Chiswell On Portland Holiday Cottages

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Your Portland, Dorset search returned 343 cottages

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  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

Beautiful 1 bedroom stable conversion in the heart of the harbour area in Weymouth. WIFI, Close to town centre and beach. Parking for one car. (Ref. 1096825)

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

7 nights from $668

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A quaint stone-built cottage resting on the outskirts of Weymouth. Open-plan living. Off-road parking. WiFi. Dorchester 6.4 miles; Fortuneswell 8.2 miles. (Ref. 1061544)

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

7 nights from $722

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A delightful, romantic bolthole in the third-floor in Weymouth, Dorset. Balconies. Romantic. Sea views. Close to beach. Close to local amenities. Dorchester 8.3 miles; Bridport 19.1 miles. (Ref. 1078324)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from $722

  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0

    Perfect

  • Sykes rating

A delightful, one-bedroom holiday home resting in Weymouth, Dorset. Contemporary. Private garden. Romantic. Close to amenities and beach. Near AONB. Open-plan. Dorchester 7 miles; Bridport 20.8 miles. (Ref. 1133982)

  • Wi-fi
  • Off-road parking

7 nights from $676

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A beautiful, second-floor apartment overlooking the harbour in Weymouth, Dorset. Romantic. Sea views. Close to beach. Close to local amenities. Dorchester 8.3 miles; Bridport 19.1 miles. (Ref. 1107011)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from $644

Last booked yesterday
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  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A charming reverse-level cottage in the village of Upwey, Dorset. Close to amenities. Woodburning stove. In an Area of Outstanding Natural Beauty. Romantic. Walkers & Cyclists. Weymouth 4.5 miles; Dorchester 4.6 miles. (Ref. 1072756)

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

7 nights from $1171

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A stylish and contemporary apartment set in the town of Weymouth, Dorset. Seaside setting. Fantastic views. Off-road parking. Fortuneswell 5.8 miles; Dorchester 7.2 miles; Bridport 20.9 miles. (Ref. 1072234)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from $952

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.8

    Outstanding

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Beautiful seafront apartment within the popular resort of Weymouth in Dorset. Incredible sea views. WiFi. Centre of Weymouth. (Ref. 1003083)

  • Wi-fi
  • Dishwasher

7 nights from $674

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

A modern ground floor annex in Weymouth, just moments from the beach. 1 well behaved pet, WiFi, parking for two cars. (Ref. 994726)

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

7 nights from $952

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

Stylish renovated ground floor apartment in Weymouth. Town centre a short walk away. WiFi. Welcomes one dog. Pub and shop 5 min. Beach 10 min. Dorchester 8.3 miles. (Ref. 994763)

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

7 nights from $849

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

Situated in the Isle of Portland, Langham Cottage is very comfortable and spacious holiday home. Accepts one dog. Pub and shop 5 min. Beach 5 min. Bridport 23 miles. (Ref. 994321)

  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • 5% off - Fri 1st Aug to 8th Aug 2025

7 nights from $625

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

The Nightingale is a stylish, semi-detached holiday home resting in Weymouth, Dorset. Designated parking. Close to a beach and amenities. Enclosed garden. Dorchester 8.8 miles; Bridport 19.6 miles. (Ref. 1133998)

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

7 nights from $869

Last booked 2 days ago
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

This quirky, converted bunker rests in Ringstead near Preston, Dorset. Open fire. In an AONB. Smart TV. Off-road parking. Weymouth 7.6 mile. (Ref. 1131689)

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

7 nights from $1103

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

A lovely terraced house resting in a quiet residential area of Weymouth, Dorset. Enclosed garden. Pet-friendly. Near to beach. Dorchester 10.1 miles; Bridport 18.8 miles. (Ref. 1053611)

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

7 nights from $633

  • Sleeps4
  • Bedrooms2
  • PetsYes
  • Sykes rating

The Nook is a charming, pet-friendly cottage resting near the beach in the town of Weymouth in Dorset, boasting a woodburning stove and enclosed garden. Dorchester 8.5 miles; Bridport 20.5 miles; Poole 32.2 miles. (Ref. 1107935)

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

7 nights from $690

Last booked 2 days ago
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

An inviting, mid-terrace house perched on the coast in Weymouth, Dorset. Sea views. Off-road parking. Near the beach. Dorchester 10.2 miles; Bridport 18.8 miles. (Ref. 1082718)

  • Wi-fi
  • Washing machine
  • Baby-friendly

7 nights from $632

  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0

    Perfect

  • Sykes rating

A boutique, two-bedroom property situated in Brewers Quay Harbour, Weymouth, Dorset. Quality finish. Sea and harbour views. Enclosed garden. Raised elevation. Dorchester 8.5 miles; West Lulworth 15.5 miles. (Ref. 1096352)

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

7 nights from $1211

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

A lovely two-bedroom, ground-floor apartment resting in Weymouth, Dorset. Near a beach. Close to amenities. Romantic. Ground-floor. Dorchester 7.5 miles; Bridport 20.5 miles. (Ref. 1083146)

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

7 nights from $864

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

Sleeping four near harbourside in Weymouth. Welcome two dogs. Pubs, restaurants and harbour 5 mins walk. (Ref. 994584)

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

7 nights from $802

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

Comfortable Spanish style holiday home in Weymouth. Off road parking for two cars. Patio garden with furniture. Sea views. Beach 5 min. Pub and shop 10 min. Dorchester 9 miles. (Ref. 994352)

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

7 nights from $857

Last booked yesterday
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Please find below a selection of self catering holiday cottages to rent in or near Chiswell On Portland.