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The best holiday homes in Portland

Check out our pick of great holiday homes in Portland

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Superb: 9+ Very good: 8+ Good: 7+ Pleasant: 6+
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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. The holiday home, set in a building dating from 19th century, is 32 km from Monkey World and 39 km from Golden Cap. The property is non-smoking and is set 500 metres from Portland Beach.

Location, house layout worked well.

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9
Superb
5 reviews
Price from
£124.31
per night

The spacious holiday home has 3 bedrooms, a TV, a fully equipped kitchen with a microwave and a toaster, and 2 bathrooms with a walk-in shower.

Guests at the holiday home can enjoy cycling and fishing nearby, or make the most of the garden.

Everything about this property is perfect. In fact, we just regretted immediately why we didn't book for more days. This property is classy for a fantastic holiday. It got everything from space, cleanliness, secure gated parking, comfortable beds and chairs, TV sets in the living room and some bedrooms, extensive balconies with chairs for relaxation while enjoying the sea view,, fully equipped kitchen etc....... Summary is that property is beyond imagination....

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9.2
Superb
6 reviews
Price from
£228.85
per night

The air-conditioned holiday home consists of 5 bedrooms, a fully equipped kitchen and 3 bathrooms. Towels and bed linen are offered in the holiday home.

Rufus Castle is 3.5 km from the holiday home, while Athelhampton House is 30 km from the property. The nearest airport is Bournemouth Airport, 67 km from SeaSky.

Really nice property, very clean and well equipped. The communication with the host was very smooth.

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9
Superb
8 reviews
Price from
£200
per night

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. The property is non-smoking and is set 2.2 km from Portland Beach.

Poppy & Sunny have made this place in to a dream! Loads of original features which are done to a very high standard. We loved our time at Dukes Cottage and cannot wait to visit again

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9.3
Superb
18 reviews
Price from
£155
per night

This holiday home features 2 bedrooms, a kitchen with a dishwasher and an oven, a TV, a seating area and 1 bathroom. The accommodation offers a fireplace.

Guests at the holiday home will be able to enjoy activities in and around Portland, like golfing, cycling and fishing.

Great location as about 5 minute walk from the beach and you get some awesome views of the sunset from the main bedroom. Really nice cottage with everything we needed for a long weekend and suitable for kids. Met the owner and he was very nice. Well looked after property and a great location for getting to see the rest of portland and surrounding areas. Would recommend

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9.1
Superb
7 reviews
Price from
£336.95
per night

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. With inner courtyard views, this accommodation provides a patio. Providing free WiFi throughout the property, the non-smoking holiday home features a hot tub.

The location was PERFECT. The four of us (two couples) had way more room than we needed and were easily able to walk to local grocery stores, hiking spots, rock climbing spots, and restaurants.

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9.3
Superb
9 reviews
Price from
£139.50
per night

Set 32 km from Monkey World, 39 km from Golden Cap and 46 km from Corfe Castle, Sunset Lodge offers accommodation located in Portland. The 4-star holiday home has sea views and is 2.4 km from Chesil Beach. Free WiFi is available throughout the property and Portland Beach is 200 metres away.

The spacious holiday home is fitted with 3 bedrooms, a fully equipped kitchen with a dining area and a dishwasher, and 2 bathrooms. The accommodation is non-smoking.

Lovely clean comfortable house with plenty of space for us all, great location. Really nice welcome pack on arrival which wasn't expected, but greatly received! Would defiantly like to stay there again. Thanks for providing a lovely homely place to stay.

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9.7
Exceptional
9 reviews

The spacious holiday home is equipped with 4 bedrooms, a fully equipped kitchen with a dining area and a dishwasher, and 2 bathrooms.

Corfe Castle is 45 km from the holiday home, while Portland Castle is 600 metres away. The nearest airport is Bournemouth Airport, 66 km from Osprey House Portland.

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

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9.2
Superb
5 reviews
Price from
£398.48
per night

The holiday home is equipped with 3 bedrooms, a TV and a fully equipped kitchen that provides guests with a dishwasher, an oven, a washing machine, a microwave and a toaster. Towels and bed linen are provided in the holiday home. The property has an outdoor dining area.

Very comfortable property ,with everything to make the stay home from home.

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9.1
Superb
15 reviews
Price from
£177.50
per night

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. Featuring sea and garden views, this holiday home also offers free WiFi. The property is non-smoking and is located 400 metres from Portland Beach.

So comfortable, clean, equipped and beautifully furnished.

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8.7
Fabulous
58 reviews
Price from
£162
per night

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.
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Most booked holiday homes in Portland this month

Enjoy breakfast in Portland!

