Chiswell On Portland Holiday Cottages

REFINE SEARCH

Your Portland, Dorset search returned 351 cottages

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
Map View
A brick apartment building with balconies and parking at Brewery View in Weymouth
22
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

  • Sykes rating

Brewery View is a stylish, first-floor apartment near the beach in Weymouth, Dorset, with an open-plan living space, balcony, and designated parking. Dorchester 8.8 miles; Bridport 19.4 miles. (Ref. 1189426)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights $712

Last booked 1 hour ago
See more details
A beach and ocean view with a clock tower in Weymouth
43
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

  • Sykes rating

Vista Mare 1 is a pleasant apartment located in the heart of Weymouth in Dorset, enjoying close proximity to a beach and pub, as well as a warm welcome to pets. Dorchester 7.5 miles; Bridport 21.1 miles. (Ref. 1164685)

  • Wi-fi
  • Dishwasher


for 7 nights $1813

See more details
A mobile home with a deck and table at Littlesea Holiday Park - Holiday Accommodation 13127 Weymouth
41

Holiday Park

Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms2
  • PetsYes

  • Sykes rating

39 Green Lands is a lovely pet-friendly caravan in Weymouth, Dorset, boasting onsite facilities and is close to the beach for a day out. Dorchester 9.2 miles; Bridport 17,6 miles. (Ref. 1185302)

  • Wi-fi
  • Swimming pool


for 7 nights $776

See more details
A house facade with windows and doors at 8 Park View Grove Weymouth
New property
40
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms3
  • PetsYes

  • Sykes rating

Park View is a welcoming house in Weymouth, Dorset, offering three bedrooms, enclosed rear garden, and easy reach of shop, pub, and beach. Dorchester 8.4 miles; Bridport 19 miles; Charmouth 25.5 miles. (Ref. 1198402)

  • Wi-fi
  • Off-road parking
  • Dishwasher


for 7 nights $832

See more details
A street with colorful buildings and lampposts at Apartment 1 Brewers Quay in Weymouth
5
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms1
  • PetsNo

  • Tourist Board rating

Apartment 1 Brewers Quay is a stylish property in Weymouth’s historic Quayside, boasting modern interiors and allocated parking. Dorchester 8.6 miles; Bridport 19.3 miles. (Ref. 1166031)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights $623

See more details
A house with a front door and windows at The Weymouth House in Weymouth
28
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsYes

  • Sykes rating

The Weymouth House is a welcoming holiday home in Weymouth, Dorset, with a private courtyard and parking permit. Dorchester 7.5 miles; Bridport 18.9 miles. (Ref. 1193951)

  • Wi-fi
  • Washing machine


for 7 nights $2478

See more details
Row of three connected houses with two having painted facades and one with pebble dash exterior
19
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsNo

    3.5★

    Good

  • Sykes rating

Ocean Swell is a lovely cottage for families or friends in Weymouth. Close to the town centre. WiFi. Shop and pub 5 min. Beach 1 mile. Dorchester 8.5 miles. (Ref. 994710)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights $702

Last booked 2 days ago
See more details
An outdoor dining area with a table and chairs overlooking the sea at Ocean Wave in Greenhill
New property
19
Greenhill, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

  • 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. 1197674)

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


for 7 nights $1095

See more details
An exterior view of a house with pink and white windows at Seahorse Cottage in Weymouth
New property
29
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

  • Sykes rating

Seahorse Cottage, a delightful stone terraced cottage near Old Harbour in Weymouth, Dorset, boasts a garden, a nearby beach and amenities, and allows pets. Dorchester 7 miles. (Ref. 1191297)

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


for 7 nights $688

See more details
The front door of a blue and white house with two blue pots containing plants and a blue wooden planter in front at Cove Cottage Hideaway in Chiswell On Portland
36
Chiswell On Portland, Dorset, DT5
  • Sleeps2
  • Bedrooms1
  • PetsNo

    3.3★

  • Sykes rating

Cove Cottage Hideaway is a romantic, terrace abode near the coast in Chiswell on Portland, Dorset. Close to amenities and beach. Sea Views. Romantic. Weymouth 5.2 miles. (Ref. 1150238)

  • Wi-fi


for 7 nights $790

See more details
Exterior view of a multi-story building with beige brick walls and blue glass balconies at Nautica in Weymouth
15
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    3.4★

