Vacation Rentals & Cottages in Castletown

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676 Houses

21

OLYMPIC COTTAGE, Sleep 4, Original olympic althlete house, WiFi, Contemporary ho

Isle of Portland / Castletown

Castletown cottage

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$88

Price per night from

$88

29

JURASSIC COAST HOUSE, Sleep 8, modern olympic athletes house, Close to Chesil be

Isle of Portland / Castletown

Castletown cottage

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Child Friendly
  • Pet Friendly
  • Private garden

Price per night from

$143

Price per night from

$143

23

THE VIEW, beautiful sea views, sleeps 6, Walk to chesil beach, Portland.

Isle of Portland / Castletown

Castletown cottage

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min

Price per night from

$115

Price per night from

$115

30

UNICORN, cute cottage, sleeps 4, sea glimpses, cottage garden, Portland

Isle of Portland / Castletown

Castletown cottage

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$81

Price per night from

$81

27

THE PALMS, sleep 4 bungalow, pet friendly, close to amenities, 2 miles to Portla

Isle of Portland / Castletown

Castletown cottage

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Child Friendly
  • Pet Friendly
  • Private garden

Price per night from

$76

Price per night from

$76

28

LANGHAM COTTAGE, Terraced cottage with sea views, Sleeps 4, Log Burner, WiFi, Po

Isle of Portland / Castletown

Castletown cottage

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$78

Price per night from

$78

19

ST JOHNS VIEW, contemporary house, sleeps 4, off road parking, Wifi, Portland

Isle of Portland / Castletown

Castletown cottage

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min

Price per night from

$81

Price per night from

$81

20

NEPTUNE COTTAGE, Sleeps 5, tradtional Portland Cottage, Pet friendly, WiFi, Port

Isle of Portland / Castletown

Castletown cottage

3 5 3 nights min

  • 3 bedrooms
  • sleeps 5
  • 3 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$84

Price per night from

$84

32

AMMONITE COTTAGE, WiFi, two bedrooms, courtyard on Isle of Portland.

Isle of Portland / Castletown

Castletown cottage

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Child Friendly

Price per night from

$78

Price per night from

$78

33

OSPREY HOUSE, contemporary house, sleeps 7, Rooftop balcony with views, WiFi, Po

Isle of Portland / Castletown

Castletown cottage

4 7 3 nights min

  • 4 bedrooms
  • sleeps 7
  • 3 nights min
  • Child Friendly

Price per night from

$109

Price per night from

$109

24

PITT HAYES COTTAGE, Breath taking views, sleeps 8, open plan living, Portland

Isle of Portland / Castletown

Castletown cottage

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$119

Price per night from

$119

27

SUNSET LODGE, modern apartment, sleeps 6, sea views, WiFi, Portland

Isle of Portland / Castletown

Castletown cottage

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Child Friendly

Price per night from

$93

Price per night from

$93

33

THE OLD PORTLAND COURTHOUSE, sleeps 8, historic building, four poster bed, Portl

Isle of Portland / Castletown

Castletown cottage

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min

Price per night from

$179

Price per night from

$179

19

BOWMAN'S COTTAGE, Traditional stone cottage, sleeps 4, close to walks, Portland

Isle of Portland / Castletown

Castletown cottage

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Private garden

Price per night from

$76

Price per night from

$76

28

QUARRY TRAILS, Sleeps 5, Close to coast walks, WiFi, Parking, Portland

Isle of Portland / Castletown

Castletown cottage

3 5 3 nights min

  • 3 bedrooms
  • sleeps 5
  • 3 nights min
  • Child Friendly

Price per night from

$93

Price per night from

$93

Great rentals within 20 miles that match your search

Distance approx 6.26 km from Castletown Show on Map

16

APPLETREE COTTAGE, pretty cottage in Dorset AONB, Osmington

Dorset / Osmington Mills

Osmington Mills cottage

1 3 3 nights min

  • 1 bedroom
  • sleeps 3
  • 3 nights min
  • Pet Friendly

Price per night from

$46

Price per night from

$46

Distance approx 14.43 km from Castletown

(7) Very Good 

16

Cogden cottages - Ketch Cottage

Bridport / Burton Bradstock

Burton Bradstock apartment

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Child Friendly
  • Private garden

Price per night from

$95

Responds fast!
avg. 2 hours 26 minutes

Price per night from

$95

Distance approx 10.14 km from Castletown

(1) Excellent 

9

Top Parts Bed and Breakfast.

Weymouth / Abbotsbury

Abbotsbury b and b

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 3 mi
  • Child Friendly

Price per night from

$249

Price per night from

$249

Distance approx 3.96 km from Castletown Show on Map

19

WEYMOUTH BAY APARTMENT C, Second floor, Sea views, parking, close to town, Weymo

Dorset / Weymouth

Weymouth cottage

3 7 3 nights min

  • 3 bedrooms
  • sleeps 7
  • 3 nights min
  • Child Friendly
  • Pet Friendly
  • Private garden

Price per night from

$88

Price per night from

$88

Distance approx 18.04 km from Castletown

27

TAVERN WAY, Stone Cottage, sleeps 4, centre village location, parking, Corfe Cas

Isle of Purbeck / Corfe Castle

Corfe Castle cottage

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Pet Friendly
  • Private garden

Price per night from

$81

Price per night from

$81

Distance approx 15.3 km from Castletown

22

POPPA'S COTTAGE, thatched cottage, perfect couple retreat, village location, Bur

Bridport / Burton Bradstock

Burton Bradstock cottage

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Pet Friendly
  • Private garden

Price per night from

$67

Price per night from

$67

Distance approx 2.79 km from Castletown Show on Map

34

HARBOURSIDE HOUSE, sleeps 8, Harbour views, stylish interior, close to beach, We

Dorset / Weymouth

Weymouth cottage

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Child Friendly

Price per night from

$202

Price per night from

$202

Distance approx 5.73 km from Castletown Show on Map

10

OCEANA, semi-detached, pet-friendly, garden, WiFi, nr Weymouth, Ref 932957

Dorset / Osmington Mills

Osmington Mills house

3 5 3 nights min

  • 3 bedrooms
  • sleeps 5
  • 3 nights min
  • Child Friendly
  • Pet Friendly
  • Private garden

Price per night from

$62

Price per night from

$62

Distance approx 19.47 km from Castletown

12

Cottage set in the middle of beautiful Dorst countryside with secure garden.

