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The best holiday homes in Portland

Check out our pick of great holiday homes in Portland

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Olympic Village Vela - Portland, hotel in Portland

Set in Portland and only 200 metres from Portland Beach, Olympic Village Vela - Portland offers accommodation with garden views, free WiFi and free private parking.

Scored 8.8
8.8
Rated fabulous
Fabulous
42 reviews
Price from
£318.30
1 night, 2 adults
The Grange, hotel in Portland

Located in Weymouth in the Dorset region, The Grange provides accommodation with free WiFi and free private parking.

Everything
Scored 9.5
9.5
Rated exceptional
Exceptional
41 reviews
Price from
£337.50
1 night, 2 adults
Cabin cottage, hotel in Portland

Cabin cottage in Castletown offers accommodation with free WiFi, 200 metres from Portland Beach, 7.6 km from Weymouth Harbour and 32 km from Monkey World.

Spotlessly clean and very well equipped. Very central for everything
Scored 9.6
9.6
Rated exceptional
Exceptional
33 reviews
Price from
£127.50
1 night, 2 adults
House with free parking and large garden, hotel in Portland

Featuring garden views, House with free parking and large garden provides accommodation with a garden and a patio, around 2.7 km from Weymouth Beach.

Great parking and plenty of amenities
Scored 9.3
9.3
Rated superb
Superb
14 reviews
Price from
£166.50
1 night, 2 adults
Blue Ensign Cottage, hotel in Portland

Located in Weymouth, 500 metres from Weymouth Beach and 25 km from Monkey World, Blue Ensign Cottage provides accommodation with free WiFi in a historic building.

excellent location, property had a very homely feel about it. The kitchen area was a lovely area to spend family time in with our family of 8, our little girl loved the toy and game corner. Would definitely stay again.
Scored 9.2
9.2
Rated superb
Superb
35 reviews
Price from
£361
1 night, 2 adults
Jurassic View 3 Bed House with Hot Tub, hotel in Portland

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.

Hot tub
Scored 7.4
7.4
Rated good
Good
102 reviews
Price from
£374.06
1 night, 2 adults
Admiralty House, hotel in Portland

Located in Weymouth, in a historic building, 600 metres from Weymouth Beach, Admiralty House is a holiday home with a garden and terrace.

Location and enough space in the kitchen for everyone.
Scored 7.4
7.4
Rated good
Good
8 reviews
Price from
£950
1 night, 2 adults
2-6 guests Holiday Home in Durdle Door, hotel in Portland

2-6 guests Holiday Home in Durdle Door has a patio and is situated in Wareham, within just 600 metres of Man O'War Beach and less than 1 km of Durdle Door Beach.

Luxurious, comfortable and very clean.
Scored 9.5
9.5
Rated exceptional
Exceptional
93 reviews
Price from
£178.60
1 night, 2 adults
2-6 guests Holiday Chalet in Durdle Door, hotel in Portland

Located 600 metres from Man O'War Beach, 1 km from Durdle Door Beach and 1.8 km from Lulworth Cove Beach, 2-6 guests Holiday Chalet in Durdle Door offers accommodation situated in West Lulworth.

Excellent property for stay
Scored 9.6
9.6
Rated exceptional
Exceptional
65 reviews
Price from
£186
1 night, 2 adults
Stable Cottage - Sleeps 6, near Lulworth Cove, hotel in Portland

Located in Dorchester, in a historic building, 12 km from Monkey World, Stable Cottage - Sleeps 6, near Lulworth Cove is a holiday home with a garden and terrace.

I recently stayed at this charming cottage, and it was exactly what we needed for a peaceful getaway. The location was ideal—close enough to explore the area but secluded enough to feel like a true retreat. The atmosphere was incredibly tranquil, making it easy to unwind and relax. The cottage itself was well-equipped with everything we needed, comfortable, and thoughtfully prepared. I highly recommend this place to anyone looking for a perfect escape from the hustle and bustle. We couldn’t have asked for a better experience!
Scored 8.6
8.6
Rated fabulous
Fabulous
29 reviews
Price from
£153.13
1 night, 2 adults
All holiday homes in Portland
Looking for a holiday home?
Great for families or large parties, holiday homes are privately owned accommodation, available for long or short-term rental. These homes are furnished and equipped with kitchen facilities for self-catering, although breakfast may be offered as an add-on. These properties have their own independent front door, which makes them different to apartments.

