50 Best Weymouth cottages, homes and apartments - Holiday Lettings - Holiday rentals

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  • Abbotsbury (5)
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  • Upwey (5)
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32 Holiday homes

Filters applied: BBQ (32) Under 5s (32) Clear all

(22) Excellent 

29

Lilystone cottage - Weymouth cottage sleeps 6

Dorset / Weymouth

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Private garden
This Cottage is in a very central location of Weymouth only a short walk to the beach and radipole lake nature reserve, it's also a very short walk to the town centre and beautiful harbour, where you can sit and enjoy a drink at one of the local bars over looking the h  …see more

from £80 / night

£600 - £850 / week

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from £80 / night

(16) Very Good 

21

Summer Lodge - Weymouth house sleeps 10

Dorset / Weymouth

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 4 km
  • Swimming pool
Summer Lodge is located a short car ride from Weymouths safe, sandy, lifguarded, beach complete with many restaurants and family attractions. Portland, Chesil Beach, West Bay, Lulworth cove,Corfe Castle, and Swanage are a few places in the surounding area.Summer lodge  …see more

from £332 / night

£1490 - £3300 / week

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from £332 / night

(21) Very Good 

13

Moonfleet Holiday Cottage - Wyke Regis cottage sleeps 5

Weymouth / Wyke Regis

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly
Moonfleet is a two bedroom cottage located on the edge of Portland Harbour; the waters that hosted the 2012 Olmpic Sailing. Presented to a high standard this accommodation sleeps 5, with two double bedrooms (one with a double and single bed) a spacious lounge/diner and  …see more

from £55 / night

£350 - £810 / week

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from £55 / night

(8) Excellent 

17

Laurel Cottage - Sutton Poyntz cottage sleeps 8

Weymouth / Sutton Poyntz

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Pet friendly
Laurel Cottage is a charming 300 year old thatched cottage in the heart of the peaceful village of Sutton Poyntz on the outskirts of the seaside resort town of Weymouth. The interior has been refurbished to a high standard combining a modern kitchen and bathrooms with  …see more

from £150 / night

£990 - £1490 / week

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from £150 / night

(1) Excellent 

12

The Brambles - Upwey cottage sleeps 2

Weymouth / Upwey

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly
The Brambles is a delightful 1 bedroom holiday cottage furnished with lone travellers, couples and pairs in mind. Situated just off the stunning Chesil Beach in the small, tranquil village of Langton Herring near Weymouth, it is one of seven family run farm holiday co  …see more

from £70 / night

£330 - £550 / week

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from £70 / night

(17) Excellent 

13

'THE NEST' HOLIDAY HOME CHICKERELL DORSET WEYMOUTH - Chickerell bungalow sleeps 4

Weymouth / Chickerell

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 4 km
  • Child friendly
The Nest Holiday Annexe is nestled quietly behind the owner's 200 year old cottage, with its own patio, beautiful planted garden with Bbq area & has an amazing Day Bed for lounging in the sunshine.The property is on one level, with Double Bedroom, shower room/toilet, ki  …see more

from £65 / night

£400 - £675 / week

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from £65 / night

(3) Excellent 

11

The Grain Store, Wears Farm, Abbotsbury - Abbotsbury barn sleeps 6

Weymouth / Abbotsbury

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 3 km
  • Child friendly
  • Pet friendly
Wears Farm holiday cottages (The Stables, The Grain Store & The Cow Byre) sit in the hills above the beautiful village of Abbotsbury; comprising three individual holiday homes with spectacular views across the Dorset countryside. Take a short walk from the cottages up o  …see more

from £72 / night

£500 - £1400 / week

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from £72 / night

(4) Excellent 

11

The Stables, Wears Farm, Abbotsbury - Abbotsbury barn sleeps 8

Weymouth / Abbotsbury

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 3 km
  • Child friendly
  • Pet friendly
Wears Farm holiday cottages (The Stables, The Grain Store & The Cow Byre) are nestled in the hills above the beautiful village of Abbotsbury; comprising three individual holiday homes with spectacular views across the Dorset countryside. Take a short walk from the cotta  …see more

