Chiswell On Portland Holiday Cottages

Your Portland, Dorset search returned 360 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

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.9

    Outstanding

  • Sykes rating

A stunning holiday home in the bustling seaside town centre of Weymouth in Dorset. Enclosed patio. Near beach. Smart TV. Isle of Portland 6.7 miles; Dorchester 8 miles; Bridport 20.2 miles. (Ref. 1054948)

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


for 7 nights From £558

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.8

    Outstanding

  • Sykes rating

The View is a charming, three-storey house resting near the beach in Weymouth, Dorset, boasting stunning sea views, a balcony, and off-road parking. Dorchester 8.9 miles; Bridport 19.2 miles. (Ref. 1173086)

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


for 7 nights From £618

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.6

    Outstanding

  • Sykes rating

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

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


for 7 nights From £695

Last booked yesterday
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  • Sleeps7
  • Bedrooms4
  • Pet FriendlyNo

    4.8

    Outstanding

  • Sykes rating

This pretty, detached cottage lies in Preston, Dorset. Smart TV. En-suite master bedroom. Close to amenities. Woodburning stove. Weymouth 3.6 mile. (Ref. 1119018)

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


for 7 nights From £661

  • Sleeps2
  • Bedrooms1
  • Pet FriendlyYes

    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)

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


for 7 nights From £552

  • Sleeps6
  • Bedrooms3
  • Pet FriendlyNo

    4.4

    Good

  • Sykes rating

Modern 3 Storey house. Close to the Harbour, Newton’s Cove and Brewers Quay. WIFI. Parking for one car. 5 minutes to local shop. 15 minute walk to town centre. (Ref. 993939)

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


for 7 nights From £786

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.8

    Outstanding

  • Sykes rating

This spacious ground-floor apartment is nestled in the gorgeous seaside town of Weymouth in Dorset. Bike/kayak storage. En-suite. WiFi. Dorchester 6.3 miles; Isle of Portland 8.6 miles; West Lulworth 12.3 miles. (Ref. 1037083)

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


for 7 nights From £492

Last booked 2 days ago
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  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    4.9

    Outstanding

  • Sykes rating

A Grade II listed, spacious maisonette apartment over the first and second floor in the Dorset town of Weymouth. WiFi. One dog welcome. Pub and shop within 0.1 miles. (Ref. 1011525)

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


for 7 nights From £823

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.8

    Outstanding

  • Tourist Board rating

Delightful, single-storey, Grade II listed cottage linked to Old Higher Lighthouse at Portland Bill on Dorset's Jurassic Coast. Amazing views. Shared access to lighthouse observatory. Shared use of seasonal outdoor heated pool and Jacuzzi. (Ref. 12494)

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


for 7 nights From £644

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.7

    Outstanding

  • Sykes rating

Modern one level apartment. Sitting room, with balcony and beautiful sea views. Short walk to the beach and a causal walk to the town centre. Wifi. (Ref. 994505)

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


for 7 nights From £610

  • Sleeps6
  • Bedrooms3
  • Pet FriendlyNo

    4.9

    Outstanding

  • Sykes rating

With off road parking for 2 cars and just a short 3-minute walk to the old harbour, town centre and beach beyond, this fully modernised 1900 cottage with 3 bedrooms, more importantly 3 bathrooms with 2 receptions and a sunny south facing garden is a steal (Ref. 1099795)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • £370 off - Sat 29th Aug to 5th Sep 2026


for 7 nights From £827

  • Sleeps5
  • Bedrooms2
  • Pet FriendlyNo

    4.5

    Outstanding

  • Sykes rating

Blue Yonder is a cheerful, terrace holiday home resting by the sea in Weymouth, Dorset. Sea views. Ground-floor living. Near beach. Close to pub. Dorchester 7.5 miles; Bridport 20.9 miles. (Ref. 1144628)

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


for 7 nights From £528

Last booked 3 hours ago
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  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.6

    Outstanding

  • Sykes rating

A delightful, mid-terrace cottage resting in Brewers Quay Harbour, Dorset. Designated parking. Pet-friendly. Enclosed garden. Weymouth 0.6 miles; Dorchester 8.8 miles; West Lulworth 15.7 miles. (Ref. 1084006)

  • Pets go free
  • Dishwasher
  • Washing machine


for 7 nights From £621

  • Sleeps7
  • Bedrooms4
  • Pet FriendlyYes

    4.7

    Outstanding

  • Sykes rating

Four bedrooms in Kellaway Court, Weymouth. Restaurants and bars close by. Near harbourside. Accepts one dog. (Ref. 994219)

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


for 7 nights From £839

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.7

    Outstanding

  • Sykes rating

Set in a lovely and quiet residential area of Weymouth, the house is a comfortable getaway for a family. One dog welcome. Wifi. Shop and pub 5 min. Beach 10 min. Dorchester 7 miles. (Ref. 994377)

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


for 7 nights From £608

Last booked 2 days ago
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  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    5.0

    Perfect

  • Sykes rating

A boutique, period home moments from Weymouth's iconic harbour. Dorchester 8.3 miles; Bridport 18.9 miles (Ref. 1177943)

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


for 7 nights From £692

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.6

    Outstanding

  • Sykes rating

Traditional Portland Cottage. Beautiful scenery walks. Close to pubs. (Ref. 993922)

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


for 7 nights From £529

Last booked yesterday
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  • Sleeps2
  • Bedrooms1
  • Pet FriendlyYes

    4.5

    Outstanding

  • Sykes rating

A lovely one-bedroom holiday home resting in Weymouth, Dorset. Romantic. Off-road parking. Private garden. Near a beach. Dorchester 10.2 miles; Bridport 18.8 miles. (Ref. 1092449)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Electric vehicle charging
  • Dishwasher
  • Washing machine


for 7 nights From £493

  • Sleeps6
  • Bedrooms3
  • Pet FriendlyNo

    4.4

    Good

  • Sykes rating

Modern and well-furnished Hops House is an ideal family holiday home in Weymouth. WiFi. Pub and shop 5 min. Beach 1 mile. Dorchester 9 miles. (Ref. 994277)

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


for 7 nights From £798

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.8

    Outstanding

  • Sykes rating

Comfortable cottage for couples or small family in Nottington, Dorset. Beaches and historic harbour 3 miles. Wifi. Lawn garden. Wheelchair access. (Ref. 994199)

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


for 7 nights From £511