Most booked holiday homes in Portland this month

Enjoy breakfast in Portland!

  • Our Place In Portland Holiday Home with Sea View
    Scored 9.3
    9.3
    Rated superb
    Superb
     · 9 reviews

    Housed in a historic building, the recently renovated Our Place In Portland Holiday Home with Sea View offers accommodation with a garden and free WiFi.

  • Lyme View
    Breakfast options
    Scored 9.4
    9.4
    Rated superb
    Superb
     · 5 reviews

    Lyme View, a property with a garden, is located in Portland, 33 km from Monkey World, 40 km from Golden Cap, as well as 46 km from Corfe Castle.

  • The Blue Cottage
    Breakfast options
    Scored 9.1
    9.1
    Rated superb
    Superb
     · 7 reviews

    Situated in Portland and only 500 metres from Portland Beach, The Blue Cottage features accommodation with sea views, free WiFi and free private parking.

    Homely feel and had everything we needed for our holiday

  • SeaSky
    Breakfast options
    Scored 9.1
    9.1
    Rated superb
    Superb
     · 16 reviews

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

    The sauna is a real treat and we enjoyed it. Every room has a theme.

  • Duke’s Cottage
    Breakfast options
    Scored 9.0
    9.0
    Rated superb
    Superb
     · 24 reviews

    Situated in Portland, near Portland Museum and Rufus Castle, the historic Duke’s Cottage has a garden. Featuring sea and garden views, this holiday home also includes free WiFi.

    Location, comfort,cleanliness,responsive to any need

  • Pebbles Reach
    Breakfast options
    Scored 9.0
    9.0
    Rated superb
    Superb
     · 5 reviews

    Located in Portland in the Dorset region, with Portland Beach and Portland Castle nearby, Pebbles Reach provides accommodation with free WiFi and free private parking.

  • The View
    Breakfast options
    Scored 9.0
    9.0
    Rated superb
    Superb
     · 6 reviews

    Offering sea views, The View is an accommodation located in Portland, 100 metres from Portland Beach and 2.6 km from Chesil Beach.

  • Pebble Reef
    Breakfast options
    Scored 9.2
    9.2
    Rated superb
    Superb
     · 10 reviews

    Boasting a terrace with garden views, a garden and barbecue facilities, Pebble Reef can be found in Portland, close to Portland Museum and 2.7 km from Portland Beach.

    We loved this cottage and the hot tub! It is in a great location, near the coastal paths and Portland Bill. The cottage was very well-equipped and comfortable.

Save money on holiday homes in Portland – budget options available!

  • Sunset Lodge
    Budget options available
    Scored 9.7
    9.7
    Rated exceptional
    Exceptional
     · 9 reviews

    Set 32 km from Monkey World, 39 km from Golden Cap and 46 km from Corfe Castle, Sunset Lodge offers accommodation located in Portland.

    Fabulous location Beautifully appointed, very thoughtfully done - e.g. torches in each room

  • Osprey House Portland
    Budget options available
    Scored 9.3
    9.3
    Rated superb
    Superb
     · 6 reviews

    Offering a garden and sea view, Osprey House Portland is located in Portland, 200 metres from Portland Beach and 32 km from Monkey World.

    WOW what an amazing property, extremely well equipped and spacious, and the location was perfect for our stay .

  • Cornerstone
    Budget options available
    Scored 9.2
    9.2
    Rated superb
    Superb
     · 13 reviews

    Cornerstone is situated in Portland, 33 km from Monkey World, 40 km from Golden Cap, as well as 46 km from Corfe Castle. This property offers access to a terrace, free private parking and free WiFi.

    Lovely well looked after property, modern decor Great size bedrooms

  • Bright & beautiful 4 bedroom house with sea views
    Scored 8.7
    8.7
    Rated fabulous
    Fabulous
     · 7 reviews

    Bright & beautiful 4 bedroom house with sea views is situated in Portland, 8.1 km from Weymouth Harbour, 33 km from Monkey World, and 40 km from Golden Cap.

