Holiday Cottages in Portland

Holiday Cottages in Portland

Home to the biggest range at the lowest price

Check-in

{{checkInFormatted}}

Add dates

± {{flex}}
Check-out

{{checkOutFormatted}}

Add dates

± {{flex}}

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 - Old Higher Lighthouse Branscombe Lodge
  • Dorset

    Old Higher Lighthouse Branscombe Lodge

    Ref: S2422

    Reviews 40

    2
    4
    The village of Fortuneswell is on the 'Isle of Portland' peninsula, and is joined to the mainland via Chesil Beach. Fortuneswell boasts shops, pubs and restaurants with walking and climbing opportunities, watersports, and the harbour at Weymouth.

    From

    £89

    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

    £82

    per night
    View

  • Last Minute Cottages - Bed in Portland (94598)
  • Dorset

    Bed in Portland (94598)

    Ref: S842417

    2
    2
    Situated in a peaceful spot along the beautiful Isle of Portland, this charming single level stone built cottage provides fantastic accommodation for couples and small families enjoying a relaxing break. Perfect for exploring a wonderful part of...

    From

    £82

    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 - 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 - Crows Nest
  • 3

    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

    £74

    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

    £63

    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

    £63

    per night
    View

  • Last Minute Cottages - The Shambles
  • Dorset

    The Shambles

    Ref: S394516

    Reviews 15

    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 - 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

    £71

    per night
    View

  • Last Minute Cottages - The Old Police Station
  • Dorset

    The Old Police Station

    Ref: S376613

    Reviews 14

    3
    6
    Fortuneswell is a picturesque village nestled on Dorset’s wonderful Jurassic Coast. The village not only boasts access to a long stretch of golden sands, but contains a vast selection of pubs, eateries and shops; making for a great seaside break....

    From

    £125

    per night
    View

  • Last Minute Cottages - Home From Home
  • 1

    Dorset

    Home From Home

    Ref: S882044

    Reviews 1

    4
    8
    Castletown is a small, yet popular village resting on the Isle of Portland, between Fortuneswell and Wakeham. Castletown is well-known for being a conservation area, thanks to its fascinating history. Your local amenities can be found in nearby...

    From

    £73

    per night
    View

  • Last Minute Cottages - Dorset Castle
  • Dorset

    Dorset Castle

    Ref: S277119

    Reviews 9

    9
    20
    Dorset Castle is situated on the Isle of Portland, the most southernmost point on the Jurassic coast, a tied island joined to the mainland by Chesil beach. Despite being relatively small in size, there is plenty to see, do and explore without even...

    From

    £2129

    per night
    View
    LateRooms.com

  • Last Minute Cottages - 5 Coastguard Cottage
  • Dorset

    5 Coastguard Cottage

    Ref: S485332

    1
    2

    From

    £87

    per night
    View
    LateRooms.com

  • Last Minute Cottages - Lyme View
  • Dorset

    Lyme View

    Ref: S1008887

    2
    4

    From

    £72

    per night
    View
    LateRooms.com

  • Last Minute Cottages - Old Higher Lighthouse Branscombe Lodge
  • Dorset

    Old Higher Lighthouse Branscombe Lodge

    Ref: S291264

    2
    4

    From

    £101

    per night
    View
    LateRooms.com

  • Last Minute Cottages - Ammonite Cottage
  • Dorset

    Ammonite Cottage

    Ref: S301956

    2
    4

    From

    £84

    per night
    View
    LateRooms.com

  • Last Minute Cottages - Bowman's Cottage
  • Dorset

    Bowman's Cottage

    Ref: S301973

    2
    4

    From

    £81

    per night
    View
    LateRooms.com

  • Last Minute Cottages - 74 Reap Lane
  • Dorset

    74 Reap Lane

    Ref: S1016432

    2
    4

    From

    £72

    per night
    View
    LateRooms.com

  • Last Minute Cottages - The Shambles
  • Dorset

    The Shambles

    Ref: S523794

    2
    4

    From

    £98

    per night
    View
    LateRooms.com

  • Last Minute Cottages - Groves House
  • Dorset

    Groves House

    Ref: S1038253

    3
    6

    From

    £81

    per night
    View
    LateRooms.com

  • Last Minute Cottages - The Old Police Station
  • Dorset

    The Old Police Station

    Ref: S437238

    3
    6

    From

    £153

    per night
    View
    LateRooms.com

  • Last Minute Cottages - Home From Home
  • Dorset

    Home From Home

    Ref: S1016846

    4
    8

    From

    £84

    per night
    View
    LateRooms.com

  • Last Minute Cottages - The Old Portland Courthouse
  • Dorset

    The Old Portland Courthouse

    Ref: S302026

    4
    8

    From

    £192

    per night
    View
    Showing 1 - 24 of 40 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 >

    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 >

    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

    Did you mean {{ suggestedEmail }}?

    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