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
A living room with a brown sofa a coffee table with fruit a television and two light grey cabinets at Old Malthouse Apartment Weymouth
Offer
18
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    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)

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

  • 5% off - Sat 1st Aug to 5th Sep 2026


for 7 nights From €794

Last booked yesterday
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Row of three connected houses with two having painted facades and one with pebble dash exterior
19
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyNo

    3.4★

  • Sykes rating

Ocean Swell is a lovely cottage for families or friends in Weymouth. Close to the town centre. WiFi. Shop and pub 5 min. Beach 1 mile. Dorchester 8.5 miles. (Ref. 994710)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights From €615

Last booked 2 days ago
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A living room with a sofa and dining area at Old Harbour View in Weymouth
20
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

  • Sykes rating

Old Harbour View is a harbourside first-floor apartment with a balcony, resting in Weymouth and located near all bars and restaurants for convenience. Dorchester 8.5 miles; Bridport 20.5 miles. (Ref. 1192728)

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


for 7 nights From €654

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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
  • Pet FriendlyYes

    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)

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


for 7 nights From €441

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A living room with a sofa and a coffee table at Vista Mare 3 in Weymouth
31
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

  • Sykes rating

Vista Mare 3 is a delightful apartment located in the centre of Weymouth, a vibrant town in Dorset, with lovely sea views from an open-plan living space. Dorchester 7.5 miles; Bridport 21.1 miles. (Ref. 1164688)

  • Wi-fi
  • Dishwasher


for 7 nights From €1065

Last booked yesterday
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A street with colorful buildings and lampposts at Apartment 1 Brewers Quay in Weymouth
5
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms1
  • Pet FriendlyNo

  • Sykes rating

Apartment 1 Brewers Quay is a stylish property in Weymouth’s historic Quayside, boasting modern interiors and allocated parking. Dorchester 8.6 miles; Bridport 19.3 miles. (Ref. 1166031)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights From €552

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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
  • Pet FriendlyYes

    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)

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


for 7 nights From €639

Last booked 4 hours ago
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A beach and ocean view with a clock tower in Weymouth
43
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

  • 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)

  • Wi-fi
  • Dishwasher


for 7 nights From €1591

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A house with white facade and windows at NO 10 Fortuneswell
34
Fortuneswell, Dorset, DT5
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

  • Sykes rating

NO 10 is a fine, dog-friendly house situated in Fortuneswell, Dorset, featuring an electric fire, an enclosed courtyard, and easy access to the beach. Weymouth 5.1 miles. (Ref. 1200066)

  • Pets go free
  • Wi-fi
  • Dishwasher


for 7 nights From €714

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The front door of a blue and white house with two blue pots containing plants and a blue wooden planter in front at Cove Cottage Hideaway in Chiswell On Portland
36
Chiswell On Portland, Dorset, DT5
  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

    3.3★

  • Sykes rating

Cove Cottage Hideaway is a romantic, terrace abode near the coast in Chiswell on Portland, Dorset. Close to amenities and beach. Sea Views. Romantic. Weymouth 5.2 miles. (Ref. 1150238)

  • Wi-fi


for 7 nights From €583

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A house with a garden and stone wall at 12 West Street Weymouth
Offer
37
Chickerell, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

  • Sykes rating

September Cottage is a charming cottage in Chickerell, Dorset, featuring a conservatory, gas fire, and a multi-tiered garden with patio near the beach. Weymouth 3.9 miles; Abbotsbury 6 miles; Portland 7.1 miles; Dorchester 8.3 miles. (Ref. 1202453)

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

  • 10% off - Fri 7th Aug to 14th Aug 2026


for 7 nights From €638

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A living room with a sofa and television at Littlesea Holiday Park - Holiday Accommodation 19270, Weymouth
15

Holiday Park

Weymouth, Dorset, DT4
  • Sleeps8
  • Bedrooms3
  • Pet FriendlyYes

  • Sykes rating

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

  • Pets go free
  • Wi-fi
  • Swimming pool
  • Baby-friendly


for 7 nights From €601

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An outdoor view of a cottage with a thatched roof and stone wall at Bracken Cottage in
11
Osmington, Dorset, DT3
  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

  • Sykes rating

Bracken Cottage is a romantic property resting in the village of Osmington, Dorset, boasting an open-plan living area, is close to the beach and amenities. Weymouth 5.4 miles. (Ref. 1173628)

  • Wi-fi
  • Off-road parking


for 7 nights From €526

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A living room with a sofa and dining table at Vista Mare 2 in Weymouth
25
Weymouth, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

  • Sykes rating

Vista Mare 2 is a lovely apartment perched in the heart of Weymouth, a popular town in Dorset, enjoying fantastic sea views from the open-plan living space. Dorchester 7.5 miles; Bridport 21.1 miles. (Ref. 1164686)

  • Wi-fi
  • Dishwasher


for 7 nights From €762

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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
  • Pet FriendlyYes

    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)

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


for 7 nights From €929

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A stone house with wooden doors and windows along a road with slow painted on the street at Wren in Upwey
36
Upwey, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

  • Sykes rating

Wren, a stylish, two-bedroom home rests in Upwey, Dorset. Near AONB. Close to amenities. Near the beach and attractions. Enclosed garden. Contemporary. Weymouth 4.2 miles; Dorchester 4.4 miles. (Ref. 1138702)

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


for 7 nights From €601

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Two small wooden huts with open doors on grass surrounded by trees and two wooden chairs with a tree stump table at Sika in Warmwell
19
Warmwell, Dorset, DT2
  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

  • Sykes rating

Sika is a tremendous hut near the village of Broadmayne, Dorset, boasting exceptional countryside views all around as well as a woodburning stove. Dorchester 5.8 miles; Weymouth 8.2 miles; Bridport 20.6 miles; Swanage 21 miles. (Ref. 1174453)

  • Off-road parking
  • Ground floor bedroom


for 7 nights From €429

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A house with garage and pathway at Millmead House in Portesham
61
Portesham, Dorset, DT3
  • Sleeps8
  • Bedrooms4
  • Pet FriendlyNo

  • 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 From €1102

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Two small wooden cabins in a grassy area with trees and outdoor wooden table and chairs with red flowers at Fallow in Warmwell
22
Warmwell, Dorset, DT2
  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

  • Sykes rating

Fallow is a superb hut near Broadmayne, Dorset, boasting impressive countryside views to admire with the fire pit in the garden and a woodburning stove. Dorchester 5.8 miles; Weymouth 8.2 miles; Bridport 20.6 miles; Swanage 21 miles. (Ref. 1174455)

  • Off-road parking
  • Ground floor bedroom


for 7 nights From €429

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Exterior view of a multi-story building with beige brick walls and blue glass balconies at Nautica in Weymouth
15
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    3.4★

  • Sykes rating

A contemporary second-floor apartment set within the town of Weymouth, Dorset. Close to the close. Balcony with views. Dorchester 8.4 miles; Bridport 19.2 miles; Bournemouth 37.1 miles. (Ref. 1052595)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights From €572

Last booked yesterday
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