Preston Holiday Cottages

Add your dates to see accurate prices and availability.

Your Preston, Dorset search returned 399 cottages

REFINE SEARCH
Most relevant
  • Distance to Location
  • Most relevant
  • Price (lowest first)
  • Price (highest first)
  • Sleeps (lowest first)
  • Sleeps (highest first)
  • Tick Rating (lowest first)
  • Tick Rating (highest first)
20
  • 10
  • 20
  • 50
  • 100

How reviews work

A property's star rating is the average of the star ratings received from guests that wish for their review to be published

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.7

    Outstanding

  • Sykes rating

Situated in front of the Old Harbour in Weymouth, Tradewinds is perfect base for couples. Walking distance to town centre. Pub, shop 5 min. Beach 10 min. Dorchester 8.3 miles. (Ref. 994737)

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


for 7 nights From £733

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.4

    Good

  • Sykes rating

Harbourside is a charming, dog-friendly, Grade II listed house in Weymouth, Dorset, set over three stories, with open-plan living and a private courtyard. Dorchester 8.8 miles; Bridport 18.9 miles. (Ref. 1172365)

  • Pets go free
  • Wi-fi
  • Washing machine


for 7 nights From £408

Last booked today
See more details
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.9

    Outstanding

  • Sykes rating

Coastguard View is a lovely holiday cottage resting near the coast in Portland Bill on the Isle of Portland, Dorset with a Smart TV and open-plan space. Easton 2.6 miles; Fortuneswell 3.6 miles; Weymouth 9.1 miles. (Ref. 1169819)

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


for 7 nights From £600

  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    4.9

    Outstanding

  • Sykes rating

A contemporary townhouse situated just a stone’s throw from Chesil Beach. Pet-friendly. Three floors. Beach views. Weymouth 4.5 miles. (Ref. 1084822)

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


for 7 nights From £610

  • Sleeps7
  • Bedrooms3
  • Pet FriendlyYes

    4.6

    Outstanding

  • Sykes rating

An attractive, terraced, three-storey house near Chesil Beach in Fortuneswell, Dorset. Off-road parking. Dog-friendly. Enclosed terrace. Smart TV. Bedroom with en-suite. Weymouth 4.6 miles. (Ref. 1091335)

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


for 7 nights From £680

  • Sleeps12
  • Bedrooms6
  • Pet FriendlyNo

    4.4

    Good

  • Sykes rating

A spacious, detached, three-storey house nestled in Weymouth, Dorset. Close to amenities. Close to beach. Pet-free. Enclosed garden. Dorchester 6.5 miles; Bridport 18 miles. (Ref. 1080182)

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


for 7 nights From £1271

  • Sleeps7
  • Bedrooms4
  • Pet FriendlyNo

    4.9

    Outstanding

  • Sykes rating

A spacious, three-storey house settled in Castletown, Portland, Dorset. Private parking. Bedrooms with en-suite. Smart TVs. Enclosed courtyard. Close to amenities and beach. Pet-free. Weymouth 4.8 miles; Dorchester 12.4 miles. (Ref. 1107230)

  • Wi-fi
  • Ground floor bedroom
  • Dishwasher


for 7 nights From £916

Last booked 8 hours ago
See more details
  • Sleeps6
  • Bedrooms4
  • Pet FriendlyYes

    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)

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


for 7 nights From £877

  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    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)

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


for 7 nights From £729

  • Sleeps5
  • Bedrooms3
  • Pet FriendlyYes

    4.7

    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)

  • Pets go free
  • Wi-fi
  • Baby-friendly


for 7 nights From £539

  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    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)

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


for 7 nights From £916

  • Sleeps15
  • Bedrooms6
  • Pet FriendlyYes

    4.5

    Outstanding

  • Sykes rating

Anchor House is a stunning, pet-friendly townhouse with a private hot tub in the heart of Weymouth, Dorset, close to local amenities and the beach. Dorchester 7.8 miles; Bridport 19.9 miles. (Ref. 1105510)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Hot Tub
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • Games room
  • 15% off - Mon 13th Jul to 31st Dec 2026


for 7 nights From £1648