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The best vacation homes in Portland

Check out our selection of great vacation homes in Portland

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Review Score

Wonderful: 9+ Very Good: 8+ Good: 7+ Pleasant: 6+
Our top picks Lowest Price First Star rating and price Top reviewed

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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
Wonderful
6 reviews
Price from
$192
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
Wonderful
7 reviews
Price from
$254
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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9.2
Wonderful
17 reviews
Price from
$165
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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9.4
Wonderful
5 reviews
Price from
$428
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
Wonderful
9 reviews
Price from
$172
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
Price from
$445
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
Wonderful
16 reviews
Price from
$191
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
Excellent
55 reviews
Price from
$223
per night

The holiday home has 1 bedroom, a TV, a fully equipped kitchen with a microwave and a toaster, a washing machine, and 1 bathroom with a walk-in shower.

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

Lovely view of the sea and coastline. Well laid out garden. The property was geared up for rentals as all painted white.

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8
Very Good
5 reviews
Price from
$377
per night

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. This recently renovated holiday home is located 40 km from Golden Cap and 46 km from Corfe Castle. The property is non-smoking and is located 1.2 km from Portland Castle.

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

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8.6
Excellent
18 reviews
Price from
$292
per night

Looking for a vacation home?

Great for families or large parties, vacation homes are privately owned accommodations, available for long or short-term rental. These homes are furnished and equipped with kitchen facilities, though breakfast might be offered as an add-on. These properties have their own independent front door, which makes them different than apartments.
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Most booked vacation homes in Portland this month

Enjoy breakfast in Portland!

  • The Blue Cottage
    Breakfast options
    9.2
    Scored 9.2
    Wonderful
    Rated wonderful
     · 6 reviews

    The Blue Cottage offers accommodations in Portland, a 5-minute walk from Portland Beach and 20 miles from Monkey World.

  • SeaSky
    Breakfast options
    9.0
    Scored 9.0
    Wonderful
    Rated wonderful
     · 7 reviews

    SeaSky offers accommodations in Portland, a 6-minute walk from Portland Beach and 20 miles from Monkey World.

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

  • Duke’s Cottage
    Breakfast options
    9.2
    Scored 9.2
    Wonderful
    Rated wonderful
     · 17 reviews

    Duke’s Cottage is located in Portland, just 1.4 miles from Portland Beach and 22 miles from Monkey World. Featuring sea and garden views, this vacation home also includes free Wifi.

    Location, comfort,cleanliness,responsive to any need

  • The Shambles
    Breakfast options
    9.4
    Scored 9.4
    Wonderful
    Rated wonderful
     · 5 reviews

    The Shambles is located in Portland, just 20 miles from Monkey World and 25 miles from Golden Cap.

  • Pebble Reef
    Breakfast options
    9.3
    Scored 9.3
    Wonderful
    Rated wonderful
     · 9 reviews

    22 miles from Monkey World in Portland, Pebble Reef features accommodations with access to a hot tub. With inner courtyard views, this accommodation provides a patio.

    Great hot tub. The cottage had everything we needed.

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

    Sunset Lodge is located in Portland, just 20 miles from Monkey World and 24 miles from Golden Cap. The 4-star vacation home is 1.5 miles from Chesil Beach.

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

  • Osprey House Portland
    9.0
    Scored 9.0
    Wonderful
    Rated wonderful
     · 4 reviews

    Osprey House Portland is located in Portland, just a 2-minute walk from Portland Beach and 20 miles from Monkey World.

  • Cornerstone
    Breakfast options
    9.0
    Scored 9.0
    Wonderful
    Rated wonderful
     · 16 reviews

    Cornerstone is located in Portland, just a 7-minute walk from Portland Beach and 20 miles from Monkey World. This property offers access to a terrace and free private parking.

    Lovely well looked after property, modern decor Great size bedrooms

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

  • Sea View Cottage in Dorset, Portland
    8.7
    Scored 8.7
    Excellent
    Rated excellent
     · 55 reviews

    Offering a garden and a terrace, Sea View Cottage in Dorset, Portland in Portland is close to Portland Beach and Portland Castle.

    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

    Just a 4-minute walk from Portland Beach and 0.6 miles from Portland Castle, 5 Coastguard Cottage features accommodations in Portland with a garden.

  • The Old Rope House
    Budget options available
    8.6
    Scored 8.6
    Excellent
    Rated excellent
     · 18 reviews

    The Old Rope House is a recently renovated vacation home in Portland, near Portland Beach.

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

  • The View
    Budget options available
    8.7
    Scored 8.7
    Excellent
    Rated excellent
     · 7 reviews

    The View is located in Portland, just a few steps from Portland Beach and 1.6 miles from Chesil Beach. Complimentary Wifi is provided throughout the property and private parking is available on site.

