Skip to main content

The best cottages in Castletown

Check out our pick of great cottages in Castletown

Filter by:


Review score

Superb: 9+ Very good: 8+ Good: 7+ Pleasant: 6+
Our top picks Lowest price first Star rating and price Top reviewed

See the latest prices and deals by choosing your dates.

Luxurious Beach House Chesil Beach. Sleeps 6, a property with a garden, is located in Castletown, 2.5 km from Chesil Beach, 32 km from Monkey World, as well as 39 km from Golden Cap. This beachfront property offers access to a patio, free private parking and free WiFi. The property is non-smoking and is situated 90 metres from Portland Beach.

Lovely house, we really enjoyed our stay 😀 All good, great location & loved the secure gated premises.

Show more Show less
9
Superb
56 reviews
Price from
£296.65
per night

The 3-bedroom holiday home is fitted with a living room with a flat-screen TV, a fully equipped kitchen with a dishwasher and an oven, and 2 bathrooms with a hair dryer. The accommodation offers a fireplace.

Show more Show less
9
Superb
1 reviews
Price from
£180
per night

Offering a garden and sea view, Spaniels Cottage is situated in Castletown, 400 metres from Portland Beach and 8 km from Weymouth Harbour. The property is around 40 km from Golden Cap, 44 km from Corfe Castle and less than 1 km from Portland Castle. The property is non-smoking and is located 32 km from Monkey World.

Show more Show less
8
Very good
1 reviews
Price from
£179.67
per night

Offering a garden and garden view, Chiswell Cottage a large family nr WPNSA & Beach is set in Castletown, 32 km from Monkey World and 39 km from Golden Cap. The property is around 45 km from Corfe Castle, less than 1 km from Portland Castle and 4 km from Portland Museum. Free WiFi is available throughout the property and Portland Beach is 70 metres away.

Show more Show less
8.3
Very good
3 reviews
Price from
£335
per night

Set in Castletown in the Dorset region, with Portland Beach and Portland Castle nearby, Cornerstone offers accommodation with free WiFi and free private parking. The property is around 33 km from Monkey World, 40 km from Golden Cap and 44 km from Corfe Castle. The property is non-smoking and is situated 8.1 km from Weymouth Harbour.

Show more Show less
9
Superb
1 reviews
Price from
£106.43
per night

Set in Castletown, near Portland Beach and Portland Castle, Jurassic View 3 Bed House with Hot Tub is a recently renovated property, featuring, a garden and tennis court. Both free WiFi and parking on-site are accessible at the holiday home free of charge. The property is non-smoking and is located 2.8 km from Chesil Beach.

After some confusion about the booking at first, it was sorted out quickly with a discussion that satisfied both sides. From then on our host couldn't have been more welcoming. We appreciated his trust and kindness and have no hesitation in recommending this lovely house for a great place to stay.

Show more Show less
7.6
Good
91 reviews
Price from
£393.75
per night

Offering a garden and sea view, Mallams is set in Castletown, 7.8 km from Weymouth Harbour and 32 km from Monkey World. Offering free private parking, the 3-star holiday home is 300 metres from Portland Beach. The property is non-smoking and is situated 40 km from Golden Cap.

Show more Show less
8
Very good
2 reviews
Price from
£234.50
per night

Situated in Castletown and only 400 metres from Portland Beach, Host & Stay - Jurassica features accommodation with sea views, free WiFi and free private parking. This holiday home offers accommodation with a terrace. The property is non-smoking and is set 7.6 km from Weymouth Harbour.

Show more Show less
Price from
£277
per night

The holiday home features 2 bedrooms, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 1 bathroom. Towels and bed linen are featured in the holiday home. The accommodation offers a fireplace.

Show more Show less
Price from
£359.50
per night

Set in Castletown, just 200 metres from Portland Beach, Dory Cottage - Chesil Beach View offers beachfront accommodation with free WiFi. The property features sea views and is 32 km from Monkey World and 39 km from Golden Cap. The property is non-smoking and is situated 46 km from Corfe Castle.

Show more Show less
Price from
£186.67
per night

Looking for a cottage?

Cottages are perfect for travellers who enjoy feeling cosy and independent in the countryside. Usually small, traditionally built houses, cottages spread across one or two floors, making them great for families, or holidays with a little more privacy.
Search cottages in Castletown

Most booked cottages in Castletown this month

Enjoy breakfast in Castletown!

  • Luxurious Beach House Chesil Beach. Sleeps 6
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 56 reviews

    Luxurious Beach House Chesil Beach. Sleeps 6, a property with a garden, is located in Castletown, 2.5 km from Chesil Beach, 32 km from Monkey World, as well as 39 km from Golden Cap.

