Upwey Cottages

REFINE SEARCH

Your search returned 231 cottages.

Most relevant
  • Distance to Location
  • Most relevant
  • Price (lowest first)
  • Price (highest first)
  • Sleeps (lowest first)
  • Sleeps (highest first)
  • Rating (lowest first)
  • Rating (highest first)
  • Location (A to Z)
  • Location (Z to A)
  • Property name (A to Z)
  • Property name (Z to A)
10
  • 10
  • 20
  • 50
  • 100
Map View
  • A backyard patio with a glass table and chairs purple flowers a wooden bench and a wooden swing at Anchors Away in Weymouth
    34
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    A wonderful three-storey holiday cottage settled in the seaside resort of Weymouth in Dorset. (Ref. 1096129)

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

    7 nights from €786

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
    Book now
  • A row of attached houses with brick and beige facades on a street with sidewalks at Globe Cottage in Weymouth
    27
    Weymouth, Dorset
    • Sleeps7
    • Bedrooms3
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Three bedroom terraced property in central Weymouth. (Ref. 1095056)

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

    7 nights from €880

    Secure your holiday with a 30% deposit* Book now
  • A stone cottage with a white front door and a paved pathway bordered by trimmed hedges at Knapp Cottage in Chickerell
    39
    Chickerell, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    A charming, three-bedroom cottage sitting in Chickerell, Dorset. (Ref. 1086432)

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

    7 nights from €734

    Secure your holiday with a 30% deposit* Book now
  • The exterior of a brick house with white doors and windows outdoor chairs and plants at Footprint Brewers Quay Harbour
    Property has offers
    22
    Brewers Quay Harbour, Dorset
    • Sleeps5
    • Bedrooms2
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    Footprint a converted stable located in a gated development in Weymouth close to harbour and beach. (Ref. 994201)

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

    • €400 off - Mon 29th Dec 2025 to 5th Jan 2026

    7 nights from €760

    Secure your holiday with a 30% deposit* Book now
  • Exterior view of three adjacent terraced houses with bay windows and chimneys at Harbourside House in Brewers Quay Harbour
    50
    Brewers Quay Harbour, Dorset
    • Sleeps8
    • Bedrooms4
    • PetsNo

      4.4★

      Good

    • Dream Cottages rating

    Beautiful holiday cottage over three floors beside Old Harbour in Weymouth. (Ref. 994256)

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

    7 nights from €1368

    Secure your holiday with a 30% deposit* Book now
  • 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
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    A marvellous third-floor penthouse situated overlooking the harbour in Weymouth, Dorset. (Ref. 1059267)

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

    7 nights from €676

    Secure your holiday with a 30% deposit* Book now
  • A three-story red brick residential building with multiple white-framed windows and black doors at Admiral's Quarter Apartment 5 in Weymouth
    11
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    A well-presented, ground-floor apartment in Weymouth, Dorset. (Ref. 1126298)

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

    7 nights from €484

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
    Book now
  • A balcony with a round table holding a bottle and two wine glasses with two chairs and a sea view at Sunbeach in Weymouth
    24
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.5★

      Outstanding

    • Dream Cottages rating

    A neat, first-floor apartment set overlooking the Pavillion on Weymouth seafront. (Ref. 1123724)

    • Wi-fi

    7 nights from €633

    Secure your holiday with a 30% deposit* Book now
  • A window seat with two mugs and a muffin on a tray overlooking a carousel and seaside at Shore View in Weymouth
    55
    Weymouth, Dorset
    • Sleeps10
    • Bedrooms5
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    26 Esplanade, a delightful coastal holiday home nestled in the town of Weymouth in Dorset. (Ref. 1118900)

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

    7 nights from €1623

    Secure your holiday with a 30% deposit* Book now
  • A bungalow with a tiled roof and gravel front garden with plants at The Willows in Preston Weymouth
    29
    Preston, Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    This delightful, two-bedroom bungalow rests in Preston, Dorset. (Ref. 1126160)

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

    7 nights from €713

    Secure your holiday with a 30% deposit* Book now
Most relevant
  • Distance to Location
  • Most relevant
  • Price (lowest first)
  • Price (highest first)
  • Sleeps (lowest first)
  • Sleeps (highest first)
  • Rating (lowest first)
  • Rating (highest first)
  • Location (A to Z)
  • Location (Z to A)
  • Property name (A to Z)
  • Property name (Z to A)
10
  • 10
  • 20
  • 50
  • 100
Map View

Quick links

Popular Destinations