Upwey holiday cottages

Self catering holiday accommodation in Upwey, Dorset

Looking for a place to stay in the Upwey area of Dorset? Our selection of Dorset cottages range from country houses to converted barns, providing you with a variety of styles to suit your needs. Luxury, romantic and family friendly cottages.

Holiday cottages great for solo travelers, couples on romantic getaways, families with children or a group of friends.

Holiday cottage, Upwey (Little Retreat)

Upwey, Dorset

1 bedroom · Sleeps 2

This converted detached cottage is in the village of Upwey near to Weymouth in Dorset and can sleep 2 people in 1 bedroom.

Holiday cottage, Upwey (Sixpenny Cottage)

Upwey, Dorset

1 bedroom · Sleeps 2

This beautiful stone-built cottage is in the village of Upwey near to Weymouth in Dorset and can sleep 2 people in 1 bedroom.

Holiday cottage, Upwey (Budmouth)

Upwey, Dorset

2 bedrooms · Sleeps 4

This wonderful semi-detached cottage is in a courtyard location, on the edge of Upwey village near Weymouth.

Holiday cottage, Upwey (Shepherd Oak)

Upwey, Dorset

2 bedrooms · Sleeps 4 · Dog friendly

This wonderful semi-detached cottage is situated in the village of Upwey, near Weymouth and sleeps four people in two bedrooms.

Holiday cottage, Upwey (Bramshurst)

Upwey, Dorset

2 bedrooms · Sleeps 4 · Dog friendly

This wonderful terraced cottage is situated in a courtyard location, one of a group of five on the edge of Upwey near Weymouth and sleeps four people in two bedrooms.

Holiday cottage, Upwey (Riverhouse Lodge)

Upwey, Dorset

2 bedrooms · Sleeps 4

This tremendous cottage rests in Dorset and can sleep four people in two bedrooms.

Holiday cottage, Upwey (Wren)

Upwey, Dorset

2 bedrooms · Sleeps 4

Wren in Upwey, Dorset, sleeps four guests in two bedrooms.

Holiday cottage, Upwey (FCH87065)

Upwey, Dorset

3 bedrooms · Sleeps 5

This inviting property occupies an idyllic setting within the pretty suburb of Upwey. A wonderful choice for walkers and those seeking a restful break, whilst being close to man...

Holiday cottage, Upwey (Everdene)

Upwey, Dorset

3 bedrooms · Sleeps 6

This wonderful semi-detached cottage is situated in a courtyard location, on the edge of Upwey near Weymouth.

Holiday cottage, Upwey (Casterbridge)

Upwey, Dorset

3 bedrooms · Sleeps 6 · Dog friendly

This wonderful semi-detached cottage in a courtyard location is situated close to Weymouth and sleeps six people in three bedrooms.

Horizon Cottages lists over 20,000 holiday cottages all over England, Scotland and Wales.

©2026 - Horizon Cottages