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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
Rating
4.7

The Grain Store

Less than a mile from Upwey
Hot Tub
Sleeps 7
Pets 1
Bedrooms: 4
  • 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
Rating
4.8

Fisherbridge Cottage

2 miles from Upwey
Hot Tub
Sleeps 7
Bedrooms: 4
  • 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
Rating
4.8

Sunningdale Rise

2 miles from Upwey
Hot Tub
Sleeps 8
Bedrooms: 4
  • 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
Rating
4.5

Family House

2 miles from Upwey
Hot Tub
Sleeps 12
Bedrooms: 6
  • 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
Rating
4.3

Greenwell

3 miles from Upwey
Hot Tub
Sleeps 8
Bedrooms: 4
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Visitor Rating
Rating
4.9

Weymouth Bay Apartment B

3 miles from Upwey
Hot Tub
Sleeps 7
Pets 1
Bedrooms: 3
  • 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
Rating
4.9

Weymouth Bay Apartment C

3 miles from Upwey
Hot Tub
Sleeps 7
Pets 1
Bedrooms: 3
  • 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
Rating
4.8

The White Cottage

3 miles from Upwey
Hot Tub
Sleeps 9
Pets 1
Bedrooms: 4
  • 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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The Garden House

3 miles from Upwey
Hot Tub
Sleeps 8
  • Victorian elegance sleeps 8
  • Kitchen with Aga dining 9
  • Parking for 4 cars
  • Play area with toys
  • Rural estate location
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The Courtyard House

3 miles from Upwey
Hot Tub
Sleeps 8
  • 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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Park House

3 miles from Upwey
Hot Tub
Sleeps 19
  • 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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Beachaven

3 miles from Upwey
Hot Tub
Sleeps 15
Bedrooms: 7
  • 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
Rating
4.5

15 Hardwick Street

3 miles from Upwey
Hot Tub
Sleeps 9
Pets 1
Bedrooms: 4
  • 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
Rating
5

The BoBo House

3 miles from Upwey
Hot Tub
Sleeps 12
Bedrooms: 6
  • 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
Rating
4.8

Seaside House

3 miles from Upwey
Hot Tub
Sleeps 12
Bedrooms: 6
  • 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
Rating
4.9

The Esplanade

3 miles from Upwey
Hot Tub
Sleeps 18
Bedrooms: 9
  • Direct seafront location
  • Multiple group bedrooms
  • Spacious living areas
  • Georgian period features
  • Walking distance harbour
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Visitor Rating
Rating
4

Weymouth Seaside House

3 miles from Upwey
Hot Tub
Sleeps 9
Pets 1
Bedrooms: 5
  • 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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Palm Gate

3 miles from Upwey
Hot Tub
Sleeps 6
Pets 1
Bedrooms: 4
  • 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
Rating
4.6

Anchor House

3 miles from Upwey
Hot Tub
Sleeps 15
Pets 1
Bedrooms: 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
Rating
4.9

Victorian Town House

4 miles from Upwey
Hot Tub
Sleeps 8
Pets 1
Bedrooms: 5
  • 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
Rating
4.7

Hardown House

4 miles from Upwey
Hot Tub
Sleeps 8
Pets 1
Bedrooms: 4
  • 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
Rating
4.8

Baytree Lodge

4 miles from Upwey
Hot Tub
Sleeps 12
Pets 1
Bedrooms: 5
  • 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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Old Post Office Cottage Osmington

4 miles from Upwey
Hot Tub
Sleeps 8
Pets 1
Bedrooms: 4
  • 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
Rating
3.9

Low Tide

4 miles from Upwey
Hot Tub
Sleeps 10
Bedrooms: 5
  • 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
Rating
3.7

High Tide

4 miles from Upwey
Hot Tub
Sleeps 10
Bedrooms: 5
  • 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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The Beach Condo

4 miles from Upwey
Hot Tub
Sleeps 8
Bedrooms: 3
  • 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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East Cottage

4 miles from Upwey
Hot Tub
Sleeps 8
  • Group-friendly cottage layout
  • Weymouth Beach 2 miles
  • Jurassic Coast location
  • Well-equipped kitchen facilities
  • Multiple bedrooms available
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Visitor Rating
Rating
4.5

Shore View

4 miles from Upwey
Hot Tub
Sleeps 10
Pets 1
Bedrooms: 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
Rating
4.3

New Boathouse

4 miles from Upwey
Hot Tub
Sleeps 7
Bedrooms: 4
  • 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
Rating
4.7

Globe Cottage

4 miles from Upwey
Hot Tub
Sleeps 7
Bedrooms: 3
  • 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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Unit 8, Dorset Business Park, Puddletown Road, Dorchester, Dorset, DT2 8QL