Weekend Breaks in Weymouth

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British Travel Award Winners!

We are delighted to announce that we have been awarded 'Best UK Holiday Cottage/Self Catering Booking Company' at the British Travel Awards.

Weekend Breaks in Weymouth

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Your Weymouth, Dorset search returned 309 cottages

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Map View
Front exterior of a house with a black door two potted plants and pink flowers in a garden at 6 The Terrace Brewers Quay Harbour
42
Brewers Quay Harbour, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0★

    Perfect

  • Sykes rating

A boutique, two-bedroom property situated in Brewers Quay Harbour, Weymouth, Dorset. Quality finish. Sea and harbour views. Enclosed garden. Raised elevation. Dorchester 8.5 miles; West Lulworth 15.5 miles. (Ref. 1096352)

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

3 nights from £903

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A brick end terrace house with a white door and windows and a paved driveway at The Nightingale in Weymouth
33
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

The Nightingale is a stylish, semi-detached holiday home resting in Weymouth, Dorset. Designated parking. Close to a beach and amenities. Enclosed garden. Dorchester 8.8 miles; Bridport 19.6 miles. (Ref. 1133998)

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

3 nights from £502

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A row of colorful terraced houses with blue cream pink and white facades on a cobblestone street at Harbour Tales in Weymouth
38
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

A beautiful terraced fisherman’s cottage resting in the coastal town of Weymouth, Dorset. Close to a beach. Close to a pub. TV. Dorchester 8.4 miles; West Bay 18.1 miles, Lyme Regis 32.6 miles. (Ref. 1133009)

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

3 nights from £492

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A dining room with a table set for dinner at Otter Cottage in Weymouth
23
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsYes

    5.0★

    Perfect

  • Sykes rating

A boutique, period home moments from Weymouth's iconic harbour. Dorchester 8.3 miles; Bridport 18.9 miles (Ref. 1177943)

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

3 nights from £511

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A two-story house with a pitched roof on Hillcrest Road with a 20 mph zone sign and plants in Wyke Regis
46
Wyke Regis, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

A fabulous three-bedroom holiday home in Wyke Regis, Dorset. Pet-friendly. Sea views. Close to beach and amenities. Open-plan. Contemporary. Weymouth 2.2 miles; Dorchester 9.6 miles. (Ref. 1103441)

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

3 nights from £691

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A window looking out onto a harbor with fishing boats and buildings at Embassy Brewers Quay Harbour
42
Brewers Quay Harbour, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

A beautiful, second-floor apartment overlooking the harbour in Weymouth, Dorset. Romantic. Sea views. Close to beach. Close to local amenities. Dorchester 8.3 miles; Bridport 19.1 miles. (Ref. 1107011)

  • Wi-fi
  • Dishwasher
  • Washing machine

3 nights from £436

Last booked yesterday
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A garden with grass a wooden deck with a swing and a patio with chairs and a table at Blue Waters in Weymouth
25
Weymouth, Dorset, DT3
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

A delightful, one-bedroom holiday home resting in Weymouth, Dorset. Contemporary. Private garden. Romantic. Close to amenities and beach. Near AONB. Open-plan. Dorchester 7 miles; Bridport 20.8 miles. (Ref. 1133982)

  • Wi-fi
  • Off-road parking

3 nights from £480

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A living room with a grey sofa with colorful cushions a glass coffee table and a fireplace at Ocean Retreat in Weymouth
14
Weymouth, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

A stylish and contemporary apartment set in the town of Weymouth, Dorset. Seaside setting. Fantastic views. Off-road parking. Fortuneswell 5.8 miles; Dorchester 7.2 miles; Bridport 20.9 miles. (Ref. 1072234)

  • Wi-fi
  • Dishwasher
  • Washing machine

3 nights from £631

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A brick house exterior with white framed windows a door a mailbox and a small outdoor table with a bench at Goliath in Brewers Quay Harbour
24
Brewers Quay Harbour, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

Beautiful 1 bedroom stable conversion in the heart of the harbour area in Weymouth. WIFI, Close to town centre and beach. Parking for one car. (Ref. 1096825)

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

3 nights from £480

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A wooden front door next to a window with shutters and a gray mailbox numbered 20 at Smugglers Cottage in Weymouth
27
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

A contemporary, three-storey property resting by the harbour in Weymouth, Dorset. Gas Fire in Lounge, WiFi. Close to beach and amenities. Weymouth 1 mile; Dorchester 8.6 miles. (Ref. 1058500)

  • Wi-fi
  • Dishwasher
  • Washing machine

3 nights from £627

Last booked yesterday
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A corner seating area with two black armchairs near bay windows and a side table with a lamp at Two @ No36 in Weymouth
31
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

Two @ No36, a wonderful, first-floor apartment situated in the heart of Weymouth in Dorset, with the beach on your doorstep. Dorchester 7.8 miles; Bridport 19.1 miles. (Ref. 1162203)

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

3 nights from £499

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Two armchairs with striped cushions by bay windows overlooking a beach at Three @ No36 in Weymouth
34
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6★

    Outstanding

  • Sykes rating

Three @ No36, a delightful, second-floor apartment situated in the town of Weymouth in Dorset, enjoying sea views with the beach on your doorstep. Smart TV. Dorchester 7.8 miles; Bridport 19.1 miles. (Ref. 1162204)

