Castletown Vacation Rentals & Homes - 396 Rentals Available
396 Vacation rentals
The Old Council Chamber, Fortuneswell
Castletown Apartment
- 1 bedroom 1
- 1 bathroom
- sleeps 2 2
- 3 nights min
- Child friendly
- Pet friendly
$152.00
from $152.00 / night
AMMONITE COTTAGE, WiFi, two bedrooms, courtyard on Isle of Portland.
Castletown Cottage
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 3 nights min
$187.00
from $187.00 / night
SUNSET LODGE, modern apartment, sleeps 6, sea views, WiFi, Portland
Castletown Cottage
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 3 nights min
- Child friendly
$224.00
from $224.00 / night
JURASSIC COAST HOUSE, Sleep 8, modern olympic athletes house, Close to Chesil
Castletown Cottage
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- 3 nights min
- Child friendly
- Pet friendly
- Private garden
$342.00
from $342.00 / night
THE OLD PORTLAND COURTHOUSE, sleeps 8, historic building, four poster bed
Castletown Cottage
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- 3 nights min
- Private garden
$426.00
from $426.00 / night
UNICORN, cute cottage, sleeps 4, sea glimpses, cottage garden, Portland
Castletown Cottage
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 3 nights min
- Child friendly
- Pet friendly
- Private garden
$196.00
from $196.00 / night
OSPREY HOUSE, contemporary house, sleeps 7, Rooftop balcony with views, WiFi
Castletown Cottage
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- 3 nights min
- Child friendly
$259.00
from $259.00 / night
Panoramic View, Castletown, Portland
Castletown Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 3 nights min
$196.00
from $196.00 / night
Cove Cottage Hideaway, Chiswell On Portland
Castletown Cottage
- 1 bedroom 1
- 1 bathroom
- sleeps 2 2
- 3 nights min
- Private garden
$162.00
from $162.00 / night
ST JOHNS VIEW, contemporary house, sleeps 4, off road parking, Wifi, Portland
Castletown Cottage
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 3 nights min
- Child friendly
- Private garden
$178.00
from $178.00 / night
White Sails, Wyke Regis
Castletown Cottage
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 3 nights min
- Child friendly
- Private garden
$198.00
from $198.00 / night
BOWMAN'S COTTAGE, Traditional stone cottage, sleeps 4, close to walks, Portland
Castletown Cottage
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 3 nights min
- Private garden
$181.00
from $181.00 / night
LANGHAM COTTAGE, Terraced cottage with sea views, Sleeps 4, Log Burner, WiFi
Castletown Cottage
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 3 nights min
- Child friendly
- Pet friendly
$187.00
from $187.00 / night
Pitt Hayes Cottage, Fotrtuneswell
Castletown Cottage
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- 3 nights min
- Child friendly
- Pet friendly
$345.00
from $345.00 / night
Neptune Cottage, Fortuneswell
Castletown Cottage
- 3 bedrooms 3
- 2 bathrooms
- sleeps 5 5
- 3 nights min
- Child friendly
- Pet friendly
$202.00
from $202.00 / night
QUARRY TRAILS, Sleeps 5, Close to coast walks, WiFi, Parking, Portland
Castletown Cottage
- 3 bedrooms 3
- 2 bathrooms
- sleeps 5 5
- 3 nights min
- Child friendly
- Private garden
$224.00
from $224.00 / night
THE VIEW, beautiful sea views, sleeps 6, Walk to chesil beach, Portland.
