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

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11 Holiday homes

(10) Excellent 

57

Holiday cottage in Upwey

Weymouth / Upwey

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 4 km
  • Child friendly
“Shhhhhh! Dont tell anyone” This is a great place to stay in Dorset. You have the quiet setting of Upwey but with the local activities just down the road. The house was superb and enough for the 4 of us. The host , could not be more genuine and hone  …see more

from £179 / night

£899 - £1599 / week

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from £179 / night

(1) Excellent 

39

Holiday cottage in Upwey

Weymouth / Upwey

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Child friendly
Ssituated along a country lane on the edge of the picturesque village of Upwey, Cobblestone House has been skilfully refurbished to offer highly desirable, family accommodation.  …see more

from £253 / night

£1012 - £2054 / week

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from £253 / night

(13) Very Good 

24

West Country holiday home rental

Weymouth / Greenhill

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.8 km
  • Child friendly
“Wonderful house and location” When we arrived we were delighted by the airy and spacious accommodation. The dining room is bright and has a large table that the whole party (11 of us) could comfortably sit around. The kitchen is beautiful and has all  …see more

from £300 / night

£1000 - £2550 / week

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from £300 / night

(22) Excellent 

29

Cottage accommodation in West Country

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

(15) Excellent 

22

Holiday farmhouse rental

Weymouth / Wyke Regis

6 10 Min stay varies

  • 6 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Ask about pets
  • Private garden
“Great for families comfortable” We loved Dorset and the house proved to be a useful base. It was attractive although there were a few signs of damp in one of the bedrooms. we were surprised that it was in the middle of housing development but that did  …see more

from £185 / night

£1295 - £1775 / week

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from £185 / night

(1) Excellent 

12

Holiday cottage in Upwey

Weymouth / Upwey

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly
The Swallows is a 2 bedroom self catering cottage available for weekly lets or short breaks out of season. It is situated 5 miles from Weymouth just off the Fleet and Chesil beach and the Coastal Footpath literally runs past the cottage.  …see more

from £85 / night

£380 - £750 / week

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from £85 / night

(24) Very Good 

26

West Country holiday cottage rental

Weymouth / Langton Herring

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Private garden
Luxury cottage for 2 or possible 4 (cot also available)Dorset coastlineCosy cottagePeace and quietOpen log fireWarm and cosyRomantic hideawayHoneymoon WalkingJurassic coastlineDorset coastlineIf you want to unwind from a stressful lifestyle, the grooms cottage is the ri  …see more

from £120 / night

£450 - £850 / week

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from £120 / night

15

Cottage rental in Abbotsbury

Weymouth / Abbotsbury

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Child friendly
A charming 2 bedroom traditional Dorset cottage situated on a working dairy and beed farm, a short walk from Chesil Beach and an easy drive from Weymouth, surrounded by stunning country side.  …see more

from £86 / night

£600 / week

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from £86 / night

17

Holiday cottage in West Country

Weymouth / Langton Herring

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Child friendly
A charming 2 bedroom traditional Dorset cottage situated on a working dairy and beef farm, a short walk from Chesil Beach and an easy drive from Weymouth, surrounded by stunning country side ideal for walking.  …see more

from £85 / night

£410 - £750 / week

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from £85 / night

23

Barn rental in West Country

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

(2) Very Good 

28

Holiday cottage in West Country

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

Top Destination reviews

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
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
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
Fox Crossing Bed and Breakfast
Perfect

An absolutely perfect place to stay. Spotlessly clean. Excellent food. Home from home. Rosemary just could not do any more to make this any better. Thank you. … see more
Vitality Cottage
Lovely cottage in quiet village close to Dorchester and Weymouth

We stayed for a week with teenage daughters and an elderly parent, and had a wonderful time. Very quiet (apart from Saturday night when a private party at the nearby pub continued into the small hours). We ate twice in the pub, but otherwise cooked a … see more
Little Gem - Lovely Sea views
A Gem of a Holiday

We have just returned from a two week stay at Little Gem and have had a great time. The views were amazing, everything was just as advertised. And the bed was so comfortable. So much to see and do,we would love to come back again ,Thanks Jon. … see more