Chiswell On Portland Holiday Cottages

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Your Portland, Dorset search returned 341 cottages

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A glass table with sunglasses fruit bowl champagne bottle and glasses overlooking a beach and sea at 123 On The Sea in Weymouth
33
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7★

    Outstanding

  • Sykes rating

123 On The Sea is a lovely, two-bedroom apartment residing in Weymouth, Dorset. Near Dorset AONB. Sea views. Close to amenities and a beach. Private balcony. Off road parking. Dorchester 7.3 miles; Bridport 18.9 miles. (Ref. 1133961)

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


for 7 nights $697

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A white house with solar panels on the roof a lawn and a gravel garden at The White House in Weymouth
35
Weymouth, Dorset, DT3
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.7★

    Outstanding

  • Sykes rating

This fabulous three-bedroom abode resides in Weymouth, Dorset. Sea glimpses. Smart TV. Open-plan. Near an AONB. Dorchester 7 miles; Bridport 19.5 miles. (Ref. 1125198)

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


for 7 nights $830

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A living room with a beige sectional sofa and colorful cushions a wicker coffee table a small round white table with baked goods a lamp a chair with a pillow a dining area with wooden chairs and a table at Winkle Cottage in Weymouth
38
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

Winkle Cottage is a wonderful holiday home, set over three floors, situated in the popular coastal town of Weymouth in Dorset by the historic harbour. Dorchester 8.5 miles; Bridport 19.3 miles. (Ref. 1140944)

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


for 7 nights $733

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A living room with a wooden coffee table two patchwork chairs a fireplace and a window with an ocean view at Beach Retreat in Weymouth
40
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

A sea-front two-bedroom apartment fronting Weymouth bay, Dorset. Beautiful views. En-suite bedroom. Woodburning stove. Near beach. Dorchester 7.6 miles; Bridport 21.3 miles; Poole 31.4 miles. (Ref. 1100406)

  • Wi-fi
  • Dishwasher


for 7 nights $838

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A front view of a large brick and white house with bay windows and a small porch at Dream View in Greenhill
24
Greenhill, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

Located on the Esplanade in Weymouth with far reaching beach and sea views and within walking distance of the Harbour and town amenities. (Ref. 994167)

  • Wi-fi
  • Washing machine
  • Baby-friendly


for 7 nights $787

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An exterior view of a stone cottage with benches and a gate with a Follis Cottage sign in Nottington
13
Nottington, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7★

    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 $674

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A brick terraced house with a blue door and blue metal fence in front at Melanies Cottage Brewers Quay Harbour
27
Brewers Quay Harbour, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

Melanie's Cottage is a lovely mews-style holiday home located in Brewers Quay Harbour, Weymouth. Allocated parking. WiFi. Close to beach and amenities. Dorchester 8.5 miles; West Lulworth 17.4 miles. (Ref. 1146011)

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


for 7 nights $724

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The front entrance of a building with a dark door numbered 38 and a curved window with plants along the path at Flat 2 38 Preston Road Weymouth
29
Weymouth, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsNo

    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 $647

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A street view of a blue painted building with white framed windows and two white doors in a row of attached houses
18
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6★

    Outstanding

  • Sykes rating

Located on the harbourside, is this two-bedroom contemporary apartment in Weymouth, Dorset. WiFi. Fortuneswell 4.7 miles; Dorchester 9.3 miles. (Ref. 1017563)

  • Ground floor bedroom
  • Dishwasher
  • Washing machine


for 7 nights $1083

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A window view of a harbor with sailboats and buildings in the background at The Ferryman in Weymouth
16
Weymouth, Dorset, DT4
  • Sleeps5
  • Bedrooms2
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

A character-filled cottage located in the popular seaside town of Weymouth, Dorset. Fantastic views. Harbour. Ideal for families. Weymouth 0.9 miles; Isle of Portland 6 miles. (Ref. 1017295)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights $775

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An outdoor patio with a round wooden table and six chairs next to a garden and stone wall overlooking the sea at Beach View Apartment 2 in Greenhill
35
Greenhill, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.5★

