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 - Anchor Cottage
  • 1

    Dorset

    Anchor Cottage

    Ref: S1039859

    3
    5
    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

    £76

    per night
    View

  • Last Minute Cottages - Cliffwalk Cottage
  • 2

    Dorset

    Cliffwalk Cottage

    Ref: S598027

    Reviews 12

    2
    4
    An 18-mile-long stone spit called Chesil Beach connects Portland Bill, a short cape at the tip of the rough Isle of Portland peninsula, to the mainland. Portland Bill is home to three lighthouses, the most recent of which, the 35-meter-tall, white...

    From

    £84

    per night
    View

  • Last Minute Cottages - Fisherman's Cottage, King Street
  • 2

    Dorset

    Fisherman's Cottage, King Street

    Ref: S855298

    Reviews 8

    2
    4
    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

    £68

    per night
    View

  • Last Minute Cottages - Mermaid Cottage
  • 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

    £91

    per night
    View

  • Last Minute Cottages - The Blue Cottage
  • Dorset

    The Blue Cottage

    Ref: S700504

    Reviews 11

    3
    7
    The community of Fortuneswell is located on the Isle of Portland peninsula, connected to the mainland by Chesil Beach, a pebble spit that spans 18 miles towards West Bay, on Dorset's beautiful Jurassic Coast, now a World Heritage Site. Formerly a...

    From

    £80

    per night
    View

  • Last Minute Cottages - St Johns View
  • Dorset

    St Johns View

    Ref: S126721

    Reviews 33

    2
    4
    On Dorset's spectacular Jurassic Coast World Heritage Site, the village of Fortuneswell can be found on the rugged Isle of Portland, joined to the mainland via Chesil Beach, a pebble spit, which stretches 18 miles towards West Bay. Formerly a...

    From

    £91

    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

    £71

    per night
    View

  • Last Minute Cottages - 2 Bed Cottage in Portland
  • Dorset

    2 Bed Cottage in Portland

    Ref: S842417

    2
    2
    Additional information and rules No dogs allowed - 2 bedrooms – 1 double, 1 single with additional pull-out bed to make double - 1 bathroom with shower and WC - Electric oven & hob, fridge/freezer, microwave, and coffee machine - Utility...

    From

    £126

    per night
    View

  • Last Minute Cottages - Pebble Reef
  • Dorset

    Pebble Reef

    Ref: S598025

    Reviews 4

    3
    6
    Dorset's Jurassic Coast is a World Heritage Site, and the thriving community of Easton may be found near the tip of the craggy Isle of Portland Peninsula, which is connected to the mainland by the pebbled beach of Chesil Beach, which extends for...

    From

    £94

    per night
    View

  • Last Minute Cottages - Kimberlin
  • 2

    Dorset

    Kimberlin

    Ref: S425976

    Reviews 27

    3
    6
    Portland Bill is a small promontory at the tip of the mountainous Isle of Portland peninsula, connected to the mainland by Chesil Beach, an 18-mile-long shingle spit that stretches towards West Bay. Portland Bill is located on Dorset's magnificent...

    From

    £83

    per night
    View

  • 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

    £82

    per night
    View

  • Last Minute Cottages - Pebbles Reach
  • 1

    Dorset

    Pebbles Reach

    Ref: S517067

    Reviews 26

    3
    7
    The village of Fortuneswell is on the rugged Isle of Portland peninsula, joined to the mainland by Chesil Beach, a pebble spit that stretches 18 miles towards West Bay. With stunning views of the Jurassic Coast and the rolling Dorset hills beyond,...

    From

    £114

    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

    £84

    per night
    View

  • Last Minute Cottages - Crows Nest
  • 1

    Dorset

    Crows Nest

    Ref: S881497

    Reviews 3

    2
    4
    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

    £86

    per night
    View

  • Last Minute Cottages - Lyme View
  • 1

    Dorset

    Lyme View

    Ref: S777877

    Reviews 11

    2
    4
    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

    £134

    per night
    View

  • Last Minute Cottages - 2 Bed Cottage in Fortuneswell
  • 2

    Dorset

    2 Bed Cottage in Fortuneswell

    Ref: S680762

    2
    4
    Additional information and rules - 2 bedrooms – 1 king-size, 1 twin - 1 bathroom with freestanding bath, separate shower and WC - Gas hob and electric oven, microwave, fridge/freezer, air fryer dishwasher washing machine, air fryer and Tassimo...

    From

    £109

    per night
    View

  • Last Minute Cottages - 3 Bed Cottage in Portland
  • 2

    Dorset

    3 Bed Cottage in Portland

    Ref: S842358

    3
    5
    Additional information and rules - 3 bedrooms – 1 king size, 1 twin (2’6” beds) and 1 single - 1 shower room with double shower and WC - Electric oven, gas hob, fridge, freezer, microwave - Enclosed rear garden with garden furniture - Smart...

