Chiswell On Portland Holiday Cottages

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Your Portland, Dorset search returned 341 cottages

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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
  • 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 £522

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A brick house with a red door and white framed windows behind a stone wall at Weybury Cottage in Brewers Quay Harbour
18
Brewers Quay Harbour, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.3★

    Good

  • Sykes rating

A period three-storey terraced property resting in Weymouth, Dorset. In walking distance of amenities and beach. Pet-friendly. Isle of Portland 6.1 miles; Dorchester 8.7 miles. (Ref. 1055214)

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


for 7 nights £625

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A row of colorful waterfront houses with docks in front at The Boat House in Weymouth
38
Weymouth, Dorset, DT4
  • Sleeps10
  • Bedrooms5
  • PetsYes

    4.0★

    Good

  • Sykes rating

A superb, Grade II listed house set on the harbour side in Weymouth. Sleeps 10. WiFi. Close to shop, café and pub. Dorchester 8.5 miles. (Ref. 1005020)

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


for 7 nights £1420

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A building with windows and a door at Lily's Pad in Weston, Portland
25
Weston, Portland, Dorset, DT5
  • Sleeps5
  • Bedrooms2
  • PetsYes

  • Sykes rating

Lily's Pad is an intimate apartment in Weston, Dorset, with ground-floor living and is close to the picturesque coastline, alongside several amenities. Fortuneswell 1.7 miles; Weymouth 6.6 miles; Dorchester 14.5 miles; West Bay 22 miles. (Ref. 1173596)

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


for 7 nights £361

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A living room with blue chairs a wooden table dining set a large window with blinds and a view of the sea at The Kings Vista in Weymouth
21
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7★

    Outstanding

  • Sykes rating

A contemporary first-floor apartment overlooking the scenic coast of Weymouth, Dorset. Open-plan. Views. Parking. Fortuneswell 5.6 miles; Dorchester 7.6 miles; Bridport 19 miles. (Ref. 1060926)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights £724

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A living room with a blue sofa orange cushions a floral armchair green curtains a black fireplace and a wooden TV cabinet at Georgian Hideaway in Weymouth
32
Weymouth, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • PetsYes

  • Sykes rating

Georgian Hideaway, a quirky abode situated in the seaside town of Weymouth in Dorset. Near beach. Near shop. Near pub. Enclosed garden. Pet-friendly. Dorchester 7 miles; Bridport 17 miles. (Ref. 1154207)

  • Wi-fi
  • Dishwasher
  • Washing machine

  • 5% off - Fri 21st Feb to 31st Dec 2025


for 7 nights £533

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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 £352

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A backyard with a hot tub, a table with chairs, an umbrella, grass, trees, and a wooden fence at Cliffwalk Cottage in Southwell
26
Southwell, Dorset, DT5
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.3★

    Good

  • Sykes rating

This contemporary holiday home rests in Portland, Dorset. Hot tub. Barbecue. Near amenities. Pet-friendly. Easton 1.5 miles; Chiswell 3 miles; Weymouth 7.5 miles. (Ref. 1122555)

  • Wi-fi
  • Hot Tub
  • Dishwasher
  • Washing machine


for 7 nights £465

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A pedestrian street with terraced houses featuring bay windows and doors with plants in pots along the pavement at Picardy Cottage in Weymouth
43
Weymouth, Dorset, DT4
  • Sleeps8
  • Bedrooms4
  • PetsNo

    4.5★

    Outstanding

  • Sykes rating

A contemporary three-storey holiday home settled in the heart of Weymouth, Dorset. Enclosed courtyard. Close to the beach. Pet-free. Dorchester 7.9 miles; Bridport 20.1 miles. (Ref. 1088903)

  • Wi-fi
  • Dishwasher


for 7 nights £734

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A patio with wooden chairs and a table outside a brick building with open double doors at Hide-A-Way in Weymouth
31
Weymouth, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • PetsNo

  • Sykes rating

Hideaway is a fine, single-storey annex situated in Weymouth, Dorset, with open-plan living, Smart TV, and well-positioned to nearby beaches and amenities. Dorchester 8.8 miles; Bridport 19.5 miles; Bournemouth 38.4 miles. (Ref. 1169910)

  • Wi-fi
  • Ground floor bedroom
  • Baby-friendly


for 7 nights £449

Last booked yesterday
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An outdoor hot tub next to a blue house with glass doors and a garden with grass and bushes at Fisherman's Cottage in Southwell
25
Southwell, Dorset, DT5
  • Sleeps6
  • Bedrooms3
  • PetsNo

  • Sykes rating

A historic, 18th-century cottage resting in Portland, Dorset. Sea views. Character features. Hot tub. Near a pub. Easton 1.5 miles; Chiswell 3 miles; Weymouth 8 miles. (Ref. 1122551)

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


for 7 nights £765

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Exterior view of a row of houses with bay windows a blue door and a plant in a pot at The Shambles in Fortuneswell
25
Fortuneswell, Dorset, DT5
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.4★

    Good

  • Sykes rating

A well-presented two-bedroom cottage resting in Fortuneswell in Dorset. Near a beach. Close to amenities. Woodburning stove. Wakeham 1.9 miles; Weymouth 5.2 miles; Abbotsbury 11.9 miles. (Ref. 1082838)

  • Wi-fi
  • Dishwasher


for 7 nights £603

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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

  • 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 £568

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View of residential buildings a tree and a driveway seen through a window with a black railing at Crows Nest in Fortuneswell
19
Fortuneswell, Dorset, DT5
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.0★

    Good

  • Sykes rating

Crows Nest is a charming, reverse-level cottage in the seaside village of Fortuneswell, Dorset on the Jurassic Coast and close to amenities and a beach. Weymouth 5.7 miles; Dorchester 12.7 miles; West Bay 20.3 miles. (Ref. 1162358)

  • Wi-fi
  • Ground floor bedroom


for 7 nights £617

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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
  • PetsNo

    3.6★

    Good

  • 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 £494

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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
  • PetsNo

    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 £782

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An outdoor hot tub with water and jets next to a wall with ivy and a door at Pebble Reef in Easton Portland
36
Easton, Portland, Dorset, DT5
  • Sleeps6
  • Bedrooms3
  • PetsNo

    3.6★

    Good

  • Sykes rating

A lovely three-bedroom cottage perched in Easton, Dorset. Smart TV. Near a beach. Electric fire. Close to amenities. Enclosed garden. Weymouth 7 miles. (Ref. 1122341)

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


for 7 nights £658

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A street view of two attached brick houses with windows and a trimmed hedge at 18 Chamberlaine Road in Weymouth
31
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    2.8★

  • Sykes rating

18 Chamberlaine Road is a lovely and welcoming abode, near a beach, situated in the heart of Weymouth, Dorset, only a short walk to a local shop and pub. Dorchester 9.3 miles; Bridport 17.8 miles. (Ref. 1161457)

  • Wi-fi
  • Washing machine


for 7 nights £401

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A dining area with a table set with plates and a bowl and a kitchen with stools and a blue brick fireplace at Harbour Lights Apartment in Weymouth
20
Weymouth, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • PetsNo

  • Sykes rating

Harbour Lights Apartment, a nicely-decorated apartment in the seaside town of Weymouth, Dorset. Stunning harbour views. Couple's getaway. Dorchester 8.7 miles; Bridport 20.8 miles. (Ref. 1145701)

  • Wi-fi
  • Washing machine


for 7 nights £496

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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
  • PetsYes

    3.6★

    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 £367

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