from £300 / night

£695 - £2000 / week

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from £300 / night

(17) Very Good 

21

Upwey Cottage - Weymouth - Upwey cottage sleeps 4

Weymouth / Upwey

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 4 km
  • Child friendly
This cosy two bedroom cottage has its own sunny garden with garden loungers, table and chairs and BBQ. The quiet cottage is within easy reach of the beach and country walks. Set down a lane off the main link between the seaside town of Weymouth and Dorchester. Enjoy  …see more

from £110 / night

£320 - £590 / week

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from £110 / night

(1) Very Good 

10

3 Lower Farm Cottage - Weymouth cottage sleeps 5

Dorset / Weymouth

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Child friendly
3 Lower Farm is a 2 bed room stone cottage situated on our working dairy farm between Weymouth and Abbotsbury, a short distance from Dorset's stunning Chesil Beach and Jurassic coast. It is full of character features such as wooden beams and an inglenook fireplace  …see more

from £85 / night

£380 - £750 / week

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from £85 / night

(13) Very Good 

24

Number Six - Greenhill house sleeps 12

Weymouth / Greenhill

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.8 km
  • Child friendly
1920s townhouse sleeping 12. Ten minutes walk from the beach in a very desirable residential area, next to Greenhill's beautiful sea front gardens. Number 6 is a recently refurbished large house, well equipped for family holidays. The house is located right next to t  …see more

from £275 / night

£1000 - £2550 / week

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from £275 / night

(10) Very Good 

20

Les Goelands [The Seagulls] - Greenhill house sleeps 8

Weymouth / Greenhill

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly
Victorian terraced Villa - 4 bedrooms – 2 minutes seafront, 5 minutes town, pubs, restaurants, railway station. On road parking permits for two cars.2 double bedrooms, 1 bunkbedded room (only suitable for kids or teenagers as no wardrobe or cupboards in this small ro  …see more

from £200 / night

£1200 - £1510 / week

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from £200 / night

(2) Excellent 

10

Pelham Cottage - Nottington cottage sleeps 4

Weymouth / Nottington

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 4 km
  • Child friendly
Pet friendly Pelham Cottage features a shiny kitchen next to the cozy living-room. The bathroom with bathtub is on the ground floor, too. Twin and double bedrooms are upstairs. You can bring up to two pets for an extra charge per pet per week. Pelham sleeps up to 4 and  …see more

from £54 / night

£300 - £840 / week

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from £54 / night

(9) Excellent 

57

Vitality Cottage - Upwey cottage sleeps 8

Weymouth / Upwey

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 4 km
  • Child friendly
Lovely quiet cottage situated in an elevated position on the old Roman Road out of Weymouth leading to Dorchester. Some views leading to Weymouth are accessible from the outdoor elevated sun terrace. The Ridge way is no longer a through road and apart from the 16th cen  …see more

from £179 / night

£899 - £1599 / week

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from £179 / night

(5) Excellent 

24

Hazel Copse Cottage - Langton Herring cottage sleeps 4

Weymouth / Langton Herring

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 8 km
  • Child friendly
Hazel Copse Cottage is a spacious, light, comfortable barn conversion equipped with everything you'll need. Please Note: Arrival Days: Friday and Monday - minimum 3 night stay, in low season. Arrival Day: Friday - minimum 7 night stay in High Season. Located on th  …see more

from £129 / night

£581 - £850 / week

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from £129 / night

(1) Excellent 

39

Cobblestone House - Upwey cottage sleeps 8

Weymouth / Upwey

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Child friendly
Situated along a country lane on the edge of the picturesque village of Upwey, Cobblestone House has been skilfully refurbished by its current owners to offer highly desirable, family accommodation.Dating back to the 1500's, when it served as the Granary for the nearby  …see more

from £253 / night

£1012 - £2054 / week

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from £253 / night

(13) Excellent 

22

Smugglers Haunt (detached farmhouse) Weymouth - Wyke Regis farmhouse sleeps 10

Weymouth / Wyke Regis

6 10 Min stay varies

  • 6 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Ask about pets
  • Private garden
Smugglers Haunt is a detached grey stoned, characteristic farmhouse in Wyke Regis, part of bustling Weymouth. The property offers guests a comfortable stay with a contemporary feel, it is very well equipped providing a real 'home from home'. It has stand out a  …see more