  • Olympic Village Vela - Portland
    8.7
    Scored 8.7
    Excellent
    Rated excellent
     · 37 reviews

    Just a 2-minute walk from Portland Beach and 700 yards from Portland Castle, Olympic Village Vela - Portland features accommodations in Portland with barbecue facilities.

    Beautifully clean . Fab house. Really great location

  • Sea View Cottage
    Budget options available
    8.6
    Scored 8.6
    Excellent
    Rated excellent
     · 34 reviews

    With water sports facilities and a garden, Sea View Cottage is a historic vacation home that features accommodations with free Wifi. This vacation home offers accommodations with a patio.

    the location. ideal for beach and local pubs and shops

  • Fishermans Cottage
    Budget options available
    8.7
    Scored 8.7
    Excellent
    Rated excellent
     · 34 reviews

    27 miles from Golden Cap in Portland, Fishermans Cottage provides accommodations with access to a hot tub. Guests can benefit from a patio and a picnic area.

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

  • Olympic Village Home - Victory
    8.6
    Scored 8.6
    Excellent
    Rated excellent
     · 29 reviews

    Just a 4-minute walk from Portland Beach and 600 yards from Portland Castle, Olympic Village Home - Victory features accommodations in Portland with a garden.

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

Great access to the city center! Check these vacation homes in Portland

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

    Bowman's Cottage offers accommodations in Portland, 26 miles from Golden Cap and 30 miles from Corfe Castle. The 4-star vacation home is 22 miles from Monkey World.

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

    Home From Home - Sleeps 8 offers accommodations in Portland, 20 miles from Monkey World and 25 miles from Golden Cap.

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

    Vindelis Cottage Chesil Beach is located in Portland, just 24 miles from Golden Cap and 28 miles from Corfe Castle.

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

    Just a 6-minute walk from Portland Beach and 0.6 miles from Portland Castle, St Johns View features accommodations in Portland with a garden.

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

    Chesil Views is located in Portland, just a 12-minute walk from Portland Castle and 2.4 miles from Portland Museum.

  • The Old Portland Courthouse
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    The Old Portland Courthouse offers accommodations in Portland, 20 miles from Monkey World and 25 miles from Golden Cap. The 4-star vacation home is 1.6 miles from Chesil Beach.

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

    Sea Gem is located in Portland, just 24 miles from Golden Cap and 28 miles from Corfe Castle.

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

    Lyme View is located in Portland, just 20 miles from Monkey World and 25 miles from Golden Cap.

  • Fisherman's Cottage
    9.0
    Scored 9.0
    Wonderful
    Rated wonderful
     · 1 review

    Just a 18-minute walk from Portland Museum and 1.1 miles from Rufus Castle, Fisherman's Cottage features accommodations in Portland with a garden.

  • Our Place In Portland Holiday Home with Sea View
    8.8
    Scored 8.8
    Excellent
    Rated excellent
     · 4 reviews

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

  • Olympic Cottage
    Central location
    8.8
    Scored 8.8
    Excellent
    Rated excellent
     · 4 reviews

    Olympic Cottage offers accommodations in Portland, 20 miles from Monkey World and 24 miles from Golden Cap. The 4-star vacation home is 1.4 miles from Chesil Beach.

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

  • Sally Hall Large central Portland home
    8.7
    Scored 8.7
    Excellent
    Rated excellent
     · 3 reviews

    Sally Hall Large central Portland home offers accommodations in Portland, 21 miles from Monkey World and 26 miles from Golden Cap.

    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.

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

    Neptune Cottage is located in Portland, just 20 miles from Monkey World and 24 miles from Golden Cap. The 3-star vacation home is a 2-minute walk from Portland Beach.

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

    Just 1.2 miles from Portland Beach and a 11-minute walk from Portland Museum, Shell Cottage Traditional Cottage Easton features accommodations in Portland with a garden.

  • Blackford House a large home Portland Dorset
    8.5
    Scored 8.5
    Very Good
    Rated very good
     · 2 reviews

    Just a 5-minute walk from Portland Beach and 0.8 miles from Portland Castle, Blackford House a large home Portland Dorset features accommodations in Portland with a garden.

  • 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 offers accommodations in Portland, 5 miles from Weymouth Harbour and 20 miles from Monkey World.

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

    Just a 3-minute walk from Portland Beach and 600 yards from Portland Castle, Pebbles Reach features accommodations in Portland with a garden.

  • 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, 1312 feet from Portland Museum. The property features views of the garden and is 1640 feet from Rufus Castle.

  • Ammonite Cottage
    Central location
    8.3
    Scored 8.3
    Very Good
    Rated very good
     · 13 reviews

    Ammonite Cottage offers accommodations in Portland, 20 miles from Monkey World and 24 miles from Golden Cap. The 4-star vacation home is 1.4 miles from Chesil Beach.