    Location was great, lovely house, amazing main bathroom

  • Host & Stay - Jurassica

    Situated in Castletown and only 400 metres from Portland Beach, Host & Stay - Jurassica features accommodation with sea views, free WiFi and free private parking.

  • Marina View
    Breakfast options
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 1 review

    A recently renovated holiday home set in Castletown, Marina View features a garden. This property offers access to a terrace, free private parking and free WiFi.

  • 2 Bed in Portland 91468

    Offering a garden and garden view, 2 Bed in Portland 91468 is located in Castletown, 32 km from Monkey World and 39 km from Golden Cap.

  • Dory Cottage - Chesil Beach View

    Set in Castletown, just 200 metres from Portland Beach, Dory Cottage - Chesil Beach View offers beachfront accommodation with free WiFi.

  • Spaniels Cottage
    8.0
    Scored 8.0
    Very good
    Rated very good
     · 1 review

    Offering a garden and sea view, Spaniels Cottage is situated in Castletown, 400 metres from Portland Beach and 8 km from Weymouth Harbour.

  • Chiswell Cottage a large family nr WPNSA & Beach
    8.3
    Scored 8.3
    Very good
    Rated very good
     · 3 reviews

    Offering a garden and garden view, Chiswell Cottage a large family nr WPNSA & Beach is set in Castletown, 32 km from Monkey World and 39 km from Golden Cap.

  • Cornerstone
    Breakfast options
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 1 review

    Set in Castletown in the Dorset region, with Portland Beach and Portland Castle nearby, Cornerstone offers accommodation with free WiFi and free private parking.

Cottages that guests love in Castletown

  • 9.0
    Scored 9.0
    Superb
    Rated superb
     · 56 reviews
    The property was amazing! Clean, cosy, perfectly situated and family friendly!
    Lianne
    Family with young children
  • Avg. price/night: £393.75
    7.6
    Scored 7.6
    Good
    Rated good
     · 91 reviews
    View from hot tub was absolutely stunning, hot tub was ready when we got there and lots of supplies already in the propert like bread and milk. Also a bottle pf prosecco in the fridge!
    Samantha
    People with friends
  • Avg. price/night: £393.75
    7.6
    Scored 7.6
    Good
    Rated good
     · 91 reviews
    Loved the hot tub and the view! Great tv and streaming services and communication from Oliver was spot on.
    Clare
    People with friends
  • Avg. price/night: £393.75
    7.6
    Scored 7.6
    Good
    Rated good
     · 91 reviews
    Hot tub and view made our stay !!! It’s really stunning! Free car park on the front of property, Wi-Fi ok. Nice big leaving room with open kitchen. Bedrooms ok.
    Anna
    People with friends
  • Avg. price/night: £393.75
    7.6
    Scored 7.6
    Good
    Rated good
     · 91 reviews
    The view was stunning, hot tub was amazing and nice to sit by the fireplace at night. House was lovely too
    Stephanie
    Group
  • Avg. price/night: £393.75
    7.6
    Scored 7.6
    Good
    Rated good
     · 91 reviews
    Hot tub and views great. Useful supplies at property on arrival. Clean and cosy. Wifi good and available tv subscriptions good.
    Mark
    Young couple
  • Avg. price/night: £393.75
    7.6
    Scored 7.6
    Good
    Rated good
     · 91 reviews
    Comfortable cosy house, great lounge and TV, perfect for a group of friends to chill out. Hot tub was lovely and views were fantastic. easy to park and in a quiet location.
    Michele
    Group
  • Avg. price/night: £393.75
    7.6
    Scored 7.6
    Good
    Rated good
     · 91 reviews
    The location is great, free street parking. Quiet area. Amazing views! Huge hot tub is a great addition. House is very cosy and welcoming. The contact with the host is great and he is very accommodating.
    Natalia1711
    People with friends
  • 2.5
    Scored 2.5
    Very poor
    Rated very poor
     · 4 reviews
    Self catering !!! We did not stay at this apartment as the host did give us the keys and we went there then rang us up to say it was cancelled and we had to get out then another turned up and they said he’s done to them the day before the apartment was filthy anyway and the hose was very rude on the phone so we had to stay at the lovely cottage down the road .. disgusting way to be treated 😡😡😡
    Trudy
    Solo traveller
  • 8.0
    Scored 8.0
    Very good
    Rated very good
     · 3 reviews
    Lovely cottage, conform description on the website. Host was very easy to communicate with and very helpful. The house looks small, but has quite a lot of space. The location is very practical in the middle of the town and walking distance to the beach. Parking was possible in the 72 hour parking place and only a short walk from the cottage. Great beds and mattresses in the twin bedroom.
    Elisabeth
    Solo traveller
gogless