from £185 / night

£1295 - £1775 / week

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from £185 / night

(5) Very Good 

19

Ishara Apartment - Weymouth apartment sleeps 8

Dorset / Weymouth

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly
Ishara Apartment is ideally situated within a few minutes walk to Weymouth Beach with shops, pubs, restaurants, coach and rail links and leisure facilities all nearbyIt is also a great place to base yourself to explore the Dorset coast or the Dorset countryside with Por  …see more

from £65 / night

£400 - £900 / week

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from £65 / night

(5) Very Good 

12

The Cow Byre, Wears Farm, Abbotsbury - Abbotsbury barn sleeps 6

Weymouth / Abbotsbury

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 3 km
  • Child friendly
  • Pet friendly
Wears Farm holiday cottages (The Stables, The Grain Store & The Cow Byre) sit in the hills above Abbotsbury; comprising three individual holiday homes with spectacular views across the Dorset countryside. Take a short walk from the cottages up onto the South Dorset Ridg  …see more

from £69 / night

£480 - £1350 / week

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from £69 / night

(4) Excellent 

15

Clayhanger Lodge, New Barn Road, Abbotsbury - Abbotsbury barn sleeps 6

Weymouth / Abbotsbury

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Child friendly
Clayhanger Lodge, set within farmland high above Chesil Beach, is a spacious and light, detached barn conversion enjoying spectacular views across lush green fields to the ocean beyond. Clayhanger Lodge provides luxury accommodation for six people in three large, comfor  …see more

from £105 / night

£730 - £1760 / week

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from £105 / night

(1) Excellent 

12

The Swallows - Upwey cottage sleeps 4

Weymouth / Upwey

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly
Described as 'absolute bliss' and 'wonderfully peaceful' by some of our previous guests, The Swallows offers true tranquillity near the village of Abbotsbury, a short drive from the seaside town of Weymouth and the picturesque Jurassic Coast. We have  …see more

from £85 / night

£380 - £750 / week

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from £85 / night

(6) Very Good 

19

Castle Cove View: private access to sandy beach - Weymouth cottage sleeps 6

Dorset / Weymouth

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly
With sea views towards Portland and private access to sandy Castle Cove beach, Castle Cove View provides high quality modern accommodation perfect for family holidays or romantic getaways.  A downstairs shower room (including WC and basin) is ideal for washing down san  …see more

from £110 / night

£400 - £1150 / week

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from £110 / night

15

Sycamores Cottage - Abbotsbury cottage sleeps 5

Weymouth / Abbotsbury

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Child friendly
Described by previous guests as a 'lovely olde world cottage' perfect for a nice, relaxing break, Sycamores Cottage stands a short walk from the beauty of the Dorset coast.  It sleeps up to five people in 2 bedrooms and it's ideal for a family with a few  …see more

from £86 / night

£600 / week

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from £86 / night

(3) Very Good 

11

Snaffles Cottage - Nottington cottage sleeps 4

Weymouth / Nottington

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly
This cozy country cottage features a pet friendly policy but serves well for non-pet holders, too. Snaffles has an upstairs double bedroom and bathroom with a showerbath. On the ground floor the new kitchen and the twin bedroom is accessible through the classic lounge.  …see more

from £54 / night

£300 - £840 / week

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from £54 / night

(2) Excellent 

21

Orchard View Cottage - Langton Herring barn sleeps 4

Weymouth / Langton Herring

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 8 km
  • Child friendly
Orchard View is a spacious, light, comfortable property equipped with everything you'll need. Please Note: Arrival Days: Friday and Monday - minimum 3 night stay, in low season. Arrival Day: Friday - minimum 7 night stay in High Season. Located on the edge of our wi  …see more

from £122 / night

£551 - £807 / week

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from £122 / night

(2) Very Good 

6

Holiday Cottage to rent Upwey - Weymouth - Broadwey cottage sleeps 7

Weymouth / Broadwey

4 7 3 nights min

  • 4 bedrooms
  • Sleeps 7
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 6 km
  • Child friendly
This home makes a very comfortable relaxing all year round base for exploring the surrounding area, with Weymouth's Georgian seafront and beach only a few miles away. Many walks can be taken locally, or along the nearby Jurassic coastline. Popular places to visit a  …see more

