Check-in

Add dates

Check-out

Add dates

Now driving your route . . .

Holiday Cottages in Portland

Holiday Cottages in Portland

Home to the biggest range at the lowest price

Check-in

Add dates

Check-out

Add dates

Live availability

Live prices

Book instantly

Did you know? We have a dedicated site just for pet friendly holidays, take me to Dog Friendly Cottages >

Portland Cottages

  • Last Minute Cottages - 33 High Street
  • 1

    Dorset

    33 High Street

    Ref: S777334

    Reviews 4

    3
    6
    Situated on Dorset's spectacular Jurassic Coast, now a World Heritage Site, the village of Fortuneswell can be found on the rugged Isle of Portland peninsula, joined to the mainland via Chesil Beach, a pebble spit, which stretches 18 miles towards...

    From

    £126

    per night
    View

  • Last Minute Cottages - 74 Reap Lane
  • 2

    Dorset

    74 Reap Lane

    Ref: S880901

    Reviews 1

    2
    4
    Weston is a village on top of the Isle of Portland, in Dorset. Right next to the village of Easton and Southwell it forms a key part of life on Portland. Now designated a conservation area and place of special architectural and historic interest...

    From

    £100

    per night
    View

  • Last Minute Cottages - Bowman's Cottage
  • Dorset

    Bowman's Cottage

    Ref: S126494

    Reviews 50

    2
    4
    Wakeham is a small hamlet situated in a conservation area on the eastern side of the rugged ‘Isle’ of Portland above the beach at Church Ope Cove. The wide road running through the centre was constructed to accommodate the transport of Portland...

    From

    £91

    per night
    View

  • Last Minute Cottages - Coastguard View
  • Dorset

    Coastguard View

    Ref: S1053254

    2
    4
    Portland Bill is a narrow promontory on the end of the rugged Isle of Portland peninsula which is joined to the mainland via Chesil Beach, a pebble spit, which stretches 18 miles towards West Bay. Situated on Dorset's spectacular Jurassic Coast,...

    From

    £122

    per night
    View

  • Last Minute Cottages - 3 Bed Cottage in Portland
  • Dorset

    3 Bed Cottage in Portland

    Ref: S229384

    3
    6
    Additional information and rules No dogs allowed - 3 bedrooms – 1 twin zip-and-link which can be made up as a 6’ double on request, 1 double room with 5‘ bed, 1 twin room - 2 bathrooms - 1 shower room with WC, 1 bathroom with bath, shower and...

    From

    £138

    per night
    View

  • Last Minute Cottages - Sea View - Portland
  • 1

    Dorset

    Sea View - Portland

    Ref: S1228927

    3
    6

    From

    £119

    per night
    View
    Partner deal

  • Last Minute Cottages - Dory Cottage - Chesil Beach View
  • Dorset

    Dory Cottage - Chesil Beach View

    Ref: S961196

    3
    5

    From

    £182

    per night
    View
    Partner deal

  • Last Minute Cottages - Duke’s Cottage
  • Dorset

    Duke’s Cottage

    Ref: S931061

    3
    6

    From

    £137

    per night
    View
    Partner deal

  • Last Minute Cottages - Chiswell Cottage a large family nr WPNSA & Beach
  • Dorset

    Chiswell Cottage a large family nr WPNSA & Beach

    Ref: S927776

    4
    8

    From

    £251

    per night
    View
    Partner deal

  • Last Minute Cottages - Nordor - lots of parking
  • Dorset

    Nordor - lots of parking

    Ref: S357356

    4
    9

    From

    £450

    per night
    View
    Partner deal

  • Last Minute Cottages - Blackford House a large home Portland Dorset
  • 3

    Dorset

    Blackford House a large home Portland Dorset

    Ref: S927673

    3
    7

    From

    £184

    per night
    View
    Partner deal

  • Last Minute Cottages - Kearney Cottage - Artist's Retreat
  • 3

    Dorset

    Kearney Cottage - Artist's Retreat

    Ref: S928497

    3
    6

    From

    £193

    per night
    View
    Partner deal

  • Last Minute Cottages - Mallams Art House
  • 3

    Dorset

    Mallams Art House

    Ref: S1077052

    3
    6

    From

    £122

    per night
    View
    Partner deal

  • Last Minute Cottages - Fisherman's Cottage - Chesil Beach
  • Dorset

    Fisherman's Cottage - Chesil Beach

    Ref: S1001238

    2
    4

    From

    £146

    per night
    View

  • Last Minute Cottages - Mermaid Cottage
  • 1

    Dorset

    Mermaid Cottage

    Ref: S881234

    Reviews 1

    2
    4
    Wakeham is a small hamlet situated in a conservation area on the eastern side of the rugged ‘Isle’ of Portland above the beach at Church Ope Cove. The wide road running through the centre was constructed to accommodate the transport of Portland...

