Chiswell On Portland Holiday Cottages

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Your Portland, Dorset search returned 341 cottages

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A street view showing old and new boathouse buildings and inner harbour with boats in the background at Old Boathouse Weymouth
23
Weymouth, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.5★

    Outstanding

  • Sykes rating

Centrally located in Weymouth beautiful holiday home for family or friends. Walking distance to town centre. WiFi. Shop and pub 5 min. Beach 10 min. Dorchester 8.5 miles. (Ref. 994461)

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


for 7 nights £632

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An exterior view of a multi-story residential building with balconies and large windows at Townbridge Apartment in Weymouth
34
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.2★

    Good

  • Sykes rating

A gorgeous second-floor apartment nestled at the heart of Weymouth, Dorset. Open-plan living space. Private parking. Close to the coast. Chickerell 3 miles; Dorchester 8.3 miles; Swanage 28.9 miles. (Ref. 1111030)

  • Wi-fi
  • Dishwasher


for 7 nights £629

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Exterior of a white two-story house with a pitched roof and blue front door at The White Cottage in Weymouth
51
Weymouth, Dorset, DT4
  • Sleeps9
  • Bedrooms4
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

A stunning, detached home resting in Weymouth, Dorset. Enclosed garden. Near beach. Pet-friendly. Dorchester 7 miles; Bridport 19.7 miles; Poole 30.9 miles. (Ref. 1022573)

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


for 7 nights £1020

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A backyard view of a brick two-story house with patio furniture and a pond in front at Agua de Plata 16 Wakeling Island Silverlake in Dorchester
33
Dorchester, Dorset, DT2
  • Sleeps8
  • Bedrooms4
  • PetsNo

    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 £747

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A living room with a blue sofa and ottoman near a fireplace and television at Owls Rest in Weymouth
33
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

A homely, mid-terrace cottage based in Weymouth. Enclosed decking. Smart TV. Beach nearby. Dorchester 8.5 miles; Bridport 19 miles. (Ref. 1094925)

  • Wi-fi
  • Off-road parking
  • Baby-friendly


for 7 nights £519

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A harbor with sailboats docked near a quay and buildings along the waterfront at Mutiny House in Brewers Quay Harbour
24
Brewers Quay Harbour, Dorset, DT4
  • Sleeps7
  • Bedrooms4
  • PetsNo

    4.3★

    Good

  • Sykes rating

Mutiny House is situated in a harbourside location in Weymouth. Perfect for a family or group of friends. WiFi. Pub and shop 5 min. Beach 1 mile. Dorchester 8.5 miles. (Ref. 994414)

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


for 7 nights £943

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An outdoor garden area with a gravel path picnic table plastic chairs and trees at Riverhouse Lodge in Upwey
21
Upwey, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6★

    Outstanding

  • Sykes rating

A pretty village lodge, close to the seaside town of Weymouth in Dorset. Traditional. Beautiful Mediterranean-style garden. WiFi. Dorset AONB. Dorchester 4.9 miles. (Ref. 1017591)

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


for 7 nights £448

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Exterior view of three adjacent terraced houses with bay windows and chimneys at Harbourside House in Brewers Quay Harbour
50
Brewers Quay Harbour, Dorset, DT4
  • Sleeps8
  • Bedrooms4
  • PetsNo

    4.4★

    Good

  • Sykes rating

Beautiful holiday cottage over three floors beside Old Harbour in Weymouth. Harbour views. Patio with furniture. Pubs and shop 5 mins. Beach 10 mins. Bridport 22 miles. (Ref. 994256)

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


for 7 nights £1139

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A stone thatched roof cottage with white framed windows and a porch along a quiet street at Cobblers Cottage in Langton Herring
44
Langton Herring, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

Cobblers Cottage is a traditional stone built thatched cottage in the quiet Dorset village of Langton Herring, close to the Jurassic coast. Abbotsbury 5 miles; Weymouth 5.5 miles; Portland 9.4 miles; Dorchester 9.9 miles. (Ref. 1171904)

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


for 7 nights £524

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A window seat with two mugs and a muffin on a tray overlooking a carousel and seaside at Shore View in Weymouth
55
Weymouth, Dorset, DT4
  • Sleeps10
  • Bedrooms5
  • PetsYes