from £120 / night

£800 - £2200 / week

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from £120 / night

(13) Very Good 

22

Admiralty House - Greenhill townhouse sleeps 26

Weymouth / Greenhill

7 26 Min stay varies

  • 7 bedrooms
  • Sleeps 26
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.05 km
  • Child friendly
Weymouth has so much to offer. This seaside town has cinemas, a theatre, a Sea-Life centre, the restored fort, a swimming pool complex, a ten pin bowling alley. The list goes on. A trip to Weymouth wouldn't be complete without experiencing the Jurassic coastal walk  …see more

from £600 / night

£1300 - £3000 / week

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from £600 / night

(63) Excellent 

20

Pine Lodge - Warmwell log cabin sleeps 6

Weymouth / Warmwell

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Pine Lodge is in an excellent choice for families and well behavied pets. Close to Dorset's Juassic Coast and places of interest from Weymouth Beach to Ringstaed Bay - Monkey World to The Tank Museum and Sea Life Park to Colfe Castle.The larger supermarkets in the  …see more

from £60 / night

£439 - £1195 / week

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from £60 / night

17

Sycamores Cottage - Langton Herring cottage sleeps 5

Weymouth / Langton Herring

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Child friendly
Described by previous guests as a 'lovely olde world cottage' perfect for a nice, relaxing break, Sycamores Cottage is situated 5 miles to the west of Weymouth, a short walk from the stunning Chesil beach and Jurassic Coastline. It sleeps up to five people in 2 bedroo  …see more

from £85 / night

£410 - £750 / week

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from £85 / night

(2) Very Good 

28

Family Cottage Close to Beach Town Transport Links - Weymouth cottage sleeps 6

Dorset / Weymouth

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly
More photos to come currently being refurbished for 2016 Season An ideally situated terraced cottage located 400m from Weymouth Seafront. A 5 minute walk takes you to the beach and town with its shops, restaurants, coach and rail links and leisure facilities all nearby  …see more

from £65 / night

£400 - £900 / week

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from £65 / night

23

Stunning Barn Retreat near Weymouth and the beach - Weymouth barn sleeps 4

Dorset / Weymouth

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Child friendly
Nestled in the gentle rolling hills of the Dorset countryside sits the stunning Little Barn. Renovated to a very high standard with clean lines and a modern touch, Little Barn is a retreat from the stresses of modern life. With spacious living areas, under floor heating  …see more

from £175 / night

£1225 / week

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from £175 / night

(1) Very Good 

15

Cosy Victorian Cottage - Rodwell cottage sleeps 4

Weymouth / Rodwell

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Private garden
Well appointed cottage just 5 minutes from Weymouth harbour & town centre. Located in a quiet road with free parking & close to the supermarket or independent stores.Can sleep 5 people, fold up bed available on requestPrivate rear count yard, with BBQ & gard  …see more

from £79 / night

£550 / week

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from £79 / night

Top Destination reviews

Kimberwick Cottage
Wonderful area, accommodation and hosts

Andreas and Elizabeth are great hosts and the accommodation is perfect . There are two other cottages (we have stayed in all three; we keep coming back!) and I wouldn't hesitate to recommend Kimberwick, Pelham or Snaffles cottage to visitors. … see more
Weymouth Family Caravan
more like a holiday cottage

Been a long time since last caravan holiday and was not expecting such a lovely, well appointed holiday cottage. … see more
Number Six
Excellent holiday house for families

Our stay at Number Six was faultless. We had a wonderful welcome with a generous hamper, and were allowed into the property early as we had arrived well in advance of the agreed arrival time. The house is fabulous. From the ground floor layout, wi … see more
Seaview Self Catering
Excellent

Good Value, nice accommodation. Close to amenities and bus route to Weymouth. Would definately recommend. … see more
Tidmoor Barn
Fantastic place to stay

Top notch accomadation Sarah a lovely host fantastic holiday lovely view from the barn great to have secure parking a lovely place to stay a nice garden with great decking area to chill when weather good … see more
The Brambles
Cosy cottage with a blazing log fire.

We rented The Brambles over February half term and enjoyed its ambience greatly, especially the log fire. It's perfect for a couple. Open plan, nicely furnished and very peacefully situated. Abbotsbury is only four miles away on a scenically stunnin … see more

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