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Upwey Holiday Cottages
Our curated collection of Upwey cottages has something for everyone... Whether you're idea of a great holiday is a modern glamping pod, or a rustic thatched cottage that's a hundred years old, we've got you covered! Each of our rentals features a private hot tub and everything you need for your next family holiday, romantic retreat or that getaway with a group of friends. Discover find your perfect Upwey holiday home today.
Visitor Rating
4.7
- Sleeps seven across four bedrooms
- Two living rooms with Smart TVs
- Open fire for cosy evenings
- Safe enclosed courtyard garden
- Walking distance to village pub
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Visitor Rating
4.8
- Four bedrooms sleeping seven
- Enclosed garden with patio
- Off-road parking two cars
- Walking distance Bowleaze Cove
- Fully-fitted kitchen facilities
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Visitor Rating
4.8
- Sleeps 8 guests comfortably
- Four well-appointed bedrooms
- Open-plan social living space
- Private enclosed garden area
- Near Jurassic Coast attractions
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Visitor Rating
4.5
- Sleeps 12 across six bedrooms
- Multi-level garden with play area
- Near Weymouth beach and attractions
- Jacuzzi bath and spacious interiors
- Off-road parking for two cars
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Visitor Rating
4.3
Visitor Rating
4.9
- Stunning sea views to Portland
- Sleeps 7 in 3 bedrooms
- Garage parking space included
- 2 minutes walk to beach
- Dog-friendly with secure garden
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Visitor Rating
4.9
- Stunning sea views from bedrooms
- Just 2 minutes to beach
- Sleeps 7 across 3 bedrooms
- Secure garage parking space
- Shared garden for groups
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Visitor Rating
4.8
- Sleeps nine across four bedrooms
- Three bathrooms including ground floor
- Enclosed garden with patio furniture
- Off-road parking for two cars
- Walking distance to Weymouth Beach
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- Victorian elegance sleeps 8
- Kitchen with Aga dining 9
- Parking for 4 cars
- Play area with toys
- Rural estate location
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- Victorian elegance with modern comfort
- Four bedrooms sleeping eight guests
- Large courtyard with BBQ facilities
- Parking for four cars included
- Two miles from historic Dorchester
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- Two Palladian houses sleeping 19
- 8 bedrooms with 6 bathrooms
- Jurassic Coast 10 minutes drive
- Lift access and play area
- Came Estate countryside location
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- Sleeps 15 across seven bedrooms
- Six bathrooms prevent morning queues
- Kitchen table seats 14 people
- Ground floor bedroom and facilities
- Blue Flag beach 0.3 miles
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Visitor Rating
4.5
- Sleeps 9 across 4 bedrooms
- 3 minutes walk to beach
- HD TVs in every bedroom
- Enclosed garden with storage
- Two car parking permits
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Visitor Rating
5
- Six themed bedrooms sleeping twelve
- Games room with Xbox entertainment
- Enclosed garden with astro turf
- Just 0.1 miles from beach
- Walking distance to major attractions
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Visitor Rating
4.8
- Sleeps 12 across six bedrooms
- Seven bathrooms including ensuites
- Five minutes walk to beach
- Contemporary kitchen with high-spec appliances
- Ground floor bedroom for accessibility
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Visitor Rating
4.9
- Direct seafront location
- Multiple group bedrooms
- Spacious living areas
- Georgian period features
- Walking distance harbour
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Visitor Rating
4
- Five bedrooms sleeping nine
- Beach just 0.3 miles away
- Enclosed garden with patio
- Pet friendly for dogs
- Central Weymouth location
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- Sleeps six across four bedrooms
- Private parking for two cars
- Enclosed garden with BBQ facilities
- Half mile walk to beach
- Pet-friendly welcomes two dogs
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Visitor Rating
4.6
- Sleeps 15 with private hot tub
- Games room with Xbox and football
- Three bathrooms and six bedrooms
- Private parking for three cars
- Half mile walk to beach
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Visitor Rating
4.9
- Five bedrooms sleeping eight
- Central Weymouth location
- Off-road parking for two
- Small gym facility
- Beach 0.6 miles away
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Visitor Rating
4.7
- Sleeps 8 with Lyme Bay views
- Half-acre south-facing landscaped grounds
- Glass-fronted garden room extension
- Four bedrooms with three bathrooms
- Four miles from Bridport beaches
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Visitor Rating
4.8
- Indoor swimming pool facility
- Games room with entertainment
- Five en-suite bedrooms available
- Enclosed garden with BBQ
- Near Jurassic Coast beaches
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- Grade II-listed thatched cottage
- Sleeps eight across four bedrooms
- Enclosed garden with summer house
- Traditional AGA in equipped kitchen
- Two miles from coastal paths
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Visitor Rating
3.9
- Spacious group lodge accommodation
- Multiple vehicle parking spaces available
- Minutes from Weymouth sandy beaches
- Open plan living areas
- Close to Portland Bill Lighthouse
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Visitor Rating
3.7
- Direct beachfront Georgian house
- Five en-suite bedrooms available
- Spectacular sea views throughout
- Sleeps ten guests comfortably
- Prime Weymouth seafront location
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- Beachfront location with sea views
- Sleeps 8 adults in 3 bedrooms
- Three bathrooms including two en-suites
- Walking distance to bars and restaurants
- Large Smart TV and games room
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- Group-friendly cottage layout
- Weymouth Beach 2 miles
- Jurassic Coast location
- Well-equipped kitchen facilities
- Multiple bedrooms available
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Visitor Rating
4.5
- Seafront location with sea views
- Five bedrooms sleeping ten guests
- Two cosy woodburning stoves
- Pet-friendly for two dogs
- Walking distance to attractions
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Visitor Rating
4.3
- Seconds from Old Harbour
- Modern kitchen dining area
- Two parking permits included
- Five minute beach walk
- Four bedrooms sleep seven
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Visitor Rating
4.7
- Minutes from beach and harbour
- Three bedrooms sleeping seven guests
- Open-plan living and dining area
- Recently added en-suite bathroom
- Central Weymouth town centre location
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