Preston Holiday Cottages

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Your Preston, Dorset search returned 380 cottages

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  • 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 $822

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

Upper ground floor apartment in the Admiral’s Quarter development. Partial sea views from the full length windows in the sitting rooms. Modern furnishings. Perfect for a family holiday exploring the delights of Weymouth. Wifi. (Ref. 994438)

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


for 7 nights $772

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

Sleeping four in Maltings area of Weymouth, pet friendly. Off road parking. WiFi. Garden. Close to harbour. (Ref. 994596)

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


for 7 nights $716

  • 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 $792

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

This picturesque cottage, situated in the village of Upwey, with parking. Short drive to Weymouth. Close to pub and tea rooms. Lovely walks nearby. (Ref. 994658)

  • Wi-fi
  • Washing machine
  • Baby-friendly


for 7 nights $634

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

Tucked in a quiet location in Weymouth, The Pines is a modern holiday home for families or couples. Welcomes two dogs. Pub and shop 10 mins. Beach 1 mile. Dorchester 9 miles. (Ref. 994549)

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


for 7 nights $849

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

Beautiful apartment, that welcomes one well behaved dog, located on the esplanade, perfect for discovering the delights of Weymouth. With wifi and off-road parking for two small to mediums sized cars. (Ref. 994451)

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


for 7 nights $1053

  • Sleeps8
  • Bedrooms4
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

Sunningdale Rise is a striking, detached home on a gated development with off-road parking, close to a beach, in the village of Preston in Dorset. Weymouth 2.5 miles. (Ref. 1149947)

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


for 7 nights $1872

  • 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 $850

  • 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 $721

  • 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 $723

Last booked yesterday
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  • 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 $598

  • Sleeps7
  • Bedrooms4
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

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

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


for 7 nights $1050

Last booked yesterday
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  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

Wonderfully positioned townhouse just moments from Sandsfoot beach and the South West Coast path. Sea views. Sleeps 6. Off road parking (Ref. 1059103)

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


for 7 nights $1041

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

A stylish apartment resting on Weymouth's beautiful esplanade. Sleeps 4. Opposite beach. Off road parking. WiFi. Dorchester 7.3 miles; Bridport 20.3 miles. (Ref. 1067722)

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


for 7 nights $811

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6

    Outstanding

  • Sykes rating

Modern ground floor Apartment. Lovely walks through the Nothe Gardens. Short walk to town centre and the beach. Wi-Fi. Gated Parking. (Ref. 993910)

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


for 7 nights $626

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

A quality semi-detached holiday home, one of five in a courtyard location, close to Weymouth. En-suite, modern features. Shop and pub within walking distance. Weymouth 3.5 miles. (Ref. 932160)

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


for 7 nights $920

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

Large kitchen diner. Beautiful rural location. Short walk to the sea. Wi-Fi. In the heart of the Jurassic coastline. Picture postcard thatched cottage. (Ref. 994553)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • 10% off - Sat 1st Nov to 22nd Nov 2025


for 7 nights $1251

  • 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 $847

  • 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 $692