doors two upper windows and two front doors with canopies at Sea Pebbles in Weymouth
34
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsNo

    3.8★

    Good

  • Sykes rating

Close to the harbour in Weymouth, Semi detached house, access to South West Coast path, WIFI, Close to shops, restaurants and café’s, suitable for families. (Ref. 994639)

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


for 7 nights £733

See more details
A living room with a sofa, green armchair, round mirrors, dining table with dishes and wine bottle at The Cottage in Weymouth
28
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.1★

    Good

  • Sykes rating

The Cottage is a charming, two-bedroom townhouse resting in Weymouth, Dorset. Close to amenities. Smart TV. Enclosed balcony. Dorchester 8.5 miles; Bridport 20.6 miles. (Ref. 1137088)

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


for 7 nights £634

Last booked 2 days ago
See more details
A living room with a sofa, coffee table, and dining area at Beachcomb in Weymouth
Offer
28
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

  • Sykes rating

Beachcomb is a fine third-floor apartment located close to a beach in the town of Weymouth in Dorset, well-positioned to nearby attractions and amenities. Dorchester 7.7 miles; Bridport 21.2 miles; Poole 31.2 miles. (Ref. 1083686)

  • Wi-fi
  • Washing machine

  • 8% off - Wed 15th Apr to 4th Jul 2026


for 7 nights £582

Last booked yesterday
See more details
A garden with leafless trees and a small fence next to a stone and white brick building with solar panels on the roof at Carnotze in Owermoigne
18
Owermoigne, Dorset, DT2
  • Sleeps2
  • Bedrooms1
  • PetsYes

    3.8★

    Good

  • Sykes rating

This rustic, single-storey holiday cottage rests in Owermoigne near Broadmayne, Dorset. Private parking. Pet-friendly. Romantic. Dorchester 6.8 miles; Weymouth 9 miles; Swanage 20.2 miles; Bridport 21.6 miles. (Ref. 1126079)

  • Wi-fi
  • Off-road parking
  • Electric vehicle charging
  • Ground floor bedroom


for 7 nights £377

See more details
A building with an outdoor seating area and garden at Overcombe Mill Nottington near Weymouth
47
Nottington near Weymouth, Dorset, DT3
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

Overcombe Mill is a wonderful lodge nestled into the countryside of Nottington near Weymouth, Dorset. Dog-friendly. Off-road parking. Barbecue. Family-friendly. Weymouth 3.4 miles; Dorchester 6.4 miles; Fortuneswell 7.1 miles. (Ref. 1105455)

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


for 7 nights £632

See more details
a living room with a sofa, TV, and fireplace at Littlesea Holiday Park - Holiday Accommodation 19270, Weymouth
15

Holiday Park

Weymouth, Dorset, DT4
  • Sleeps8
  • Bedrooms3
  • PetsYes

  • Sykes rating

We have a lovely Salisbury caravan for hire. 3 bedrooms, sleeps 8. (Ref. 1186911)

  • Wi-fi
  • Swimming pool
  • Baby-friendly


for 7 nights £587

Last booked yesterday
See more details
A view of fields houses cars and the sea through a large window at Lighthouse View in Portland
26
Portland, Dorset, DT5
  • Sleeps2
  • Bedrooms1
  • PetsNo

    3.9★

    Good

  • Sykes rating

A lovely, second-floor apartment resting in Portland. Sea views. Pet free. Studio-style. Fortuneswell 2.7 miles; Weymouth 7.7 miles; Dorchester 15.3 miles; West Bay 22.9 miles. (Ref. 1099649)

  • Wi-fi
  • Off-road parking


for 7 nights £290

See more details
A row of cottages with wooden fences and outdoor furniture at Emminster in Nottington near Weymouth
33
Nottington near Weymouth, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsYes

    3.3★

  • Sykes rating

Emminster is a lovely abode resting in Nottington near Weymouth, Dorset. Dog-friendly. Off-road parking. Shared garden. Barbecue. Family-friendly. Weymouth 3.4 miles; Dorchester 6.4 miles; Fortuneswell 7.1 miles. (Ref. 1105445)

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


for 7 nights £576

See more details
A patio area with a yellow barbecue grill a dining table with chairs and a wooden fence at Mellstock in Nottington near Weymouth
40
Nottington near Weymouth, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.0★

    Good

  • Sykes rating

Mellstock is a charming property resting in Nottington near Weymouth, Dorset. Dog-friendly. Off-road parking. Shared garden. Barbecue. Family-friendly. Weymouth 3.4 miles; Dorchester 6.4 miles; Fortuneswell 7.1 miles. (Ref. 1105443)

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


for 7 nights £556

See more details
A row of terraced houses with colorful doors and windows along a street with railings and street lamps at Belvedere Cottage in Weymouth
43
Weymouth, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.0★

    Good

  • Sykes rating

Belvedere Cottage is a delightful holiday home nestled in the town of Weymouth, Dorset. Enclosed garden. En-suite. Close to beach. Near amenities. Dorchester 8.2 miles; Bridport 20.3 miles. (Ref. 1147966)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights £803

See more details
A white two-story building with a blue door and black framed windows labeled Neptune Cottage in Fortuneswell
20
Fortuneswell, Dorset, DT5
  • Sleeps5
  • Bedrooms3
  • PetsYes

    3.8★

    Good

  • Sykes rating

Neptune cottage situated in the Isle of Portland is very cosy and comfortable. Perfect for dog walks. Beach 2 min. Welcomes two dogs. Pub 5 min, shop 10 min. Weymouth 5 miles. (Ref. 994425)

  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights £617

See more details
A living room with a television on a cabinet at Arum in Portland Bill
32
Easton, Portland, Dorset, DT5
  • Sleeps4
  • Bedrooms2
  • PetsYes

  • Sykes rating

Arum is a single-storey bungalow resting in Wakeham, Portland, with off-road parking, Smart TV, and a small patio. Portland 0.3 miles; Weymouth 6.9 miles; Dorchester 14.1 miles. (Ref. 1183330)

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


for 7 nights £508

See more details
A brick house with a grey door garage and driveway at Dotties Retreat in Weymouth
46
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsYes

    3.8★

    Good

  • Sykes rating

Dotties Retreat, a lovely, three-storey abode located in the seaside town of Weymouth, Dorset. Near beach. Off-road parking. Enclosed garden. Pet-friendly. Dorchester 8.7 miles; Bridport 18.8 miles. (Ref. 1157026)

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


for 7 nights £711

See more details
Map View

Quick links

Popular Destinations