Chesil Cottage Holidays

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Your Chesil Beach, Dorset search returned 423 cottages

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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
  • PetsNo

    4.6★

    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 £529

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A house with a pink door on a street at Shrimp Cottage in Brewers Quay Harbour
37
Brewers Quay Harbour, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsYes

    5.0★

    Perfect

  • Sykes rating

Shrimp Cottage is a tasteful house in Brewers Quay Harbour, Dorset, this pet-friendly abode boasts Smart TVs and is near the beach and other amenities. Dorchester 9 miles; West Lulworth 15.9 miles (Ref. 1173548)

  • Wi-fi
  • Dishwasher
  • Washing machine

  • 15% off - Mon 29th Dec 2025 to 5th Jan 2026


for 7 nights £660

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A row of terraced houses with flowers and bushes in front and a view of the sea at Langham Cottage in Portland
35
Portland, Dorset, DT5
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

Situated in the Isle of Portland, Langham Cottage is very comfortable and spacious holiday home. Accepts one dog. Pub and shop 5 min. Beach 5 min. Bridport 23 miles. (Ref. 994321)

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


for 7 nights £488

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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
  • PetsYes

    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)

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


for 7 nights £493

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A small outdoor seating area with chairs and a table surrounded by flowers in front of a brick house with blue shutters at Garibaldi Cottage in Weymouth
38
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

Garibaldi Cottage is a lovely, coastal home resting in the town of Weymouth in Dorset, enjoying close proximity to a nearby shop, beach, and pub. Dorchester 8.2 miles; Bridport 20.1 miles. (Ref. 1156408)

  • Wi-fi
  • Washing machine
  • Baby-friendly


for 7 nights £595

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An outdoor garden area with a gravel path picnic table plastic chairs and trees at Riverhouse Lodge in Upwey
21
Upwey, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6★

    Outstanding

  • Sykes rating

A pretty village lodge, close to the seaside town of Weymouth in Dorset. Traditional. Beautiful Mediterranean-style garden. WiFi. Dorset AONB. Dorchester 4.9 miles. (Ref. 1017591)

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


for 7 nights £351

Last booked yesterday
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A stone building facade with multiple windows flower boxes and a wrought iron fence at The Esplanade in Weymouth
85
Weymouth, Dorset, DT4
  • Sleeps18
  • Bedrooms9
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

The Esplanade is a stunning, nine-bedroom holiday dwelling residing in Weymouth, Dorset. Sea views. En-suite bedrooms. Close to amenities and a beach. Parking. Dorchester 7.2 miles; Bridport 18.7 miles. (Ref. 1123341)

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


for 7 nights £2610

Last booked yesterday
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A brick house with a sloped roof and skylights with a gravel driveway at Baytree Lodge in Osmington
59
Osmington, Dorset, DT3
  • Sleeps12
  • Bedrooms5
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

Luxurious 5 star contemporary property. Games room. Indoor swimming pool. WiFi. Stunning views. Five en-suite bedrooms, one family bathroom. Large sitting room and generous sitting/dining room/kitchen. (Ref. 993982)

  • Wi-fi
  • Off-road parking
  • Swimming pool
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • Games room


for 7 nights £3550

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A rocky shoreline with a small beach a stone wall and garden plants at Weymouth Bay Apartment A in Weymouth
49
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

A lovely two-bedroom, ground-floor apartment resting in Weymouth, Dorset. Near a beach. Close to amenities. Romantic. Ground-floor. Dorchester 7.5 miles; Bridport 20.5 miles. (Ref. 1083146)

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


for 7 nights £659

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A garden with a shed and patio overlooking a bay with sailboats at Rainbow's End in Cove Castle
27
Cove Castle, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

2-minute walk to Sandsfoot beach and the South West Coast path. Uninterrupted sea views to Portland and beyond, sleep 5, parking. (Ref. 994582)

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


for 7 nights £708

Last booked yesterday
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A patio with a round table and chairs under a green umbrella surrounded by potted plants and garden furniture at Sixpenny Cottage in Upwey
18
Upwey, Dorset, DT3
  • 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 £486

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A garden with flowers a wooden arch and a raised deck attached to a brick house at Little Retreat in Upwey
22
Upwey, Dorset, DT3
  • Sleeps2
  • Bedrooms1
  • PetsNo

    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 £485

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A living room with black leather sofas a glass coffee table with flowers and a lamp by the window at Harbourside Haven Apartment 3 in Weymouth
17
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7★

    Outstanding

  • Sykes rating

An immaculate second-floor apartment resting in the centre of Weymouth. Marina views. Open-plan living room. WiFi. Dorchester 8.4 miles; Bridport 20.5 miles. (Ref. 1059264)

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


for 7 nights £648

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An outdoor patio area with a wooden table and six wooden chairs in front of a modern concrete structure with large sliding glass doors at Standby Generator Bunker Ringstead near Weymouth
68
Ringstead near Weymouth, Dorset, DT2
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

Standby Generator Bunker, an impressive abode, rests in rural Ringstead in Dorset, enjoying sea views, a pet-friendly policy, and a woodburning stove. Dorchester 8.3 miles; Bridport 23.1 miles. (Ref. 1137374)

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


for 7 nights £1091

Last booked yesterday
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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

    4.8★

    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 £617

Last booked 2 days ago
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A street view of a row of attached brick houses with dormer windows and a sidewalk at Marina Reach in Weymouth
30
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.5★

    Outstanding

  • Sykes rating

Ground floor apartment in Weymouth, sleeps 4, wifi, allocated parking, close to the beach, shops and marina. Open plan living kitchen diner. (Ref. 1091449)

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


for 7 nights £536

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An outdoor dining area with a table and six chairs set in front of a bunker entrance with grass on the roof at The Transmitter Bunker in Ringstead
33
Ringstead, Dorset, DT2
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

This quirky, converted bunker rests in Ringstead near Preston, Dorset. Open fire. In an AONB. Smart TV. Off-road parking. Weymouth 7.6 mile. (Ref. 1131689)

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


for 7 nights £822

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Quay Cottage - 994576 - photo 1
29
Weymouth, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

Quay cottage is a period terraced property in Weymouth. Short walk to town centre. Close to Old Harbour. WiFi. Pub and shop 5 min. Beach 10 min. Dorchester 8.5 miles. (Ref. 994576)

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


for 7 nights £610

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Exterior of a row of white buildings with balconies and doors including a restaurant named ENZO at Bliss On The Bay Weymouth
24
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6★

    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 £631

Last booked yesterday
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A thatched roof cottage with white walls green bushes and a blue door at Lime Cottage in Burton Bradstock
35
Burton Bradstock, Dorset, DT6
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7★

    Outstanding

  • Sykes rating

A charming, two-bedroom, thatched cottage resting in Burton Bradstock, Dorset. In AONB. Original features. Close to amenities and beach. Private garden. Bridport 3 miles; Dorchester 15.3 miles; Weymouth 16.2 miles; Yeovil 22.2 miles. (Ref. 1124979)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights £628

Last booked yesterday
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