  • Our Place In Portland Holiday Home with Sea View
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 5 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.

  • The Blue Cottage
    Breakfast options
    9.2
    Scored 9.2
    Superb
    Rated superb
     · 6 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.

  • SeaSky
    Breakfast options
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 8 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.

    Very spacious modern house, great location, nice view from the top room etc

  • Duke’s Cottage
    Breakfast options
    9.3
    Scored 9.3
    Superb
    Rated superb
     · 18 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

  • The Shambles
    Breakfast options
    9.1
    Scored 9.1
    Superb
    Rated superb
     · 7 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

  • Pebble Reef
    Breakfast options
    9.3
    Scored 9.3
    Superb
    Rated superb
     · 9 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.

    Great hot tub. The cottage had everything we needed.

  • Sunset Lodge
    Breakfast options
    9.7
    Scored 9.7
    Exceptional
    Rated 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.

    n/a no breakfast. location fantastic overlooking chesil beach close to pubs and garage for parking very handy

  • Osprey House Portland
    9.2
    Scored 9.2
    Superb
    Rated superb
     · 5 reviews

    Offering sea views, Osprey House Portland is an accommodation 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 .

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

  • Cornerstone
    Budget options available
    9.1
    Scored 9.1
    Superb
    Rated superb
     · 15 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

  • Sea View Cottage in Dorset, Portland
    8.7
    Scored 8.7
    Fabulous
    Rated fabulous
     · 58 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.

    Beautifully decorated, very clean and well equipped.

  • 5 Coastguard Cottage
    Budget options available
    8.0
    Scored 8.0
    Very good
    Rated very good
     · 5 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 Old Rope House
    Budget options available
    8.6
    Scored 8.6
    Fabulous
    Rated fabulous
     · 18 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.

    Very spacious even for 6 people, had everything we needed!

  • The View
    Budget options available
    8.7
    Scored 8.7
    Fabulous
    Rated fabulous
     · 7 reviews

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

  • Olympic Village Vela - Portland
    8.9
    Scored 8.9
    Fabulous
    Rated fabulous
     · 37 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

  • Sea View Cottage
    Budget options available
    8.7
    Scored 8.7
    Fabulous
    Rated fabulous
     · 33 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

  • Fishermans Cottage
    Budget options available
    8.7
    Scored 8.7
    Fabulous
    Rated fabulous
     · 34 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....

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

  • Bowman's Cottage
    Central location
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    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.

  • Home From Home - Sleeps 8
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    Home From Home - Sleeps 8 is located in Portland, 33 km from Monkey World, 40 km from Golden Cap, and 46 km from Corfe Castle.

  • Vindelis Cottage Chesil Beach
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 3 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.

  • St Johns View
    Central location
    10.0
    Scored 10.0
    Exceptional
    Rated 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.

  • Chesil Views
    Central location
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    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 Portland Courthouse
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    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
    10.0
    Scored 10.0
    Exceptional
    Rated 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.

  • Lyme View
    Central location
    9.5
    Scored 9.5
    Exceptional
    Rated exceptional
     · 2 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.

  • Fisherman's Cottage
    9.0
    Scored 9.0
    Superb
    Rated 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.

  • Olympic Cottage
    Central location
    8.8
    Scored 8.8
    Fabulous
    Rated fabulous
     · 4 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.

  • Shell Cottage Traditional Cottage Easton
    8.5
    Scored 8.5
    Very good
    Rated 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.

  • Bright & beautiful 4 bedroom house with sea views
    8.5
    Scored 8.5
    Very good
    Rated very good
     · 4 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.

  • Pebbles Reach
    Central location
    8.5
    Scored 8.5
    Very good
    Rated very good
     · 2 reviews

    Located in Portland and only 300 metres from Portland Beach, Pebbles Reach provides accommodation with sea views, free WiFi and free private parking.

  • Olympic Village Home - Victory
    8.5
    Scored 8.5
    Very good
    Rated very good
     · 27 reviews

    Offering a garden and quiet street view, Olympic Village Home - Victory is set in Portland, 2.3 km from Chesil Beach and 32 km from Monkey World.

    Lovely modern house, clean, bright, very comfortable, good location.

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

    Nordor - lots of parking is a holiday home with a garden, set in Portland, 400 metres from Portland Museum. The property features views of the garden and is 500 metres from Rufus Castle.

  • Neptune Cottage
    Central location
    8.4
    Scored 8.4
    Very good
    Rated very good
     · 9 reviews

    Neptune Cottage, a property with a garden, is set in Portland, 39 km from Golden Cap, 46 km from Corfe Castle, as well as 1.1 km from Portland Castle.