    4.7★

    Outstanding

  • Sykes rating

26 Esplanade, a delightful coastal holiday home nestled in the town of Weymouth in Dorset. Smart TV. Pet-friendly. Sea views. Close to amenities. Dorchester 7.9 miles; Bridport 20.6 miles. (Ref. 1118900)

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


for 7 nights £1177

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A living room with two blue sofas a wooden coffee table a rug a TV a bookshelf and a fireplace at Ammonite Cottage Fortuneswell Portland
32
Fortuneswell Portland, Dorset, DT5
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7★

    Outstanding

  • Sykes rating

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

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


for 7 nights £515

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A stone cottage with a thatched roof next to a road with green planters under windows at Ivy Cottage in West Lulworth
27
West Lulworth, Dorset, BH20
  • Sleeps6
  • Bedrooms3
  • PetsYes

    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)

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


for 7 nights £707

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A house with outdoor seating area at Budmouth Upwey near Weymouth
42
Upwey near Weymouth, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.4★

    Good

  • Sykes rating

Stylish semi-detached holiday cottage, one of five on-site, in Dorset's River Wey Valley, on the edge of Upwey near Weymouth. Open plan living, en-suite facilities, private patio. Furnished and equipped to a very high standard. Weymouth 3.5 miles. (Ref. 932157)

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


for 7 nights £626

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A living room with sofas a patterned rug a TV and a fireplace at Brewers House in Weymouth
38
Weymouth, Dorset, DT4
  • Sleeps7
  • Bedrooms4
  • PetsNo

    4.3★

    Good

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

A tasteful, three-storey Victorian terrace cottage in the popular Dorset resort of Weymouth. Central location. WiFi. Near Dorset AONB. (Ref. 1002126)

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


for 7 nights £827

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A stone building with a conical roof and blue chimney pipes next to brick and blue wooden sections at The Oast House in Brewers Quay Harbour
45
Brewers Quay Harbour, Dorset, DT4
  • Sleeps10
  • Bedrooms4
  • PetsNo

    4.4★

    Good

  • Sykes rating

Electronically gated property. Gated parking for three cars. Sleeps 10. Two min walk to harbour and amenities. (Ref. 994443)

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


for 7 nights £1335

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A living room with sofas facing a brick fireplace and a TV on a wooden cabinet at The Grain Store in Weymouth
39
Weymouth, Dorset, DT3
  • Sleeps7
  • Bedrooms4
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

A detached property sitting in a country location on the outskirts of Weymouth. Off-road parking. Open fire. Smart TV. Dorchester 4.4 miles; Bridport 15.3 miles; Poole 28.3 miles. (Ref. 1108920)

  • Wi-fi
  • Washing machine
  • Baby-friendly


for 7 nights £693

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A garden with flowers a wooden arch and a raised deck attached to a brick house at Little Retreat in Upwey
21
Upwey, Dorset, DT3
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

Village pubs and tea rooms. Sleeps two. Parking for one car. 10 mins from Weymouth. Patio and garden. (Ref. 994358)

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


for 7 nights £485

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A street view of brick buildings including Bay View Hotel and a pop-up pizza shop at The Loft @ No36 in Weymouth
31
Weymouth, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.7★

    Outstanding

  • Sykes rating

The Loft @ No36, a contemporary, third-floor apartment situated in the heart of Weymouth in Dorset, enjoying sea views with the beach on your doorstep. Dorchester 7.8 miles; Bridport 19.1 miles. (Ref. 1162205)

  • Wi-fi
  • Off-road parking


for 7 nights £502

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A stone cottage with a wooden door and white framed windows with a stone wall and gate in front at Blueberry Cottage in Sutton Poyntz
28
Sutton Poyntz, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.6★

    Outstanding

  • Sykes rating

An enchanting refurbished cottage in the centre of the lovely village of Sutton Poyntz. Fully furnished and comfortable. Sunny patio garden. WiFi. Weymouth 4 miles. (Ref. 994009)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights £419

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Exterior view of a brick building with balconies windows and surrounding garden at Ocean Watch 5 in Greenhill
17
Greenhill, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.5★

    Outstanding

  • Sykes rating

Modern, bright apartment with sea views over to Weymouth Bay. Short walk to the beach and a casual stroll to the town centre. Wifi and off-road parking. Great base for exploring Weymouth and the surrounding areas. (Ref. 1098447)

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


for 7 nights £676

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