    Very well equipped and nicely furnished Comfortable and clean

  • Sea View Cottage in Dorset, Portland
    Scored 8.7
    8.7
    Rated fabulous
    Fabulous
     · 77 reviews

    Sea View Cottage in Dorset, Portland, a property with a garden and a terrace, is set in Portland, 2.5 km from Chesil Beach, 32 km from Monkey World, as well as 39 km from Golden Cap.

    So comfortable, clean, equipped and beautifully furnished.

  • The Shambles
    Budget options available
    Scored 8.5
    8.5
    Rated very good
    Very good
     · 11 reviews

    Offering a garden and sea view, The Shambles is situated in Portland, 33 km from Monkey World and 40 km from Golden Cap.

    Lovely house, quite fresh and clean looking with a very homely vibe

  • 5 Coastguard Cottage
    Budget options available
    Scored 8.3
    8.3
    Rated very good
    Very good
     · 6 reviews

    5 Coastguard Cottage, a property with a garden, is located in Portland, 2.5 km from Chesil Beach, 33 km from Monkey World, as well as 40 km from Golden Cap.

    The gorgeous views made this place an absolute gem! Nothing better to wake up with views of the sea!

  • The Old Rope House
    Budget options available
    Scored 8.5
    8.5
    Rated very good
    Very good
     · 19 reviews

    Set in Portland, 500 metres from Portland Beach and 33 km from Monkey World, The Old Rope House provides accommodation with amenities such as free WiFi and a flat-screen TV.

    Location, large enough for family with teens Lovely home

Great access to the city centre! Check these holiday homes in Portland

  • Fisherman's Cottage, King Street
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 1 review

    Offering a garden and sea view, Fisherman's Cottage, King Street is set in Portland, 7.8 km from Weymouth Harbour and 32 km from Monkey World.

  • St Johns View
    Central location
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 2 reviews

    St Johns View, a property with a garden, is set in Portland, 2.7 km from Chesil Beach, 33 km from Monkey World, as well as 40 km from Golden Cap.

  • The Old Portland Courthouse
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 2 reviews

    The Old Portland Courthouse, a property with a garden, is located in Portland, 32 km from Monkey World, 40 km from Golden Cap, as well as 46 km from Corfe Castle.

  • Sea Gem
    Central location
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 2 reviews

    Sea Gem, a property with a garden and barbecue facilities, is situated in Portland, 2.5 km from Chesil Beach, 32 km from Monkey World, as well as 39 km from Golden Cap.

  • Vindelis Cottage Chesil Beach
    Scored 9.8
    9.8
    Rated exceptional
    Exceptional
     · 4 reviews

    Set in Portland in the Dorset region, with Portland Beach and Portland Castle nearby, Vindelis Cottage Chesil Beach features accommodation with free private parking.

  • Bayview Villa
    Central location
    Scored 9.5
    9.5
    Rated exceptional
    Exceptional
     · 2 reviews

    Offering a garden and sea view, Bayview Villa is located in Portland, 33 km from Monkey World and 40 km from Golden Cap.

  • Bowman's Cottage
    Central location
    Scored 9.0
    9.0
    Rated superb
    Superb
     · 2 reviews

    Set 42 km from Golden Cap, 49 km from Corfe Castle and 200 metres from Portland Museum, Bowman's Cottage offers accommodation situated in Portland. The 4-star holiday home is 35 km from Monkey World.

  • Fisherman's Cottage
    Scored 9.0
    9.0
    Rated superb
    Superb
     · 1 review

    Offering a garden and sea view, Fisherman's Cottage is located in Portland, 44 km from Golden Cap and 50 km from Corfe Castle.

  • Fishermans Cottage
    Scored 8.8
    8.8
    Rated fabulous
    Fabulous
     · 42 reviews

    Boasting a terrace with sea views, a garden and barbecue facilities, Fishermans Cottage can be found in Portland, close to Portland Museum and 37 km from Monkey World.

    Clean and comfortable...all you needed for a stay away....

