Chiswell On Portland Holiday Cottages

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Your Portland, Dorset search returned 363 cottages

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A property's star rating is the average of the star ratings received from guests that wish for their review to be published

Holiday Park

  • Sleeps6
  • Bedrooms2
  • Pet FriendlyNo

    4.5

    Outstanding

  • Sykes rating

2x Bedroom Holiday Home at Chesil Beach Holiday Park with Veranda and Sea Views over the Beautiful Jurassic Coast in Dorset. (Ref. 1186144)

  • Wi-fi
  • Swimming pool


for 7 nights From €639

  • Sleeps8
  • Bedrooms4
  • Pet FriendlyNo

    4.9

    Outstanding

  • Sykes rating

16 Wakeling Island is a stylish, detached home resting in Crossways, Dorset. On-site facilities. Family-friendly. Lakeside views. Woodburning stove. Puddletown 5.3 miles; Dorchester 5.6 miles; Weymouth 10 miles. (Ref. 1138508)

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


for 7 nights From €938

  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

    4.8

    Outstanding

  • Sykes rating

This picturesque cottage, situated in the village of Upwey, with parking. Short drive to Weymouth. Close to pub and tea rooms. Lovely walks nearby. (Ref. 994658)

  • Wi-fi
  • Washing machine
  • Baby-friendly


for 7 nights From €567

  • Sleeps8
  • Bedrooms4
  • Pet FriendlyNo

    4.6

    Outstanding

  • Sykes rating

The Old Portland Courthouse is spacious, comfortable luxury holiday home. Sleeps 8 people. Wifi. Pub and shop 10 min. Beach 5 min. Weymouth 5 miles. (Ref. 994487)

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


for 7 nights From €1414

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.9

    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)

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


for 7 nights From €785

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.4

    Good

  • Sykes rating

A pretty, renovated terraced cottage, close to the old harbour and Brewers Quay in Weymouth. WiFi. Pet-friendly. Close to beach. Dorchester 8.4 miles; Bridport 19.2 miles. (Ref. 1043009)

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


for 7 nights From €681

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    5.0

    Perfect

  • Sykes rating

Located on the Esplanade in Weymouth with far reaching beach and sea views and within walking distance of the Harbour and town amenities. (Ref. 994167)

  • Wi-fi
  • Washing machine
  • Baby-friendly


for 7 nights From €711

  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    4.6

    Outstanding

  • Sykes rating

A bright and airy lodge resting in Osmington near Preston, Dorset. Open-plan. Close to beach. Pet-friendly. Weymouth 5.4 miles; Poole 23.4 miles; Bournemouth 29.1 miles. (Ref. 1093891)

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


for 7 nights From €842

  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    4.6

    Outstanding

  • Sykes rating

Lovely thatched Grade II listed cottage for a family or friends. Welcomes two dogs. Original beams. Beach 1 mile. Pub 5 min. Seasonal shop 10 min. (Ref. 994302)

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


for 7 nights From €881

  • Sleeps7
  • Bedrooms3
  • Pet FriendlyYes

    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)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Washing machine
  • Baby-friendly


for 7 nights From €669

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.6

    Outstanding

  • Sykes rating

Modern ground floor Apartment. Lovely walks through the Nothe Gardens. Short walk to town centre and the beach. Wi-Fi. Gated Parking. (Ref. 993910)

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


for 7 nights From €564

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.4

    Good

  • Sykes rating

Located on the harbourside, is this two-bedroom contemporary apartment in Weymouth, Dorset. WiFi. Fortuneswell 4.7 miles; Dorchester 9.3 miles. (Ref. 1017563)

  • Ground floor bedroom
  • Dishwasher
  • Washing machine


for 7 nights From €963

  • Sleeps8
  • Bedrooms3
  • Pet FriendlyNo

    4.8

    Outstanding

  • Sykes rating

On Weymouth Harbourside this is an extraordinarily spacious apartment, sleeps 8, tastefully renovated, Large en-suite showers to all rooms, harbour views, WiFi. (Ref. 994463)

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


for 7 nights From €2348

  • Sleeps6
  • Bedrooms3
  • Pet FriendlyNo

    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


for 7 nights From €812

  • Sleeps8
  • Bedrooms4
  • Pet FriendlyNo

    4.9

    Outstanding

  • Sykes rating

Sunningdale Rise is a striking, detached home on a gated development with off-road parking, close to a beach, in the village of Preston in Dorset. Weymouth 2.5 miles. (Ref. 1149947)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • 10% off - Fri 17th Jul to 2nd Oct 2026


for 7 nights From €1593

Last booked yesterday
See more details
  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

    4.5

    Outstanding

  • Tourist Board rating Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon

A modern studio apartment on the seafront on Weymouth, Dorset. Open-plan living. Sea views. Perfect for couples. (Ref. 1003545)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights From €524