Chiswell On Portland Holiday Cottages

Your Portland, Dorset search returned 361 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 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
42
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 £615

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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

    4.3★

    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 £1209

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A brick residential building with multiple windows a gated entrance and a small staircase at Ocean Watch 1 in Greenhill
20
Greenhill, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7★

    Outstanding

  • Sykes rating

Modern one level apartment. Sitting room, with balcony and beautiful sea views. Short walk to the beach and a causal walk to the town centre. Wifi. (Ref. 994505)

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


for 7 nights £610

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Front view of a stone cottage with white framed windows and door at Alpen Rose Cottage Easton Portland
16
Easton Portland, Dorset, DT5
  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

A stone Fisherman's cottage on Portland, WIFI, ideal location for exploring Portland, sail at the National Sailing academy and the Jurassic Coast. (Ref. 993918)

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


for 7 nights £638

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A brick residential building with white doors and windows next to a small lawn and paved driveway at Lodmoor House in Weymouth
25
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

A lovely two-bedroom house resting in Weymouth, Dorset. Family-friendly. Enclosed garden. Near a beach. Pet-friendly. Dorchester 6.7 miles; Bridport 19.6 miles. (Ref. 1120462)

  • Wi-fi
  • Washing machine


for 7 nights £471

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A two-story house with yellow brick facade and bay window with bushes in front at Amaranta Brewers Quay Harbour
33
Brewers Quay Harbour, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.3★

    Good

  • Sykes rating

A wonderful, newly renovated three-bedroom house resting in Weymouth, Dorset. Pet-friendly. Near a beach. Family-friendly. Enclosed patio. Dorchester 8.8 miles; Bridport 20.9 miles. (Ref. 1094065)

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


for 7 nights £690

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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

    4.2★

    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 £485

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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 £581

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Two beige houses with black doors and windows on a paved street at Jurassic Coast House in Portland
42
Portland, Dorset, DT5
  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.4★

    Good

  • Sykes rating

Modern and comfortable holiday house for up to 8 people in the Isle of Portland. Enclosed garden with patio. Pub and shop 5 min. Beach 5 min. Weymouth 5 miles. (Ref. 994310)

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


for 7 nights £998

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A brick house with white framed windows a white garage door and a paved driveway at Portside Greenhill Weymouth
24
Greenhill Weymouth, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.4★

    Good

  • Sykes rating

This plush, two-storey property is located in the Greenhill suburb of Weymouth, Dorset. Bedroom with en-suite. Off-road parking. Pet-friendly. Close to amenities. Close to beach. Dorchester 7 miles; Abbotsbury 9 miles; Bridport 19.9 miles. (Ref. 1093991)

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


for 7 nights £559

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A white cottage with a thatched roof and potted plants outside on a roadside at Amy Cottage in West Lulworth
43
West Lulworth, Dorset, BH20
  • Sleeps6
  • Bedrooms4
  • PetsYes

    4.6★

    Outstanding

  • Sykes rating

Amy Cottage is a beautiful thatched cottage with a toasty gas fire and accepting pets, located in Dorset's West Lulworth on the Jurassic coastline. Wareham 8.7 miles; Weymouth 14.6 miles. (Ref. 1166887)

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


for 7 nights £858

Last booked yesterday
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A row of attached houses with different exterior finishes on a street at Home From Home in Fortuneswell
57
Fortuneswell, Dorset, DT5
  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.5★

    Outstanding

  • Sykes rating

Home From Home is a delightful cottage nestled in the village of Fortuneswell in Dorset, Isle of Portland and is pet-friendly and near the beach. Weymouth 5.5 miles (Ref. 1158103)

  • Wi-fi
  • Washing machine


for 7 nights £499

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A sandy beach with tire tracks and footprints beside a paved promenade with pedestrians and buildings at Sunrise Apartment in Weymouth
Offer
22
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6★

    Outstanding

  • Sykes rating

A contemporary first-floor apartment overlooking the coast in Weymouth, Dorset. Open-plan. Sea views. WiFi. Close to amenities. Dorchester 7.4 miles; Bridport 20.2 miles. (Ref. 1097676)

  • Wi-fi

  • 10% off - Fri 22nd May to 3rd Jul 2026


for 7 nights £686

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An old stone building with multiple gables and windows behind a stone wall at The Old Portland Courthouse in Portland
33
Portland, Dorset, DT5
  • Sleeps8
  • Bedrooms4
  • PetsNo

    4.6★

    Outstanding

  • Sykes rating

The Old Portland Courthouse is spacious, comfortable luxury holiday home. Sleeps 8 people. Wifi. Pub and shop 10 min. Beach 5 min. Weymouth 5 miles. (Ref. 994487)

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


for 7 nights £1209

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A living room with sofas a coffee table a fireplace a television and wall art at Victorian Town House in Weymouth
36
Weymouth, Dorset, DT4
  • Sleeps8
  • Bedrooms5
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

Victorian Town House is a large, coastal property resting in the seaside town of Weymouth, Dorset. Close to a shop, a pub, and a beach. Large property. Dorchester 7.5 miles; West Bay 17.5 miles. (Ref. 1035186)

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


for 7 nights £653

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The front door and window of a brick house with plants growing around the entrance at 11 Beech Road Weymouth
43
Weymouth, Dorset, DT3
  • Sleeps7
  • Bedrooms4
  • PetsYes

    4.7★

    Outstanding

  • Sykes rating

A spacious, semi-detached house resting in Weymouth, Dorset. Pet-friendly. Off-road parking. Open-plan. Bedroom with en-suite. Enclosed garden. Dorchester 4.7 miles; Bridport 17.2 miles. (Ref. 1105244)

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


for 7 nights £836

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A white brick exterior of two adjacent houses with black and green doors and windows at Wey Cottage in Weymouth
17
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.3★

    Good

  • Sykes rating

Traditional terraced cottage, 3 minutes' walk to the harbour, shop and café. WiFi. Pet-friendly. Enclosed courtyard garden. Dorchester 7 miles. (Ref. 998260)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights £531

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A blue building with bay windows and two white doors behind a black metal fence at Brewers Quay Harbour
23
Brewers Quay Harbour, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.5★

    Outstanding

  • Sykes rating

All second floor. Two bedrooms: 1 x double bed with en-suite shower, basin and WC, 1 x twin single. Bathroom with bath, basin and WC. Open plan living area with kitchen, dining area and sitting area. (Ref. 994293)

  • Wi-fi


for 7 nights £659

Last booked yesterday
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A living room with two sofas a coffee table a TV and paintings on the wall at Harbour Watch 2 in Weymouth
Offer
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

  • 10% off - Fri 17th Apr to 25th Jul 2026


for 7 nights £831

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A white semi detached house with blue doors and a blue fence under a clear sky at Ashwood Brewers Quay Harbour
22
Brewers Quay Harbour, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.4★

    Good

  • Sykes rating

Modern 3 Storey house. Close to the Harbour, Newton’s Cove and Brewers Quay. WIFI. Parking for one car. 5 minutes to local shop. 15 minute walk to town centre. (Ref. 993939)

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


for 7 nights £786

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