  • Sea View Cottage
    Central location
    Scored 8.8
    8.8
    Rated fabulous
    Fabulous
     · 34 reviews

    Situated in Portland, Sea View Cottage is a historic holiday home that features free WiFi, and guests can enjoy water sports facilities and a garden.

    the location. ideal for beach and local pubs and shops

  • Olympic Village Vela - Portland
    Scored 8.8
    8.8
    Rated fabulous
    Fabulous
     · 42 reviews

    Set in Portland and only 200 metres from Portland Beach, Olympic Village Vela - Portland offers accommodation with garden views, free WiFi and free private parking.

    Beautifully clean . Fab house. Really great location

  • Olympic Cottage
    Central location
    Scored 8.8
    8.8
    Rated fabulous
    Fabulous
     · 6 reviews

    Olympic Cottage, a property with a garden, is located in Portland, 32 km from Monkey World, 39 km from Golden Cap, as well as 45 km from Corfe Castle.

    Location, lovely and clean. All the kitchen things you might need.

  • Foundry Cottage
    Central location
    Scored 8.5
    8.5
    Rated very good
    Very good
     · 2 reviews

    Foundry Cottage, a property with a garden, is set in Portland, 34 km from Monkey World, 42 km from Golden Cap, as well as 48 km from Corfe Castle.

  • Shell Cottage Traditional Cottage Easton
    Scored 8.5
    8.5
    Rated very good
    Very good
     · 4 reviews

    Offering a garden and garden view, Shell Cottage Traditional Cottage Easton is situated in Portland, 10 km from Weymouth Harbour and 34 km from Monkey World.

  • Trevina
    Central location
    Scored 8.5
    8.5
    Rated very good
    Very good
     · 4 reviews

    Trevina, a property with a garden, is situated in Portland, 35 km from Monkey World, 42 km from Golden Cap, as well as 49 km from Corfe Castle.

    Fantastic location and a lovely little house. Amazing coastal path walks nearby which we and the dogs loved!

  • Nordor - lots of parking
    Scored 8.4
    8.4
    Rated very good
    Very good
     · 7 reviews

    Nordor - lots of parking, a property with a garden, is situated in Portland, 35 km from Monkey World, 42 km from Golden Cap, as well as 49 km from Corfe Castle.

  • Blackford House a large home Portland Dorset
    Scored 8.3
    8.3
    Rated very good
    Very good
     · 3 reviews

    Boasting garden views, Blackford House a large home Portland Dorset provides accommodation with a garden and a terrace, around 500 metres from Portland Beach.

  • Ammonite Cottage
    Central location
    Scored 8.2
    8.2
    Rated very good
    Very good
     · 12 reviews

    Ammonite Cottage, a property with a garden, is situated in Portland, 32 km from Monkey World, 39 km from Golden Cap, as well as 46 km from Corfe Castle.

    Lovely comfortable little cottage. Well placed in the island

  • Sally Hall Large central Portland home
    Scored 8.0
    8.0
    Rated very good
    Very good
     · 4 reviews

    Sally Hall Large central Portland home is located in Portland, 34 km from Monkey World, 41 km from Golden Cap, as well as 48 km from Corfe Castle.

    Stylish , spacious and well set out, especially the living area. Well equipped , warm and cosy. All enjoyed the space, never felt on top of each other.

  • Kearney Cottage - Artist's Retreat
    Scored 8.0
    8.0
    Rated very good
    Very good
     · 4 reviews

    Kearney Cottage - Artist's Retreat, a property with a garden, is located in Portland, 2.6 km from Chesil Beach, 32 km from Monkey World, as well as 39 km from Golden Cap.

  • Chesil Views
    Central location
    Scored 8.0
    8.0
    Rated very good
    Very good
     · 3 reviews

    Chesil Views, a property with a garden, is located in Portland, 33 km from Monkey World, 40 km from Golden Cap, as well as 46 km from Corfe Castle.

  • The Old Police Station
    Scored 8.0
    8.0
    Rated very good
    Very good
     · 1 review

    Offering a garden and sea view, The Old Police Station is located in Portland, 32 km from Monkey World and 39 km from Golden Cap.