  • Chesil View House
    8.3
    Scored 8.3
    Very good
    Rated very good
     · 22 reviews

    Located in Fortuneswell, Chesil View House offers self-catering accommodation with free WiFi access.

    Nicely decorated. Very comfortable beds. Fully equipped kitchen nice small garden

  • Blackford House a large home Portland Dorset
    8.3
    Scored 8.3
    Very good
    Rated 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
    8.3
    Scored 8.3
    Very good
    Rated very good
     · 13 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

  • Foundry Cottage
    Central location
    8.0
    Scored 8.0
    Very good
    Rated very good
     · 1 review

    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.

  • Sally Hall Large central Portland home
    8.0
    Scored 8.0
    Very good
    Rated 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
    8.0
    Scored 8.0
    Very good
    Rated very good
     · 3 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.

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

    Offering a garden and sea view, The Old Police Station is located in Portland, 400 metres from Portland Beach and 32 km from Monkey World.

  • Jurassic Coast House
    7.8
    Scored 7.8
    Good
    Rated 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.

  • Chesil View House
    7.0
    Scored 7.0
    Good
    Rated good
     · 2 reviews

    Offering sea views, Chesil View House is an accommodation situated in Portland, 2.8 km from Chesil Beach and 33 km from Monkey World.

  • Lime Cottage
    Central location
    6.0
    Scored 6.0
    Pleasant
    Rated pleasant
     · 1 review

    Lime Cottage, a property with a garden, is situated in Portland, 41 km from Golden Cap, 48 km from Corfe Castle, as well as 1.2 km from Portland Museum.

  • Cliffwalk Cottage
    6.0
    Scored 6.0
    Pleasant
    Rated 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.

  • Spring Rose Cottage
    4.0
    Scored 4.0
    Disappointing
    Rated disappointing
     · 1 review

    Spring Rose Cottage, a property with a terrace, is located in Portland, 33 km from Monkey World, 40 km from Golden Cap, as well as 46 km from Corfe Castle.

FAQ about holiday homes in Portland






Holiday homes that guests love in Portland

  • 9.1
    Scored 9.1
    Superb
    Rated superb
     · 80 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: £140
    7.8
    Scored 7.8
    Good
    Rated good
     · 874 reviews
    Easy parking, very clean, very pleasant / efficient / helpful staff. Lovely food (breakfast, lunch & dinner)
    Graham
    Young couple
  • 9.1
    Scored 9.1
    Superb
    Rated superb
     · 7 reviews
    Property was very clean and tidy on arrival, fantastic appliances and well equipped kitchen. Bedrooms were very comfortable and the bathroom excellent, with a great shower! Parking was tight, but all neighbours were very respectful and there was aways space to park outside property.
    Dave
    Family with young children
  • Avg. price/night: £189
    8.7
    Scored 8.7
    Fabulous
    Rated fabulous
     · 58 reviews
    Great location for what we needed visiting friends for the night. The cottage was very clean and comfortable with tea's and coffee provided.
    Adrian
    Young couple
  • Avg. price/night: £140
    7.8
    Scored 7.8
    Good
    Rated good
     · 874 reviews
    It was quiet, very clean , friendly helpful staff. Just what we wanted
    Pauline
    Young couple
  • 8.5
    Scored 8.5
    Very good
    Rated very good
     · 27 reviews
    Very clean and tidy, well equipped accommodation. Close to marina and beach. Short walk to bus stops for easy access into Weymouth or Portland Bill
    sue
    People with friends
  • 8.9
    Scored 8.9
    Fabulous
    Rated fabulous
     · 13 reviews
    Fantastic location, beautiful views, parking right next to the property. The studio was very clean and had everything needed for our stay. We were visiting friends on Portland, the property was just a few minutes away which was very convenient.
    Glenda
    Young couple
  • 8.9
    Scored 8.9
    Fabulous
    Rated fabulous
     · 13 reviews
    The studio was lovely, very clean, bright and comfortable. Great views. All the staff we met on the estate were very friendly and helpful. Very peaceful and delightful stay.
    LORNA
    Solo traveller
  • 8.9
    Scored 8.9
    Fabulous
    Rated fabulous
     · 37 reviews
    Very clean and comfortable
    Jeremy
    People with friends
  • 8.9
    Scored 8.9
    Fabulous
    Rated fabulous
     · 513 reviews
    Great location right on the waterfront, ideal for exploring the Dorset coast. Very clean and comfortable.
    Susan
    Young couple

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