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

3 nights from £486

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A row of brick terraced houses with bay windows and plants in front on a street at Seaside House in Weymouth
46
Weymouth, Dorset, DT4
  • Sleeps12
  • Bedrooms6
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

Elegant end of terrace Georgian Townhouse located in Weymouth. Close to amenities. Off-road parking. Pet-free. Courtyard with furniture. Dorchester 7.2 miles; Bridport 20.5 miles. (Ref. 1071940)

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

3 nights from £1180

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Boats docked in a harbor in front of buildings including Old Coastguard Apartment 2 in Weymouth
30
Weymouth, Dorset, DT4
  • Sleeps8
  • Bedrooms3
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

On Weymouth Harbourside this is an extraordinarily spacious apartment, sleeps 8, tastefully renovated, Large en-suite showers to all rooms, harbour views, WiFi. (Ref. 994463)

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

3 nights from £978

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A small blue house with patio furniture and potted plants on a tiled patio at Outlook Lodge in Bowleaze
28
Bowleaze, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0★

    Perfect

  • Sykes rating

A lodge sleeping four people, Bowleaze area of Weymouth. Dog friendly. Large garden. Parking for two cars. (Ref. 994500)

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

3 nights from £641

Last booked yesterday
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A stone cottage with a white door and windows a wooden gate and gravel driveway at Little Brook in Nottington near Weymouth
26
Nottington near Weymouth, Dorset, DT3
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

A quaint stone-built cottage resting on the outskirts of Weymouth. Open-plan living. Off-road parking. WiFi. Dorchester 6.4 miles; Fortuneswell 8.2 miles. (Ref. 1061544)

  • Wi-fi
  • Off-road parking
  • Electric vehicle charging
  • Ground floor bedroom
  • Washing machine

3 nights from £524

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A two-story brick house with a white entrance porch and cobblestone driveway at The Chocolate Box in Weymouth
37
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

A lovely three-storey house resting in Weymouth, Dorset. Dog-friendly. Near a beach. Off-road parking. Private garden. Dorchester 8.7 miles; Bridport 19.1 miles. (Ref. 1092302)

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

3 nights from £671

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An exterior view of Wren Cottage in Weymouth
16
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

An inviting, mid-terrace house perched on the coast in Weymouth, Dorset. Sea views. Off-road parking. Near the beach. Dorchester 10.2 miles; Bridport 18.8 miles. (Ref. 1082718)

  • Wi-fi
  • Washing machine
  • Baby-friendly

3 nights from £360

Last booked yesterday
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A brick exterior of a cottage with white doors and windows at Rupert Cottage Brewers Quay harbour
27
Brewers Quay harbour, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7★

    Outstanding

  • Sykes rating

Sleeping 4 cosy cottage in Weymouth. Close to harbour and all amenities. Gated development. (Ref. 994605)

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

3 nights from £594

Last booked yesterday
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A brick building with multiple bay windows and doors along a street at The BoBo House in Weymouth
56
Weymouth, Dorset, DT4
  • Sleeps12
  • Bedrooms6
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

The BoBo House is a delightful terraced holiday home resting in the popular coastal town of Weymouth in Dorset set over four floors and near the beach. Dorchester 7 miles; Bridport 17 miles. (Ref. 1059621)

  • Wi-fi
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Games room

3 nights from £917

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Map View

A weekend break in Weymouth is the perfect idea! Look forward to strolling along the iconic Esplanade, enjoying fresh seafood by the harbour and visiting the beautiful Weymouth Harbour with its colourful boats.  

A short break in Weymouth promises relaxation, adventure, and lasting memories; book today! 

Why a Weymouth Short Break? 

Weymouth makes for an ideal destination for a short break, thanks to the picturesque town’s beautiful sandy beaches, where you can enjoy a relaxing day by the sea and soak up the sun.  

The town also boasts a lively waterfront with charming cafés, restaurants, and pubs, where you can enjoy some fresh local seafood and stunning views.  

A little out of town, you can head along the Jurassic Coast, a UNESCO World Heritage site that showcases stunning views, several great walking trails, and even opportunities for fossil hunting.  

A short break in Weymouth is the perfect place to escape for a refreshing getaway by the coast. For other things to do, take a look at our Dorset travel guide. 

Places to Visit Near Short Breaks in Weymouth 

Short breaks in Weymouth allow you the option to explore several nearby destinations that are well worth a visit during your getaway.  

Just a short distance from Weymouth, the Isle of Portland is a must-visit, known for its rugged coastline and stunning views as well as the historic Portland Castle. The island also offers the beautiful Portland Cove, which is an ideal spot for birdwatching. 

A visit to Lulworth Cove and Durdle Door is a must during your weekend break in Weymouth. Marvel at the iconic limestone arch and take in some of the most picturesque coastal views in the UK. 

With these nearby gems close by, your Weymouth short break can easily turn into an exploration of the wider Dorset coast. 

Unveil more top spots for your Weymouth short break: 

Bournemouth 

Corfe Castle 

Dorchester 

Poole 

Swanage 

West Bay 

Types of Weymouth Holidays 

Secure your break to the coast today with a short break in Weymouth! 

If you want to take your dog with you, then head along to one of these dog-friendly cottages in Weymouth. Or, if you are looking for a quick getaway, head along on a last-minute break in Weymouth. To find the right property at the best price, see cheap cottages in Weymouth.  

If you still haven’t found what you’re looking for, view the full collection of Weymouth cottages or these other short breaks in Dorset.