    Lovely comfortable little cottage. Well placed in the island

  • Chesil View House
    8.1
    Scored 8.1
    Very Good
    Rated very good
     · 23 reviews

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

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

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

    Just 1.2 miles from Portland Beach and a 11-minute walk from Portland Museum, Foundry Cottage features accommodations in Portland with a garden.

  • Chesil View House
    8.0
    Scored 8.0
    Very Good
    Rated very good
     · 1 review

    Chesil View House offers accommodations in Portland, 29 miles from Corfe Castle and a 16-minute walk from Portland Castle.

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

    Just a 5-minute walk from Portland Beach and 0.6 miles from Portland Castle, Kearney Cottage - Artist's Retreat features accommodations in Portland with a garden.

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

    Just a 4-minute walk from Portland Beach and 0.4 miles from Portland Castle, The Old Police Station features accommodations in Portland with a garden.

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

    Just a 6-minute walk from Portland Beach and 500 yards from Portland Castle, Jurassic Coast House features accommodations in Portland with a garden.

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

    Just a 14-minute walk from Portland Museum and 0.9 miles from Rufus Castle, Lime Cottage features accommodations in Portland with a garden. The 4-star vacation home is 21 miles from Monkey World.

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

    Cliffwalk Cottage is located in Portland, just 27 miles from Golden Cap and 31 miles from Corfe Castle.

  • Beautiful Town house on the beach
    5.7
    Scored 5.7
    Above average
    Rated okay
     · 6 reviews

    Just a few steps from Portland Beach and a 14-minute walk from Portland Castle, Beautiful Town house on the beach features accommodations in Portland with a garden.

FAQ about vacation homes in Portland






Vacation Homes That Guests Love in Portland

  • Avg. price/night: $127.14
    8.9
    Scored 8.9
    Excellent
    Rated excellent
     · 513 reviews
    Great location right on the waterfront, ideal for exploring the Dorset coast. Very clean and comfortable.
    Susan
    Young couple
  • Avg. price/night: $105.53
    8.9
    Scored 8.9
    Excellent
    Rated excellent
     · 37 reviews
    Exceptional customer service from Cat. The room was very clean, with a nice bathroom. The property features a cool roof terrace. Excellent value.
    Thomas
    Young couple
  • Avg. price/night: $127.14
    8.9
    Scored 8.9
    Excellent
    Rated excellent
     · 513 reviews
    Great location, great use of space. Very clean, modern, had everything we needed.
    Kelly
    Travelers with friends
  • 8.3
    Scored 8.3
    Very Good
    Rated very good
     · 3 reviews
    The location and view were incredible. The room was very clean, and it was helpful to have full cooking facilities.
    Kate Heaphy
    Solo traveler
  • Avg. price/night: $178
    7.8
    Scored 7.8
    Good
    Rated good
     · 872 reviews
    There was plenty of parking, great location, friendly staff, spacious rooms & very clean. We had afternoon tea which was lovely. The staff were very friendly & changed some of the sandwiches we didn't like for us, plenty of choice of cakes !! the views from the Bistro were amazing.
    jill
    Family with young children
  • Avg. price/night: $127.14
    8.9
    Scored 8.9
    Excellent
    Rated excellent
     · 513 reviews
    The apartments were very clean and tidy, bed was comfortable and facilities catjtered for everything you needed for self catering. The sea view was amazing. Location was spectacular with lots of history.
    Amy
    Young couple
  • Avg. price/night: $127.14
    8.9
    Scored 8.9
    Excellent
    Rated excellent
     · 513 reviews
    The flat was very clean and well presented. The flat was warm. The towels and bedding were to a high standard. The kitchen had a good amount of items provided.
    William
    Family with young children
  • 10
    Scored 10
    Exceptional
    Rated exceptional
     · 3 reviews
    Very clean and modern. Good use of space. Parking immediately outside the property. Outside tap for washing off muddy / sandy footwear etc. Pet free is important for us. Immaculately clean. Well equipped. Modern, functional furniture. Warm. Lots of information provided about places to eat. We went to the nearest seafront pub and enjoyed a lovely meal - so nice to have this as a close by stroll.
    Amanda
    Young couple
  • Avg. price/night: $127.14
    8.9
    Scored 8.9
    Excellent
    Rated excellent
     · 513 reviews
    Beautiful holiday home. Clean and spacious.
    Beverley
    Family with young children
  • Avg. price/night: $127.14
    8.9
    Scored 8.9
    Excellent
    Rated excellent
     · 513 reviews
    Very clean the decor was lovely and very comfortable
    Luke
    Young couple

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