Dorset / Dorchester

Dorchester cottage

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$128

Price per night from

$128

Distance approx 3.27 km from Castletown Show on Map

(7) Excellent 

Certificate of Excellence

12

Bittern House

Dorset / Weymouth

Weymouth house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Nearest beach 0.8 mi
  • Child Friendly
  • Private garden

Certificate of Excellence

Price per night from

$83

Responds fast!
avg. 44 minutes

Price per night from

$83

Distance approx 6.9 km from Castletown Show on Map

15

Sycamores Cottage

Weymouth / Abbotsbury

Abbotsbury cottage

2 5 7 nights min

  • 2 bedrooms
  • sleeps 5
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 5 mi
  • Child Friendly

Price per night from

$110

Price per night from

$110

Distance approx 12.42 km from Castletown

(25) Excellent 

35

Tincleton Lodge

Dorchester / Tincleton

Tincleton cottage

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 16 mi
  • Child Friendly

Price per night from

$363

Responds fast!
avg. 3 hours 22 minutes

Price per night from

$363

Distance approx 6.83 km from Castletown Show on Map

(1) Very Good 

10

3 Lower Farm Cottage

Dorset / Weymouth

Weymouth cottage

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 5 mi
  • Child Friendly

Price per night from

$128

Responds fast!
avg. 2 hours 47 minutes

Price per night from

$128

Distance approx 17.77 km from Castletown

(1) Very Good 

11

Twine Cottage - Bridport, West bay

Bridport / West Bay

West Bay cottage

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child Friendly
  • Pet Friendly

Price per night from

$140

Price per night from

$140

Distance approx 18.69 km from Castletown

(8) Excellent 

17

Great Coombe, Bookham Court

Dorset / Cerne Abbas

Cerne Abbas cottage

4 9 min stay varies

  • 4 bedrooms
  • sleeps 9
  • min stay varies
  • Nearest beach 30 mi
  • Child Friendly
  • Pet Friendly

Price per night from

$135

Responds fast!
avg. 1 hour 37 minutes

Price per night from

$135

Distance approx 1.77 km from Castletown Show on Map

20

Fleet Retreat over looking Portland, Chesil Beach and the Fleet Lagoon

Dorset / Weymouth

Weymouth caravan/mobile home

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly

Price per night from

$128

Price per night from

$128

Distance approx 3.84 km from Castletown Show on Map

(3) Excellent 

10

Tidmoor Farmhouse B&B 1

Weymouth / Chickerell

Chickerell b and b

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Nearest beach 4 mi
  • Car not necessary
  • Private garden

Price per night from

$96

Price per night from

$96

Distance approx 18.66 km from Castletown

(36) Excellent 

34

Bluebell Cottage at Binghams Farm Barns

Bridport / Melplash

Melplash cottage

3 5 min stay varies

  • 3 bedrooms
  • sleeps 5
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 6 mi
  • Child Friendly

Price per night from

$105

Responds fast!
avg. 3 hours 15 minutes

Price per night from

$105

Distance approx 12.75 km from Castletown

(10) Very Good 

Certificate of Excellence

20

Dorset Cottage near coast (Puncknowle, Dorchester)

Dorset / Puncknowle

Puncknowle house

4 9 min stay varies

  • 4 bedrooms
  • sleeps 9
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 mi
  • Child Friendly

Certificate of Excellence

Price per night from

$128

Price per night from

$128

Distance approx 3.25 km from Castletown Show on Map

(12) Very Good 

21

Privately owned 3 bed.Brand new 2017 model on 5* haven site in Dorset.

Weymouth / Chickerell

Chickerell caravan/mobile home

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool

Price per night from

$83

Responds fast!
avg. 2 hours 45 minutes

Price per night from

$83

Distance approx 6.13 km from Castletown Show on Map

(14) Excellent 

18

Dorset period cottage sleeps 6

Dorset / Osmington Mills

Osmington Mills house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 2 mi
  • Child Friendly
  • Pet Friendly

Price per night from

$128

Responds fast!
avg. 2 hours 15 minutes

Price per night from

$128

Distance approx 8.9 km from Castletown

(16) Very Good 

15

Stable Cottage near Lulworth Cove

Dorchester / East Chaldon

East Chaldon cottage

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
  • Pet Friendly

Price per night from

$121

Price per night from

$121

Distance approx 5.71 km from Castletown Show on Map

(3) Excellent 

9

Church View, Family Friendly Holiday Home In Dorset

Dorset / Weymouth

Weymouth house

3 4 7 nights min

  • 3 bedrooms
  • sleeps 4
  • 7 nights min
  • Nearest beach 2 mi
  • Child Friendly
  • Pet Friendly

Price per night from

$78

Responds fast!
avg. 3 hours 25 minutes

Price per night from

$78