  • Chesil View House
    Scored 7.9
    7.9
    Rated good
    Good
     · 16 reviews

    Chesil View House has a balcony and is situated in Portland, within just 500 metres of Portland Beach and 1.4 km of Portland Castle. This holiday home provides accommodation with a patio.

    Nice clean and tidy. Nice decor. Homely feel. Great view from the top room. Very cosy.

  • Jurassic Coast House
    Scored 7.8
    7.8
    Rated good
    Good
     · 5 reviews

    Offering a garden and sea view, Jurassic Coast House is located in Portland, 500 metres from Portland Beach and 32 km from Monkey World.

  • Cliffwalk Cottage
    Scored 6.0
    6.0
    Rated pleasant
    Pleasant
     · 1 review

    Cliffwalk Cottage, a property with a garden, is set in Portland, 43 km from Golden Cap, 50 km from Corfe Castle, as well as 2.2 km from Portland Museum.

  • Crows Nest
    Central location
    Scored 2.0
    2.0
    Rated very poor
    Very poor
     · 1 review

    Offering sea views, Crows Nest is an accommodation located in Portland, 8 km from Weymouth Harbour and 33 km from Monkey World.

  • Alpen Rose Cottage

    Alpen Rose Cottage, a property with a garden, is set in Portland, 42 km from Golden Cap, 48 km from Corfe Castle, as well as 700 metres from Portland Museum.

  • Pebble Reef
    Central location

    Featuring a hot tub, Pebble Reef is located in Portland. The property is situated 35 km from Monkey World, 42 km from Golden Cap and 49 km from Corfe Castle.

FAQ about holiday homes in Portland

Holiday homes that guests love in Portland

  • Scored 8.9
    8.9
    Rated fabulous
    Fabulous
     · 24 reviews
    Great property in a great location. Communication from the owners was well received. The property was very clean.
    Steven
    Family with young children
  • Scored 8.5
    8.5
    Rated very good
    Very good
     · 22 reviews
    Lovely accommodation, right next to Chesil Beach which was great as we were there for a fishing trip. Very clean property with everything you need. Parking space right outside very handy.
    Mark
    People with friends
  • Avg. price/night: £119
    Scored 7.8
    7.8
    Rated good
    Good
     · 513 reviews
    Wonderful property with a great view out our windows staff were amazing and friendly- nothing was too hard. Make sure you add breakfast it’s very worth it. We ate dinner there also and had a few drinks at the bar all were great! Room was renovated and very clean. Loved our stay thank you
    Naomi
    Family with young children
  • Avg. price/night: £80.10
    Scored 9.0
    9.0
    Rated superb
    Superb
     · 139 reviews
    lovely location, lovely building, very clean, well organised, and a wonderful landlady, Cat is amazing!
    Christina
    People with friends
  • Avg. price/night: £180
    Scored 7.9
    7.9
    Rated good
    Good
     · 990 reviews
    Staff was very friendly and helpful. Breakfast was nice and hot, hotel very clean and tidy and nice location. Would definitely go back.
    Wayne
    Young couple
  • Avg. price/night: £180
    Scored 7.9
    7.9
    Rated good
    Good
     · 990 reviews
    Breakfast was OK. Location good. Very clean hotel.
    Sean
    Young couple
  • Scored 8.9
    8.9
    Rated fabulous
    Fabulous
     · 592 reviews
    The service, location and the apartment layout and compartmentalisation. Very clean, well equipped and nice colour theme and interior design.
    Roxy
    Young couple
  • Avg. price/night: £80.10
    Scored 9.0
    9.0
    Rated superb
    Superb
     · 139 reviews
    Ideal location for exploring the area. Cat was a fantastic host. The room was very clean and comfortable, and the breakfast was superb.
    Paula
    Young couple
  • Scored 9.1
    9.1
    Rated superb
    Superb
     · 91 reviews
    Lovely house and very comfortable room which was also very clean. Vienna and Joe were friendly and helpful.
    simon
    Solo traveller
  • Avg. price/night: £180
    Scored 7.9
    7.9
    Rated good
    Good
     · 990 reviews
    Easy parking, very clean, very pleasant / efficient / helpful staff. Lovely food (breakfast, lunch & dinner)
    Graham
    Young couple

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