Dorchester Cottage Holidays

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Your Dorchester, Dorset search returned 707 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 sofas and cushions near glass doors with curtains and a rug at Admirals Retreat in Weymouth
25
Weymouth, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

    4.6★

    Outstanding

  • Sykes rating

Perfect couples retreat with WIFI. Located in The Nothe in Weymouth, surrounded by beauitful walks and moments from the harbour. (Ref. 993912)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights From $682

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A white three-story residential building with a black and white tiled walkway leading to a black door at 66 3 Compass Point in Weymouth
22
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.8★

    Outstanding

  • Sykes rating

3 Compass Point is a stylish, ground-floor apartment resting in Weymouth, Dorset. Near beach and amenities. Contemporary. Open-plan. Private parking. Dorchester 6.7 miles; Bridport 20.5 miles. (Ref. 1129014)

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


for 7 nights From $871

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A stone house exterior with green door and lattice windows surrounded by garden at The Old School House in Piddletrenthide
32
Piddletrenthide, Dorset, DT2
  • Sleeps5
  • Bedrooms3
  • Pet FriendlyYes

    4.6★

    Outstanding

  • Sykes rating

An attractive, converted Victorian school resting within Piddletrenthide. WiFi. Woodburning stove. Pet-friendly. Off-road parking. Dorchester 8 miles. (Ref. 933650)

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


for 7 nights From $790

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A street view of brick buildings including Bay View Hotel and a pop-up pizza shop at The Loft @ No36 in Weymouth
31
Weymouth, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

    4.7★

    Outstanding

  • Sykes rating

The Loft @ No36, a contemporary, third-floor apartment situated in the heart of Weymouth in Dorset, enjoying sea views with the beach on your doorstep. Dorchester 7.8 miles; Bridport 19.1 miles. (Ref. 1162205)

  • Wi-fi
  • Off-road parking


for 7 nights From $738

Last booked 9 hours ago
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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

    4.8★

    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 $811

Last booked 1 hour ago
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A hallway with door opening to the sea at 123 On The Sea - The Cubby in Weymouth
New property
19
Weymouth, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

  • Sykes rating

123 On The Sea – The Cubby is a charming apartment overlooking the beach in Weymouth, Dorset, boasting ample nearby attractions. Dorchester 7.6 miles; Bridport 21.2 miles. (Ref. 1179902)

  • Wi-fi
  • Dishwasher


for 7 nights From $756

Last booked 3 hours ago
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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 $711

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A balcony with two chairs a table with a bottle of champagne and glasses overlooking greenery and water at Waters Edge in Wyke Regis
35
Wyke Regis, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • Pet FriendlyYes

    4.8★

    Outstanding

  • Sykes rating

Modern family house located on the edge of Weymouth, with sea views. Short drive to town centre. Welcomes two dogs. Garden. Pub and shop 10 min. Beach 2 min. Bridport 19 miles. (Ref. 994759)

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


for 7 nights From $885

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Exterior view of a stone house with multiple wooden windows and a wooden door next to outdoor dining furniture at The Granary Burton Bradstock
33
Burton Bradstock, Dorset, DT6
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyNo

    4.8★

    Outstanding

  • Sykes rating

A beautifully presented property resting in the pretty village of Burton Bradstock. Off-road parking. WiFi. Woodburning stove. Bridport 2.9 miles; Weymouth 15.8 miles; Dorchester 16.4 miles. (Ref. 1069147)

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


for 7 nights From $1383

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A brick terraced house with a white front door gravel front garden and small plants at Home Waters in Wyke Regis
23
Wyke Regis, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • Pet FriendlyYes

    4.8★

    Outstanding

  • Sykes rating

Off road parking. Sleeping 6 close to Portland marina. Dog friendly. (Ref. 994270)

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


for 7 nights From $772

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A stone cottage with a thatched roof near the coast with grass and gravel paths at Pitt Cottage Ringstead
30
Ringstead, Dorset, DT2
  • 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 $1210

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A mobile home with a deck and fence at Freshwater Beach Holiday Park - Holiday Accommodation 17116 in Burton Bradstock near Bridport
Offer
17

