Upwey Holiday Cottages

Find your perfect Upwey holiday cottage including pet-friendly Upwey holiday cottages. Whether you are looking for a romantic break or a family holiday, we have a great collection of cottages to choose from.
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The Old Stable - Upwey

Enjoy the convenience of a well-appointed village whilst making the most of a convenient location, perfect for exploring the coastline and countryside alike. Take a stroll into the heart of...

Secure your 2022 Weymouth holiday cottage with just a 33% deposit when booking 9 weeks or more in advance.
  • From £331
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Casterbridge - Upwey

Casterbridge is a quality semi-detached cottage, one of five on-site in a courtyard setting, on the edge of Upwey near Weymouth. This superb holiday home is set mostly on the...

Secure your 2022 Weymouth holiday cottage with just a 30% deposit
  • From £473
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Riverhouse Lodge - Upwey

Riverhouse Lodge is a brilliant property located in the Dorset Area of Outstanding Natural Beauty. The cottage has two bedrooms both with en-suite shower rooms and is suitable to sleep...

Secure your 2022 Weymouth holiday cottage with just a 30% deposit
  • From £299
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40 The Ridgeway - Upwey

40 The Ridgeway is a delightful cottage resting within Upwey, Dorset. It comes with two bedrooms, comprising of a double and a twin, together sleeping up to four people and...

Secure your 2022 Weymouth holiday cottage with just a 30% deposit
  • From £397
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Wishing Well Cottage - Upwey

Wishing Well Cottage is an attractive stone-built cottage lying in the village of Upwey near Weymouth, Dorset. Hosting two double bedrooms this cottage can sleep up to four people. The...

Secure your 2022 Weymouth holiday cottage with just a 30% deposit
  • From £560
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Budmouth - Upwey

Budmouth is a superb semi-detached cottage, one of five on-site, on the outskirts of Upwey and 3.5 miles from Weymouth in Dorset. This wonderful cottage is set mostly on the...

Secure your 2022 Weymouth holiday cottage with just a 30% deposit
  • From £415
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Bramble Cottage Upwey - Upwey

Upwey is 4 miles north of the vibrant town centre of Weymouth where you can take a stroll around the historic old harbour, visit Nothe Fort or enjoy the sandy...

Secure your 2022 Weymouth holiday cottage with just a 33% deposit when booking 9 weeks or more in advance.
  • From £440
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Bramshurst - Upwey

Bramshurst is a superb terraced cottage, the middle one of three, in a courtyard development of five holiday cottages, on the outskirts of Upwey village near Weymouth. This wonderful cottage...

Secure your 2022 Weymouth holiday cottage with just a 30% deposit
  • From £377
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Everdene - Upwey

Everdene is an outstanding semi-detached cottage, one of five in a courtyard setting on the outskirts of the village of Upwey, 3.5 miles from Weymouth. This superb holiday home is...

Secure your 2022 Weymouth holiday cottage with just a 30% deposit
  • From £475
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Little Retreat - Upwey

Little Retreat is a converted detached property located in the picturesque village of Upwey, near Weymouth and is situated in the grounds of ‘The Retreat’. Just perfect for two, once...

Secure your 2022 Weymouth holiday cottage with just a 30% deposit
  • From £365
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The Cabin At Cackleberry Farm - Upwey

Located in the tranquil village of Upwey and set on a smallholding with sheep and chickens, this property offers a wide network of walking and cycling routes from the doorstep,...

Secure your 2022 Weymouth holiday cottage with just a 33% deposit when booking 9 weeks or more in advance.
  • From £374
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Sixpenny Cottage - Upwey

Sixpenny Cottage is a beautiful semi-built cottage situated in the village of Upwey near to the town of Weymouth in Dorset and benefits from spacious and charmingly furnished accommodation. The...

Secure your 2022 Weymouth holiday cottage with just a 30% deposit
  • From £372

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