    From

    £126

    per night
    View

  • Last Minute Cottages - Sea Gem
  • Dorset

    Sea Gem

    Ref: S517329

    Reviews 8

    4
    7
    Castletown is a small village in Underhill, Dorset. It is close to Fortuneswell, on the shores of Portland Harbour, and features a sandy beach, Portland Castle, and the Weymouth and Portland National Sailing Academy. Castletown, like Portland's...

    From

    £172

    per night
    View
    Partner deal

  • Last Minute Cottages - Foundry Cottage
  • Dorset

    Foundry Cottage

    Ref: S927991

    3
    5

    From

    £151

    per night
    View
    Partner deal

  • Last Minute Cottages - Sea View Cottage in Dorset, Portland
  • 3

    Dorset

    Sea View Cottage in Dorset, Portland

    Ref: S926056

    3
    5

    From

    £156

    per night
    View

    Reviews

    What our customers say about their holidays

    • Mary - Verified booking

      The cottage was pristine clean when we arrived - bathroom, kitchen etc all spotless.

      It is very well equipped - the owners have thought of almost everything. The only thing we would have liked was a bath mat. There was a plastic mat to put in the bath, but we couldn't find one to put on the floor so had to use a towel. The bathroom is small, but we didn't find that a problem. The living room was very comfortable and although the cottage is on a main road it is still very quiet at night. Being on a bus route was a big plus for us as we were able to go into Weymouth without having to worry about car parking. There is no off-street parking at the cottage, but we never had any problems finding a space close by. There was a very good selection of pots and pans in the kitchen, which you don't always find in a holiday property, and the appliances all worked very well. The main bedroom is huge, very welcoming and has plenty of storage space with lots of hangers to use. We loved the summer house, which gets the afternoon sun. It was great to return after a half-day out and relax inside it with a cup of tea. Many thanks to Dream Cottages for their prompt response when, on arrival, we found that the key to the summer house had sheared and we were unable to unlock it. A member of staff came round the next day to sort it out. Great service. There was a lot of information provided by the owners about restaurants, pubs and places to visit which we found very useful. This cottage was much more like home than many holiday cottages we have stayed in. The décor was very tasteful, the property felt very cosy and we didn't want to leave. It was one of the best cottages we have stayed in and we would like to come back.

      Read more less >

    • Mrs Vanessa Peters - Verified booking

      We were delighted with Bowman's Cottage.

      It exceeded our expectations. The actual accommodation is much better than the photo's imply. The decor was charming; the cottage was very clean and tidy and the equipment and facilities provided were entirely adequate. It really felt to us like 'home from home' We were particularly impressed by the comfy beds and bedlinen; the excellent shower - the water pressure is so good it was like a power shower. One word of warning though - the height in the shower is limited so a tall person may struggle. Likewise, the bath is limited in length so a tall person may struggle. Outside is the garden room with table and chairs - delightful on a warm evening. Parking outside the cottage was never a problem. The location was perfect as it was not too near to the busier areas of the island but at the quieter end. Nevertheless, the shops were close enough to walk to for supplies. We used the bus several times and the service is very frequent and takes you in to the heart of Weymouth. We couldn't fault a single thing. Stayed June 2018

      Read more less >

    • Lindsey - Verified booking

      We’d return here tomorrow if we could!

      Mermaid Cottage is one of our favourite ever rental cottages. What makes it so special is that, not only is it in a lovely location, with a beautiful garden and all the facilities you’d expect, but also that all of the facilities are particularly perfect. For example, the kitchen is extremely well stocked. The internet is fast. The beds are very comfortable. There are items for dogs, for cleaning, games, a super shower, Netflix and Prime, and just lots of little extras that a home has but often a rental property doesn’t. We lacked for nothing except more time here! The location is very close to the beautiful Church Ope Bay—a climb down many steps and fine if you’re a strong walker, certainly worth it—but it also has a butterfly reserve just at the back, which was perfect for an older member of our group. Thank you for making the cottage such a welcoming place for us. We’re very much looking forward to returning soon!

