Chiswell On Portland Holiday Cottages

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Your Portland, Dorset search returned 341 cottages

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A blue two-story building with bay windows and white doors on a brick street at Tradewinds Brewers Quay Harbour
17
Brewers Quay Harbour, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7★

    Outstanding

  • Sykes rating

Situated in front of the Old Harbour in Weymouth, Tradewinds is perfect base for couples. Walking distance to town centre. Pub, shop 5 min. Beach 10 min. Dorchester 8.3 miles. (Ref. 994737)

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


for 7 nights £714

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The front view of a two-story brick house with a green door and multiple windows and a paved driveway at Bridge Apartment in Weymouth
20
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7★

    Outstanding

  • Sykes rating

Ground Floor modern accommodation. Near to Weymouth Town centre and nature reserve. Perfect for families or couples. Allocated parking. Modern property. WIFI. (Ref. 994034)

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


for 7 nights £445

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A garden with red roses and a metal chair beside a brick house at The Corner House in Weymouth
39
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6★

    Outstanding

  • Sykes rating

The Corner House is a delightful terrace home resting in the popular seaside town of Weymouth, Dorset. Close to amenities. Near beach. Enclosed courtyard. Dorchester 7.1 miles; Bridport 19.1 miles. (Ref. 1129331)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights £566

Last booked 2 days ago
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The exterior of a brick house with white doors and windows outdoor chairs and plants at Footprint Brewers Quay Harbour
22
Brewers Quay Harbour, Dorset, DT4
  • Sleeps5
  • Bedrooms2
  • PetsYes

    4.6★

    Outstanding

  • Sykes rating

Footprint a converted stable located in a gated development in Weymouth close to harbour and beach. En-suite master bedroom. Beach 1 mile. Dorchester 9 miles. (Ref. 994201)

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


for 7 nights £637

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A small dining area with a round glass table set for two and wicker chairs by two windows with ocean views at 6 The Beaches in Weymouth
16
Weymouth, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.5★

    Outstanding

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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 £413

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A three-story red brick residential building with multiple white-framed windows and black doors at Admiral's Quarter Apartment 5 in Weymouth
11
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7★

    Outstanding

  • Sykes rating

A well-presented, ground-floor apartment in Weymouth, Dorset. Open-plan. Close to beach. Near an AONB. Ground-floor living. Dorchester 8.8 miles; Bridport 19.6 miles. (Ref. 1126298)

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


for 7 nights £424

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A backyard with a brick house a blue wooden shed a small fenced garden and plants at Sandpiper in Weymouth
41
Weymouth, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.7★

    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)

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


for 7 nights £480

Last booked yesterday
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A brick house with blue door windows and a blue fence at Poppies Brewers Quay Harbour
24
Brewers Quay Harbour, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7★

    Outstanding

  • Sykes rating

Situated in a gated complex near Weymouth harbour. WiFi. Parking. Close to bars and restaurants. (Ref. 994560)

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


for 7 nights £566

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A row of terraced houses with different colored facades along a street at Old Harbour Townhouse in Weymouth
31
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.7★

    Outstanding

  • Sykes rating

Old Harbour Townhouse, a delightful, three-storey abode set in the seaside town of Weymouth in Dorset. Near coast. Woodburning stove. Open-plan. Near pub. Dorchester 8.7 miles; Bridport 19.4 miles. (Ref. 1159836)

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


for 7 nights £608

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A street view of brick terraced houses with windows and front doors under a blue sky at Victoria House in Weymouth
37
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

Victoria House is a pleasant holiday home resting in the coastal town of Weymouth in Dorset. Public car parking. Over three floors. Near amenities. Dorchester 8 miles; Bridport 20.2 miles. (Ref. 1148491)

  • Wi-fi


for 7 nights £459

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A lighthouse and white buildings with a stone wall and grassy area at Old Higher Lighthouse Branscombe Lodge Portland Bill
40
Portland Bill, Dorset, DT5
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

Charming detached Grade II listed lighthouse cottage at Portland Bill on Dorset's Jurassic Coast. Upside down accommodation with sensational sea views. Shared access to Lighthouse observatory. Shared use of heated pool and Jacuzzi. (Ref. 12497)

