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

  • Snaptrip - 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

    £83

    per night
    View

  • Snaptrip - 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

    £76

    per night
    View

  • Snaptrip - 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

    £67

    per night
    View

  • Snaptrip - The Blue Cottage
  • Dorset

    The Blue Cottage

    Ref: S700504

    Reviews 11

    3
    6
    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

    £109

    per night
    View

  • Snaptrip - 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

    £76

    per night
    View

  • Snaptrip - 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

    £89

    per night
    View

  • Snaptrip - 3 Bed Cottage in Portland
  • 1

    Dorset

    3 Bed Cottage in Portland

    Ref: S1342512

    3
    6
    Additional information and rules . Please enquire if you wish to bring more than 1 dog - 3 bedrooms – 1 king-size, 2 doubles - 2 bathrooms – 1 bathroom with bath and WC, 1 ground floor shower room with WC - Electric oven, gas hob,...

    From

    £81

    per night
    View

  • Snaptrip - 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

    £131

    per night
    View

  • Snaptrip - 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

    £100

    per night
    View

  • Snaptrip - 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

    £92

    per night
    View

  • Snaptrip - 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

    £173

    per night
    View

  • Snaptrip - 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

    £76

    per night
    View

  • Snaptrip - 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

    £2403

    per night
    View
    Partner deal

  • Snaptrip - Fisherman's Cottage on Chesil Beach
  • 3

    Dorset

    Fisherman's Cottage on Chesil Beach

    Ref: S1278870

    4
    Fisherman's Cottage on Chesil Beach is set in Castletown, 7.4 km from Weymouth Harbour, 32 km from Monkey World, as well as 38 km from Golden Cap. Both free WiFi and parking on-site are available at the holiday home free of charge. The property is...

    From

    £101

    per night
    View
    Partner deal

  • Snaptrip - Dory Cottage - Chesil Beach View
  • Dorset

    Dory Cottage - Chesil Beach View

    Ref: S961196

    3
    5
    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 7.7 km from Weymouth Harbour and 32 km from Monkey World. The property...

    From

    £157

    per night
    View
    Partner deal

  • Snaptrip - No. 231 Waterfront
  • Portland

    No. 231 Waterfront

    Ref: S2111001

    3
    5
    Situated in Portland in the Victoria region, No. 231 Waterfront features accommodation with free WiFi and free private parking. The property features sea views. The holiday home has 3 bedrooms, a flat-screen TV, a fully equipped kitchen with a...

    From

    £233

    per night
    View
    Partner deal

  • Snaptrip - Beach Views Cottage, Portland - Stunning & Cosy
  • 3

    Dorset

    Beach Views Cottage, Portland - Stunning & Cosy

    Ref: S1278780

    3
    6
    Housed in a historic building, Beach Views Cottage, Portland - Stunning & Cosy provides accommodation with a garden and free WiFi in Castletown, 200 metres from Portland Beach. It is set 32 km from Monkey World and offers private check-in and...

    From

    £300

    per night
    View
    Partner deal

  • Snaptrip - Blackford House a large home Portland Dorset
  • 3

    Dorset

    Blackford House a large home Portland Dorset

    Ref: S927673

    3
    7
    Boasting garden views, Blackford House a large home Portland Dorset provides accommodation with a garden and a terrace, around 500 metres from Portland Beach. The property is located 32 km from Monkey World, 39 km from Golden Cap and 44 km from...

    From

    £173

    per night
    View
    Partner deal

  • Snaptrip - Storm View
  • Dorset

    Storm View

    Ref: S2157835

    1
    6
    Located in Castletown in the Dorset region, with Portland Beach and Portland Castle nearby, Storm View provides accommodation with free WiFi and free private parking. The property is set 32 km from Monkey World, 38 km from Golden Cap and 44 km...

    From

    £231

    per night
    View
    Partner deal

  • Snaptrip - Dream view holiday home
  • 3

    Dorset

    Dream view holiday home

    Ref: S2062524

    3
    6
    Offering a garden and garden view, Dream view holiday home is set in Castletown, 8.3 km from Weymouth Harbour and 33 km from Monkey World. This property offers access to a terrace, a pool table, free private parking and free WiFi. The property is...

    From

    £270

    per night
    View
    Partner deal

  • Snaptrip - The Old Rope House
  • Dorset

    The Old Rope House

    Ref: S919287

    3
    8
    Set in Portland, 500 metres from Portland Beach and 8 km from Weymouth Harbour, The Old Rope House provides accommodation with amenities such as free WiFi and a flat-screen TV. The property is around 39 km from Golden Cap, 44 km from Corfe Castle...

    From

    £200

    per night
    View
    Partner deal

  • Snaptrip - Bright & beautiful 4 bedroom house with sea views
  • Dorset

    Bright & beautiful 4 bedroom house with sea views

    Ref: S928198

    4
    8
    Situated in Portland, 300 metres from Portland Beach, Bright & beautiful 4 bedroom house with sea views features recently renovated accommodation with free WiFi and a terrace. Housed in a building dating from 1900, this holiday home is 33 km from...

    From

    £148

    per night
    View
    Partner deal

  • Snaptrip - Castle Road
  • Dorset

    Castle Road

    Ref: S2199308

    2
    6
    Comfortable Accommodation Castle Road in Castletown offers a holiday home with two bedrooms and a bathroom. Guests enjoy a balcony with garden views and a fully equipped kitchen. Essential Facilities The property features a garden and free...

    From

    £160

    per night
    View
    Partner deal

  • Snaptrip - Sally Hall Large central Portland home
  • Dorset

    Sally Hall Large central Portland home

    Ref: S1302293

    5
    8
    Sally Hall Large central Portland home is situated in Portland, 10 km from Weymouth Harbour, 34 km from Monkey World, as well as 40 km from Golden Cap. The property is located 46 km from Corfe Castle, 1.1 km from Portland Museum and 1.3 km from...

    From

    £219

    per night
    View
    Showing 1 - 24 of 94 properties

    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.