  • Sykes rating

A contemporary second-floor apartment set within the town of Weymouth, Dorset. Close to the close. Balcony with views. Dorchester 8.4 miles; Bridport 19.2 miles; Bournemouth 37.1 miles. (Ref. 1052595)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights $670

See more details
A living room with a sofa and a coffee table at Vista Mare 3 in Weymouth
31
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

  • Sykes rating

Vista Mare 3 is a delightful apartment located in the centre of Weymouth, a vibrant town in Dorset, with lovely sea views from an open-plan living space. Dorchester 7.5 miles; Bridport 21.1 miles. (Ref. 1164688)

  • Wi-fi
  • Dishwasher


for 7 nights $1203

See more details
An outdoor view of a cottage with a thatched roof and stone wall at Bracken Cottage in
Offer
11
Osmington, Dorset, DT3
  • Sleeps2
  • Bedrooms1
  • PetsNo

  • Sykes rating

Bracken Cottage is a romantic property resting in the village of Osmington, Dorset, boasting an open-plan living area, is close to the beach and amenities. Weymouth 5.4 miles. (Ref. 1173628)

  • Wi-fi
  • Off-road parking

  • 10% off - Mon 12th Jan to 31st Dec 2026


for 7 nights $601

See more details
A living room with a sofa and dining table at Vista Mare 2 in Weymouth
25
Weymouth, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • PetsNo

  • Sykes rating

Vista Mare 2 is a lovely apartment perched in the heart of Weymouth, a popular town in Dorset, enjoying fantastic sea views from the open-plan living space. Dorchester 7.5 miles; Bridport 21.1 miles. (Ref. 1164686)

  • Wi-fi
  • Dishwasher


for 7 nights $856

See more details
A stone house with wooden doors and windows along a road with slow painted on the street at Wren in Upwey
36
Upwey, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsNo

  • Sykes rating

Wren, a stylish, two-bedroom home rests in Upwey, Dorset. Near AONB. Close to amenities. Near the beach and attractions. Enclosed garden. Contemporary. Weymouth 4.2 miles; Dorchester 4.4 miles. (Ref. 1138702)

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


for 7 nights $686

See more details
Vinney Cottage - 1164354 - photo 1
Offer
30
Owermoigne, Dorset, DT2
  • Sleeps5
  • Bedrooms3
  • PetsYes

  • Sykes rating

Vinney Cottage is a Grade II listed traditional, farm-style thatched home in Owermoigne near Broadmayne, Dorset, with ground-floor living and a pet-friendly policy. Dorchester 6.8 miles; Puddletown 7.6 miles; Weymouth 8.6 miles. (Ref. 1164354)

  • Wi-fi
  • Ground floor bedroom
  • Washing machine

  • 10% off - Fri 1st May to 16th Jun 2026


for 7 nights $1104

See more details
A living room with a staircase and a sofa at Harbourside in Weymouth
New property
34
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

  • 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)

  • Wi-fi
  • Washing machine


for 7 nights $585

Last booked 2 days ago
See more details
A living room with a fireplace and kitchen visible at Fisherman’s Cottage
27
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

  • Sykes rating

Fisherman’s Cottage, a pleasant house nestled in Weymouth, Dorset, with an open-plan design, an enclosed courtyard and proximity to the beach and amenities. Dorchester 8.4 miles; Bridport 19 miles. (Ref. 1172825)

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


for 7 nights $657

See more details
A living room with a sofa and dining area at Betty's Buoy Weymouth
28
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

  • Sykes rating

Betty’s Buoy is a stylish first-floor apartment in Weymouth, Dorset, with open-plan living and easy access to the beach. Dorchester 7.5 miles; Bridport 18.8 miles. (Ref. 1168986)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights $659

See more details
A cottage with a patio and chairs at Bubbs Cottage
39
Winfrith Newburgh, Dorset, DT2
  • Sleeps4
  • Bedrooms2
  • PetsYes

  • Sykes rating

Bubbs Cottage is a charming thatched cottage near Winfrith Newburgh, Dorset, boasting proximity to the Jurassic Coast, WiFi, a garden and allows pets. Dorchester 9 miles; Wareham 8 miles. (Ref. 1183195)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights $833

See more details
Map View

Quick links

Popular Destinations