Holiday Park

Burton Bradstock near Bridport, Dorset, DT6
  • Sleeps6
  • Bedrooms2
  • Pet FriendlyNo

  • Sykes rating

Holiday Accommodation 17116 offers stunning views near Bridport, with two bedrooms, enclosed decking and easy access to Dorset’s coast and countryside. Lyme Regis 10 miles; West Bay 2 miles. (Ref. 1186216)

  • Wi-fi
  • Swimming pool
  • Baby-friendly

  • 5% off - Sat 1st Aug to 30th Sep 2026


for 7 nights From $723

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A stone cottage with a thatched roof a white door and wooden garage door on a street at Stable Cottage in Burton Bradstock
39
Burton Bradstock, Dorset, DT6
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyNo

    4.8★

    Outstanding

  • Sykes rating

Stable Cottage is a charming, three-bedroom dwelling residing in Burton Bradstock, Dorset. En-suite master bedroom. Close to amenities and a beach. In the Dorset AONB. Bridport 3.1 miles; Weymouth 15.9 miles; Dorchester 15.2 miles; Yeovil 21.4 miles (Ref. 1133658)

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


for 7 nights From $1024

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A living room with a sofa, coffee table, and dining area at Beachcomb in Weymouth
28
Weymouth, England, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

  • Sykes rating

Beachcomb is a fine third-floor apartment located close to a beach in the town of Weymouth in Dorset, well-positioned to nearby attractions and amenities. Dorchester 7.7 miles; Bridport 21.2 miles; Poole 31.2 miles. (Ref. 1083686)

  • Wi-fi
  • Washing machine


for 7 nights From $763

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A house with garage and pathway at Millmead House in Portesham
61
Portesham, Dorset, DT3
  • Sleeps8
  • Bedrooms4
  • Pet FriendlyYes

  • Sykes rating

Millmead House is a welcoming house in Portesham, Dorset, within the Dorset National Landscape, featuring a toasty woodburning stove and a garden. Weymouth 7.8 miles; Dorchester 8.1 miles (Ref. 1200773)

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


for 7 nights From $1245

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A beach with houses alongside at Cove Cottage in Weymouth
New property
35
Weymouth, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • Pet FriendlyNo

  • Sykes rating

Cove Cottage is a well-located cottage in Weymouth, Dorset, boasting close proximity to the beach and easy access to local shops and nearby amenities. Dorchester 9.7 miles; Bridport 18.9 miles. (Ref. 1094256)

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


for 7 nights From $885

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The front view of a two-story brick house with a green door and multiple windows and a paved driveway at Bridge Apartment in Weymouth
20
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    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 From $590

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A house with patio furniture at The Old Inn in Winterborne Whitechurch
New property
52
Winterborne Whitechurch, Dorset, DT11
  • Sleeps8
  • Bedrooms4
  • Pet FriendlyYes

  • Sykes rating

The Old Inn is a stunning, pet-friendly house in Winterborne Whitechurch, Dorset, with rural views, a hot tub, woodburning stoves, and private parking. Blandford Forum 6.5 miles; Dorchester 9.8 miles. (Ref. 1191860)

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


for 7 nights From $1938

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A two-story brick house with a white enclosed porch shrubs in front and a driveway leading to a detached garage at Casa Carmen in Weymouth
18
Weymouth, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • Pet FriendlyNo

    4.1★

    Good

  • Sykes rating

Modern, detached cottage resting on the edges of Weymouth in Dorset. Off-road parking. Garden. WiFi. Close to harbour, shops, restaurants and pubs. (Ref. 1001584)

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


for 7 nights From $872

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A house with a garden and stone wall at 12 West Street Weymouth
37
Chickerell, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

  • Sykes rating

September Cottage is a charming cottage in Chickerell, Dorset, featuring a conservatory, gas fire, and a multi-tiered garden with patio near the beach. Weymouth 3.9 miles; Abbotsbury 6 miles; Portland 7.1 miles; Dorchester 8.3 miles. (Ref. 1202453)

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


for 7 nights From $727

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