      Read more less >

    • Margaret - Verified booking

      This is a very comfortable & spotless cottage, well located for various walks and short drives.

      Portland is more interesting than I expected and we were helped by a glorious week of sunshine. The owners were very generous, leaving plenty of necessities that other places we’ve been to don’t provide & there’s pubs/small supermarket/excellent fish and chip shop within walking distance. Our only quibble would be the master bedroom which had a double sized bed, although there was ample room for a king size one. We have a super king size at home, so struggled on the first night to get comfortable in the double. If the window is open (we sleep with open window at home), the room gets very noisy from early morning traffic. We just decamped into the back room & its single beds, which was fine for two of us but you couldn’t do that obviously if there were more than 2 occupants. The shower was great & the courtyard was pleasant to sit & eat lunch in. All in all, we had a lovely week there.

      Read more less >

    • Valerie - Verified booking

      We had problems with getting the television to work when we arrived.

      It was a signal problem, for some reason there was no signal at all. We reported this but then the reception came back briefly on Sunday morning so we cancelled the call. On Sunday evening we had no reception again. I contacted Dream Cottages again on Monday morning and they said they would send someone out. We were out for the day but received a call from a very polite gentleman called Dave who said he would call in and see if he could fix the problem. When we arrived back Monday afternoon, the TV was working and worked for the rest of our stay. Even though Dave said he could not detect a problem and the TV was working when he arrived, he said that if we had any other issues with it, to call straight back.

      Read more less >

    Best price guarantee

    No one can beat our prices

    Best price guarantee

    Our cottages are professionally managed by our partners and payments are taken by them, but rest assured, by booking via Snaptrip you'll pay the lowest possible price for your trip.

    We never charge you more than you would pay booking directly on the partner's site and if you become a member you can save even more. If you find a property priced lower anywhere else on the internet (we’d be amazed if you do), simply email us at marketing@snaptrip.com and we'll refund you the difference.

    We bring it all together

    Biggest range of self-catering holiday properties

    We connect you to a range of great suppliers with a huge selection of properties. We've done the research, so that you don't have to.

    View properties >

    We get you
    the lowest price

    We help you to complete your booking whilst giving you discounts, member only prices and our best price guarantee.

    A marketplace
    you can trust

    We connect you with the best professionally managed properties and our marketing leading customer services can help you every step of the way.

    Start your journey >

    Things to do near Portland

    • Natural Landmark Natural Landmark
    • Activity Activity
    Durdle Door
    One of the most iconic landmarks in the whole of the UK, the towering natural limestone arch of Durdle Door can be found tucked away on Devon’s magnificent Jurassic Coast. Stretching on for 95 miles, the whole of the Jurassic Coast is a UNESCO World Heritage Site, due to its ancient history and wild, windswept beauty. However, this dramatic arch of rock rising straight out of the sea is a particularly picturesque spot, even by Jurassic Coast standards.
    Lulworth Cove
    Lulworth Cove is a stunning secluded cove on the Jurassic Coast UNESCO World Heritage Site which owes its existence to the collision of continents and the birth of the Alps and is considered one of the best places in the world to study geology.

    The Tank Museum

    The Tank Museum in Bovington houses 300 military machines and moving exhibitions representing the key battles of every major conflict since the First World War. Cafe & Shop.

    Monkey World

    Monkey World is a must-visit attraction for animal lovers. Home to over 250 primates, the park is dedicated to rescuing and rehabilitating monkeys from all over the world. Highlights include watching the monkeys in their natural habitats and learning about their stories and behaviors. With play areas for kids, a picnic spot, and a gift shop, it's an excellent day out. Located at Longthorns, Wareham, Dorset BH20 6HH

    The Dinosaur Museum

    Located close to the Jurassic Coast, this award-winning museum is perfect for dinosaur lovers of any age. Exhibits include dinosaur skeletons, lifesize reconstructions and hands on displays. Dog friendly.

    Join for free to get access to exclusive prices on thousands of properties.

    Login to see

    • Discounts exclusive to members
    • Save & share your favourite properties
    • See your previously viewed properties

    Sign up to see

    Login to see

    • Discounts exclusive to members
    • Save & share your favourite properties
    • See your previously viewed properties

    or

    Already a member login here

    Not a member?

    By entering my email address, I agree to Snaptrip's Terms of service, Privacy policy and to receive email updates, news, & offers from Snaptrip.

    Welcome, member discounts are now available.

    Your browser is out of date and we can't guarantee a consistent experience when using our site. Please consider updating or switching. More info on browser support