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


for 7 nights £617

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A stone walkway with plants along the side of a stone house at The Apple Loft at Jordan House in Preston
21
Preston, Dorset, DT3
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.3★

    Good

  • Sykes rating

The Apple Loft at Jordan House is a contemporary cottage resting in Bowleaze, on the outskirts of Weymouth, Dorset. Off-road parking. Open-plan. Garden. Dorchester 6.1 miles; Abbotsbury 9.8 miles; Bridport 19.3 miles. (Ref. 1149531)

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


for 7 nights £494

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A modern residential area with brick and stone buildings a driveway and a streetlamp at Sea Gem in Castletown Portland
43
Castletown, Portland, Dorset, DT5
  • Sleeps7
  • Bedrooms4
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

A spacious, three-storey house settled in Castletown, Portland, Dorset. Private parking. Bedrooms with en-suite. Smart TVs. Enclosed courtyard. Close to amenities and beach. Pet-free. Weymouth 4.8 miles; Dorchester 12.4 miles. (Ref. 1107230)

  • Wi-fi
  • Ground floor bedroom
  • Dishwasher


for 7 nights £922

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A row of brick terraced houses with bay windows and small front gardens at Covecastle Cottage in Weymouth
26
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.5★

    Outstanding

  • Sykes rating

Charming Edwardian terraced cottage located close to Sansfoot castle in Weymouth. Near to shops and town centre. Beach 10 minutes away. WiFi. Dorchester 8.5 miles. (Ref. 994072)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights £515

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A street view of a row of attached brick houses with dormer windows and a sidewalk at Marina Reach in Weymouth
30
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.5★

    Outstanding

  • Sykes rating

Ground floor apartment in Weymouth, sleeps 4, wifi, allocated parking, close to the beach, shops and marina. Open plan living kitchen diner. (Ref. 1091449)

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


for 7 nights £521

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Front of a white building with black door and window frames flowers in front at Harbour Reach Brewers Quay Harbour
36
Brewers Quay Harbour, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.6★

    Outstanding

  • Sykes rating

Stylish fisherman’s cottage just a few minutes’ walk from Old Harbour in Weymouth. Beach 1 mile. Harbour, shop and pub 5 min. Welcomes one dog. Poole 33 miles. (Ref. 1058438)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights £578

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A brick house with a sloped roof and skylights with a gravel driveway at Baytree Lodge in Osmington
59
Osmington, Dorset, DT3
  • Sleeps12
  • Bedrooms5
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

Luxurious 5 star contemporary property. Games room. Indoor swimming pool. WiFi. Stunning views. Five en-suite bedrooms, one family bathroom. Large sitting room and generous sitting/dining room/kitchen. (Ref. 993982)

  • Wi-fi
  • Off-road parking
  • Swimming pool
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • Games room


for 7 nights £3359

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A garden with grass and flowerbeds in front of a blue bungalow with a veranda and outdoor chairs at Harbour View Bungalow in Weymouth
30
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.5★

    Outstanding

  • Sykes rating

Overlooking the beautiful Nothe Gardens and, through the trees, the coastal views of Weymouth Bay and Portland Harbour is Harbour View Bungalow. (Ref. 994244)

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


for 7 nights £1206

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A brick house with white framed windows a pale green door and parking signs outside at Anchor Cottage in Weymouth
23
Weymouth, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

Anchor Cottage is a delightful, terraced home resting in the seaside town of Weymouth, Dorset. Close to a shop, a pub, and a beach. Family-friendly. Dorchester 7.6 miles; West Bay 17.8 miles. (Ref. 1150151)

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


for 7 nights £476

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A living room with sofas and a television at Weyside in Weymouth
20
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

  • Sykes rating

Weyside is a fantastic apartment in the seaside town of Weymouth, located in Dorset, boasting close proximity to the beach as well as several amenities. Dorchester 8.2 miles; Bridport 18.8 miles. (Ref. 1164944)

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


for 7 nights £642

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