    Outstanding

  • Sykes rating

Excellent period apartment in Weymouth close to the esplanade. Two en-suite shower rooms and three bedrooms. WiFi. Enclosed patio area. Beach 1 min away. (Ref. 993988)

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


for 7 nights $1402

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A driveway with a silver van parked next to a house with a garage and trees at Redcliff View Lodge in Weymouth
24
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.2★

    Good

  • Sykes rating

Sleeps six in Weymouth, patio garden. Off road parking. 10 mins walk from Weymouth harbour. (Ref. 994586)

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


for 7 nights $853

Last booked 2 days ago
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A brick exterior with white doors windows hanging plants and a sculpture at Barley Mews Brewers Quay Harbour
50
Brewers Quay Harbour, Dorset, DT4
  • Sleeps9
  • Bedrooms4
  • PetsNo

    4.4★

    Good

  • Sykes rating

A beautiful conversion of the Devenish Brewery malthouse, just moments from the harbourside. Sleeps 9, WIFI, stylish curved kitchen. Games Room (Ref. 993976)

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


for 7 nights $1591

Last booked yesterday
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A row of houses with white and blue walls and small gardens along a brick pathway at Little Tern Brewers Quay Harbour
31
Brewers Quay Harbour, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.5★

    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)

  • Dishwasher
  • Washing machine


for 7 nights $768

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A dining area with a glass table set with plates wine glasses bread and flowers overlooking a living room with black sofas and large window at Harbourside Haven Penthouse 2 in Weymouth
16
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

A marvellous third-floor penthouse situated overlooking the harbour in Weymouth, Dorset. Underfloor heating. Smart TV. Allocated Off road parking. Dorchester 8.4 miles; Bridport 20.5 miles. (Ref. 1059267)

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


for 7 nights $801

Last booked 2 days ago
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A street view showing the entrance door of Little Gull Cottage with steps and potted plants in Weymouth
21
Weymouth, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

Little Gull Cottage is a lovely, three-storey holiday home close to Weymouth’s harbour in Dorset. Patio with furniture. Close to amenities. Smart TV. Dorchester 8.2 miles; Bridport 18.7 miles. (Ref. 1144645)

  • Wi-fi
  • Baby-friendly


for 7 nights $726

Last booked yesterday
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A brick terraced house with a black front door two windows with shutters and a street lamp in front at Harbour Catch Cottage in Weymouth
18
Weymouth, Dorset, DT4
  • Sleeps3
  • Bedrooms2
  • PetsYes

    4.7★

    Outstanding

  • Sykes rating

Traditional cute cottage, in the town centre side of Weymouth harbour. WIFI, Close to Shops, restaurants and bars. Perfect for a couples retreat. (Ref. 994240)

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


for 7 nights $639

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A row of yellow terraced houses with street lamps and paved walkways at Olympic Cottage in Portland
23
Portland, Dorset, DT5
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7★

    Outstanding

  • Sykes rating

Modern and spacious cottage for couples or family in the Isle of Portland. Enclosed garden. Welcomes one dog. Pub and shop 10 min. Beach 5 min. Weymouth 5 miles. (Ref. 994497)

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


for 7 nights $790

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A backyard patio with a glass table and chairs purple flowers a wooden bench and a wooden swing at Anchors Away in Weymouth
34
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.6★

    Outstanding

  • Sykes rating

A wonderful three-storey holiday cottage settled in the seaside resort of Weymouth in Dorset. Washing machine. Enclosed garden. Close to the beach. Dorchester 7.7 miles; Bridport 19.9 miles. (Ref. 1096129)

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


for 7 nights $876

Last booked yesterday
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A balcony with a round table holding a bottle and two wine glasses with two chairs and a sea view at Sunbeach in Weymouth
24
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6★

    Outstanding

  • Sykes rating

A neat, first-floor apartment set overlooking the Pavillion on Weymouth seafront. Excellent location. Smart TV. WiFi. Dorchester 7.4 miles; Bridport 18.8 miles. (Ref. 1123724)

  • Wi-fi


for 7 nights $740

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