    From

    £75

    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

    £132

    per night
    View

  • Last Minute Cottages - Sunset Lodge
  • Dorset

    Sunset Lodge

    Ref: S1064878

    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

    £90

    per night
    View

  • Last Minute Cottages - Groves House
  • Dorset

    Groves House

    Ref: S1029433

    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

    £72

    per night
    View

  • Last Minute Cottages - Sea View - Portland
  • 1

    Dorset

    Sea View - Portland

    Ref: S1228927

    3
    6

    From

    £108

    per night
    View

  • Last Minute Cottages - Fisherman's Cottage
  • Dorset

    Fisherman's Cottage

    Ref: S598026

    3
    6
    Portland Bill, a promontory at the tip of the wild Isle of Portland peninsula, is connected to the mainland by Chesil Beach, a gravel spit that extends 18 miles in the direction of West Bay. Portland is home to three lighthouses, the most recent...

    From

    £109

    per night
    View

  • Last Minute Cottages - The Old Portland Courthouse
  • Dorset

    The Old Portland Courthouse

    Ref: S126658

    Reviews 28

    4
    8
    On Dorset's spectacular Jurassic Coast World Heritage Site, the village of Fortuneswell can be found on the rugged Isle of Portland, joined to the mainland via Chesil Beach, a pebble spit, which stretches 18 miles towards West Bay. Formerly a...

    From

    £168

    per night
    View

  • Last Minute Cottages - Spring Rose Cottage
  • 1

    Dorset

    Spring Rose Cottage

    Ref: S268136

    Reviews 42

    3
    8
    Fortuneswell on the Isle of Portland, Dorset, situated just five miles away from Weymouth. The village is connected to the mainland by the Chesil Beach, a pebble spit, which stretches 18 miles towards West Bay. Within the village you will find a...

    From

    £73

    per night
    View
    Showing 1 - 24 of 62 properties

    Portland Holiday Cottages

    Escape it all and head to the stunning, wilds of Portland for an action-packed getaway that you won't forget! The Isle of Portland, in Dorset, is a beautiful rugged landscape at the southern point of the Jurassic Coast. The isolated setting offers visitors breathtaking scenery, wonderful walks and pretty villages. Joined to the mainland by Chesil Beach, you can enjoy sweeping sea views and lots of history and culture here.

    From Portland Bill lighthouse in the south to Portland Castle in the north, the island has lots of beautiful places to stay and plenty of fun activities to keep you busy. We've hand-picked a selection of the finest holiday cottages from homes that are perfect for single travellers, couples, families, groups, parties and even dog-friendly accommodation. Our homes come in all shapes and sizes from historic cottages with open fires, modern apartments with sleek kitchens and luxury pads with hot tubs.

    Our team is on hand to help make your booking process as easy as possible and we can answer any questions you have. But best of all, we can offer you our best price guarantee so you can find a home within budget. This tiny isle has lots of fun packed into a small landmass and is home to amazing wonderful wildlife. Get back to nature with a stay in Portland - and let Snaptrip help you find the perfect home away from home, without the stress.

    More locations in Dorset

    The great outdoors awaits in Dorset and there are many picture-perfect villages and bustling towns to visit if you're planning a getaway. We've put together some inspiration to help you find the ideal destination for your staycation.

    Read more > less >

    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 >

    • Wendy - Verified booking

      From the minute we arrived at the cottage, we knew we were going to fall in love with it.

      I had a quick glance over the reviews but unless they are consistent, I don't pay too much attention. Yes, it took me a few minutes to get the car parked, but I did it! I have a Nissan Juke and it fitted in the space perfectly. So we enter the cottage and the dogs go off for a sniff....straight to the care box provided by the hosts!! We loved this sentiment. Unpacked the car and settled straight in. The sun was shining, considering we'd just had weeks of rain! Husband read the welcome folder and started planning our walks. I felt immediately at home, as did my dogs. We always take blankets to dog friendly stays but there were some provided if required. Another sweet touch. Everything available to us were perfect. All furniture was comfortable and the wood burner was my favourite touch. I would definitely recommend this stay to anyone and everyone. Great value for money. The surrounding facilities are great. The Cove pub on the front of Chesil beach is fab and also dog friendly. The walks are brilliant. And most of all, people were incredibly friendly. Super tasty big portions of fish and chips up the road at Salty Towers. We couldn't fault a thing. Only 1 thing I'd agree with, with someone else's review would be a little side lamp in the living room. But it didn't affect a thing. We will return with our dogs and we cannot wait to.ezplore more of Portland. The hosts have put a lot of thought into all aspects of their cottage and we thank them for it.

      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 >

    • Kristie - Verified booking

      We had a fantastic holiday at Blue Cottage.

      Very well presented and lovely decor. I'll start from bottom of the house to 4th floor. The house had everything you needed from cooking facilities: oven/hob, microwave, kettle including all the utensils. The trays were a very thoughtful item to help carry dinner up the 2-3 flights of stairs. Lounge/dining room was spacious, TV had access to Netflix, little touches like board games too. Bedding was well presented with plenty of hanging space for your holiday clothes. 2 bathrooms with a bath and shower. Top bedroom with balcony was stunning, we ended up cancelling our table reservation out for evening dinner to instead sit on the balcony and eat watching the sunset. Constructive feedback- List all the little details on the website as we were not aware of absolutely everything they had in the house - for example, we brought our own high chair, bath anti slip mat for the little one, own iron, etc when we could have saved space in the very full car as the holiday house had it all.

      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 >

    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.