Castletown Cottage
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 3 nights min
$275.00
from $275.00 / night
OLYMPIC COTTAGE, Sleep 4, Original olympic althlete house, WiFi, Contemporary
Castletown Cottage
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 3 nights min
- Child friendly
- Pet friendly
- Private garden
$212.00
from $212.00 / night
Telltales, Fortuneswell
Castletown Cottage
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 3 nights min
- Child friendly
- Pet friendly
- Private garden
$212.00
from $212.00 / night
Jurassica House, Fortuneswell
Castletown House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- 3 nights min
- Child friendly
- Pet friendly
- Private garden
$361.00
from $361.00 / night
Spring Rose Cottage, Fortuneswell
Castletown Cottage
- 3 bedrooms 3
- 1 bathroom
- sleeps 8 8
- 3 nights min
- Child friendly
- Pet friendly
- Private garden
$189.00
from $189.00 / night
Your search has been expanded 19 miles to include more rentals
WEYMOUTH BAY APARTMENT B, First floor, sleeps 7, Sea views, close to town
Weymouth Cottage - 4 miles away
- 3 bedrooms 3
- 1 bathroom
- sleeps 7 7
- 3 nights min
- Child friendly
- Pet friendly
- Private garden
$216.00
from $216.00 / night
Pennsylvania Castle, Wakeham, Portland
Weston Cottage - 2.1 miles away
- 9 bedrooms 9
- 11 bathrooms
- sleeps 20 20
- 3 nights min
- Swimming pool
- Child friendly
$2,652.00
from $2,652.00 / night
Casa Carmen, Weymouth
Weymouth House - 2.6 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 5 5
- 3 nights min
- Private garden
$239.00
from $239.00 / night
SEA-ESTA, All en-suites, WiFi, Electric fire, Weymouth
Weymouth Cottage - 3.6 miles away
- 12 bedrooms 12
- 6 bathrooms
- sleeps 12 12
- 3 nights min
- Child friendly
$420.00
from $420.00 / night
Castle View, Fortuneswell
Weymouth Cottage - 3.3 miles away
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 3 nights min
- Pet friendly
- Private garden
$197.00
from $197.00 / night
WOODLANDERS, Woodburner, Open-plan living, WiFi, Symondsbury
Chideock Cottage - 19 miles away
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 3 nights min
- Child friendly
- Private garden
$161.00
from $161.00 / night
Sailors Watch, Weymouth
Weymouth Cottage - 2.8 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 3 nights min
- Pet friendly
- Private garden
$255.00
from $255.00 / night
Chestnut Cottage, Puncknowle
Puncknowle Cottage - 12.8 miles away
- 3 bedrooms 3
- 1 bathroom
- sleeps 6 6
- 3 nights min
- Child friendly
- Pet friendly
- Private garden
$255.00
from $255.00 / night
Westbay Penthouse, West Bay
West Bay Apartment - 17 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 3 nights min
- Child friendly
- Private garden
$357.00
from $357.00 / night
Willow Cottage, Bridport
Askerswell Cottage - 15.4 miles away
- 3 bedrooms 3
- 1 bathroom
- sleeps 6 6
- 3 nights min
- Pet friendly
$131.00
from $131.00 / night
Rose Cottage, Bridport
Askerswell Cottage - 15.4 miles away
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 3 nights min
- Pet friendly
- Private garden
$124.00
from $124.00 / night
The Old Grainstore, Buckland Newton
Plush Cottage - 17.2 miles away
- 6 bedrooms 6
- 3 bathrooms
- sleeps 12 12
- 3 nights min
- Child friendly
- Private garden
$434.00
from $434.00 / night
Ivy Cottage, Bridport
Askerswell Cottage - 15.4 miles away
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 3 nights min
- Pet friendly
$124.00
from $124.00 / night
Riverhouse Lodge, Upwey
Upwey Log cabin - 6.5 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 3 nights min
- Child friendly
$145.00
from $145.00 / night
Lavender Cottage, Bridport
Askerswell Cottage - 15.4 miles away
- 1 bedroom 1
- 1 bathroom
- sleeps 2 2
- 3 nights min
- Pet friendly
$125.00
from $125.00 / night
Cobweb Cottage, Sutton Poyntz
Osmington Cottage - 6.3 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 3 nights min
- Child friendly
- Private garden
$211.00
from $211.00 / night
Brewers Retreat, Weymouth
Weymouth Cottage - 2.6 miles away
- 3 bedrooms 3
- 1 bathroom
- sleeps 4 4
- 3 nights min
- Child friendly
- Pet friendly
$208.00
from $208.00 / night
Rafters, West Lulworth
West Lulworth House - 9.2 miles away
- 10 bedrooms 10
- 10 bathrooms
- sleeps 20 20
- 3 nights min
- Swimming pool
- Child friendly
$3,146.00
from $3,146.00 / night
Harbour View, Weymouth
Weymouth Caravan/mobile home - 2.1 miles away
- 2 bedrooms 2
- 1 bathroom
- sleeps 3 3
- 3 nights min
$215.00
from $215.00 / night
What is Travelers’ Choice award?
Tripadvisor gives a Travelers’ Choice award to accommodations, attractions and restaurants that consistently earn great reviews from travellers and are ranked within the top 10% of properties on Tripadvisor.