Chiswell On Portland Holiday Cottages

Your Portland, Dorset search returned 364 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
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
  • Pet FriendlyNo

    4.8★

    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 From £511

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A row of attached houses with one blue house covered in climbing plants and flowers in front at Fenders Brewers Quay Harbour
30
Brewers Quay Harbour, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.4★

    Good

  • Sykes rating

Delightful terraced cottage. Central Weymouth location. Close to Harbour and beach . sleeping 4. Enclosed garden. WiFi. Weymouth beach just 10 minutes away. (Ref. 998253)

  • Pets go free
  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights From £617

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An exterior courtyard with stone buildings a staircase and no parking signs at George's House in Brewers Quay Harbour
28
Brewers Quay Harbour, Dorset, DT4
  • Sleeps7
  • Bedrooms4
  • Pet FriendlyYes

    4.7★

    Outstanding

  • Sykes rating

Four bedrooms in Kellaway Court, Weymouth. Restaurants and bars close by. Near harbourside. Accepts one dog. (Ref. 994219)

  • Pets go free
  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights From £832

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A balcony with a table and chairs overlooking a garden and sea at The View in Weymouth
46
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.6★

    Outstanding

  • Sykes rating

The View is a charming, three-storey house resting near the beach in Weymouth, Dorset, boasting stunning sea views, a balcony, and off-road parking. Dorchester 8.9 miles; Bridport 19.2 miles. (Ref. 1173086)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine


for 7 nights From £618

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A brick townhouse with multiple windows and green hedges in front at Plain Sailing in Weymouth
25
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    4.7★

    Outstanding

  • Sykes rating

Plain Sailing, a gorgeous holiday home located in the heart of the marvellous seaside town of Weymouth, Dorset. En-suite master. Lake view. Pet-friendly. Dorchester 7.8 miles; Bridport 18.6 miles. (Ref. 1153879)

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


for 7 nights From £713

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A house with a garden and pathway at 29 Bincleaves Road Weymouth
New property
55
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

  • Sykes rating

Coast Path Cottage is a delightful, pet-friendly house near a beach in Weymouth, Dorset, featuring a conservatory, enclosed garden, and off-road parking. Dorchester 8.9 miles; Bridport 20.5 miles. (Ref. 1204253)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Dishwasher


for 7 nights From £796

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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
  • Pet FriendlyYes

    4.5★

    Outstanding

  • 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)

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


for 7 nights From £998

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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
  • Pet FriendlyYes

    4.6★

    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)

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


for 7 nights From £493

Last booked yesterday
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The exterior of a brick house with a tiled roof a black door a paved path and plants at Badbury Lodge Brewers Quay Harbour
26
Brewers Quay Harbour, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.7★

    Outstanding

  • Sykes rating

Victorian Semi located in Weymouth, Short walk to Brewers Quay and the Harbour. (Ref. 993971)

  • Wi-fi
  • Washing machine
  • Baby-friendly


for 7 nights From £512

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A house with a deck and garden at Little Retreat in Upwey
27
Upwey, Dorset, DT3
  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

    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 From £485

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Stone buildings covered with greenery along a street with a white gate at Market House in Abbotsbury
41
Abbotsbury, Dorset, DT3
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyNo

    4.9★

    Outstanding

  • Sykes rating

This wonderful renovated cottage is situated in the village of Abbotsbury, near the coastal town of Weymouth, Dorset. Rustic, cosy interior. stove, Weymouth 8.8 miles. (Ref. 992021)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights From £593

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A building with apartments and boats at Harbourside Apartment Weymouth
23
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.4★

    Good

  • Sykes rating

Harbourside Apartment is a waterfront retreat in Weymouth, Dorset, offering views of the town bridge and harbour with convenient access to amenities. Dorchester 8.4 miles; Bridport 20.4 miles. (Ref. 1189387)

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


for 7 nights From £644

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A living room with a TV on a stand a coffee table with board games a clock on the wall and large windows showing a sea view at Beach View Apartment 3 in Greenhill
19
Greenhill, Dorset, DT4
  • Sleeps5
  • Bedrooms2
  • Pet FriendlyNo

    4.7★

    Outstanding

  • Sykes rating

Directly on the seafront. First floor period apartment. Bright and comfortable. Breath-taking sea views. En-suite shower room. WiFi. Off road parking with garage. (Ref. 993989)

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


for 7 nights From £673

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A living room with a sofa, table, and kitchen area at Royal Terrace Sunset in Weymouth
21
Weymouth, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

    5.0★

    Perfect

  • Sykes rating

Royal Terrace Sunset is a contemporary apartment situated along the coast in the heart of Weymouth, Dorset, boasting a short walk to a pub and shop. Dorchester 7.7 miles; Bridport 18.9 miles. (Ref. 1173496)

  • Wi-fi


for 7 nights From £533

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A white building with a stone wall and flowers in front and a lighthouse behind at Old Higher Lighthouse Stopes Cottage in Portland Bill
55
Portland Bill, Dorset, DT5
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.8★

    Outstanding

  • Tourist Board rating

Delightful, single-storey, Grade II listed cottage linked to Old Higher Lighthouse at Portland Bill on Dorset's Jurassic Coast. Amazing views. Shared access to lighthouse observatory. Shared use of seasonal outdoor heated pool and Jacuzzi. (Ref. 12494)

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


for 7 nights From £648

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A living room with two silver sofas a glass coffee table and two large windows at Royal Terrace View in Weymouth
23
Weymouth, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

    4.9★

    Outstanding

  • Sykes rating

This seafront, second-floor apartment sits in Weymouth, Dorset. Pay and Display parking nearby. Romantic. Sea views. Open-plan. Pet-free. Dorchester 7.6 miles; Bridport 20.3 miles. (Ref. 1107825)

  • Wi-fi


for 7 nights From £497

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Side view of a house with windows and plants at Osmington Cottage Annex
New property
19
Osmington near Preston, Dorset, DT3
  • Sleeps6
  • Bedrooms2
  • Pet FriendlyNo

  • Sykes rating

Osmington Cottage Annex is a charming cottage in Osmington, Dorset, featuring off-road parking, a garden patio, and close access to the beach nearby. Weymouth 4.7 miles. (Ref. 1211408)

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


for 7 nights From £648

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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
  • Pet FriendlyNo

    4.4★

    Good

  • 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 From £666

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Front view of two adjoining houses with black doors and white brick walls with a paved driveway at Maisy Cottage in Weymouth
25
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.7★

    Outstanding

  • Sykes rating

Modern and beautiful cottage in the heart of Weymouth. Close to town centre. Wifi. Parking for two cars. Landscaped garden with patio. Shop and pub 5 min. Bridport 22.5 miles. (Ref. 994369)

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


for 7 nights From £581

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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
  • Pet FriendlyNo

    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 From £1168

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